Chesapeake Bay Yacht Charter Guide

So convenient for North American residents and a fascinating place to visit from all over the world, Chesapeake Bay offers lovely summertime conditions for keen sailors and vacationing families. And all around this extensive sunken river valley are exciting places to explore, from secluded bays to modern cities with just about everything this part of USA has to offer.

Living in North America and looking for a bareboat charter destination close to home? Seeking to experience the natural beauty and the modern lifestyle of the USA? Wanting to vacation under sail but not bothered about snorkelling in clear blue tropical waters? Then take a look at Chesapeake Bay as a destination. 

Top places to visit on a Chesapeake Bay sailboat vacation

Chesapeake Bay is a vast waterway, 200 miles long draining  64,000 square miles in six states via the more than 150 rivers that feed it. In the upper section of Chesapeake Bay you are in Maryland. The state's big city is Baltimore, while the capital is historic Annapolis, your likely starting point on a Chesapeake Bay sailing vacation. Annapolis is a lovely city that lies at the heart of the region's, some would say the nation's, sailing culture. It is also home of the National Sailing Hall of Fame and US Naval Academy - try to spare the time for a tour.

The Chesapeake's Upper Bay

Sailing out of Annapolis, turn the corner and you are immediately far from the bustle of the city. It doesn't take long to get a sense of the geography here – inlet after countless inlet formed as the sea level rose after the last ice age, beyond which wooded lowlands share the landscape with cultivated farm properties and a generous sprinkling of picturesque settlements.

Head south and a huge expanse of tidewater opens up. Bear northeast and sail under the monstrous dual-span Chesapeake Bay Bridge towards Baltimore, or on the eastern shore Rock Hall and the Chester River.

Rock Hall is a pleasant fishing village that offers an overnighting choice on a marina or at anchor in nearby Swan Creek. Just 15 nautical miles from base, getting to Rock Hall is an easy first day's sail. It's also a convenience stepping-off point for an upriver journey in either direction - to Baltimore's Inner Harbor or Chestertown, both with appeal in their own different ways. If you want to spend longer in the Bay's upper reaches, sail up to the Sassafras River and you can easily fill a week-long itinerary without going south of Annapolis. 

But to see more of this huge Bay with its 11,600 miles of shoreline, you need to head back under the big bridge. Immediately south of  Kent Island is Eastern Bay that brings you into the Wye River area. Here St Michaels is a popular stopover, a waterfront village with excellent marina facilities, shops and restaurants catering for the nautical crowd. St Michaels is also home to the Chesapeake Bay Maritime Museum. A short sail further south are Tilghman Island and Oxford, at the mouth of the Choptank River, setting for James A Michener's great novel Chesapeake

This may well be all you have time to see on your Chesapeake Bay sailing vacation. However if you have longer, continue on south, exploring the eastern shore around Crisfield or crossing to Solomons Island if needing supplies or a marina berth.

The Middle Bay and South

Sail by the mouth of the Potomac River and across the state line into Virginia. Call at Smith or Tangier Island for an appreciation of the Chesapeake way of life and the wonderful natural environment in these parts. Most of the residents of Tangier Island make their living from crabbing, one of the Bay's big industries.

As you proceed south, you may wish to stop over at Deltaville for a berth and supplies, before heading across to the up-market coastal resort are of Cape Charles, with all its amenities for young and old. If time is still on your side, you can go as far as Portsmouth, rent a marina and take off by car to explore the area of Newport News, Norfolk and Virginia Beach.

As you sail back to Annapolis, there are numerous top spots you missed on your way out – Onancock,St Leonard's Creek on the Patuxent, and all those other inviting bays and rivers you observed on the way south. So leave plenty of time to stopover and make your return a leisurely sail.

Around these parts there is many a yachtsperson who will talk about sailing on the Chesapeake. How they've been doing it all their lives and still not been into half the bays and rivers. Head out and find your own special place, perhaps it'll be one that even the locals haven't  come across yet.

Chesapeake Bay Sailing Season and Climate

USA residents will be familiar with the seasonal variations in this part of North America. For international visitors be aware of the short transitions between summer and winter. That notwithstanding, the Chesapeake Bay sailing season runs from late April to early November. he most popular time for charter is mid-May to mid-October, when the winds can generally be relied on to range between 7 and 20 knots. 

In Annapolis the temperatures range from 68° F (20° C) in April to 89° (32°) in July (with high humidity), then down to a cool 60° (15°) by November. There is little monthly variance in rainfall, so expect the posibility of rain showers during any month. 

Chesapeake Bay is surprisingly shallow over much of its area, with an average depth of only 21 feet. The tidal range varies between approximately one and two feet. With all the rivers flowing into it, about half of the bay's overal volume of water is fresh (considerable more so in the upper bay).. 

Enquire Now - Click Here   or view our bareboats and crewed yachts.

The Sail Connections Guarantee

One contact - every option - advice you can trust.

  • Matching any competitive offer 
  • Sourcing boats with discounts available
  • Personalising our proposal just for you
  • Qualifying the operator as well as the boat
  • Advising without bias based on 25+ years of experience

We will match any discount website offer on charter boat price, and still provide our customary high level of service. We do more than just book yachts!

Read our free charter guide for all you need to know about planning your sailing holiday.

Yachts in Chesapeake Bay

Lagoon 52
Lagoon 52 - 52' (15.8m) 8 Guests
Lagoon 450
Lagoon 450 - 45' (13.7m) 8 Guests
Bali 4.0
Bali 4.0 - 40' (12.2m) 8 Guests
Lipari 41
Lipari 41 - 40' (12.2m) 8 Guests
Sun Odyssey 409
Sun Odyssey 409 - 40' (12.2m) 6 Guests

Enquire about Chesapeake Bay

Receive a personalized proposal with boat, cost and extra options as applicable.
required fields