Sailboat rental in Annapolis

Add your dates
With or without a captain
Price per day
0 - $1,350+
Boat length
0 - 196+ ft
Engine power
0 - 400+ hp
Year of manufacture
2003 - 2024
Search radius
50 Max MI
8 sailboats available

43' Landfall Sailboat (1987)

With captain

From $1,614 per day

30' Pearson (1977)

With or without a captain

From $1,128 per day

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These are our available boats around Annapolis, United States

Hunter Passage 42 for Day Charters (1995)

With captain

From $1,239 per day

Beneteau Oceanis 40 (2010)

With captain

From $1,222 per day

Custom 41' Historic Sloop (1926)

Saint Michaels
With captain

From $1,270 per day

Sailboat Custom Sailboat 15.2m (1926)

St. Michaels
With or without a captain

From $1,320 per day

S/V Sea Hawk, C&C 37+ (1989)

With captain

From $1,596 per day

Sailboat Custom Sailboat 8.53m

With or without a captain

From $720 per day

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Sailboat Rental Annapolis with Click&Boat

Sailing is a must when it comes to visiting Annapolis, Maryland. Annapolis is known as the epicenter of America’s boating culture, boasting a long tradition as a sailing capital of the United States.

With a sailboat charter in Annapolis, take advantage of visiting the US Naval Academy, which has served as the US Navy’s most prestigious academic institution since 1845. You can also visit the famous Ego Alley, a narrow waterway in downtown Annapolis. If you are interested in exploring the rest of the Chesapeake Bay by sailboat, we highly recommend checking out Rock Hall, St. Michaels, and Chestertown!

How much does it cost to rent a sailboat in Annapolis?

The cost of a sailboat rental in Annapolis, Maryland may depend on a few factors. Depending on the size and model of the boat, as well as if it is high or low tourism season in the area. Extras like fuel, water sports equipment, and the services of a captain may come at an additional cost. So to be sure, contact the boat owner via Click&Boat’s messaging platform to ask any questions you may have.

  • Sailboat rentals in Annapolis start at $150/hour and range from $600/day to $1,200/day for 6 guests onboard.

Since you are interested in renting a sailing boat on the Chesapeake Bay, we also recommend you check out our fleet in nearby destinations:

Setting sail in Annapolis, Maryland!

This summer, choose Annapolis as your starting point for an adventurous (or relaxing!) day out on the water. Here are our top recommendations when it comes to setting sail on the Chesapeake Bay:

Charter a boat in Annapolis and get to know some of the Bay’s small and historical towns. For example, St. Michaels was voted one of the ‘Top 10 Best Coastal Towns” by USA Today, home to excellent shopping and dining options.

Rock Hall is an absolute must, it is a waterfront village settled in 1706, with plenty of restaurants and bars on the docks with live music in the summer. Crabbing is a way of life here, so during your next visit be sure to try this local delicacy. We also recommend dropping an anchor at one of the local shorefronts for a swim. And we can’t forget charming Chestertown, embellished with 18th-century mansions and townhouses- the perfect day trip destination.

The city of Baltimore is also stunning to see by the water, especially if you take the time to visit its inner harbor. And Chesapeake City is a classic sailing destination for all those cruising out on the bay.

So, hoist the sails and set off for one of these destinations!

When is the best time for a sailboat rental in Annapolis?

The best time for a sailboat charter in Annapolis, Maryland is during the warm summer months. From May to late September, you can comfortably cruise the Chesapeake Bay and enjoy warm water temperatures for swimming.

If you are interested in booking a yacht charter in Annapolis, we highly recommend that you make a reservation in advance with Click&Boat to ensure that you can set sail on board your dream boat.

Can I rent a sailboat with a captain in Annapolis?

Yes! With Click&Boat, most sailboat rentals in the Annapolis area are available with an experienced captain and crew. All you have to do is sit back and relax while the skipper and crew take care of everything from mooring, navigating, docking, and more! This is also a great option for those who are planning parties or celebrations on board!

Our captains are local experts who know the area best! Let them show you all the top places to see including, charming villages, sandy beaches, waterways, sandbars as well as give you recommendations on the best restaurants and bars- if you are interested in a dock’n’dine experience on the Chesapeake!

For those interested in bareboat charters, don’t hesitate to contact our owners on Click&Boat for more information and availabilities.

Why charter a sailboat for your next sailing adventure?

Sailboat rentals are ideal for anyone interested in learning to sail, wanting a unique experience on board, or who plan to set sail for a longer period of time and need to be able to sleep on board.

Depending on the model and length of the sailboat, they can typically accommodate 4 to 6 guests comfortably. This is a great option for small families and couples.

Imagine yourself cruising along the bay, stopping for a quick picnic and swim, and most importantly- creating unforgettable memories with your loved ones. Sailing charters are definitely a bucket-list-worthy adventure!

Renting a sailboat with Click&Boat

With Click&Boat, the leading peer-to-peer boat rental service, guests can select from a range of sailboat brands like Beneteau, Catalina, etc... And rest assured that we will help you find a boat that fits your budget and suits your needs.

Once you have found the perfect sailboat charter, send a message to a boat owner using our internal messaging system in order to clarify any questions you may have. After that, all that is left to do is book your rental. And after your experience aboard, be sure to leave a review.

However, if you prefer, you can request a free quote from our team of knowledgeable sailing advisors. They will help you find the crewed yacht charter of your dreams, as well as help you plan all the details of your world-class trip on the Chesapeake Bay.

Rent a sailboat near Annapolis

In Annapolis, privately owned sailboat are available for rent. See other boats in the area

Rent another type of boat in Annapolis

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