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Sail Chesapeake Bay

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Explore the USA's Largest Estuary and Discover America

Living in North America and looking for a bareboat charter destination close to home? Seeking to experience the natural beauty and the modern lifestyle of the USA? Wanting to vacation under sail but not bothered about snorkeling in clear blue tropical waters? Then take a look at Chesapeake Bay as a destination. 

So convenient for the locals and a fascinating place to visit from all over the world, Chesapeake Bay offers lovely summertime conditions for keen sailors and vacationing families. And all around this extensive sunken river valley are exciting places to explore, from secluded bays to modern cities with just about everything this part of USA has to offer.

It All Starts in Annapolis, America's Sailing Capital

Chesapeake Bay is a vast waterway, 200 miles long draining  64,000 square miles in six states via the more than 150 rivers that feed it. In the upper section of Chesapeake Bay you are in Maryland. The state's big city is Baltimore, while the capital is historic Annapolis, your likely starting point on a Chesapeake Bay sailing vacation. Annapolis is a lovely city that lies at the heart of the region's, some would say the nation's, sailing culture. It is also home of the National Sailing Hall of Fame and US Naval Academy - try to spare the time for a tour.

The Chesapeake's Upper Bay

Sailing out of Annapolis, turn the corner and you are immediately far from the bustle of the city. It doesn't take long to get a sense of the geography here – inlet after countless inlet formed as the sea level rose after the last ice age, beyond which wooded lowlands share the landscape with cultivated farm properties and a generous sprinkling of picturesque settlements.

Head south and a huge expanse of tidewater opens up. Bear northeast and sail under the monstrous dual-span Chesapeake Bay Bridge towards Baltimore, or on the eastern shore Rock Hall and the Chester River.

Rock Hall is a pleasant fishing village that offers an overnighting choice on a marina or at anchor in nearby Swan Creek. Just 15 nautical miles from base, getting to Rock Hall is an easy first day's sail. It's also a convenience stepping-off point for an upriver journey in either direction - to Baltimore's Inner Harbor or Chestertown, both with appeal in their own different ways. If you want to spend longer in the Bay's upper reaches, sail up to the Sassafras River and you can easily fill a week-long itinerary without going south of Annapolis. 

But to see more of this huge Bay with its 11,600 miles of shoreline, you need to head back under the big bridge. Immediately south of  Kent Island is Eastern Bay that brings you into the Wye River area. Here St Michaels is a popular stopover, a waterfront village with excellent marina facilities, shops and restaurants catering for the nautical crowd. St Michaels is also home to the Chesapeake Bay Maritime Museum. A short sail further south are Tilghman Island and Oxford, at the mouth of the Choptank River, setting for James A. Michener's great novel Chesapeake. 

This may well be all you have time to see on your Chesapeake Bay sailing vacation. However if you have longer, continue on south, exploring the eastern shore around Crisfield or crossing to Solomons Island if needing supplies or a marina berth.

The Middle Bay and South

Sail by the mouth of the Potomac River and across the state line into Virginia. Call at Smith or Tangier Island for an appreciation of the Chesapeake way of life and the wonderful natural environment in these parts. Most of the residents of Tangier Island make their living from crabbing, one of the Bay's big industries.

As you proceed south, you may wish to stop over at Deltaville for a berth and supplies, before heading across to the up-market coastal resort are of Cape Charles, with all its amenities for young and old. If time is still on your side, you can go as far as Portsmouth, rent a marina and take off by car to explore the area of Newport News, Norfolk and Virginia Beach.

As you sail back to Annapolis, there are numerous top spots you missed on your way out – Onancock,St Leonard's Creek on the Patuxent, and all those other inviting bays and rivers you observed on the way south. So leave plenty of time to stopover and make your return a leisurely sail.

Around these parts there is many a yachtsperson who will talk about sailing on the Chesapeake. How they've been doing it all their lives and still not been into half the bays and rivers. Head out and find your own special place, perhaps it'll be one that even the locals haven't  come across yet.

Browse our yachts for charter in Chesapeake Bay

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We will match any discount website offer on charter boat price, and still provide our customary high level of service.

