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Your Guide to the BEST Maine Sailing Tours | Windjammers, Sailboats, & Schooner Tours

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Everyone knows that Maine has a stunning coastline and breathtaking views of the Atlantic Ocean from pristine beaches to rugged cliff walks. But, have you ever considered seeing Maine from the water? Set sail on an exciting adventure on one of the best Maine sailing tours onboard a windjammer, sailboat, or schooner.

We think it’s the best way to view the Maine coast , and what could be more exhilarating than setting sail out of a Maine harbor aboard a tall-masted schooner? Down the coastline from the Downeast & Acadia region to the Southern Maine Coast , there are so many sailing excursions to choose from.

The best part? You can sit back and relax while someone else does the sailing and navigating. Or, you may lend a hand and hoist a sail if you prefer. There’s no better way to experience the beauty of Maine than on a historic sailing trip, so check out these options for your next visit to Maine.

Downeast & Acadia Sailing Tours

Downeast windjammer cruise lines.

If you’re looking for a variety of options for sailing, Downeast Windjammer Cruise Lines in Bar Harbor has you covered. Offering a Sunset Sail, a Morning Sail, and an Afternoon Sail, there’s a wonderful experience no matter the time of day. Each sail has its own vibe.

The Sunset Sail is the most popular cruise that Downeast offers. It includes live folk music, beer, and wine for sale. Or, enjoy sailing in Frenchman Bay during the Morning Sail, which is more relaxed but still offers breathtaking views of Acadia National Park .

The Afternoon Sail is perfect for those looking for a narration during the sail. The captain will point out points of interest, regale you with the local history, and discuss wildlife.

No matter the sail, you can bring a picnic of snacks along, and most sails are pet-friendly.

Downeast Sailing Adventures

Southwest Harbor

Step aboard the Real Maine for an unforgettable experience sailing around the Cranberry Islands, Acadia, and Somes Sound. This tour will take you by lighthouses, past gorgeous homes on the shore, and by working fishing boats.

Book a private charter or a group day sailing adventure for up to six passengers. Downeast Sailing Adventures has daily sails on its 33-foot boat Surprise and its 38-foot boat Swan .

Sail Acadia

Northeast Harbor & Southwest Harbor

Sail Acadia offers trips out of two harbors, Northeast Harbor and Southwest Harbor . Sailing trips can be either shared or privately chartered. Private charters can be catered to your preferences with sailing instructions or a stop at an island for a picnic included.

Book a morning sail for calm waters with gentle sea breezes and good opportunities to view local wildlife. The morning sail is suggested for first-timers and children.

Or, book an afternoon sail for stronger winds that will make the sailboat cruise faster. This sail typically sees seals along the route, and the captain will often give a narration of the wildlife and history of the area.

Another option is a sunset sail for a romantic experience. This sail will have you seeing gorgeous sunset views on calm waters.

Schooner Tours in MidCoast Maine

Schooner stephen taber.

If you’re looking for an all-inclusive overnight experience, book a sail aboard the 150-year-old Stephen Taber . Each sail includes accommodations in one of 12 cabins, meals, wine (on evening sails), a lobster bake and barbecue on the beach, and evening entertainment.

Guests can choose from a themed trip or a private charter from Rockland Maine . Themed trips are a lot of fun and span from three to six nights, depending on your preference.

Enjoy trips such as Culinary Explorations; ‘Wine, Dine, and Chocolate;’ Yacht Racing Regatta; Penobscot Bay’s Hidden Gems; and more. These trips are sure to be memorable experiences, and by the end of the trips, you’ll feel like family with the other guests on board.

Here are more MidCoast Maine boat tours that are part of the Maine Windjammer Association like the Schooner Stephen Taber : Schooner American Eagle | Captain Tyler King | Rockland, ME Windjammer Angelique | Captain Dennis Gallant & Candace Kuchinski | Camden ME Schooner Grace Bailey | Captain Sam Sikkema | Rockland, ME Schooner Heritage | Captains Sean Grims & Ben Welzenbach | Rockland, ME Schooner Ladona | Captain J.R. Braugh  | Rockland, ME Schooner Lewis R. French | Captain Becky Wright and Nathan Sigouin | Camden, ME Schooner Mary Day | Captain Barry King and Jen Martin | Camden, ME

A Morning in Maine

If you’re strapped for time and want a shorter sail, A Morning in Maine’s sailing trips are a wonderful experience. The two-hour sailing adventures take place aboard a 55-foot ketch that passes lighthouses and other schooners.

The morning trip is perfect for those looking for calm sailing. The mid-afternoon sail has windier conditions for a faster sail. Evening and sunset sails feature beautiful sunset views and a relaxing ride. Guests are often given the chance to try to steer the boat as well.

Schooner Surprise

The Schooner Surprise has been sailing for over 105 years, with 30 of those years setting sail out of Camden Maine . Guests can book a two-hour sail with views of the lighthouse, summer houses and views of Penobscot Bay .

These family-friendly sails let guests, including children, take the wheel while out at sea. Special sails include a Full Moon Sail that features live music during sunset and a trip lasting two hours into the night. Or, book a fireworks view sail or a Birding and Marine Life Tour with an ornithologist.

Portland & Casco Bay Sailing Tours

Portland schooner co..

Portland Schooner Co. sets sail from Portland Maine and cruises through Casco Bay for a delightful trip along the coastline and past lighthouses and ocean life, like seals. On the two-hour sail, bring your own picnic and even alcoholic beverages for a relaxing, scenic time on the water.

