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Private Yacht & Boat Rentals in Annapolis, MD

1 - 18 of 37 boats

Try TOP Yacht Charters in Annapolis with Sailo!

Looking for a boat rental Annapolis, MD? Annapolis - the charming capital of Maryland — is quintessentially maritime. Home of the US Naval Academy, this amazing town preserves the authentic Colonial atmosphere: cobblestone streets, original lamp posts and brick row houses. Sailing is ingrained in Annapolis — a boat rental comes naturally if you choose to spend a few days around here.

How to rent a boat in Annapolis, Maryland?

Check out our extensive inventory and pick the yacht rental in Annapolis, MD that suits your plans for having fun on the water. Whether you are into watersports, looking for a relaxed cruise, or to go for a fishing trip, this famous boating destination has something for every taste. If you’re around for the 4th of July, you’ll get the chance to enjoy the amazing fireworks right from your boat!  

A boat rental to Chesapeake bay is the perfect choice for a romantic sunset cruise to enjoy the scenic skyline, or a  visit to the historic Kent island. There are many things to do by boat in “America’s Sailing Capital”. Browse, pick your Annapolis, MD boat rental and get ready for a memorable nautical adventure! We also invite you to check our top boat selections in other locations in Maryland: Pasadena and  Solomons Island.

Sailo concierge team  is here to help you rent the perfect Annapolis boat charter to go sailing in Maryland. To ask for more details or request special arrangements on your yacht rental in Annapolis, MD, please send a direct message to the boat representative, or reach out to us on live chat.

Annapolis, MD could be the ideal yachting playground for you

Boating in Annapolis is a thrilling experience and one best savoured with your own private yacht charter. Choose your perfect boat rental in Annapolis and step aboard with your family or friends for a spectacular day on the water. Escape the crowds and enjoy some of the most beautiful scenery in Maryland from the deck of your own yacht charter.

Top private boat rentals in Annapolis, MD

Want to rent a boat in Annapolis, MD? You’ll find 9 boats waiting for you to take them on an adventure here on Sailo. Choose from our 3 elegant and classic sailboats. A catamaran is also a great choice, with 6 available in Annapolis. Fans of luxury motor yachts will be spoiled for choice with our multiple motor yacht charters. Maryland is an excellent place to enjoy a boat party, so discover our various larger party boats for 13+ guests in Annapolis and see for yourself.

Learn how to find the best yacht charter in Annapolis, Maryland

Choosing the perfect Sailo boat for you in Annapolis, MD is easy and quick thanks to our advanced filters! First we recommend filtering by date and trip duration. Whether you look for a 2, 4 hrs or a full day rental in Annapolis, the group size is very important, as well as the type of boat you want for your adventure in the waters of Maryland. Use the price filter to see only options according to your budget and click on the 'Crew' button to choose if you want a boat with a captain or you want to drive it yourself (option Bareboat). Once a Annapolis charter catches your eye, click on it to see the boat page with more photos and a detailed description. Check the reviews and send a direct message to the boat owner to ask more details!

How much does it cost to rent a yacht in Annapolis, MD for a day?

Boat charter prices in Annapolis, MD vary significantly. You can find great budget friendly rentals starting from $250 for a daily trip. Luxury or party yacht rentals for the day can cost up to $6500 where service fees and mandatory extras are not included. Your budget per day will vary depending on whether you are renting the boat in Annapolis with captain and/or crew, fuel cost, special requests for pick-up and drop-off or other special arrangements you may want to make with the owner.

Can I pay in installments for my Sailo Annapolis 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.

Responsible boating guidelines

However long you’re on a boat, it’s always a thrilling and fun experience. Here at Sailo, we like to make sure that the stunning beauty of the seas, lakes and rivers of our planet stay as pristine as possible. If you’re going to charter a yacht, from a few hours to week, try to follow these sustainable boating tips:
  • Take your rubbish home
  • Use eco-friendly sunblock
  • Avoid single use plastic
Much of the world’s plastic ends up in the sea, so reduce, reuse and recycle. Read more about responsible boating.