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Boat rentals in Annapolis, MD, USA


1 - 12 of 12 boats

Annapolis, MD could be the ideal yachting playground for you

A boating trip is always a great way to experience Annapolis. Choose your perfect boat rental or yacht charter with Sailo and set a course for adventure! When you rent a boat in Annapolis, you can choose your own itinerary and explore at your leisure. Want to relax on deck? Prefer to do some fishing? Or maybe you just want to escape the crowds? Find your ideal yacht rental in Annapolis with Sailo.

Our finest collection of sailboat charters in Annapolis, MD

We’ve been asked many times if a sailboat rental is a good choice to explore Annapolis, MD from the water. With more than 22 charters rented every day during the season, our answer is YES, you’re set for an amazing experience when you rent a sailboat in Annapolis! Our boats are available with or without captain, with prices starting at $250 per day, depending on the boat type you choose. Browse, find, and book in minutes the best sailboat for you in Annapolis, MD!

Looking for a weekly charter? Learn how to find the perfect one for you

If you are interested in a weekly sailing vacation, after you filtered for weekly trip duration, you can search through 22 boats in Annapolis, MD by price ranging between $2760 and $10500, type of boat, such as motorboats, sailboats monohulls or catamarans, and number of guests. Some boats in Annapolis have additional discounts for more than a week charters. If you can’t make up your mind right away, you can use the 'Free reservation' to put the boat on hold.

How much is it to rent a sailboat for a week in Annapolis, MD?

The price for a sailboat rental in Annapolis starts at $2760 per week. Your quote varies depending on the season, with low prices off-season or for early booking and sometimes double during high-season. Luxury sailboat charters from Annapolis, MD can cost up to tens of thousands of $ for a week-long vacation with captain and crew included.

Can I pay in installments for my Sailo boat rental?

A lot of our boat owners allow payment in installments, particularly for the weekly charters. First installment is always charged at the time the booking is confirmed. To find out if a boat has an installment plan, reach out to the boat representative and ask details via 'Message Owner' before you submit the booking or check out the Payment Schedule at top of the booking page.

Sustainable boating tips

Sailing is a great way to experience nature. So we like to remind everyone that keeping nature as beautiful as possible involves a little effort from all of us. Some of our tips for responsible boating include:
  • Don’t litter or throw waste overboard - take rubbish home and dispose of it responsibly
  • Eco-friendly sunblock can help prevent damage to marine life
  • buy local and sustainable food products
However long you’re sailing for, a little goes a long way. Read more about responsible boating.