Herrington Harbour: Begin sailing at Herrington Harbour, just south of Annapolis. This protected harbour is a great place to start your sailing adventure. Herrington Harbour offers two marinas, Herrington South and Herrington North, as well as a shipyard and Yacht Club. There are also plenty of restaurants and shops in the area, so you can find anything you need for your trip.

Oxford: After a day of sailing, head to Oxford for a night on the town. This quaint little town is full of history and charm. Stroll down Main Street and explore the shops and restaurants. Don't forget to stop by the Oxford-Bellevue Ferry for a ride across the Tred Avon River.

Cambridge: After a day in Oxford, head to Cambridge for some more sailing. Cambridge is located on the Eastern Shore of Maryland and is a popular spot for sailing and fishing. There are several marinas in the area, so you can easily find a place to dock for the night. Cambridge is very well-known as a blue crabbing destination, so make sure to try some of the local seafood while you're in town!

Leonard Creek: Let us sail to Leonard Creek, a beautiful and protected anchorage on the Western Shore of Maryland. This is a great spot for swimming, fishing and relaxing on the beach. One of the highlights of Leonard Creek is the view of the Baltimore skyline. There are also several restaurants and shops in the area, so you can find anything you need.

Solomons Island: After a day at Leonard Creek, head to Solomons Island for some more sailing, one of the most popular destinations for sails. Solomons Island is a beautiful and historic town located on the Chesapeake Bay. Solomons Island has a lot to offer, from restaurants and shops to museums and parks.

Waterfront Village, St. Michael's: St. Michael's is a charming and historic town located on the Eastern Shore of Maryland. This town is known for its amazing seafood, so make sure to try some of the local fares while you're in town. There are also several shops and restaurants, as well as a waterfront park and marina.

Travel back! You can enjoy the beautiful view way back to the base because it takes 5-7 hours. You’ll want to have an extra battery for your camera or phone to get some pictures while on the picturesque sail back. Enjoy your last trip and make it worthwhile.