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

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Rent a boat in Annapolis. MD

18 boats available for bareboat or crewed charter

Yachts from professional fleet operators in Annapolis. MD

Free cancellation of reservation without obligations within 4 days

Yacht types available in Annapolis. MD

Catamaran charter

Sailboat charter

Power boat charter

Most affordable boats for rent in annapolis. md list of boats sorted by the price per week. starting with the most affordable boats from ₽323,010 per week (like sun odyssey 389 - 2018) going to more premium yachts available in annapolis. md from ₽1,206,090 per week..

Sun Odyssey 389 (2018)

Sun Odyssey 440 - 3 cab. (2018)

Dufour 430 - 3 cab. (2021)

Jeanneau NC 33 (2018)

Jeanneau 53 - 3 cab. (2018)

Dufour 530 - 4 cab. (2021)

Jeanneau 58 (2017)

Fountaine Pajot Astrea 42 - 3 + 1 cab. (2024)

Fountaine Pajot Isla 40 - 3 cab. (2022)

Fountaine Pajot Astrea 42 - 3 + 1 cab. (2021)

Most popular sailboat rentals in annapolis. md, popular catamarans charters in annapolis. md.

Fountaine Pajot Elba 45 (2022)

Fountaine Pajot Aura 51 (2023)

Lagoon 50 - 6 + 1 cab. (2022)

Fountaine Pajot Saona 47 - 5 cab. (2024)

Fountaine Pajot Aura 51 (2024)

Fountaine Pajot Tanna 47 Maestro - 3 cab. (2025)

Fountaine Pajot Saona 47 (Quintet) - 3 + 1 cab. (2019)

Annapolis. md yacht charter options, bareboat charter, crewed yachts, skippered boats, cost of boat rental in annapolis. md.

The prices for yacht charters in Annapolis. MD are closely tied to the weather and sailing conditions throughout the year. They tend to be at their lowest in January, corresponding to the low season, and reach their peak in July when demand is high and sailing conditions are optimal.

Sailing Charters, Lessons & Captain Services in Annapolis, MD & Abroad

We Have a Chronic Sailing Condition

sail with us and you will too!

Annapolis Sailing Charters.

Sail the Chesapeake Bay on your own private yacht. Select a trip from our popular itineraries below, see more sailing trips in the Chesapeake Bay or contact us to customize an itinerary just for you.

Annapolis Sunset Cruise

Catch the gorgeous Chesapeake Bay sunset aboard a luxury catamaran. Perfect for a romantic evening, cocktails with friends or a way to end a day exploring Annapolis.

Mid-Week “3 Hour Tour”

“Just sit right back and…” feel the wind in your hair, go for a swim or just enjoy the views. Great for office outings and happy hour hangs.

Celebrate Your Special Event

Birthdays, anniversaries, bachelorette parties and other occasions are more fun on your own private yacht! We’ll tailor a cruise for your special day.

Chesapeake Overnight Sail

Get away for a night (or 2) and enjoy adventures on the water, excursions into nearby towns, sunset cocktails and sleeping under the stars.

Annapolis Sailing Lessons

ASA certified instructor, Captain Shawn Owen helps students of all skill levels become confident and safe sailors. With decades of experience teaching snowboarding and music, Shawn has a laid back, positive attitude and a passion for sailing and seamanship that will be contagious when you sail with us.

If you’ve never sailed before and are interested in trying it out to see what all the fuss is about, this class may be the perfect way to give it a shot.

Intro to Sailing

Interested in one on one training? Or maybe you want to get you and your crew up to speed before an upcoming charter? We can customize private instruction for up to 4 people for an extremely competitive rate.

Private Sailing Instruction

New boat owner needing insurance checkout or just looking to brush up skills on your own boat? We offer instruction and certifications aboard your boat to maximize benefit and personal knowledge of your vessel.

Learn on your Boat

The American Sailing Association is a national and global leader in sailing education and bareboat chartering certifications. We offer ASA Courses 101-106, as well as the 114 catamaran certification. If bareboat chartering is something you see in your future, then this could be your best avenue to achieve the necessary skills and qualifications required to handle your own charter vessel.

ASA Courses

Learn To Sail

Browse our charter fleet.

This modern marvel stands out with sleek lines and a spacious deck layout, ideal for leisurely cruises or adventurous voyages.

American Honey

This state-of-the-art catamaran seamlessly combines performance, comfort, and elegance to provide an unforgettable chartering adventure.

Dos Milagros

Experience the ultimate luxury sailing adventure on the stunning Chesapeake Bay aboard the exquisite 2017 Beneteau Oceanis 45, a true gem in the world of yacht chartering.

