Sign up and
GET 20% OFF
Your first boat rental
Welcome to Sailo !
Your code is:
We currently offer 13 boat and yacht charters in MD, Annapolis. See other options available for rent in these nearby locations:
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.
Check out our extensive inventory and pick the sailboat 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 boat to go sailing in Maryland. To ask for more details or request special arrangements on your sailboat rental in Annapolis, MD, please send a direct message to the boat representative, or reach out to us on live chat.