The waterfront at sunset, in Annapolis, Maryland.

Sample Annapolis Long Weekend Itineraries

Escape for a long weekend in the sailing capital of the United States: Annapolis, MD! A 4-day charter is the perfect amount of time to explore hidden gems along the Chesapeake Bay with friends and family.

Day 1

Set sail from Annapolis Harbor and head to the Thomas Point Lighthouse, a historic lighthouse built in 1875 and still an important navigation beacon for boaters. Once past the lighthouse, go southwest towards Herrington Harbor (~17 nm). We assume the boats have an average speed of 5 to 7 nm/hr, so this sail may take around 3 hours depending on wind speed. Once you reach Herring Bay, go to the southern end to Herrington Harbor South for a relaxing, resort experience complete with swimming pool, private beaches, and plenty of dining and shopping options. The marina’s restaurant, Ketch 22, is a great option for delicious, locally sourced food or poolside drinks. The marina is very popular, so it’s best to reserve a slip ahead of time. 

Day 2

After some rest and relaxation, begin the sail to Solomon’s Island. It is a long haul, but fairly open sailing (~33.6 nm). As the sail will take between 5 to 7 hours, eating lunch on board, and preferably while still under sail, is best. Solomons Island is a picturesque island town nestled in the joining of the Patuxent River and the Chesapeake Bay in Calvert County, Maryland. Once a renowned seafood packing house supported the local economy, but now tourism is its mainstay. Solomons remains a fishing village — alive with workboats and an active charter fishing fleet. It’s also a place to escape and to learn about the Bay’s past, present, and future. One particularly popular place for kids and adults alike is the Calvert Marine Museum! Solomons’ mile and a half long town offers numerous dining options, shopping, and special happenings. Be sure to visit The Tiki Bar — the first completely open-air bar in Southern Maryland. The annual opening of the Tiki Bar has become a firmly entrenched Southern Maryland tradition with crowds in excess of 10,000 people at the event. We recommend the house drink: the Mai-Tai. 

Day 3

In the morning, or the afternoon if you had a little too much fun the night before, head to Cambridge and get a slip for the night with Cambridge Yacht Basin or River Marsh Marina – Hyatt Regency (~40.7 nm). Settled in 1684, Cambridge is the county seat of Dorchester County, Maryland and one of the oldest towns in the state! You can still walk past relics of its history with elegant 19th century homes lining the shaded streets (many with markers describing their past) or learn about the town’s time as an economic and social center on the coast at the Richardson Museum and Ruark Boatworks which reopen in 2024. It was also an important stop on the Underground Railroad. You can learn about Harriet Tubman’s journey at many museums (Bucktown Store and Harriet Tubman Museum and Educational Center) as well as through historical markers scattered throughout the town.  

Day 4

Time to begin the beautiful sail back to Annapolis (~39.23 nm). On the way back, if you’ve made good time, you can anchor in Whitehall Bay or Mill Creek to enjoy a short swim and snacks before returning to our docks (~2.75 nm).