These sails are perfect for all ages. Sails take place throughout the day on one of the five historic wooden schooners. The sails are relaxing and do not include narration, but the crew is available to answer any questions that guests may have.

Maine Sailing Adventures

Maine Sailing Adventures offers traditional two-hour and themed sails through Casco Bay . What sets it apart from other sailing companies is its unique themed sails. Try an acoustic sail that features live music. Or, try a wine sail that includes a wine tasting for adults.

Have you ever heard of a yoga sail? This ship can accommodate up to 12 guests for a yoga class that you won’t experience anywhere else. Enjoy amazing views of the water while working on your poses.

Sail Portland Maine

If you’re looking for an intimate sailing adventure, Sail Portland Maine has you covered. Guests can choose a private charter or a public trip. The public trips’ capacity is 12 people, so you know that your sail won’t be too crowded.

Day and sunset trips are two hours in length and pass by all of the famous Casco Bay features — like historic forts, lighthouses, and if you’re lucky to spot them, seals. Guests are welcome to bring their own food and drinks, while bottled water is complimentary on board.

Schooner Tours on the Southern Maine Coast

The pineapple ketch.

Kennebunkport

There’s no better way to see the Kennebunk River than sailing on it. The Pineapple Ketch departs from Nonantum Resort for a dazzling trip along the river and the Kennebunkport coastline.

You’ll see gorgeous seasonal cottages, including the famous cottage of President George H.W. Bush. Enjoy views of the Goat Island Lighthouse, local harbors, seabirds, and seals.

Each sail includes complimentary bottled water and sodas, but guests are also welcome to bring their own food and beverages.

Silverlining Sailing

Silverlining Sailing offers one of the most intimate sails in Ogunquit Maine . Each boat has the capacity for up to six passengers, making for a small group sail. Sails typically last two hours, departing from the quaint Perkins Cove village.

There are five trips daily (weather permitting) from early morning through to a sunset sail in the evening. Enjoy stunning ocean views, gorgeous waterfront homes, views of local beaches, and harbors.

Since this is a smaller group sail, guests get the opportunity to try their hand at taking the wheel and steering the schooner.

Broad Reach Adventures

Broad Reach Adventures has two-hour sails, half-day and full-day sails, and chartered sails from Saco Maine , so there’s a sail to accommodate your busy schedule.

Each one allows guests to see beautiful views of the Saco River, Saco Bay, Biddeford Pool, Old Orchard Beach , and lighthouses along the way. Longer sails provide guests with the opportunity to disembark and explore uninhabited islands.

A unique feature that Broad Reach Adventures offers is the opportunity to add a massage or professional photographer. These experiences are available on certain dates and times, so book ahead if you’re interested in these add-ons.

Sailing Lessons & Boat Rentals

If you want to learn to sail, sailing instruction is often available as part of your charter package.  Private charters  of sailboats on the Maine coast allow experienced sailors to explore the coastline on their own.

Private sailors will find  hotel marinas  for lodging in Maine’s best harbors. If you time your sailing cruise right, you might witness seals, porpoises, whales, or other tall ships.

Watching the sunrise from the deck of a schooner is one of life’s simplest, most satisfying pleasures. Of course, the spectacular Maine scenery is always included on your sail.

Set Sail on Sailboat & Schooner Tours From Maine This Season

Now that you know about all of the sailing trip options, it’s time to set sail into the open waters of Maine. From two-hour trips of the bays and harbors to overnight excursions, there’s an experience awaiting you on your next getaway.

Each Maine sailing company offers its own unique trips aboard safe, well-maintained schooners. Relax, unwind, and feel the ocean breeze in your hair as you cruise through the lapping waves of Maine’s Atlantic shoreline.

The VisitMaine.Net team is the small team of authors and editors that research and write our in-depth guides throughout the site and update past articles to make sure they're still super valuable to you. We have one goal: to help you fall more in love with the state of Maine!

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Travel+Discover Maine – The unofficial guide to exploring the great state of Maine. Not affiliated with any official tourism entities.

Copyright Travel+Discover Maine 2024 Images Courtesy Greg and Heather Burke unless otherwise noted.

Portland, Maine Historic Fort & Lighthouse Tours

Family friendly civil war fort tours, maine’s iconic lighthouses tour, and 21+ sunset cruises. a local craft beer, canned cocktail, or wine is included for every guest.

• Most Popular!
• Hour Glass 2 Hours
• User All Ages

Fort Tour on a Private Island

Casco Bay’s stone fortresses are captivating characters in the story of Maine history. For the first time, SeaPortland is bringing you to the historic site Fort Scammel via the Elizabeth Grace . Join us for a boat tour no other Portland harbor tour company can offer.    

• Hour Glass 1.5 Hours

Sunset Lighthouse Harbor Cruise

 There is nothing quite like a Maine sunset, especially from the water . Aboard the Elizabeth Grace , with local craft beers in hand, we will take you on a stunning journey through the waters of Casco Bay. Don’t miss this tour!

Scenic Lighthouse Harbor Tour

This epic tour is the best way to take in the historic lighthouses, stone forts, and rocky islands that make Casco Bay a world-renowned destination.

Limited Edition Tour

• Limited Time - Monthly Tour

Maine Island Rum Tasting and Boat Tour

Embark on a one-of-a-kind rum tasting adventure with Sea Portland and Three of Strong Spirits. Cruise Casco Bay to House Island aboard the Elizabeth Grace for a 90-min journey through Portland’ Maine’s candid history with prohibition and rum.