Let us plan your customized “escape” on this well appointed catamaran sailing the Chesapeake Bay out of Annapolis, MD

A magnificent vessel that seamlessly blends luxury, performance, and comfort on the open seas.

This sleek and modern vessel feature 3 cabins, each equipped with its own private en-suite bathroom. Expansive deck with plenty of seating and lounging areas.

JEHM of the Sea

A versatile and comfortable sailboat designed for cruising, well-suited for exploring the waters of the Chesapeake Bay.

Stay in the Loop

I want to know about new classes, specials, events and offers from Chronic Sailing.

Life is Just Better on a Boat

sail with us!

Sailing changed my life for the better in nearly every way. It makes me more present, more thoughtful, more focused, healthier, happier, just better as a person in most every way. I would be honored to help share it with you and then watch it become a part of your life.

Keep it chronic.

- Captain Shawn

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Sailing Charters in Annapolis, MD

Classic Sail Charters offers Chesapeake Bay sailing adventures on our thoroughly refined sailing yacht, the Licentia. It is exquisitely appointed, safe, and ready for you to call home while you enjoy the mystique and allure of some of the best sailing grounds in the world.

Select A Time

1 - 6 people | 3-hour (am/pm) - 2.5-hour (sunset) sailing yacht cruise | 25% deposit, minimum age: 7 years., gratuity not included in pricing.

• Most Popular!
• Hour Glass 2.5 Hours
• Users Up to 6 Passengers

Sunset Sail - Licentia

Come join us for an unforgettable cruise on one of our world-class sailing yachts and enjoy the beautiful sunsets in Chesapeake bay!

• Hour Glass 3 Hours

Morning Sail - Licentia

Classic Sail Charters offers Chesapeake Bay sailing adventures on a thoroughly refined sailing yacht Licentia, a 2008 Catalina 42 MKII.

Afternoon Sail - Licentia

Come sail with us on the Chesapeake Bay! As the largest estuary in the world, the Chesapeake Bay is stunningly beautiful!

Other Times

• Hour Glass 8 Hours

Full Day Sail - Licentia

Come sail with us on the Chesapeake Bay! As the largest estuary in the world, the Chesapeake Bay is stunningly beautiful, fed by countless navigable rivers and home to an abundance of wildlife.

Chesapeake Bay - Annapolis

Looking for a unique sailing experience on the Chesapeake Bay? Our charters are the perfect way to explore the Bay and its navigable rivers. As the largest estuary in the world, the Chesapeake Bay is a natural beauty filled with an abundance of wildlife. Create your own sailing adventure on the Chesapeake Bay as we work with you to define your perfect excursion and then you may leave the rest to us!

Annapolis, located less than an hour from Washington, D.C., is noted not only as the location of the US Naval Academy but as America’s ‘Sailing Capital.’ It is home to a rich history that includes the oldest working state capitol building in the U.S., noted as the location where General Washington resigned his commission, as well as dozens of first-class bed and breakfasts, hotels, and fantastic restaurants. As a sailing venue, it is second to none.

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Celebrate or relax in style on a private yacht charter

Charter a luxury catamaran yacht for a few hours, days or weeks.

Enjoy the scenic views, sailing yacht charter amenities and the adventure that lays ahead for you and your guests. Our experienced captains provide local knowledge and nautical skills to ensure a safe and fun experience for everyone. We can’t wait to have you aboard!

Destinations

Charters available in these beautiful destinations

Key West, FL

The Abacos, Bahamas

U.S., British & Spanish Virgin Islands

St. Vincent & The Grenadines

Make your special occasion a one of a kind experience.

Our mission at Sail Away Catamarans is to provide you and your party a one of a kind experience. Chartering a private yacht is a fun and decadent way to celebrate birthdays, weddings, anniversaries and retirements. Or get the gang together for a family trip, bachelorette party, or a corporate event. Our experienced charter agents are standing by to help make your event a memorable one.

Book Today and Set Sail

Select a Yacht or Itinerary

Search for the yacht or find an itinerary that best fits your event.

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" Book Now " to submit your preferences and make your payment. You will receive a confirmation number & email.

We Will Review

One of our specialists will call and review your booking with you as your date nears. Let’s go sailing!

"Can not recommend Sail Away Catamarans enough! I was planning a bachelorette party with 12 girls and they could not have been more accommodating. They were very responsive, reasonably priced and the day of went off without a hitch! ...the boat was just beautiful! All the girls had wonderful things to say and a great time!

