The Top Charter Yachts in Annapolis and Chesapeake Bay

Visit the gorgeous buildings in Annapolis and Chesapeake Bay

Boatbookings curated list of the best charter yachts to Explore Annapolis and the Chesapeake Bay

The Chesapeake Bay is an enormous inland waterway in the Mid-Atlantic States of Virginia and Maryland. It is a sailor’s paradise with over 5,000 miles of shoreline to explore.

You will enjoy delicious seafood (especially the famous Bay crabs!), gorgeous sandy beaches, inland rivers, and historic towns like Annapolis, home of the US Naval Academy, and the vibrant port city of Baltimore. In the Southern part of the Bay, you can see the famous wild horses on the islands of Chincoteague and Assateague.

Sailing northward into Maryland, you can stop in Soloman’s Island, visit St. Mary’s City, and sail up the Patuxent and St. Mary’s Rivers. You won’t want to miss Smith and Tangiers islands, written up in National Geographic for maintaining their traditional lifestyles. In the northern part of the Bay, you can stop in Baltimore, Annapolis, Georgetown, and Chestertown. The sailing around the Chesapeake Bay is all “line of sight” with the breeziest times of the year in the spring and the fall.

In the middle of the summer, the weather can be very hot and humid and less breezy (or even still) with afternoon thunderstorms that break the heat. The waters of the Bay are brackish (a mixture of salt and fresh) varying from very salty near the mouth of the Bay to almost fresh at the northern end. We have a fantastic selection of the best bareboat charter yachts from Annapolis or contact us if you would like us to find the right bareboat for you. 

Annapolis/Chesapeake Catamarans. If you're looking for a comfortable and relaxing catamaran, we have a great selection of Annapolis Catamarans here.

If you love sailing, you owe yourself the thrill of sailing up to the Naval Academy, as well as the experience of sailing to some of the prettiest areas on America's storied East Coast. Please see below our curated list of the best charter yachts out of Annapolis and please let us know which one best meets your needs for a Chesapeake Bay charter!

See our Chesapeake sailing itinerary

CYNDERELLA
    Hargrave 101 - 4 Cabins - St Thomas - Virgin Islands - Bahamas - Chesapeake - Annapolis
  • Hargrave 101 Luxury Crewed Motor Yacht
  • Length: 30.78 m
  • Year: 2010 (2018 Refit)
  • Cabins: 4
  • Berths: 8
  • From $44000 to $50600 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 30.78 m (104' 6")
  • Year: 2010 (2018 Refit)
From $44000 to $50600
per week

BOATBOOKINGS SAYS:
"CYNDERELLA has two master cabins, well suited to two couples or families looking to explore New England in the summer in pure luxury."

Fountaine Pajot Saona 47
    3 cabins (3 double) - 2019 - Annapolis
  • 3 cabins (3 double) Bareboat Catamaran
  • Length: 14.02 m
  • Year: 2019
  • Cabins: 3
  • Berths: 8
  • From $9100 per week
Details Enquire
  • Berths: 8
  • Cabins: 3
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 14.02 m (47' 10")
  • Year: 2019
From $9100
per week

BOATBOOKINGS SAYS:
"This brand-new owners version Saona 47 with great amenities is an ideal boat for exploring the Chesapeake Bay!"

Hondo
    Fountaine Pajot MY 44 - 3 Cabins - 2019 - Annapolis
  • Fountaine Pajot MY 44 Crewed Power Catamaran
  • Length: 13.41 m
  • Year: 2019
  • Cabins: 3
  • Berths: 6
  • From $12950 to $12950 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 13.41 m (45' 9")
  • Year: 2019
From $12950 to $12950
per week

BOATBOOKINGS SAYS:
"A luxurious catamaran motor yacht perfect for friends and family cruising the Chesapeake Bay!"

Fountaine Pajot Lucia 40
    3 Cabins - 2019 - Annapolis
  • 3 Cabins Bareboat Catamaran
  • Length: 11.7 m
  • Year: 2019
  • Cabins: 3
  • Berths: 6
  • From $5387 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11.7 m (39' 6")
  • Year: 2019
From $5387
per week

BOATBOOKINGS SAYS:
"Hop aboard for an amazing experience sailing the Chesapeake Bay in a 2019 Fountaine Pajot Lucia 40!"

CHRISTINE
    Jeanneau Power NC 33 - Annapolis
  • Jeanneau Power NC 33 Bareboat Motor Yacht
  • Length: 10.006 m
  • Year: 2020
  • Cabins: 2
  • Berths: 4
  • From $4675 per week
Details Enquire
  • Berths: 4
  • Cabins: 2
  • Crew: Bareboat
  • Type: Motor
  • Length: 10.006 m (34' 4")
  • Year: 2020
From $4675
per week

BOATBOOKINGS SAYS:
"Explore the Chesapeake waters in a brand new 2020 Jeanneau Power NC 33!"

Jeanneau Sun Odyssey 41DS
    2 Cabins - 2016 - Annapolis - Chesapeake Bay
  • 2 Cabins Bareboat Sailing Yacht
  • Length: 12.5 m
  • Year: 2016
  • Cabins: 2
  • Berths: 4
  • From $3738 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 4
  • Cabins: 2
  • Crew: Bareboat
  • Type: Sail
  • Length: 12.5 m (42' 2")
  • Year: 2016
VIEW 1 REVIEW
From $3738
per week

BOATBOOKINGS SAYS:
"Perfect for two couples to explore Annapolis and the Chesapeake Bay in a sporty yacht that sails beautifully"

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