SeaPortland brings you straight into the heart of authentic Maine.

Aboard the Elizabeth Grace and other vessels in our fleet, we show you the parts of Casco Bay unseen by most. We provide experiences that strike at the heart of what makes this part of the world so magical.

Join us for boat tours of previously unexplored early nineteenth-century forts. Bathe in the warm lights of a summer sunset over the water. Breathe in the ocean air while viewing Maine’s famous lighthouses. Toast local craft beverages. What could be better?

Join us for a tour today.

• Chevron down Is there a head (bathroom) on the boat?

There is no bathroom on the boat. We highly recommend using the facilities before boarding. If you are on the Private Island Fort Tour there is a bathroom on the island.

• Chevron down Can I purchase more drinks on the boat?

Yes! Every SeaPortland tour includes 1 canned alcoholic beverage per person (local beer, hard seltzer, wine, canned cocktails). We have complimentary non-alcoholic beverages stocked aboard.

Following the first included beverage, additional beverages can be purchased via credit / debit card on the boat.

• Chevron down Should I tip the crew?

Yes. The boat crew is there to help keep you safe and to tell you about the sights in the harbor. They work hard to make it a great experience! The crew will split tips and for those wondering 20% is the common amount.

• Chevron down Can we bring our own alcohol on board?

No, we have our own license that prohibits guests from bringing their own alcohol on the boat.

• Chevron down Can we bring food on board?

Yes, feel free to bring food on board. We just ask that you also take any trash away with you as well.

• Chevron down Do we have to be 21 to take a tour?

Both our Sunset Tour and Rum Tasting Cruise are 21+.

Our daytime Lighthouse Tour and morning Fort Scammel Tour are for all ages!

• Chevron down What should I wear?

Dress appropriately for the weather. We will have a canopy which will protect you from direct sunlight and rain, however it can be significantly cooler out on the water so we recommend bringing a jacket. On the Fort Tour we highly encourage closed toed shoes.

• Chevron down What is your Cancellation Policy?

All ticket sales are final without Ticket Protection.

Tours cannot be exchanged, rescheduled, or refunded.

Ticket Protection allows you to cancel or reschedule your tour with at least 24 hours’ notice. We will reschedule or reimburse you for your full tour ticket price (minus booking and ticket protection fees).

We operate rain and shine as long as the waters are safe and we have met our minimum number of guests to operate the tour

“The Best Harbor Charters in Portland, ME”

Join Sail Portland Maine for a more intimate trip around the waters of Casco Bay aboard our 6 passenger sailing vessel, the Eleanor Hawkes, or our 12 passenger Classic Motor Yacht Picnic Boat, the Calista Ann.

Eleanor Hawkes → Set Sail on the Eleanor Hawkes

The Eleanor Hawkes is a Friendship sloop, a beautiful traditional-style sailboat that glides effortlessly over the water. With space for up to 6 guests , this is the most private sail you can get in Portland shy of owning a boat!

The Eleanor Hawkes is based on the Friendship sloop, also known as a Muscongus Bay sloop or lobster sloop, which is a traditional style of gaff-rigged sloop that originated in Friendship, Maine around 1880. Fishermen in Friendship and neighboring Bremen collectively originated the design, one influenced by the fishing sailboats of Gloucester, Massachusetts, particularly the schooner Fredonia of 1889.

Although familiar as a pleasure craft today, the Friendship sloop was the traditional fishing boat used off the coast of Maine, especially for lobstering, until the introduction of the gasoline engine early in the 20th century. Friendship-area boat builder Wilbur A. Morse produced many examples from the 1880s and into the early 1900s.

Calista Ann → Go for a Cruise on the Calista Ann

The Calista Ann is our newest addition to the Sail Portland Maine fleet! This motor vessel, also sometimes referred to as a picnic boat or cocktail cruiser, has slightly more seating and space to move about, so if you’re looking for a private cruise for a larger party, Calista Ann is the boat for you!

We offer cruises for up to 12 guests on public and private charters to keep the intimate feel for your group.

We provide multiple trip options to ensure that your Portland, Maine boat cruise fits into your schedule. You can see all our available charter times here !

Harbor Charters in Portland, Maine

Want to learn more about the history of Portland and the ships of its past? Come join us! You’ll experience the most scenic harbor charters in Portland, Maine, aboard the Eleanor Hawkes or Calista Ann. Sit back, relax and enjoy the cruise of a lifetime through the glassy waters of Casco Bay with the best sailing Portland has to offer. Book your trip with us today!

Choose Which Harbor Charter is Right for You

207.415.9698

SEAGLASS SAILING CO.

We're Not Just Better, We're the Best

S/V Seaglass, a 1965 Pearson Rhodes 41 turns heads everywhere she sails.  

The 41' masthead sloop can comfortably accommodate up to 6 passengers for 1/2 day, full day, and overnight voyages around Casco Bay.  

A comfortable cabin and spacious cockpit provide gracious space for relaxing and entertaining.  

Captain Paul Leddy, who grew up sailing the waters of Casco Bay, is looking forward to helping you plan an unforgettable Maine Experience.  

Contact us today, or learn more about voyages aboard S/V Seaglass .  

Inspired Work

Get in Touch

Captain Paul and Seaglass Sailing Co. are here to share the beauty of Casco Bay and a passion for sailing with all of their visitors. Questions, comments or special requests? We’d love to hear from you, so don’t hesitate to reach out today.

