About Boatsy : Who we are and how it works.

From Yachts , Catamarans and Gulets, Boatsy is the home of yacht charters and experiences. Connecting you with hosts in a similar way to airbnb. More than a charter service Boatsy goes the extra mile with a dedicated concierge team, 100s of the word’s mosts beautiful sailing routes all matched with boats and crew to ensure a seamless sailing experience.

How do payments work?

There are two main payment options in the system, depending on the host's preferences. Some boats allow for a partial upfront deposit with the remaining balance due on the day of the trip, while others require full payment upfront. During the payment process, you will see if the host requires a card payment or cash payment for the second installment, if applicable.

What is Boatsy’s Price Match Policy?

While we’re confident in the value and exclusivity of our offerings, we’re happy to match verified competitor pricing to ensure you can experience the best with Boatsy. This applies to your first trip with us, provided the offer is available.

What is the Boatsy Wallet and How Does it Work?

The Boatsy Wallet lets you earn credit for future bookings. For bookings over $5,000, you’ll receive 10% of the total price as credit, which can be used on your next trip or for add-ons like crew and provisions.

What insurance options are available?

Flexible Cancellation : Cancel up to 2 days before without having to submit any proof or justification and get an 80% refund. Justified Cancellation : Receive a full refund for your booking up until your departure if you are unable to travel due to a covered event

Annapolis Yacht Charter: Chesapeake Maryland Capital

Cast off from Annapolis City Dock at noon, sail to a St Michaels Eastern Shore village, eat at an Eastport seafood restaurant. 5-day Chesapeake Bay base.

Boat RentalsDaily Experiences

When?Any date

Lets find the best sailing itineraries of Annapolis based on your preferences

From stunning bays to culinary delights, choose below to explore the world’s best itineraries tailored to your preferences.
By selecting your itinerary in advance, our platform uniquely allows you to view boats that can deliver selected tinerary with full cost transparency, including fuel etc..

Foodie

Party

Exploration

History

Less Miles More Smiles

Minimal

Private

Serenity

Annapolis

Annapolis is the capital of the US state of Maryland and the long-running self-described \"Sailing Capital of America\" — on the western shore of the Chesapeake Bay, the largest estuary in the United States (300 kilometres long, 50 kilometres wide at maximum). The city holds the US Naval Academy (the United States Navy officer training school, 1845 onwards), with the largest concentration of marinas on the US East Coast and the annual US Sailboat Show (October) — the largest in-water sailboat show in North America. The Chesapeake Bay is sailable on charter routes connecting St Michaels, Oxford, Solomons Island, and the Eastern Shore tidewater towns — together one of the most-sailed inland sailing regions in the world. Season runs April through November; the bay holds Maryland blue crab and Chesapeake oyster traditions.