Chesapeake Bay (Annapolis MD) Catamaran Sailing Vacations: Bareboat & Yachts with Crew
Catamaran Sailing Vacations in Chesapeake Bay
The East Coast of the United States boasts some extraordinary bays and inlets that are ideal for navigating with your bareboat yacht charter. Chesapeake Bay is one of the coasts best-loved sailing destinations with its rich history and picturesque scenery.


The Catamaran company features catamaran sailing vacations in Chesapeake Bay with popular stops at anchorages like Annapolis. The Catamaran company's yachts with crew boast comforts and amenities that will complement your Chesapeake Bay yacht charter sailing vacation.

Catamaran sailing vacations Chesapeake Bay

The Sailing Capital of the World: Chesapeake Bay

Catamaran sailing vacations in Chesapeake Bay will acquaint you with this area that has long been dubbed America's sailing capital. The region's love for sailing is legendary, and you'll be able to experience this love first hand as you board your Chesapeake Bay yacht charter. The Catamaran company features Chesapeake Bay by the cabin at a fraction of the cost of other yacht charters; you can even design your own sailing itinerary, which makes for a perfectly customized catamaran sailing vacation in Chesapeake Bay. Consider including the following stops as you create your travel plan.

Catamaran sailing vacations Annapolis

Annapolis, Maryland

Annapolis is a sailing hub as well as an historic Maryland city boasting a myriad of attractions. Dock your bareboat yacht charter here to enjoy a lunch of steamed crabs before visiting landmarks like the U.S. Naval Academy, the Annapolis Maritime Museum, or the Thomas Point Shoal Lighthouse. Famous for its historic architecture and quaint fishing villages, Annapolis is a slice of America you definitely can't miss on your Chesapeake Bay sailing vacation.

Catamaran sailing vacations south river Maryland

Blackwater National Wildlife Refuge

Blackwater National Wildlife Refuge is a celebrated waterfowl sanctuary. Enjoy the pristine scenery as your yacht charter cruises through the tea-colored waters of the Blackwater River. With any luck, you might even catch as sight of a bald eagle as you dangle your feet over the side of your catamaran.

Catamaran sailing vacations Maryland

The James River and Richmond, Virginia

The James River features largely in early American History. Early explorers sailed up this river to found the city of Richmond. The city is a great anchorage for bareboat yacht charters with its historic and cultural attractions like the Virginia Museum of Fine Arts, the Lee Monument, and the Edgar Allan Poe Museum. It also boasts exciting nightlife venues and plenty of luxurious boutique hotels and bed and breakfasts.

Smith Island

The historic community of Smith Island makes for an enchanting stop on your Chesapeake Bay sailing vacation. Captain John Smith first mapped the island in 1608. Many visitors enjoy exploring its famed marshlands at the Martin National Wildlife Refuge. Don't leave the island without picking up a few slices of its famous Smith Island cake to enjoy back on board your yacht charter!

Deal Island, Maryland

Time seems to have forgotten. With its oyster boats and blue skies, this is a great site to add to your yacht charter itinerary. Witness some of the last skipjacks (old sailing vessels) on the water at Wenona Harbor.

Cape Charles, Virginia

With its myriad of Victorian architecture, Cape Charles has retains its historic aura. Upon docking your bareboat yacht charter here, you'll want to enjoy a meal on the waterfront or visit sites like Kiptopeke State Park or explore the Eastern Shore National Wildlife Refuge.

Chesapeake Beach

With its celebrated water park and splendid piers and marinas, Chesapeake Beach is a favorite stop for many sailing excursions on the bay. Explore its scenic beach or check out the renowned Chesapeake Beach Railway Museum. There's something for everyone in this coastal town.

Of course, Chesapeake Bay offers throngs of other great sites to visit too. You might want to include visits to Norfolk, Cambridge, or even Baltimore on your Chesapeake Bay Sailing Vacation. The marvelous thing about this part of the world is that it offers great sailing opportunities, historical cultural attractions, scenic wonders, and modern attractions too. With both urban and rural charms, Chesapeake Bay will delight you in so many ways.
Catamaran Sailing Vacations in Chesapeake Bay: Sample Itinerary

  • Day 1 and 2: Explore the James River and the city of Richmond
  • Day 3: Tour the Victorians of Cape Charles
  • Day 4: Visit Smith Island
  • Day 5: Explore Deal Island
  • Day 6: Tour Chesapeake Beach
  • Day 7: Visit the Blackwater National Wildlife Refuge
  • Day 8 and 9: Explore historic Annapolis