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seaglass sailing co.

©2018 by Seaglass Sailing Co.

Casco Bay Custom Charters

Embark on an unforgettable journey: customizable private boat charters & tours of casco bay, celebrating a decade on the water.

Experience Casco Bay’s Splendor with Our Private Boat Charters & Tours. 

At Casco Bay Custom Charters, we invite you to explore the captivating beauty of Maine from the unique vantage point of our classic wooden vessels. For the past decade, we’ve shared more than just boat tours. Our charters are personal introductions to the coastal landscapes, lighthouses, and culinary delights that define our region. 

With a focus on customization, each voyage with us is tailored to uncover the genuine essence of Casco Bay, enhanced by our commitment to exceptional service. Led by experienced crews passionate about sharing their knowledge and love for Maine, we ensure your journey is not only enjoyable but truly memorable.

SEARCH CHARTERS BY GROUP SIZE

Designed for exclusivity, our charters accommodate intimate groups of up to 6 guests or larger gatherings of 7-16. Our friendly captains and knowledgeable stewards ensure a personalized boating experience.

Small Groups aboard MONHEGAN

Intimate cruises for up to 6 on a vintage lobster boat

Learn More »

Large Groups aboard MARIE L

Classic coastal tours for up to 16

DINING CHARTERS

The best way to eat locally-sourced Maine cuisine is aboard our Dining Charters. Specialty menu dining charters, chef’s dinner sunset cruises, and bottomless mimosa brunch cruises available. Local catering and all-inclusive drink upgrades are available aboard EVERY Casco Bay Custom Charter!

Private Sunset Dinner Cruise

Small Groups (up to 6 guests) aboard MONHEGAN

Bottomless Mimosas & Croissant Brunch

Large Groups (7-16 guests) aboard MARIE L

ELOPE ON A PRIVATE ISLAND

Experience the magic of saying ‘I do’ on a private island with our Fortland Elopement Package. Escape to Fortland for an intimate, and unique wedding ceremony set against the backdrop of a stunning coastal landscape. An unforgettable way to share your vows and begin your new adventure in love

FORTLAND ISLAND ELOPEMENT PACKAGE

Unique, intimate wedding ceremonies on Fortland.

SAIL WITH GLEAM

For a limited-time, we’re partnering with GLEAM to offer sailing charters off the coast of Maine. GLEAM is a fully restored vintage 12 meter yacht that hosts up to 13 guests. Each captivating sailing excursion includes captain and crew for an effortless Maine summer sail.

GLEAM Private Sailing Charters

Sailing Excursions along Maine's Coast

CREATE YOUR OWN CUSTOM CHARTER

Tailor any of our curated tours and experiences for your group’s needs, from corporate bleisure to family-friendly outings and celebrations. Collaborate with our team to craft your perfect day, selecting from diverse food, beverage, and tour itinerary options. Your bespoke Maine adventure awaits.

Unforgettable 5-Star Maine Experiences ⭐⭐⭐⭐⭐

Embrace authentic maine with casco bay custom charters.

Journey with us and unlock the essence of Maine on our signature boat tours. Enjoy the serenity of coastal cruises while indulging in gourmet locally-sourced food and craft beverages. Our classic wooden vessels offer a truly authentic Maine experience for unforgettable memories.

Eager for an unparalleled experience? Book your private boat charters and coastal tours to navigate the beautiful waters of Casco Bay!

Guided Tours + Cruises

Sample the sights and sounds of the region.

When you visit the Greater Portland, Maine region you get a hands-on experience. Get up close and personal with our rocky coastline and sandy beaches. The region is your oyster and you can take on everything from kayak trips to lobstering tours to brews cruises.

Learn More On The Blog

Portland Discovery Land & Sea Tours

The perfect way to experience the coastal and inland areas of Greater Portland Maine.

Offering specialty food cruises, harbor tours, and private charters. Complimentary beer and wine with all cruises!

Visiting Maine and want to see whales, puffins, or the sights? Cap’n Fish is the way to experience Boothbay Harbor.

Portland's iconic ferry system with year-round ferry services, specialty cruises and private charters to the islands of Casco Bay.

Discover the wonder of Casco Bay with Fogg's Water Taxi & Charters, offering a diverse range of services across our seven boats.

Join us for a guided tour, pedicab ride, or explore the region at your own pace with a worksman bike rental.

Private sightseeing tours are available for couples and all size groups, from minivan to motor coach.

Highly interactive tours that will educate and entertain you all along the way. Foodie tours, history tours, and more!

Come aboard Frances, our 74’ traditional British cutter for a day sail, evening sail, wine sail, or an acoustic sunset series sail. Private charter available.

Home to the best tours and activities in Maine. Authentic experiences led by locals. Your gateway to an unforgettable Maine.

Jump aboard New England Eco Adventure’s small, intimate excursions that blend adventure and education into one amazing trip.

Witness the beauty of Maine from above with Pine Tree Helicopters' extraordinary flight services, offering breaking aerial views of Maine's iconic lighthouses and more.

Experience unforgettable storytelling—rich with heart, humor, and humanity—on a walking tour with Maine's top-rated guide!

Don't just see Portland- Discover it! Offer a wide variety of sightseeing and charter options by Land and Sea.

Operate a unique multimedia history tour aboard a Vintage Fire Engine. We explore the peninsula of Portland.

Refresh your spirit with a two-hour sail on Casco Bay and witness first-hand the forts, lighthouses, sea life and rugged coastline.

