Discover our selection of yachts below and contact our Charter Experts at Boatbookings to receive a bespoke proposal and embark on the ultimate yacht charter vacation.

Let us take over and do the work for you by completing our enquiry form. Or, contact us directly at [email protected] with details of your group size, type of yacht, destination and budget. One of our Charter Experts will call you so please leave your phone number.

We look forward to hearing from you!

WEATHER OR KNOT
WEATHER OR KNOT
  • Bareboat Sailing Yacht
  • Length: 12.53 m
  • Year: 2017
  • 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: 2017
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
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
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
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
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
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
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

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