Charter a sailing boat in Annapolis

Where
Dates
Add your dates
Sail
With or without a skipper
Price per day
0 - €1,200+
Boat length
0 - 60+ m
Engine power
0 - 400+ hp
Year of manufacture
2003 - 2024
Search radius
100 Max Km
22 boats available

60' Motoryacht charter in Annapolis (1989)

Annapolis
55
With skipper

From €2,800 per day

34' Formula Cruiser (1988)

Annapolis
4
With skipper
 1

From €1,453 per day

43' Landfall Sailboat (1987)

Annapolis
5
With skipper
 1

From €1,453 per day

30' Pearson (1977)

Annapolis
6
With or without a skipper
Private

From €1,015 per day

See more nearby boats
These boats are available around Annapolis, United States

Hunter Passage 42 for Day Charters (1995)

Edgewater
6
With skipper

From €1,115 per day

Sea Ray 450 Sundancer Luxury Cruising Yacht near Annapolis MD (1998)

Edgewater
13
With skipper

From €1,500 per day

Fishingboat 23' (2012)

Edgewater
4
With skipper

From €796 per day

Beneteau Oceanis 40 (2010)

Pasadena
8
With skipper
Private

From €1,100 per day

Custom 41' Historic Sloop (1926)

Saint Michaels
4
With skipper

From €1,143 per day

Sailboat Custom Sailboat 15.2m (1926)

St. Michaels
0
With or without a skipper

From €1,188 per day

Motorboat Custom Fishing Boat 450hp (2016)

Baltimore
6
With skipper

From €970 per day

Motorboat Custom Markley / Meekins Deadrise 100hp (2014)

Baltimore
8
With skipper

From €678 per day

Motorboat Custom 41 200hp (2017)

Baltimore
12
With skipper

From €1,204 per day

46' Markley for Fishing Charters in Baltimore, Maryland!! (2015)

Baltimore
14
With skipper

From €1,404 per day

Motorboat Carman 32 315hp (2017)

Baltimore
6
With skipper

From €610 per day

Motorboat Sea Ray 380 Sundancer 750hp (2015)

Washington
6
With skipper

From €2,407 per day

Discount offer

Premium Boating @ DCs best Waterfront destinations (2014)

Washington
12
With skipper

From €4,000 per day

Bayliner Cierra (2005)

Washington
6
With skipper

From €1,942 per day

Yacht Charter Annapolis- the U.S. sailing metropolis

Annapolis is the epicenter of America's boating culture, boasting a long tradition as the sailing capital of the United States. A private boat rental in Annapolis is a unique experience, particularly from late April up to the end of the summer.

The Chesapeake Bay is a boating paradise in the summer, with plenty of waterfront towns that are not only historically significant but each charming in their own way. Some of our favorite towns include Rock Hall, Chestertown, and St. Michaels.

So whether you are looking to sail away for the weekend or rent a motorboat for a day of water sports or anchoring by a beach to relax, in Annapolis you will find the right boat.

What is the cost of a boat rental in Annapolis?

When it comes to the average price for renting a boat in Annapolis, Maryland, there are several factors that may influence the cost. Such as the rental duration, the season of the rental, age and model of the vessel, as well as if a skipper and/or crew is requested. Make sure you take these factors into consideration, so that you can rent the perfect boat within your budget.

  • If you’re looking to set sail, prices for a sailboat rental in Annapolis start at €500/day for 6 guests on board. But the average prices are around €1,000/day to €1,200/day during high season.
  • Catamaran rentals on average cost between €800/day and €900/day and may accommodate up to 12 people aboard.
  • A motorboat rental costs €650/day to €1,100/day in Annapolis, however large party boats are also available starting at €13,5000/day for 80 guests.

Where to sail to… 

Annapolis is the perfect location to start your boating adventure. Explore the wonders of the Chesapeake Bay or take an even longer sailing trip and discover all that the Atlantic coast has to offer. When you charter a boat in Annapolis, consider these destinations:

  • St. Michaels- voted one of the ‘Top 10 Best Small Coastal Towns’ in USA Today, boosting many dining and shopping options.
  • Rock Hall- a waterfront village settled in 1706 that has many waterfront boutiques, restaurants, and bars- be sure to enjoy the live music and local catches- crab!
  • Chestertown- sail up the Chester River and visit this charismatic town’s eighteenth century brick townhouses and mansions.
  • Chesapeake City- a charming and welcoming sailing destination for boats all over the bay.
  • Baltimore- a city that holds historical significance and is worth visiting for its Inner Harbor, an urban waterfront park.
  • Chesapeake Bay Bridge- by boat, catch a glimpse of this stunning bridge!

What to do and see in Annapolis ? 

Nestled in the Chesapeake Bay, Annapolis, MD has plenty of things to do and see in the area:  

  • Visit the US Naval Academy, has been serving as the US Navy’s most prestigious academic institution since 1845.
  • Enjoy downtown Annapolis with its variety of bars, restaurants, and shops
  • The biggest sailing attraction in Annapolis is the US Sailboat Show, attracting boating aficionados from all over the world every October.
  • Walk around the Annapolis Dock and have a glimpse of some of the world’s most stunning or in some cases, peculiar sailboats.
  • Check out Ego Alley, a narrow waterway that every respectable boatman has navigated at least once.
  • Grab the family and take a hike at Sandy Point State Park.

Can I charter a boat in Annapolis with a captain?

In Annapolis there are many boat rental options available with a captain. Guests can set sail at their own pace and follow their own itinerary. By having a local in their midst, guests will have the opportunity to explore and enjoy secluded anchorages and stunning beaches, that they might have not otherwise visited.

All that there is left to do is to sit back and enjoy your time on board. Let the captain (and crew- if requested!) take care of everything from navigating, docking, and anchoring. Your charter in Annapolis will be unforgettable!

Captain and crew may be an additional cost to your rental. The cost depends on the size of the boat, number of crew members and other specific requests.

Finding boat rentals in Annapolis with Click&Boat

If you are looking for a yacht charter in Annapolis at an affordable price, look no further than Click&Boat, the leading boat rental service.

Rely on the best prices and availability, our integrated messaging tool for renters and owners, as well as our team of expert advisors ready on deck, to help you plan your boating vacation.

Whether you are planning to rent a catamaran, sailboat, motorboat or party boat in Annapolis, with or without a captain, you are sure to find your dream boat with Click&Boat. So what do you say? Are you ready to set sail?

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