Hosted on a traditional lobster boat, Rugosa’s lobster tour offers the most exclusive, personal, and educational cruise in Kennebunkport.

For 20 years we have been offering cycling, walking, and multi-sport vacations in the most beautiful places in Maine.

Portland's #1 party boat! Join us on the water for a fully immersive way to experience Casco Bay and the islands, all while live bands set the soundtrack.

Explore the best of Maine with private sightseeing tours featuring chef prepared local cuisine and drinks. Unforgettable experiences await on our historic boats.

A unique island experience within Fort Scammel on the private House Island in Casco Bay. Camp and tour the historic island!

A lobstering excursion for all ages while enjoying close-up views of historic lighthouses, civil war forts, and seals.

Maine’s first human-powered party boat. Book individual seats or the whole boat for a private tour of Portland.

All-inclusive tours providing guests a behind-the-scenes look at Maine’s breweries, distilleries, wineries, and more.

Scenic train ride along beautiful Casco Bay. Activities, historic railroad cars & exhibits.

Experience the Old Port's rich history since 1632. Over 50 historic stops! Memorable tour experiences not to miss!

Join our family owned and operated tour company for unforgettable explorations. Customized year-round tours.

Residents and guides, with enthusiasm and expertise in Portland’s history, food, drinks, art, music, and literature.

A day in the life of a lobsterman from pulling traps and setting traps to examining sea life and selling the catch.

We offer unique boat-based tours and experiences on the beautiful waters of Casco Bay!

City & 3 lighthouses Historical Sightseeing Tour with a REAL local, born & raised in Portland!

A family-owned and operated tour company sharing what we love about our charming city and the state of Maine.

BOOK YOUR KENNEBUNK OR PORTLAND TOUR BEFORE SUMMER SLIPS AWAY!

BOAT TOUR & WHALE WATCHING ADVENTURES

Portland, me kennebunkport, me, leave the crowds behind.

Jump aboard New England Eco Adventure’s small, intimate excursions that blend adventure and education into one amazing trip. We get there faster. We stay longer. And we go places other tour boat tours can’t reach – in a style they can’t match. From our top-notch customer service to our custom RIB boat, we provide you with a first-class experience.

Checkmark Small group sizes

Checkmark Every seat has 360° views

Checkmark View wildlife up close

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Book your tour in Kennebunk, Maine

• Star Outline Whale watching
• Hour Glass 4 hours
• Map Marker Kennebunk

The Ultimate Whale Watch – Kennebunkport, ME

This is our most adventurous tour and has something to offer for everyone! From the sightseer, the thrill-seeker to the marine lover, our Ultimate Whale Watching tour in the Gulf of Maine is the way to go!

• Most Popular!
• Star Outline Scenic cruise
• Hour Glass 1 hour

Kennebunkport Scenic Adventure

The entire Kennebunkport Coastline in an epic 1 – Hour adventure. This tour has it all – Walkers Point, Seals, Cape Porpoise, Goat Island Lighthouse, and if time permits, Goose Rocks Beach. You get all this while enjoying your own personal front-row seat!

The captain will make every effort to take requests and will tailor the tour according to the weather.

• Most Popular
• Star Outline Lighthouse tour
• Hour Glass 2 hours

Nubble & Boon Island Lighthouses

Explore Boon Island Lighthouse and Nubble Lighthouse on this tour that cruises up the coastline. See these historic lighthouses first-hand. Join us today!

Book your tour in Portland, Maine

• Star Outline Seal watching , Lighthouse tour , Scenic cruise
• Hour Glass 1.5 hours
• Map Marker Portland, Maine

Best of Casco Bay

Depart with us from bustling Portland Harbor as we tour one of Maine’s most picturesque boating destinations. Casco Bay is littered with islands, historic forts, wildlife, birds, and lighthouses in our unique 14-passenger RIB boat.

• Hour Glass 3 hours

Adventure Whale Watch – Portland

Experience the breathtaking beauty of the Atlantic Ocean on our whale-watching tour departing from Portland, Maine. Set sail from the historic harbor, where you’ll board a comfortable vessel equipped for a thrilling marine adventure.

• Star Outline Oyster Farm Tour
• Hour Glass 2.5 hours

Mere Point Oyster Farm Tour

Join us on a scenic ride of Casco Bay on our way to tour one of Maine’s premier oyster farms. Along the way we will cruise through some of Casco Bay’s less visited waters for great wildlife viewing before arriving at Mere Point Oyster Farm.

• Hour Glass 2.25 hours

Portland’s Ultimate Lighthouse Tour

Experience the picturesque beauty of the Maine coastline with our exhilarating boat tour from Portland, Maine. This guided adventure will take you on a breathtaking journey along the rugged shoreline to view more lighthouses than any other tour in the state!

Kennebunk, Maine

See the crown jewel of coastal New England

Portland, Maine

See the crown jewel of Portland, Maine

Our Customers Rave About Us

My 17-year old daughter and I took the trip to see Boon and Nubble Island lighthouses. We had a fantastic time- saw lots of seals too. The crew was great- friendly and accommodating. Captain Gary has great stories to tell. I highly recommend this trip for a fun morning adventure.

My family and I had an awesome trip with Captain Gary and Wess on the one hour Thrill Ride! They were entertaining, knowledgeable about the sea life that we saw, and gave us a thrill ride that is not to be missed! We are already planning another trip. Thank you for being such great hosts!

