The largest and at most famous estuary in the United States, Chesapeake Bay (or “the Chesapeake”) is truly an extraordinary place. Stretching across six states and the District of Columbia, the Bay watershed never ceases to amaze with its rich history, vital economic importance, and astounding beauty. And the wonders of sailing the Chesapeake Bay could fill a lifetime.

The history, natural beauty and wonderful ecosystem combine to present visitors with endless possibilities, and there’s a new adventure around every corner. However if you only have a limited amount of time to explore, it’s best to get an understanding of what there is on offer before your trip.

The following are a couple of tips for planning your sailing adventure on the bay.

How to Stay (Find Airbnbs & Hotels)

Here is an interactive map of hotels and airbnbs you can book in the Chesapeake area.

Be Realistic

If you try to see everything, it’s likely that you’ll miss a lot. Considering the scale of Chesapeake Bay, you will have to be realistic. It is not somewhere to speed around trying to encompass it all in one visit.

Do it right, and you will enjoy the experience so much more and thereafter, who knows, you may return to continue the adventure.

Remember the Definition of Cruising

To sail about for pleasure in an unhurried or unconcerned fashion, to move leisurely about an area. Let the Bay dictate your pace, stimulate your interest, suggest stops and places to see.

Be flexible in your approach, do plan, but don’t think that the plans cannot be altered once you arrive.

Best Time

Summers are hot and humid, whereas Spring and Autumn are long, and much more comfortable. Even being on the Bay cannot always provide sufficient respite from the still humidity of the summer months, so be warned.

How to Travel

Cruising can take two forms. You can charter a vessel either bareboat or crewed.

Bareboat – You take charge of the boat yourself and provide the crew, and if you are a competent sailor, then this may heighten the excitement, but it is also less of a vacation and more of an adventure. Don’t forget also the issue of stopovers, are you mooring, docking, or anchoring the boat!

Crewed – the cruiser is manned with a captain and crew, and you can sit back and enjoy the trip and all the sights without having to worry about any of the mundane logistics and duties.

Itinerary Suggestions

There is simply so much, in a sense too much, to see, so it may be a good starting point to pick a more defined area of the Bay and concentrate on that.

Though you’re looking for variety then sailing the Chesapeake area is a natural cruising route for discovery, made for simply hopscotching from one shore to the next, with things to see, visit, experience, taste and indulge all of your senses at once.

Commonly visited areas include Havre de Grace via the Chesapeake & Delaware Canal built in 1829. Many people choose to visit the inner harbour of Baltimore travelling along the Sassafras River with its steep banks and from there to Rock Hall, a sailors town famed for its seafood; travel from St Michaels to Annapolis, known as the sailing capital of the World; onward to Oxford on the Trent Avon, a sleepy, quaint and picturesque town, or finally on to Washington DC should the mood take you.

You will find yourself with so many options and avenues of adventure, so many that a sense of spontaneity should be a prerequisite. Whilst you slowly absorb the sights, sounds and scenery as you are cruising, you can smile to yourself and be proud that you chose to sail the Chesapeake Bay.

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Dry Bag – 20L Floating Waterproof Bag

The Complete Sailing Manual, Third Edition

Hat Leash Hat Clip – Don’t Lose Your Hat!

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Megan is an Australian Journalist and award-winning travel writer who has been blogging since 2007. Her husband Mike is the American naturalist and wildlife photographer behind Waking Up Wild; a website dedicated to opening your eyes to the wild & natural world.

Committed to bringing you the best in adventure travel from all around the globe, there is no mountain too high, and no fete too extreme! They haven’t been everywhere, but it’s on their list.

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