Our Most Popular Itineraries

Sunset cruise on the bay, so maryland: crab feast + sail, overnight in annapolis or saint michaels, custom itinerary, book your sailing charter now.

Annapolis Yacht Charters

Captain and Bareboat, Cruising or Fishing

Daily through weekly rates

1505 Shipsview Road

Annapolis, MD 21409

[email protected]

410-353-8242

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New Model Charter Yachts In Annapolis, MD

Waypoints Annapolis offers a variety of new model sailing monohulls, catamarans, and powerboats for multi-day charters on the Chesapeake Bay. Our team prides itself in providing an elevated charter experience for each of our guests aboard our meticulously maintained yachts equipped with all of the comforts of home. Come charter with us and discover the Waypoints difference.

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Annapolis Fall Charter Special. Get One Night FREE!*

Elite Charters of Annapolis

Luxury yacht charter experiences.

Unique and Unforgettable Memories Await in Annapolis and on the Chesapeake Bay

Why Choose Elite Charters of Annapolis

Exclusive Yacht Charter Experiences

Let us host your next special occasion, cocktail cruise, relaxing weekend, or wedding cruise aboard one of our luxury yachts.  

Located in the heart of Annapolis, our professionally crewed charter yachts are easily accessible and create stunning and memorable experiences on the Chesapeake Bay. 

Our yachts are equipped with state-of-the-art amenities, including air conditioning, comfortable seating, and entertainment systems.

Professional Captains and Crew

Our crew members are experienced and knowledgeable about the Chesapeake Bay. They will ensure that you have a safe and memorable experience on your charter.

Muse - 87' Warren Yacht

• This sleek 87 ft sport yacht is available in Annapolis and the Chesapeake Bay.
• Invite up to 12 guests for half or full-day private yacht charters.
• She boasts beautiful teak decks, dual salons, and a spacious aft entertainment area.
• With a 5 ft draft, Muse can navigate secluded coves and anchorages.
• A 27-knot cruise speed ensures fast travel and exploration of multiple destinations.
• Overnight guest accommodations for six plus crew.

Shredder - 54' Eastbay

• Built by Grand Banks, the 54 ft Shredder is the quintessential Downeast-style cruiser.
• Accommodates up to 12 guests for half or full-day private yacht charters.
• Ideal for multi-day or week-long luxury Chesapeake Bay cruises for a couple in the spacious master stateroom.
• Perfect for day excursions to quaint Chesapeake Bay towns, romantic dinners, and water activities.

Firefly - 68' Azimut

• The Italian-designed and built Firefly turns heads with its sleek lines and lavish leather interiors.
• With a 6 ft draft, Firefly can access secluded Chesapeake Bay coves and shallow rivers.
• Features two spacious staterooms, making it an ideal overnight retreat for two couples or accommodating up to 12 guests on a day charter.
• Suitable for various experiences, from an elegant sunset cruise to a week-long excursion along the Chesapeake Bay, Annapolis, and Baltimore.
• Firefly ensures your private yacht charter is marked by style, comfort, and luxury.

Photo Gallery

The stunning yacht Muse at her winter home in Miami

Reserve Your Charter Today!

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326 1st Street, Suite 403, Annapolis, MD 21403

Mike Esposito / [email protected] 239-227-7879

Copyright © 2024 Elite Charters of Annapolis - All Rights Reserved.

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Trip duration, multiple days (less than 1 week), weekly trip show boats that have weekly prices. most weekly boats outside of the us are available only saturday to saturday., boat length: 5ft -, manufacturer, boat build year: -, weekly trip, price: $ - $, 24 annapolis boat rentals: private yacht charters md.

Annapolis, MD

boating guide

In addition to the best offers we have for boat and yacht charters in Annapolis, MD, see also options available for rent in these nearby locations:

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Rent a Boat Charter in Annapolis, Maryland with Sailo!

Looking for a boat rental Annapolis, MD? Let's start choosing the right private yacht rental in Annapolis, MD - the charming capital of Maryland — is quintessentially maritime. Home of the US Naval Academy, this amazing town preserves the authentic Colonial atmosphere: cobblestone streets, original lamp posts and brick row houses. Sailing is ingrained in Annapolis — a boat rental comes naturally if you choose to spend a few days around here.