We did the 1 hr thrill ride.What a ride! Awesome crew. Better then the Codzilla in Boston Ma. Or the Banana boat. We will be back next year to do the whale watch with you.

We recently went on the one hour Thrill Ride and it was by far the best part of our vacation. Our group included children, teenagers, parents, and a grandparent and everyone was raving about how fun and exciting the ride was... Definitely will do it again and highly recommend it!

As a lighthouse Enthusiast it was an awesome adventure out to Boon Island and then to see Nubble from the water. Could not have asked for more! We will definitely be taking another tour with you! We have been sharing our experience with other lighthouse lovers too. Thank you so much!

THE BEST AND MOST FUN BOAT RIDE EVER! INCREDIBLY KNOWLEDGEABLE TOUR GUIDE INFO ABOUT SO ME COASTLINE. PLAYS TO THE CROWD: "WANNA GO FAST?!" THERE WERE YOUNG KIDS ON THERE, ENGAGED COUPLE, PARENTS, AND MY RIDE WAS A BIRTHDAY PRESENT FOR MY 70th BIRTHDAY, AND I CAN'T WAIT TO GET BACK ON THAT BOAT! UNFORGETTABLE!

We hope to see you in 2025!

Nautilus Sailing Company is closed for the 2024 season.

With great regret, we must close the 2024 season on a sad note.

The Nautilus was damaged by another vessel while at the marina in her slip, and is unable to sail. We hope more than anything to be sailing with you on the water again in 2025.

Until then, far winds and following seas on all your journeys.

--Sam and Crow, owners.

If Nautilus has provided you or loved ones with good memories on the water, or if you haven't yet been aboard and nonetheless generously wish to support us during this time, we have a GoFundMe running in an attempt to cover a portion of the repair costs to get this gorgeous boat sailing again next year.  

https://www.gofundme.com/f/help-sam-and-crow-keep-the-nautilus-sailing

Relax and enjoy the best views of Portland aboard Nautilus

Grab your favorite bottle of wine and step aboard for an experience you'll always remember. Sail past lighthouses, the historic Fort Gorges, and learn about the rich history of Portland Harbor from our seasoned and passionate crew.

Sail on Casco Bay with us!

Book a sailing adventure for a day trip, sunset cruise or your own private charter in Portland, Maine!

DAY SAILS &

PRIVATE CHARTERS

11:00 AM - 1:00 PM | Morning Sail

3:00 PM - 5:00 PM | Afternoon Sail

$80 per Person | $450 Private Charter

Hop on one of our 2-hour morning or afternoon sails to explore Maine’s diverse and scenic Portland Harbor.

Choose our first trip for a calm morning outing, or join us in the afternoon when the wind picks up. Get on the water with Nautilus Sailing Company for a uniquely memorable Portland, Maine excursion.

SUNSET SAILS & PRIVATE CHARTERS

6:00 - 8:00 PM | Sunset Sail

Fall Hours May Vary

$95 per Person | $550 Private Charter

Sunset sails depart each evening for 2 hours to enjoy golden hour views of Maine’s diverse and scenic Portland Harbor.

Bring your camera and favorite cocktail and get on the water with Nautilus Sailing Company to enjoy the best sunset views of Portland, Maine.

CUSTOM CHARTERS

Starting at $450 |  Call for a Quote

Need an extra hour or some additional flexibility? From intimate wedding ceremonies, to memorable anniversary celebrations, to unique bachelor and bachelorette parties, to corporate outings, our custom private charters are fully customizable to meet your needs.

Call to plan your ideal Portland Harbor sail charter and make your next special event epic!

BOOKING CALENDAR

Have a date in mind? View our Booking Calendar below:

Designed and built to look and feel like the sailing vessels of days gone by, our 37' ketch Nautilus perfectly combines traditional form and modern function.

With a large cockpit and wide cabin tops, you'll find plenty of comfortable seating options for all. Guests are free to move up to the bow for a great view while we're underway. The spacious cabin offers ample space for lounging, eating, or a brief respite from the elements. The galley has all the amenities of home, including an ice box and stove, and there is also a large head (bathroom) with push button facilities-- everything you need to create your ideal Portland excursion. Join us! We're certain you'll be glad you did.

Step aboard the sailboat Nautilus and experience the real magic of Casco Bay.

Relax and unwind as we silence the motor and let the wind take us sailing past lighthouses, between the islands, past historic forts, and even alongside playful porpoises and seals. With Captain Sam and first mate Crow as your seasoned guides, sit back and enjoy the view while you learn about our treasured Maine coast.

