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Charter a sailing boat in Annapolis

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From €533 per day


From €667 per day


From €445 per day

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 charter 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 skipper in Annapolis?

Yes! With Click&Boat, most sailboat hires 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!

Chartering 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 sailing boat 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 hire. 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.

  • Sailboat
  • Motorboat
  • RIB
  • Catamaran
  • Gulet
  • Jet ski
  • Houseboat
  • Yacht
0 - 1 000+ € /day
0 - 60 m
  • Discounts
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0 - 250 hp
2001 - 2022
100 km max.
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Sailboat Charter 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 charter a sailboat in Annapolis?

The cost of a sailing boat 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 charters in Annapolis start at 125€/hour and range from 490€/day to 980/day for 6 guests onboard.

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

Charter a sailboat near Annapolis

In Annapolis, privately owned sailboat are available for charter. See other yachts in the area

Charter another yacht type in Annapolis

You are interested in other yachts than Sailboat in Annapolis?
Look up at other yachts to charter on our website

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