tropical yachts Home About us CARIBBEAN / AMERICAS: Antigua Bahamas Baja Mexico Belize Grenada Guadeloupe Honduras Martinique Ft Lauderdale - Key West Panama Puerto Rico St. Lucia St. Martin St. Vincent Virgin Islands - British Virgin Islands - US ASIA / INDIAN OCEAN: Seychelles Thailand MEDITERRANEAN: Croatia France Greece Italy Montenegro Spain Turkey SOUTH PACIFIC: Australia New Caledonia Tahiti ITINERARIES: Caribbean US & Mexico Indian Ocean & Asia Mediterranean South Pacific MENU ☰

Before embarking, seeing the sights of Annapolis is a must. Stroll down to “Ego Alley” at Annapolis Harbor, and then grab a sandwich at Chick & Ruth’s Delly on Main Street. Visit the Maryland State House – the oldest state capitol in continuous legislative use topped by the largest wooden dome in the nation. The Chesapeake Bay takes its name from a Powhatan word, “Chesepioc,” or “Great Shellfish Bay.” The French founded Annapolis as a settlement called Port Royal in 1605, and Captain John Smith became the first European to explore and thoroughly map the Chesapeake Bay in 1609, writing in his journal that “heaven and earth have never agreed better to frame a place for man’s habitation.” With so many delightful creeks, coves, rivers, towns and villages to visit, Annapolis makes for a dream sailing vacation.

Day 1 – Solomon’s Island

Solomon’s Island is an island town between the Patuxent River and the Chesapeake Bay. Solomon’s is a fishing village, alive with work-boats and an active fishing fleet, but also offers numerous dining options, shopping and special events.

Day 2 – Deltaville

Cruise to Deltaville and visit Dozier’s Regatta Point Yachting Center with floating docks, a southern-style clubhouse, and a courtesy car. Dinghy to Railway Restaurant across the creek from the marina, or drive into town (about 3 miles) to sample other local joints.

Day 3/4 – Ocean Marine Yacht Center

Ocean Marine Yacht Center is just 0.5 miles south of mile marker zero on the Intracoastal Waterway in Portsmouth, VA. This complex features a modern marina. Getting hungry? There are plenty of great restaurants minutes away from the marina.

Day 5 – Bay Creek

Bay Creek has the perfect blend of elegant homes, great dining, a word-class golf resort, plus a state-of-the-art beach club and fitness center – coastal living at its best. Bay Creek is a true escape, and it neighbors historic Cape Charles on the Chesapeake Bay, minutes away from Norfolk and Virginia Beach.

Day 6 – Chesapeake Bay Marina

Chesapeake Bay Marina at the Tides Inn Resort provides the beauty and tranquility of a secluded harbor and the facilities of a world-class destination resort. Located on Carters Creek, 11 miles from Windmill Point, the marina accommodates up to 24 vessels of various sizes.

Day 7 – The channel to Onancock Wharf

The channel to Onancock Wharf twists and turns, but never fear – it’s plenty deep and easy to follow. There’s no grocery in walking distance, but special arrangements can be made with the harbormaster for transportation. They can provide a list of restaurants in town, where you’ll also find plenty of shops and art galleries.

Day 8 – Somers Cove Marina

Somers Cove Marina in Crisfield offers a swimming pool, picnic tables, barbecues and golf packages. If you’d like to pick up provisions, there’s a grocery store about a mile away. Excursions at Janes Island State Park and boat trips to Smith Island and Tangier Island are tried-and-true favorites.

Day 9 – Back to Solomon’s Island

It’s back to Solomon’s Island, where Zahniser’s Yachting Center offers a full service resort marina and boatyard. Centrally located to town, it also features a swimming pool, restaurant, courtesy bicycles, a grocery shuttle and more.

Day 10 – Oxford

Sail to Oxford, located on the eastern shore and bordered on three sides by the Tred Avon River and Town Creek. The community makes visitors feel like old friends and works hard to maintain a serene, boater-friendly atmosphere. It boasts a walkable downtown with plenty of shops, restaurants, and attractions.

Day 11 – Cambridge

Cambridge, with its elegant 19th-century homes, lies about 13 miles from the mouth of the Choptank River. It was settled in 1684, and is one of the oldest towns in Maryland. Highlights include the Richardson Maritime Museum, Meredith House, the Skipjack Nathan, Sailwinds Park, and the Choptank River Fishing Pier. Cambridge Creek offers ample anchorage.

Day 12 – Harringtor Harbour

Herrington Harbour South and Herrington Harbour North on the western shore of the Chesapeake Bay offer overnight slips, several restaurants and lounges, and a wide range of amenities. It’s best to make reservations. We recommend Mango’s Bar & Grill for beautiful waterfront dining in a classy but laid-back atmosphere.

Day 13 – St Michael

Another quaint waterfront village, St. Michael’s sits on a bucolic peninsula. It became an important shipbuilding center especially noted for its Baltimore Clippers – the fastest sailing vessels of their time. Today, it is a popular yachting center, and the site of the Chesapeake Bay Maritime Museum.

Day 14– Back to base

It’ll take about 5-7 hours to sail back to base – the Chesapeake will always welcome you back!


Or click-to-call, toll free: