5 Best Yacht Charters In Annapolis, Maryland

| 3 min read

Annapolis boasts itself as a museum without walls and “America’s Sailing Capital.” As Maryland’s capital, it brims with an upbeat, modern vibe that blends well with centuries-old architectural works. It is renowned for its rich, nautical heritage, with its connection to Chesapeake Bay so you can expect to find various accommodations near the water, from luxury hotels to Vrbo waterfront vacation rentals. Famously, it is home to US Naval Academy (USNA), which has been providing education and training to US Navy officers since 1845. USNA has a museum commemorating the achievements and traditions of the US Navy and Marines. A trip to this historic city is not complete without touring Maryland State House, which once served as the capital of the fledgling United States. To have a genuine, local experience here, try sailing and rent a boat or yacht. Check out some of the best yacht charters in Annapolis, Maryland.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on February 08, 2024.

1. Two-cabin yacht with a fully equipped galley (from USD 299)

This 13.11-m (43-ft) Annapolis boat rental is docked in Eastport, only a short walk away from the historic Downtown Annapolis and USNA. It features two private cabins, one with a queen-sized bed and another with bunk beds. Hosting up to four people, it has a fully functional galley where you can conveniently prepare home-cooked meals.

This galley is furnished with a coffee machine, a fridge, an ice maker, a microwave, a toaster, and a two-burner cooktop. In the main salon, you will find a couch that can serve as an additional sleeping space.

Stayed at this property?

1.11 km (0.7 mi) from Annapolis City Dock
44 reviews   Wifi Available
Boat 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
it was very clean and we had a wonderful view
the accommodations are clean and very unique place to stay compared to the land alternatives
boat was amazing—spacious clean as a whistle beautiful view
lena and her husband were perfect hosts—communicative gracious attentive (but not too much so)
mena was very helpful and responsive
a great experience on the water and walking distance from annapolis
an easy walk to many places to eat and explore
beautiful views walking distance to great food and unique atmosphere
excellent location with great views
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

2. Two-bedroom sailboat with a cozy cockpit (from USD 174)

This charter boat in Annapolis is essentially a two-bedroom apartment that will make you feel at home right by the sea, definitely, a great alternative to the equally amazing hotels on land. Accommodating a maximum of four guests, it has a full bathroom, a dining saloon with couches, and a fully stocked galley.

Since it is a family-friendly rental, you can request a folding bassinet in the forward cabin or a travel bassinet in the aft cabin for your little one. The boat also has a cozy cockpit up on the deck where you can unwind comfortably on a lazy afternoon. It is safely tied at the marina, so you have nothing to worry about during your stay.

Stayed at this property?
Annapolis, Maryland, United States
616 meters (0.4 ft) from Annapolis City Dock
349 reviews   Superhost Wifi Available
Boat 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
and we got great restaurant reviews from ryan including iron rooster and preserve
the boat itself is in great condition and had all the amenities that a small apartment would have
my studio was exceptionally clean upon arrival
beautiful clean and convenient
everything was convenient and clean
ryan’s studio was impeccably clean and very well kept overall
super clean comfortable and convenient though a little exotic
ryan is the perfect host
ryan was a wonderful host
ryan was an excellent host
ryan is a great host everything is explained in great detail
ryan is a great and attentive host
walking distance to many great places
great accommodations in an ideal location
the location is so convenient to many great restaurants and just a short walk to the downtown
great location right across the bridge from annapolis within walking distance of restaurants historic sites and stores
great location with easy walking access to eastport and annapolis
Read more reviews

3. Luxury yacht with a double trampoline (from USD 475)

This 15.24-m (50-ft) luxury yacht rental in Annapolis is only a few minutes away from the downtown area. During winter, it is situated in the Bahamas. It features three bedrooms, which can host up to two adults each, and three full bathrooms. It can accommodate a maximum of 8 people, and it offers 83.61 sq. m (900 sq. ft) of living space. The salon can host two people with its king-sized dropdown table.

On the main deck, you will find a double trampoline that is perfect for sunbathing. Several chaise loungers are provided, so you will get to sit back, relax, and enjoy breathtaking views anywhere on the deck.

Stayed at this property?
Annapolis, MD, US
8 Guests 3 Bedrooms 3 Bathrooms
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

More options for boat rentals in Annapolis

4. Two-cabin sailboat at a full-service marina

This 10.97-m (36-ft) Annapolis sailboat rental accommodates up to 4 guests and offers 2 cabins and a salon. It is docked at a full-service marina in Back Creek where you will find a bathhouse, a cafe, a supply store, a swimming pool, and a water taxi service. At the cafe, you can have your sumptuous breakfast and lunch meals.

The water taxis can take you to Downtown Annapolis and other nearby seafood restaurants and other waterfront dining options. If you are bringing a private vehicle, you can park for free in the marina’s parking area. The city center is only a 10-minute drive away.

Stayed at this property?
Annapolis, Maryland, United States
1.8 km (1.2 mi) from Annapolis City Dock
172 reviews   Wifi Available
Boat 4 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
amenities are nice including the bath house and pool
the boat is a comfortable stay with all the amenities you would need
we enjoyed sleeping on a boat we made the most of the pool in the marina
so we knew what to expect cool alternative to a hotel room in annapolis
the boat offers a small tv and dvd play for watching movies and regular cable networks
clean bathhouse is 100ft away
the bath house is convenient and clean
bath house was very clean and close
marina was great bath house was clean and the pool was super
the marina facilities are clean and convenient
ken is a great host
ken was an excellent host
ken was very responsive to questions and direction even though he was out of the country
everyone was very friendly
ken is a fantastic host
the location is perfect with close proximity to everything
location was great and very safe
the location is quite private and safe
safe place to stay and great location
i returned for another trip because the location in the marina atmosphere is outstanding
Read more reviews

5. Cozy sailboat with access to the marina’s swimming pool

Only a few minutes away from Downtown Annapolis and roughly 45 minutes away from Washington DC, this cozy 9.14-m (30-ft) sailboat hosts up to 3 people. During your stay here, you will have access to all of its facilities, including the saloon and V berth. You will also have access to all other amenities that the marine provides, including the bathhouse, car park, and swimming pool. If you are bringing a private vehicle, you can take advantage of the marina’s complimentary parking. Wi-Fi is also available, so you can always stay online.

Stayed at this property?
Annapolis, Maryland, United States
824 meters (0.6 ft) from Annapolis City Dock
Wifi Available
Private room in boat 3 Beds 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Find out why Annapolis is "America's Sailing Capital"

With its connection to Chesapeake Bay and USNA, Annapolis thrives on its rich, nautical heritage. Of course, you can always choose to stay in one of the hotels with tub or Airbnbs with pool on dry land but staying in one of these best yacht charters in Annapolis, Maryland, will likely make you realize how and why the city is known as “America’s Sailing Capital,” so go ahead and check them out.

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Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Ninna, a writer and traveler, encourages everyone to explore the world one city at a time, unveiling its myriad surprises.

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