How to rent a boat in Annapolis, Maryland?

Check out our extensive inventory and pick the yacht rental in Annapolis, MD that suits your plans for having fun on the water. Whether you are into watersports, looking for a relaxed cruise, or to go for a fishing trip, this famous boating destination has something for every taste. If you’re around for the 4th of July, you’ll get the chance to enjoy the amazing fireworks right from your boat!

A boat rental to Chesapeake bay is the perfect choice for a romantic sunset cruise to enjoy the scenic skyline, or a visit to the historic Kent island. There are many things to do by boat in “America’s Sailing Capital”. Browse, pick your Annapolis, MD boat rental and get ready for a memorable nautical adventure! We also invite you to check our top boat selections in other locations in Maryland: Pasadena boat charters and Solomons Island boat rentals .

Sailo concierge team is here to help you rent the perfect private boat charter in Annapolis to go sailing in Maryland. To ask for more details or request special arrangements on your private yacht rental in Annapolis, MD, please send a direct message to the boat representative, or reach out to us on live chat.

Annapolis, MD could be the ideal yachting playground for you

Boating in Annapolis is a thrilling experience and one best savoured with your own private yacht charter. Choose your perfect boat rental in Annapolis and step aboard with your family or friends for a spectacular day on the water. Escape the crowds and enjoy some of the most beautiful scenery in Maryland from the deck of your own yacht charter.

Top private boat rentals in Annapolis, MD

Want to rent a boat in Annapolis, MD? You’ll find 9 boats waiting for you to take them on an adventure here on Sailo. Choose from our sailboat rentals in Annapolis, MD . Another great choice is a catamaran rental in Annapolis, MD . Fans of luxury motor yachts will be spoiled for choice with our multiple motor yacht charters in Annapolis . Maryland is an excellent place to enjoy a party, so discover our party boat rentals in Annapolis, MD for 13+ guests in Annapolis and see for yourself.

How to find a boat charter in Annapolis, Maryland?

Choosing the perfect Sailo boat for you in Annapolis, MD is easy and quick thanks to our advanced filters! First we recommend filtering by date and trip duration. Whether you look for a 2, 4 hrs or a full day boat rental in Annapolis, MD, the group size is very important, as well as the type of boat you want for your adventure in the waters of Maryland. Use the price filter to see only options according to your budget and click on the 'Crew' button to choose if you want a Annapolis boat charter with a captain or you want to drive it yourself (option Bareboat). Once a Annapolis yacht charter catches your eye, click on it to see the boat page with more photos and a detailed description. Check the reviews and send a direct message to the boat owner to ask more details!

How much does it cost to rent a yacht charter in Annapolis, MD for a day?

Annapolis boat rentals prices vary significantly. You can find great budget friendly private yacht rentals in Annapolis, MD starting from $250 for a daily trip. Luxury or party yacht rentals for the day can cost up to $6500 where service fees and mandatory extras are not included. Your budget per day will vary depending on whether you are renting the boat in Annapolis with captain and/or crew, fuel cost, special requests for pick-up and drop-off or other special arrangements you may want to make with the owner.

Can I pay in installments for my Sailo Annapolis boat rental?

A lot of our boat owners allow payment in installments, particularly for the weekly yacht charters in Annapolis, MD. First installment is always charged at the time the booking is confirmed. To find out if a boat has an installment plan, reach out to the boat representative and ask details via 'Message Owner' before you submit the booking or check out the Payment Schedule at top of the booking page.

Responsible boating guidelines

• Take your rubbish home
• Use eco-friendly sunblock
• Avoid single use plastic

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Sailing Yacht Charter Annapolis Sailboat Charters & Rentals

Top-rated yacht charters in annapolis - preselected yacht rentals:.

Yacht Sun Odyssey 389 for rent in Annapolis

• Sun Odyssey 389 [Yacht Price incl. Taxes]
• Barbeque Grill
• Yacht Insurance
• Final cleaning
• Damage waiver
• Cancellation insurance
• Maryland Amusement Tax
• VAT or sales tax
• Credit Card Payments (surcharge)

Yacht Dufour 430 available for charter in Port Annapolis Marina

• Dufour 430 [Yacht Price incl. Taxes]

Yacht Sun Odyssey 440 available for charter in Port Annapolis Marina

• Sun Odyssey 440 [Yacht Price incl. Taxes]

