Popular Chesapeake Bay Boating Destinations

By September 20, 2017May 29th, 2021Explore
Chesapeake Bay Boating Destinations

‘Hot Spots’ Around the Chesapeake Bay With Great Boating and Endless Fun

Fall boating is some of the best boating in the country, and especially in the Chesapeake Bay. With the season still going strong, but the crowds thinning out, it’s a great time to visit some of the most popular Chesapeake Bay marinas and destinations. So, if you’re still in the water, be sure to cap off your season with these amazing Chesapeake Bay boating destinations.

Annapolis, Maryland

Marinas in Annapolis, Maryland - Chesapeake Bay Boating Destinations

Annapolis, Maryland, USA State House and St. Mary’s Church viewed over Annapolis Harbor.

Annapolis is one of the best-known boating hubs in the world, and we agree! We don’t only love Annapolis because it’s our hometown, it’s undeniably a must-do getaway with so much to offer in addition to amazing boating. Great restaurants, shops and historical monuments are a water taxi or quick walk to your slip. There’s never a dull moment here!

Sears Marina
Horn Point Harbor
Port Williams Marina
Eastport Yacht Center
Watergate Pointe Marina
Annapolis City Marina
Annapolis Maryland Capital Yacht Club
Podickory Point Marina
Chesapeake Harbour Marina
Port Annapolis Marina

St. Michaels, Maryland

Marinas in St Michaels Maryland - Chesapeake Bay Boating Destinations

Strolling the streets in St Michaels, Maryland.

Oh, St Michaels – how we love you! This charming little town on the Bay is a weekend warrior’s paradise. St Michaels is a great family getaway spot. Be sure to  check out the Chesapeake Maritime Museum to learn about the area’s rich history – and then stroll the quaint streets for shopping. There’s no shortage of great bars, restaurants and bakeries here, so you are sure to find something for every palate.

St. Michaels Marina
St. Michaels Harbour Inn and Spa


Oxford, Maryland

Oxford, MD - Chesapeake Bay Boating Destinations

Oxford is a sailor’s paradise.

For serene sailor’s paradise, be sure to check out Oxford, Maryland. The small waterside community is one of the oldest towns in America and has a long history in maritime activities. The picturesque views of the Chesapeake here are sure to leave you breathless, and two new dock bars on either side of town will keep you entertained will into the fall!

Hinckley Yacht Services
Town Creek Marina by Campbell’s
Bachelor Point Marina by Campbell’s
Boatyard at Jacks Point by Campbell’s

Rock Hall, Maryland

Rock Hall Marinas - Chesapeake Bay Boating Destinations

It’s crab decks and sunsets in Rock Hall, Maryland.

Known as ‘the Pearl of the Chesapeake,’ Rock Hall is one of the Bays most beloved destinations. The waterfront town is filled with live music and other great sources of entertainment. Visitors can dine on local oysters, crabs and freshly caught rockfish. If adventure is what you’re searching for, you can go hunting, fishing, biking or hiking and learn about the Eastern Shore’s heritage during your visit.

Deckelman’s Long Cove Marina
The Sailing Emporium
Lankford Bay Marina
Swan Creek Marina 
Moonlight Bay Marina and Inn
Gratitude Marina
Osprey Point Marina
Rock Hall Landing

Baltimore, Maryland

Baltimore Marinas

The Baltimore Inner Harbor is full of fun activities for kids.

Baltimore is a must-visit boating destination while cruising the Chesapeake. Charm City is filled with world-renowned restaurants and also hidden gems in need of discovery. Great shopping, art museums, the aquarium, music, sports and so much more are awaiting you this summer. OH- and go O’s!

Harbor East Marina
Tidewater Yacht Service
Baltimore Yacht Basin

Washington D.C.

Washington D.C. Marinas - Chesapeake Bay Boating Destinations

The Yards is Washington D.C.’s hottest new neighborhood.

Not many may think to boat to the Nation’s Capital, but we promise it’s worth it! The city is filled with so much to do, so you may need more than one weekend to fit it all in. D.C., of course, is home to much of our nation’s history, but it is also filled with so many activities every member of the family can enjoy. Tour the museums, stroll through the Mall or catch a National’s ball game while you’re in town –  it is still the season!

The Yards Marina

Share this Share on Facebook
Tweet about this on Twitter

Author Alexa

Born and raised in Annapolis, Alexa travels far and often with Snag-A-Slip for Marketing and other cool ventures. She loves Mexican food, with an emphasis on Queso, and being somewhere on a beach. Commonly known as the crazy cat lady among friends, she will most likely end up with her own TV show along the lines of “58 Cats and Counting.”

More posts by Alexa

Join the discussion 2 Comments

  • Kathleen says:

    Great post! I love visiting St. Michael’s, but I will definitely have to try out some of these other destinations!

  • Vivit-Tours says:

    Remember to stop by Tent C-7 and say hi to your friends at Herrington Harbour. Rent a boat slip or schedule services at our display.