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Explore Annapolis, MD with Sailo - an yachting playground waiting 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 Annapolis, MD private yacht charters

Want to rent a boat in Annapolis, MD? You’ll find 20 boats waiting for you to take them on an adventure here on Sailo. Choose from our 6 elegant and classic sailboats. A catamaran is also a great choice, with numerous available in Annapolis. Fans of luxury motor yachts will be spoiled for choice with our 4 motor yacht charters. Maryland is an excellent place to enjoy a boat party, so discover our 10 larger party boats for 13+ guests in Annapolis and see for yourself.

How to choose your weekly charter for a memorable sailing experience

If you are interested in a weekly sailing vacation, after you filtered for weekly trip duration, you can search through 20 boats in Annapolis, MD by price ranging between $1 and $15000, type of boat, such as motorboats, sailboats monohulls or catamarans, and number of guests. Once you find the perfect boat, you can click on 'Extras' and choose additional options and services to add to your yacht vacation. Some of the services offered can be provisioning, jet skis or a cook.

What is Sailo FREE 24 hours Reservation?

Not sure if the boat you like suits your vacation plans? You can place a free reservation for 24 hrs, no credit card required, for most of our weekly boat rentals, allowing you more time to discuss details with the boat owner, talk to your family or friends or customize your budget to suit your needs. Once you have placed the reservation, boat is blocked for 24 hours. During the 24 hours of your reservation, you can book the boat, cancel the reservation or ask for a one-time extension of 24 hours by contacting us at reserve@sailo.com. If you do nothing, your reservation will automatically expire and the boat will become available for other renters. Read more about free reservations.

Be a responsible boater

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.