Yacht Dufour 530 for charter in Annapolis

• Dufour 530 [Yacht Price incl. Taxes]

Sailing yacht Jeanneau 58 for rent in Port Annapolis Marina

• Jeanneau 58 [Yacht Price incl. Taxes]
• Skipper (food not included)

Sailing boat Jeanneau 51 for rent in Port Annapolis Marina

• Jeanneau 51 [Yacht Price incl. Taxes]

Sailboat Dufour 56 Exclusive available for charter in Annapolis

• Dufour 56 Exclusive [Yacht Price incl. Taxes]
• Cockpit cushion
• Outboard engine for dinghy
• Service fee

Yacht Dufour 390 Grand Large for rent in Annapolis

• Dufour 390 Grand Large [Yacht Price incl. Taxes]
• Virgin Islands Search and Rescue (VISAR)
• Cruising tax
• Fuel (for outboarder)

Yacht Catalina 42 for rent in Annapolis

• Catalina 42 [Yacht Price incl. Taxes]

Yacht Oceanis 30.1 available for charter in Annapolis

• Oceanis 30.1 [Yacht Price incl. Taxes]

Sailboat Oceanis 45 available for charter in Annapolis

• Oceanis 45 [Yacht Price incl. Taxes]

Rent a sailing boat in Annapolis, U.S

Sailing boat rentals in annapolis.

The most common boat booked for charters throughout the world is the sailing boat . With more than 20 available for rent in Annapolis , Yachtico.com can provide you with a fantastic deal for your next sailing trip around this beautiful city and the surrounding eastern U.S. coastline.

Annapolis is found on the coastline of the state of Maryland, in the picturesque Cheseapeake Bay. Charter a sailing boat from this fantastic location and you can sail up the Atlantic and visit locations such as the Big Apple - New York City and Rhode Island. Sailing boats are an ideal option if you are looking for a relaxing vacation aboard the water and enjoy time to yourself on deck. They are also a more economical on fuel and costs in general, also making them a great option for holiday-goers on a budget.

Yachtico is always working on providing more boats in Annapolis and other locations throughout the U.S. so if you are searching for something that you cannot find here, we suggest you check out our United States page for Sailing boat rental for other locations where your perfect boat is available. Otherwise, check out the great sailing yachts available below and book online today for your next charter holiday in Annapolis.

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Annapolis Bay Charters

Location & Hours

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7080 Bembe Beach Rd

Annapolis, MD 21403

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Charter a late model monohull or catamaran to enjoy a sailing vacation in and around the breathtaking Chesapeake Bay. Our agents can help you choose the best boat for your family and friends and the itinerary that will make your holiday special. …

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Annapolis Bay Charters (aka Dream Yacht Charter at same address) Should you use Dream Yacht Charter? Read this and then decide. Our bareboat charter sailboat was advertised to have several convenient and appealing systems that would make a family's vacation safe and comfortable. However, we quickly found that some of the critically important and desirable ones were broken: - Broken windlass (no way to anchor safely - like having no brakes in a car) - Broken fresh-water maker (fresh-water rationing) - Broken AC (sleepless nights from the sweltering heat) - Incompatible propane tank valve (no way to cook our provisions - forced to dinghy in to buy expensive restaurant food) - Bad dinghy motor (unable to leave and return to boat reliably and safely) I heard from one of their USVI technicians that they know at least one onboard system was broken before they sent us out on our 10-day USVI vacation. Within 24 hours after leaving the marina, we discovered other broken systems. Over the next eight days I made 40 calls to their emergency mechanical hotline. On the rare occasions that a human answered (the voice mailbox was always full so no messages could be left), they repeatedly assured us that someone would be sent out immediately to repair all the issues. Finally, eight days later, they sent two technicians to fix one issue - they brought a propane tank with proper fittings so that we could now cook our provisions. Why did they lie about fixing the issues immediately? Why didn't they respond sooner? Why didn't they fix the issues before the charter? Why didn't they swap out the boat for one that was known to be usable? In addition to the broken items mentioned above there were other things that underscored negligence and chronically poor maintenance: - Heavily encrusted hull bottoms (looked like it had not been cleaned in years) - Badly damaged, unrepaired bow (potential water intrusion) - Failure to provide prearranged extras (they have yet to provide a refund) - Leaking windows (significant rain intrusion) - Filthy condition of cushions (appeared not to have not been cleaned for years) - Numerous broken snaps and Velcro (loss of cushions while underway) - Ripped helm bimini We were trapped on the boat in survival mode instead of joyous vacation mode with limited ability to stay at the locations we had planned to visit because the windlass was broken. It was unsafe, uncomfortable, and disappointing. It was worse than renting a camper van in the peak of summer in Florida, and finding that the brakes, AC, stove, motor, and other systems were malfunctioning or completely unusable. Wouldn't you at least expect a refund from the car rental company. I have detailed documentation on everything that happened - lists of all calls made and numerous damning images/descriptions of all the broken and deficient systems. These have been shared with DYC and I will gladly share any of this information with anyone who is interested to see proof of these claims. Upon returning home after the "vacation" I made numerous attempts (calls, e-mails, and certified letters) to seek restitution. After weeks of delay, they finally responded with a paltry and insulting compensation offer for ruining our vacation, and at this time they have refused to provide a refund or negotiate further to reach a fair settlement. They cannot and have not refuted the facts stated above. They know them to be true. They just don't care or want to provide fair restitution. This charter was not the only contentious interaction I had with them. Prior to this disastrous charter, I had two other unpleasant encounters. In the first one, they refused to honor a promise that was used to convince me not to cancel my reservation during the 2020 Covid shutdown. They promised to add two free days to the charter but never honored the promise. In the second interaction, they failed to return phone calls in a timely manner causing an important deadline to pass. Their sloth cost me a great deal of aggravation to prove, with documentation through numerous e-mails and telephone calls, that it was their fault that the deadline was missed. My experiences with them have convinced me that they don't care about anything, except getting your money. There are better more customer focused competitors out there. They have demonstrated that this customer's satisfaction was not a high priority for them. #dreamyachtcharter