• What is the maximum passenger capacity? Nautilus's passenger capacity is 6 people maximum. This is determined by the U.S. Coast Guard so it is not flexible.
• Do infants count towards passenger capacity? Yes. The passenger limit is based on the number of human lives aboard, rather than by seating room.
• Do you take same-day bookings? YES we do! Our booking software with FareHarbor allows for same-day bookings. If a sail during a time slot you are interested in appears to be greyed out, you can give us a call to see if there are any seats remaining. One important thing to note: if the crew are not currently on the boat, it will take us roughly one hour to arrive at the boat and complete an all-systems safety check, so please call as far in advance as possible.
• Will we tip (heel) over? As a sailboat, the Nautilus is designed to lean to one side or the other with the pressure of the wind in her sails, with the extent of that heeling depending on the strength of the wind. If you’d like a more spirited sail, we recommend checking the forecast for winds of 13 knots (roughly 15 miles per hour) or higher. Morning and Sunset Sails tend to be the calmest, while Afternoon Sails are generally more lively. In Portland we usually receive the strongest winds in May, June, September, and October, while July and August are the calmest months.
• Is there a bathroom on board? Yes! We have a marine toilet, also called a head. The marina also has facilities for all guests in the form of 3 single-stall restrooms.
• Are life jackets required to be worn? Due to Federal law, anyone under 13 years of age is required to wear a life jacket on board any commercial vessel that is off the dock. Adults can choose to wear one if it would make them feel comfortable, but it is not required.
• What is your general cancellation policy? Please cancel one week in advance of your sail to receive a full refund. Cancellations made with under one week’s notice will not receive a refund unless they are due solely to sudden illness (see covid-19 policy below).
• What happens if it rains? Nautilus will still depart in mist, light rain, and passing showers. In the event of poor weather or unsafe conditions determined by the Captain at the time of the sail, we will offer to rebook your sail to a more pleasant day or provide you with a refund.
• Do you have a covid-19 / illness refund policy? If you become sick with covid-19, the flu, or any other contagious illness and need to cancel, you will receive a full refund. We appreciate your help in not spreading any illnesses to the crew!

Fore Points Marina

1 Marina Way

Portland, ME 04101

Get in Touch

[email protected]

207.544.5757

© Nautilus Sailing Company

• Mailboat Run

Hop on the Mailboat Run! The locals’ favorite way to experience Casco Bay – this true working boat carries passengers, mail and freight to Little Diamond, Great Diamond, Long, Cliff and Chebeague Islands. Year-round availability. Check out our blog for more information!

Narration provided with 10 or more cruise passengers.

Duration : 2.5-3.5 hrs. (times vary based upon route and cargo volume)            Runs : Daily

• Sunrise Run
• Diamond Pass Run
• 2024 Cruising Casco Bay Concert Series

Closed for the Season

Maine Duck Tours

Duck Tours In Portland, Maine

Experience Portland by Land and Sea

Land & sea historical tour of portland and casco bay.

On our history and sightseeing tour of Portland, we’ll travel by land & by sea to explore many different points of interest.

Fun for all ages aboard a modern amphibious vehicle!

As you twist and turn through the Old Port aboard Maine’s famous, modern land and sea vehicle, or “Duck”, we’ll tell you about the legends and lore that have shaped Portland into one of the most historical cities in the nation.

Learn about places of interest to visit and many little known facts about the city that is nicknamed “The Phoenix.” Then, hold onto your tail feathers as we DRIVE into the waters of Casco Bay to view Portland’s working waterfront, Calendar Islands and marine wildlife.  This is Maine sightseeing at it’s best!

For all of our tour details, please visit our Portland Maine Tour page.

Top 10 Boat Tours & Water Sports in Portland!

We did it as a part of our Portland trip with small kids aged 3-7. We all enjoyed the tour of the city as well as the boat time as well. Dugan was very helpful in getting us oriented after the ride as well. Highly recommend this!

What a fun tour, we enjoyed our trip on land and water. Truly, it quacked us up! I would recommend this tour on the beginning of your stay in Portland, it will give you a nice overview of the area.

Dugan and captain Mike did an excellent job. Both were very professional. Dugan was a great host, he was very knowledgeable and friendly-I would highly recommend this tour if you are in Portland.

The Maine Duck Tours is a good way to oversee the city. You get taken on land and water so it is entertaining and fun!

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* Terms & Conditions Package not available on sailings less than 5 days or charter sailings.

Shore Excursion Details

A day in maine, portland, maine.

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• 7 hrs Estimate Duration

Spend a carefree day exploring Portland and Kennebunkport, two deeply historical cities whose architectural treasures have been well preserved. In Portland alone, you will pass through several Victorian neighborhoods and the New Arts District, which has become the hub for the city’s cultural resurgence. The house where poet Henry Wadsworth Longfellow grew up is also there. He frequently visited the Portland Head Light, which is said to have inspired his poem “The Lighthouse.” You will stop to see this beacon up close on the picturesque drive to Kennebunkport, a charming seaside village with an abundance of Victorian- and Federal-style homes that wealthy sea captains and merchants built. Perhaps even more well-known is the compound on Walker’s Point that served as the summer retreat for president George H.W. Bush and his family. During free time in Kennebunkport’s waterfront Dock Square, you might shop, browse the galleries and dine on your own.

• View the most meaningful landmarks in Portland on a panoramic drive through the city. • Pause at Maine’s oldest lighthouse, which was first illuminated with whale oil lamps. • Explore the village of Kennebunkport independently and dine on your own if you wish.

HELPFUL HINTS

• Dress in weather-appropriate clothing. • Wear flat comfortable walking shoes.

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Scenic & City Tours

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• 3 Challenging

Copy My Trip: 3 days in Portland, Maine

Sep 12, 2024 • 6 min read

Be inspired to spend a weekend in Portland, Maine, with these top tips from a recent visitor. Rachel Lewis/Lonely Planet

Lonely Planet’s senior social media manager, Rachel Lewis, recently returned from a weekend with her wife in  Portland , Maine . Here she shares her trip highlights and what to prepare for before you go.

