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

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 $10725 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 13.41 m (45' 9")
  • Year: 2019
From $10725
per week

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

Fountaine Pajot Lucia 40
    4 Cabins - 2020 - Annapolis
  • 4 Cabins Bareboat Catamaran
  • Length: 11.7 m
  • Year: 2020
  • Cabins: 4
  • Berths: 8
  • From $6052 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11.7 m (39' 6")
  • Year: 2020
From $6052
per week

BOATBOOKINGS SAYS:
"This 2020 Fountaine Pajot Lucia 40 is the perfect boat for family charters out of Annapolis!"

Jeanneau 51
    3 Cabins - 2019 - Annapolis
  • 3 Cabins Bareboat Sailing Yacht
  • Length: 15.4 m
  • Year: 2019
  • Cabins: 3
  • Berths: 6
  • From $5363 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 15.4 m (52' 4")
  • Year: 2019
From $5363
per week

BOATBOOKINGS SAYS:
"A new boat perfect for up to three couples sailing out of Annapolis!"

Jeanneau Sun Odyssey 44DS
    2 Cabins - 2013 - Annapolis - Nassau
  • 2 Cabins Bareboat Sailing Yacht
  • Length: 13.35 m
  • Year: 2013
  • Cabins: 3
  • Berths: 6
  • From $5580 to $6200 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 13.35 m (45' 3")
  • Year: 2013
From $5580 to $6200
per week

BOATBOOKINGS SAYS:
"Pure Sailing Pleasure!"

Jeanneau 54
    3 Cabins - 2017 - Annapolis
  • 3 Cabins Bareboat Sailing Yacht
  • Length: 16.15 m
  • Year: 2017
  • Cabins: 3
  • Berths: 6
  • From $5985 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 16.15 m (54' 6")
  • Year: 2017
From $5985
per week

BOATBOOKINGS SAYS:
"Take your family sailing out of Annapolis in this stylish Jeanneau 54!"

PADRIGIAN II
  • Crewed Sailing Yacht
  • Length: 17.8 m
  • Year:
  • Cabins: 3
  • Berths: 6
  • From $6175 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 17.8 m (60' 4")
  • Year:
From $6175
per week

BOATBOOKINGS SAYS:
"A Jeanneau 58 suitable for family charters in 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!"

Jeanneau Sun Odyssey 490
    3 Cabins - 2020 - Annapolis
  • 3 Cabins Bareboat Sailing Yacht
  • Length: 14.43 m
  • Year: 2020
  • Cabins: 3
  • Berths: 6
  • From $4875 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 14.43 m (49' 3")
  • Year: 2020
From $4875
per week

BOATBOOKINGS SAYS:
"Great size yacht for friends or family!"

Jeanneau 51
    3 Cabins - 2020 - Annapolis
  • 3 Cabins Bareboat Sailing Yacht
  • Length: 15.37 m
  • Year: 2020
  • Cabins: 3
  • Berths: 6
  • From $5363 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 15.37 m (52' 1")
  • Year: 2020
From $5363
per week

BOATBOOKINGS SAYS:
"Sail the Chesapeake Bay in a brand new 2020 Jeanneau 51!"

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!"

SOULSHINE
  • Bareboat Sailing Yacht
  • Length: 12.38 m
  • Year: 2019
  • Cabins: 3
  • Berths: 6
  • From $3965 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 12.38 m (42' 2")
  • Year: 2019
From $3965
per week

BOATBOOKINGS SAYS:
"A brand new boat made for exploring the Chesapeake Bay with family or friends!"

WEATHER OR KNOT
  • Bareboat Sailing Yacht
  • Length: 12.53 m
  • Year:
  • Cabins: 3
  • Berths: 6
  • From $3965 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 12.53 m (42' 5")
  • Year:
From $3965
per week

BOATBOOKINGS SAYS:
"The Jeanneau Sun Odyssey 419 is the perfect boat for sailing the Chesapeake Bay!"

Jeanneau Sun Odyssey 410
    2 Cabins - 2020 - Annapolis
  • 2 Cabins Bareboat Sailing Yacht
  • Length: 12.34 m
  • Year: 2020
  • Cabins: 2
  • Berths: 4
  • From $3738 per week
Details Enquire
  • Berths: 4
  • Cabins: 2
  • Crew: Bareboat
  • Type: Sail
  • Length: 12.34 m (41' 10")
  • Year: 2020
From $3738
per week

BOATBOOKINGS SAYS:
"Sailing out of Annapolis has never been so stylish!"

SUMMER SALT
  • Bareboat Sailing Yacht
  • Length: 13.41 m
  • Year:
  • Cabins: 3
  • Berths: 6
  • From $4225 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 13.41 m (45' 9")
  • Year:
From $4225
per week

BOATBOOKINGS SAYS:
"Experience the Chesapeake Bay in a spacious Jeanneau Sun Odyssey 440!"

Jeanneau Power NC 33
    2 Cabins - 2019 - Annapolis
  • 2 Cabins Bareboat Motor Yacht
  • Length: 10.49 m
  • Year: 2019
  • Cabins: 2
  • Berths: 4
  • From $4675 per week
Details Enquire
  • Berths: 4
  • Cabins: 2
  • Crew: Bareboat
  • Type: Motor
  • Length: 10.49 m (35' 5")
  • Year: 2019
From $4675
per week

BOATBOOKINGS SAYS:
"An elegant Jeanneau Power NC 33 perfect for cruising out of Annapolis!"

Lucia 40
    4 Cabins - 2018 - Annapolis - Grenadines
  • 4 Cabins Bareboat Catamaran
  • Length: 11.73 m
  • Year: 2018
  • Cabins: 4
  • Berths: 8
  • From $5568 to $6091 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11.73 m (39' 9")
  • Year: 2018
From $5568 to $6091
per week

BOATBOOKINGS SAYS:
"A brand new 4 cabin catamaran."

Jeanneau 409
    2 Cabins - Annapolis
  • 2 Cabins Bareboat Sailing Yacht
  • Length: 12.3 m
  • Year: 2012
  • Cabins: 2
  • Berths: 4
  • From $4725 to $5200 per week
Details Enquire
  • Berths: 4
  • Cabins: 2
  • Crew: Bareboat
  • Type: Sail
  • Length: 12.3 m (41' 6")
  • Year: 2012
From $4725 to $5200
per week

BOATBOOKINGS SAYS:
"A delight to sail"

Jeanneau Sun Odyssey 41DS - 2 Cabins - 2016 - Annapolis - Chesapeake Bay VIEW 1 REVIEW 
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"

Bavria 45
    3 cabins - Annapolis
  • 3 cabins Bareboat Sailing Yacht
  • Length: 46 m
  • Year: 2011
  • Cabins: 3
  • Berths: 6
  • From $4399 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 46 m (156' 4")
  • Year: 2011
From $4399
per week

QUICK ENQUIRY

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Top Rated Yachts
  • Hondo - Fountaine Pajot MY 44

    Hondo - Fountaine Pajot MY 44

    Details
  • Fountaine Pajot Lucia 40 - 4 Cabins

    Fountaine Pajot Lucia 40 - 4 Cabins

    Details
  • Fountaine Pajot Saona 47

    Fountaine Pajot Saona 47

    Details
  • Jeanneau 51 - 3 Cabins

    Jeanneau 51 - 3 Cabins

    Details
  • Jeanneau Sun Odyssey 44DS - 2 Cabins

    Jeanneau Sun Odyssey 44DS - 2 Cabins

    Details
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