Absolutely horrible boat and company to work with. We spent 32k for a month and boat was almost unusable. On top of this, the company was contacted several times during and after the charter and they wont respond to emails or calls.

They are an agent for Dream Yacht Charters. We had absolutely the worst cruise ever! If you're reading this, you're likely considering Dream Yacht Charters (DYC) for a charter. I've been sailing for a long time and my best advice is to find another company...no matter how good DYC sounds, YOU CANNOT TRUST THEM. There is a detailed Terms and Conditions (T&C Contract) for their charters, that apparently only apply if it is in their favor. We did a 'Cabin Charter' from Nassau to the Exumas (Bahamas). There were several things that the booking agents and charter operators disregarded that ruined our trip. 1) Our cruise was ruined by a screaming 2.5 year old brat that threw screaming tantrums several times a day. The parents were unfamiliar with any form of discipline. All of the DYC descriptive information indicated it was an 'Adults Only' cruise. Their home office even admitted they discouraged booking young children. However, the agent who booked the screaming-kid-family said it was a "Family Friendly" cruise. The disruption in the peace desired when sailing was complete. DYC actually has a written policy in their T&C Contract (Clause 8.5: "The Captain will disembark any Passenger whose behavior could endanger or seriously inconvenience other Passengers..."). Even though the Captain was completely aware of the negative impact of the child's disruptive behavior, he took no action (likely because they would have had to reimburse the charter fee) and all of the other passengers were seriously impacted by the child's behavior. You may think you can ask the agent if there are any kids onboard, but their answer means nothing because of the potential for late bookings and they can move you to a different boat as they desire and without any consultation with you. 2) There were 2 non-meat eaters aboard our trip. DYC is supposed to provision adequately to accommodate any dietary needs of their passengers... which they did not do. As a result, the 2 non-meat eaters were given a majority of the fish rations intended for everyone else. There was an opportunity at our first stop to acquire appropriate provisions, but the Captain and cook did not do so. The non-meat eaters ate well and the rest of us did not. 3) The departure on our voyage was delayed by several hours while we waited for someone who never showed up. We never actually caught up on the intended schedule because of the delay. Once again, DYC actually has a written policy in their T&C Contract (Clause 9. 6: "If Charterer is not present at the time of Embarkation... this will be treated as a cancellation of reservation... the Charterer will lose its entire charter fee.") There was no word from the missing passengers that they would be arriving late, but we waited anyway. 4) We were told by the booking agent that we would have first choice of cabins, as they are supposedly assigned in the order of booking for the cruise. This was confirmed as the policy by the DYC Customer service office. However, the Captain decided to assign cabins by raffle. We got LAST choice. 5) The agents indicated COVID vaccination status would be checked at the base (all passengers were required to be vaccinated). This check was never performed and as we learned later one of the passengers had been ill with COVID less than a week earlier. Again, DYC did not hold to their verbally stated policy. There were several other issues that affected our enjoyment of the trip. In summary, the DYC policies (written or verbal) are easily disregarded by them and apparently only apply if it is their interest to enforce them. AVOID THIS COMPANY. There are many other good quality charter companies and, as I discovered recently when looking for a bareboat to charter, the DYC prices were higher for the exact same boat at the exact same period. They screw you on both the price and service provided. Their "Customer Service" apparently only exists to defend their actions and not to provide any actual service to a customer.

Last year family of four chartered a 47 foot Catamaran with the name Kilamanjaro from Dream Yacht Charters, also doing business as Annapolis Yacht Charters. The charter was a nightmare! We received a broken boat, were left at seat with no engines and our two small kids and the company did nothing to help us. When we returned the boat early the base owner agreed we deserved a full refund that never happened. Buyer beware. Do not vacation with Dream Yacht Charters DBA Annapolis Yacht Charters. We arrived on the first day of our 10 day trip to a boat with a lot of visual wear at tear. The trip was wrought with one mechanical issue after another. First the boat was not stocked with the correct equipment that fit, then we lost an engine, then the air conditioning, then a bad impeller on the engine, lost the second engine, a part of the generator rusted off and after 7 days of drama we returned the boat early. Not only was the boat was a mechanical disaster the interior was compromised and the stove was without a gamble (necessary for a stove on a moving object) the stove gave way and boiling water poured down my stomach. At one point we were sailing with our two small children, without both engines and asked to meet on the other end of the island for repairs. Given the seas and the conditions, this was neither safe nor what you would call a vacation. When we called the main office NO ONE was interested in actually helping us. During that trip we called as many people as we could begging for help/new boat/out of our existing boat and we were offered little more than a sorry. After 7 days of sitting around wasting our vacation waiting for Dream yacht charter to repair the boat we finally returned it early. Upon returning the boat we spoke with the manager who agreed we did not get to enjoy our vacation nor did we get to do anything that wasn't focused on repairs. The manager of the branch, Paschal, assured us he would work on a full refund. When we arrived home I followed up with Dream Yacht Charters booking agent, who couldn't do anything more than say she would forward my message. Then I spoke to the GM of the Dream Yacht, Dan Lockyer, he offered me credit on a future trip. Which I turned down, my family was in an unsafe scenario due to their neglect of their equipment. He offered to credit us a for the two days we returned it early and a small inconvience fee which was nothing compared to the full refund that Paschal had agreed we deserved. Chartering from this company is a vacation roulette. I tried to take legal action upon my return but because of the way the company is structured any ligation would need to take place in the Republic of France. Even though the GM I spoke with was part of the US company and I booked with a US company. BUYER BEWARE. UNSAFE BOAT!

Poor diligence by Annapolis Yacht ruins perfect plan. We chartered a 40 foot catamaran named The Doghouse for two days. The cat was built in 2012. Looked great. Caterer great. Boat was not checked out. We toured Annapolis harbor by motor. Once out on the bay, we could not raise main as main halyard was twisted and knotted. Tried sailing with Genny to find steering or rudder fouled. Beautiful day, motored over to St Michaels where accommodations and transport met us. Annapolis Yacht pretty unresponsive and offered minimal restitution. Use someone else.

I am a delivery captain and was asked to take a Bali catamaran named off call to the Bahamas. It was a danger to be on. Safety equipment was out of date doors locked us out twice. And then I had to break into the aft cabin where my mate was locked in with no way to get out. Life raft deployed in moderate seas. Head was leaking into bilge, And after 16 days of BS we made it to Hollywood FL. With many needed repairs. Worse of all. I still haven't been paid. Nor will they return my calls. They should be shut down and sued. Going on 6 months of nothing. I guess I'm going to have to hire a marine lawyer. I have all my records and paperwork with pictures with dates starting on day 1 of all the problems. The persons name was Erin. I hope she was fired. Worst company I've ever worked for. And I've been delivering boats for years on both coasts. I hope they pay me soon. I even had to buy my own return flight back home and my mates ticket. I lost money on this job. Stay away from dream Yacht Charters. There boats are a danger to the industry.nightmare Yacht Charters.

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