Come Explore the Chesapeake Bay with flotilla cruising by Let’s Go Cruising.
Our First Flotilla Cruise will take place 4th of July weekend.
The sailing flotilla will leave Annapolis Saturday June 29th and return back to Annapolis on Friday evening July 4th before the fireworks. Guests are then welcome to stay on their boats for the rest of the weekend in Annapolis.
Flotilla Sailing is popular because of the following:
- Sailing with groups is fun!
- Meet new and exciting families and groups
- Explore new territory with confidence
- Sail some of the nicest boats on the bay
- Sailing itinerary, slips and planning is done for you, just show up with your family and friends.
Trip Itinerary:
Day 1:
North Wind: Sail to Herrington Harbour
Herrington Harbour South and its sister marina Herrington Harbour North are both located on the western shore of the Chesapeake Bay and offer a plethora of overnight slips, several restaurants and lounges, and a wide range of amenities.
Note: due to Herrington Harbour South’s popularity, it’s best to reserve a slip in advance 1-800-213-9438
Mango’s Bar & Grill: 410-257-0095 Beautiful waterfront dining in a classy but casual atmosphere. Serving a wide selection of steaks and seafood by Chef de Cuisine Mark Brewer in a quiet non-smoking atmosphere.
South Wind (northern route): Sail to Rock Hall
Rock Hall is a quaint fishing town that sits picturesquely on the eastern shore. As a top cruising destination, it offers a bevy of marinas, interesting shops, a variety of restaurants and a burgeoning artist colony.
Waterman’s Crab House: 410-639-2261 Overlooking Rock Hall Harbor and the Chesapeake Bay, Waterman's Crab House Restaurant and Dock Bar is well-known for its award-winning steamed crabs, jumbo lump crab cakes and barbecued baby-back ribs.
Swan Creek has long been a favorite destination for cruisers because of its rural beauty. Located directly north of Rock Hall harbor, this well-protected creek offers a wonderful place to anchor.
Day 2:
Sail to Oxford
Oxford is located on the Eastern Shore and bordered on three sides by the Tred Avon River and Town Creek. Oxford’s allure is its quiet small townishness where townspeople make visitors feel like old friends. Oxford works hard to maintain its serene, boater-friendly atmosphere and boasts a small, easily walkable downtown with enough shops, restaurants and attractions to satisfy most visitors.
(northern route) Sail to Baltimore Harbor
The harbor itself is actually the end of the Northwest Branch of the Patapsco River and includes any water west of a line drawn between the National Aquarium in Baltimore and the Rusty Scupper Restaurant. You'll find a variety of things to see and do at Inner Harbor, all within walking distance! Baltimore's Inner Harbor is one of the most visited features of the city. Distinct in function and form, Baltimoreans and visitors alike enjoy Baltimore's Inner Harbor and the surrounding neighborhoods that offer a variety of fine dining, cultural experiences and exciting nightlife.
Day 3:
Sail to Cambridge (re-supply)
Cambridge lies about 13 miles up-river from the mouth of the Choptank River. Cambridge is the county seat of Dorchester County, Maryland. Cambridge was settled in 1684 and is one of the oldest towns in Maryland. The elegant 19th century homes lining Cambridge’s shaded streets hail from a time when the town was an economic and social center—a heritage also proudly preserved in its maritime museums. Town attractions include several museums (Brannock Maritime Museum, Richardson Maritime Museum, and Merideth House), the Skipjack Nathan, Sailwinds Park, and the Choptank River Fishing Pier.
Cambridge Creek offers ample anchoring room for those looking for a protected spot to relax.
(northern route) Sail to Chester River
The second-longest river on the Eastern Shore, the Chester River is bordered along much of its shoreline by beautiful, rolling countryside and lovely estates. Nearly three miles across at its widest point, the Chester gradually narrows to about a quarter mile at Chestertown, with good navigating depths in its well-bouyed channel. Above Eastern Neck Island, a the Chester fans out in four generous, cruisable branches: Gray’s Inn Creek, Langford Creek, the main extension of the Chester that leads to Chestertown and the Corsica River. All are inviting.
Day 4:
Sail to St. Leonard’s Creek, up the Patuxent River (Anchor or dock at Vera’s)
St. Leonard Creek, about seven miles upriver from Solomons, has been said to be the most beautiful on the Patuxent. This five-mile-long creek is on the river’s northern shore. The shoreline is a mix of marshes, rolling hills and wooded bluffs. At the mouth of Johns Creek lies Vera’s White Sands Beach Club. This fanciful place looks like a Polynesian island misplaced on the Chesapeake. Decorated with South Sea treasures culled from international voyages. Vera’s is a wonderful marina that welcomes all cruisers!
(northern route) Sail around Kent Island to the Kent Narrows (boats with masts under 64 feet can go through the Narrows)
Marinas at the Narrows range from simple to elaborate, and local yards do a brisk business in maintaining and restoring boats. Excellent restaurants in all price categories, a wonderful crabhouse, a dive shop and a Visitors Center are with easy walking distance. The nightlife is lively and includes bikini contests, dancing and live bands with open-air docks, karaoke music and water oriented events.
Day 5:
Sail to Solomons Yachting Center in Solomons Island
Solomons Island is 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 work-boats and an active charter fishing fleet—but it’s also a place to escape and to learn about the Bay’s past, present and future. Solomon’s mile and a half long town offers numerous dining options, shopping and special happenings.
The Tiki Bar:(410) 326-4075 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. The house drink is the Mai-Tai, the potency of which has been know to cause people to react in a variety of ways.
(northern route) sail to St. Michaels
Saint Michaels, Maryland is a quaint waterfront village on the Eastern Shore, situated on a picturesque peninsula between Tilghman Island, Easton and Oxford. St. Michaels became an important shipbuilding center especially noted for its “Baltimore Clippers,” the fastest sailing vessels of their time. Today the town is better known as a popular yachting center and offers numerous things to do and see.
Chesapeake Maritime Museum: On permanent display at the campus is the nation's most complete collection of Chesapeake Bay artifacts, visual arts, and indigenous water craft. Interpretive exhibitions and public programs cover the range of Chesapeake Bay maritime history and culture including Native-American life, Anglo-American settlement, seventeenth- and eighteenth-century trans-Atlantic trade, naval history, the Bay's unique watercraft and boat building traditions, navigation, waterfowling, boating, seafood harvesting, and recreation.
Day 6:
Sail to St. Michaels (anchor or dock)
(northern route) sail into the Wye River on the Eastern Shore
The river—divided into three branches—embraces the Wye Island along 21 miles of shoreline. You won’t find supplies or public facilities anywhere on Wye Island but secluded anchorages and a rich historical heritage are among the charms of the Wye River. The western shore of the Wye River is well developed, but its eastern shore offer more secluded anchorages. On the Wye East, big old houses, many dating back to colonial days, stand on the banks, greeting cruisers at every turn.
Day 7:
Sail back to Annapolis
Expect a sail time between five and seven hours
Choose any of our boats available for charter that works best for your family; see a list here. (based on availability).
Flotilla includes itinerary planning, provisioning (if desired), Let’s Go Cruising Reciprocity Card, slip reservations, and more!
We have two routes planned for the flotilla trip. The exact trip will be picked based on popularity of one route, weather conditions, and dock availability. Book your flotilla trip early and let us know which route is most interesting to you!
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Flotilla Cruises