I’ve always had a clear picture in my head of what visiting Portland, Maine would be like, and, honestly, it was pretty stereotypical: buttery lobster, stripes and linen, setting sail from the Old Port and thumbing through pottery at local shops. I’d never been to Maine, period, but when I told my grandmother (who’s from Massachusetts) that I was planning a long-weekend trip with my wife, she had two recommendations: eat as much as you can manage, and go to the locally owned Cool As A Moose (and buy her a mug for Christmas – on it, Gramma). My wife and I landed with empty tums and space in our luggage for goodies, and hit it. 

I want to help you do the same. Here are a few things that made my weekend in Portland so memorable.

Where did you stay? What was the vibe?

The Longfellow Hotel in the West End is a newly opened boutique hotel with a heart for sustainability. On our first morning in Portland, we tested out room service with a breakfast order of an iced oat milk latte. I got just what I was craving, and my wife couldn’t stop raving over her breakfast sandwich – baked egg, spicy mayo and pepper jack on an English muffin.

I was particularly impressed with the creative mocktail menu at its dinner and drinks venue, Five of Clubs . Finding good alcohol-free drinks when traveling sober (or sober curious, in my case) can be tricky, but the “functional cocktails” are stunning. I had a Rosarium – bitter orange, earl grey, pomegranate – and a Vacationland Refresher – wild Maine blueberry, cardamom, lemon soda. The earl grey was a great intro to the -ber months. 

The spa, Astraea , has an  infrared sauna  (reserve it in advance!), and you can get your very own space with a bathroom, rain shower and sauna. There are a few different massage options. We chose Mindful Dreams , a meditative, rhythmic full body massage ($145/person for 60 minutes). Sip peppermint tea and feel wonderful as you lounge about in your new skin (okay, I know that’s not how it works, but it’s how it feels).

What was the best thing you ate or drank?

I'm not even going to attempt to single out a "best" meal in Portland, but with its foodie reputation , you can expect to dine well. These are the dishes, snacks and flavors that stood out for us.

Brickyard Hollow Brewing Company  is a local chain that makes gourmet pizza from Freeport to Yarmouth (the original) and beyond. We went with cheese pizza, and it was beautiful in its simplicity: 12 inches of cheesy goodness with an olive oil base. Next time, though, I’d grab something more experimental, like its blueberry pizza with Maine blueberries, rosemary ricotta, roasted shallots and lemon zest.

Green Elephant , a vegetarian bistro, does not take reservations, so get there at 11:30am when it opens for lunch. Grab yourself some deep-fried vegetarian spring rolls and king oyster mushroom tempura. If you’re a vegetarian like me, you’ll appreciate a space where you can eat literally anything without having to triple-check that the allegedly vegetarian pseudo-meat you’re taking a bite of is 100% not meat. Go for the ginger noodles and appreciate the spice (make it vegan by skipping the egg).

Another tasty lunch option includes Benkay, a Japanese restaurant and sushi bar. Consider the teriyaki tofu; it’s fast, hot and surrounded by colorful veggies. For a filling dinner, we hit  Black Cow , a burger joint. I got a veggie burger with a mushroom lentil patty, iceberg, pickled red onion, radish and black garlic mayonnaise on its signature black cow bun.

When you need a break during your Portland wanders, grab a donut at Holy Donut (consider the blueberry glaze).  Navis Café on Thames Street – about a block from the water – serves great egg-white bagels and iced decaf vanilla lattes for breakfast on the move.

What was the most touristy thing you did?

We wrapped up our final day by hopping on a sunset cruise. Portland has quite a few options, but no matter what you pick, book in advance. We saw many excited tourists get turned away when they tried to buy tickets just before sailing. We chose the Casco Bay Sunset and Lighthouse Cruise ($52/person) to see Diamond Pass and the Calendar Islands and were glad we arrived early – we snagged stellar seats on the upper deck. 

Where is the best place to shop?

In Maine’s historic Arts District, swing by Soleil , a gift shop where you’ll want pretty much everything, especially if you’re the sort of traveler who wishes they had a cuter key chain (how about a  dog wearing a sweate r?), an adorable lobster toiletry bag or a notebook with a metallic croissant on the cover.

Cross the street and make your way to Loquat . It’s alive with design, literally, considering that you can see artists working in the back. Stock up on shea butter or grab a Shirt of the Week . If all this color makes your artsy heart grow three sizes, consider swinging by any of the galleries along the way or nearby. The Portland Museum of Art is the obvious choice, and it’s free on Fridays (otherwise it’s $20 per adult). You’re almost certainly going to run into spaces showcasing student work from the Maine College of Art & Design, so keep your eyes peeled as you stroll.

What essential items did you pack?

The name of the game is layers and comfy, grippy sneakers for lots of strolls on cobblestone streets and stepping onto a sailboat. Portland is pretty chill. We saw loads of people in sneakers and jeans, and quite a few people in all black. I packed a pair of jeans that could be dressed up or down, a light sweater and a linen chore jacket for layering, and a baseball cap in case of rain. Accessories are handy for nicer restaurants where you want to feel like you dressed up without dressing up.

What other tips do you have for someone planning a similar trip?

• When to arrive: Give yourself at least three days – we arrived Friday evening and left late Monday afternoon, and were glad we had time to laze about in between activities. 
• How to get from the airport: For ease, fly into the Portland International Jetport, just 2 miles from downtown Portland. From there, hop in a rideshare. Our Uber was $12 and took less than 20 minutes. Or, if you live within a few hours of Portland, consider taking the train; prices are reasonable, and bonus: you can get in views of foliage if you come during fall.
• Getting around town: Portland is walkable as long as you choose accomodations near the hub where you want to explore. We zeroed in on the West End and Old Port.

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