Sunset Sailing in Annapolis | Annapolis Sailing Adventures

Annapolis, Maryland, known as the Sailing Capital of the United States, offers a unique waterfront playground that is best experienced aboard a sailboat. Annapolis Sailing Adventures, LLC provides private charters on their elegant Beneteau 473 sloop, inviting visitors to explore the iconic Chesapeake Bay from an intimate and knowledgeable crew-led perspective. The Chesapeake Bay is the largest estuary in the U.S., defined by its expansive waters, rich marine life, and historic coastal landmarks. Sailing here offers calm yet refreshing conditions, making it ideal for sailors of all skill levels.

What sets Annapolis Sailing Adventures apart is the experienced and personable team—Rick, Annette, and Garrett—who transform a simple sail into a memorable journey. Guests have the opportunity not only to enjoy the spectacular views and breezes but actively participate, whether it's learning the ropes or steering the boat. This hands-on approach deepens appreciation for sailing, allowing visitors to connect with Annapolis’s maritime heritage firsthand.

Whether celebrating special occasions, participating in Annapolis’s famed Wednesday Night Races, or simply enjoying the serenity of a sunset sail, each trip is tailored for comfort and engagement. The S/V Celerity's spacious deck and beautiful design provide perfect vantage points for watching the sun dip below the horizon or spotting local wildlife like osprey and herons.

Annapolis Sailing Adventures plays a vital role in Annapolis’s outdoor recreation scene by offering a unique combination of relaxation, education, and excitement on the water. This business enhances the outdoor experience with its commitment to safety, sustainability, and personalized service, helping visitors truly appreciate the natural beauty and maritime culture of Maryland’s capital city. For anyone looking to escape onto the water and embrace a classic American sailing experience, this is the premier destination.