Cruising 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 S...
The USA offers an incredible variety of charter opportunities. The destinations on the East Coast range from the opulence of Miami, Ft. Lauderdale and Key West, to the remarkable Chesapeake Bay,...
Head to Annapolis to start your charter to explore the Chesapeake Bay and some of the most celebrated sailing grounds of the US! Be sure to allow some time before or after your char...
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!
- Fountaine Pajot Isla 40 Bareboat Catamaran
- Length: 11.93 m
- Year: 2022
- Cabins: 3
- Berths: 6
- From $7200 per week
BOATBOOKINGS SAYS:
"The Fountaine Pajot Isla 40 SECOND WIND is your partner in finding the most exclusive and stunning anchorages on the American East Coast."
- Fountaine Pajot MY6 Bareboat Catamaran
- Length: 15 m
- Year: 2025
- Cabins: 4
- Berths: 8
- From $14000 per week
BOATBOOKINGS SAYS:
"Experience the vitality of the American East Coast on LA DOLCE VITA!"
- Fountaine Pajot MY 44 Crewed Power Catamaran
- Length: 13.41 m
- Year: 2019
- Cabins: 3
- Berths: 6
- 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 Bareboat Catamaran
- Length: 12.2 m
- Year: 2020
- Cabins: 4
- Berths: 8
- From $6052 per week
BOATBOOKINGS SAYS:
"This 2020 Fountaine Pajot Lucia 40 is the perfect boat for family charters out of Annapolis!"
- 3 cabins (3 double) Bareboat Catamaran
- Length: 14.02 m
- Year: 2019
- Cabins: 3
- Berths: 8
- 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!"
- Bareboat Sailing Yacht
- Length: 15.4 m
- Year: 2019
- Cabins: 3
- Berths: 6
- From $5363 per week
BOATBOOKINGS SAYS:
"A new boat perfect for up to three couples sailing out of Annapolis!"
- 2 Cabins Bareboat Sailing Yacht
- Length: 13.35 m
- Year: 2013
- Cabins: 3
- Berths: 6
- From $5580 to $6200 per week
BOATBOOKINGS SAYS:
"Pure Sailing Pleasure!"
- Bareboat Sailing Yacht
- Length: 16.16 m
- Year: 2017
- Cabins: 3
- Berths: 6
- From $5985 per week
BOATBOOKINGS SAYS:
"Take your family sailing out of Annapolis in this stylish Jeanneau 54!"
- 3 Cabins Bareboat Sailing Yacht
- Length: 14.43 m
- Year: 2020
- Cabins: 3
- Berths: 6
- From $4875 per week
BOATBOOKINGS SAYS:
"Great size yacht for friends or family!"
- 3 Cabins Bareboat Sailing Yacht
- Length: 15.37 m
- Year: 2020
- Cabins: 3
- Berths: 6
- From $5363 per week
BOATBOOKINGS SAYS:
"Sail the Chesapeake Bay in a brand new 2020 Jeanneau 51!"
- Jeanneau Power NC 33 Bareboat Motor Yacht
- Length: 10.006 m
- Year: 2020
- Cabins: 2
- Berths: 4
- From $4675 per week
BOATBOOKINGS SAYS:
"Explore the Chesapeake waters in a brand new 2020 Jeanneau Power NC 33!"
- Bareboat Sailing Yacht
- Length: 12.38 m
- Year: 2019
- Cabins: 3
- Berths: 6
- From $3965 per week
BOATBOOKINGS SAYS:
"A brand new boat made for exploring the Chesapeake Bay with family or friends!"
- Bareboat Sailing Yacht
- Length: 12.53 m
- Year: 2017
- Cabins: 3
- Berths: 6
- From $3965 per week
BOATBOOKINGS SAYS:
"The Jeanneau Sun Odyssey 419 is the perfect boat for sailing the Chesapeake Bay!"
- Bareboat Sailing Yacht
- Length: 13.41 m
- Year:
- Cabins: 3
- Berths: 6
- From $4225 per week
BOATBOOKINGS SAYS:
"Experience the Chesapeake Bay in a spacious Jeanneau Sun Odyssey 440!"
- 2 Cabins Bareboat Motor Yacht
- Length: 10.49 m
- Year: 2019
- Cabins: 2
- Berths: 4
- From $4675 per week
BOATBOOKINGS SAYS:
"An elegant Jeanneau Power NC 33 perfect for cruising out of Annapolis!"
- 4 Cabins Bareboat Catamaran
- Length: 11.73 m
- Year: 2018
- Cabins: 4
- Berths: 8
- From $5568 to $6091 per week
BOATBOOKINGS SAYS:
"Perfect for smaller groups."
- 2 Cabins Bareboat Sailing Yacht
- Length: 12.3 m
- Year: 2012
- Cabins: 2
- Berths: 4
- From $4725 to $5200 per week
BOATBOOKINGS SAYS:
"A delight to sail"
- 2 Cabins Bareboat Sailing Yacht
- Length: 12.5 m
- Year: 2016
- Cabins: 2
- Berths: 4
- From $3738 per week
BOATBOOKINGS SAYS:
"Perfect for two couples to explore Annapolis and the Chesapeake Bay in a sporty yacht that sails beautifully"
- Westport 112 Crewed Motor Yacht
- Length: 34 m
- Year: 2001 (2016 refit)
- Cabins: 4
- Berths: 8
- From $55000 to $60000 per week
BOATBOOKINGS SAYS:
"Let ISLAND GIRL whisk you away to the tropical paradise of the Bahamas in style and elegance."
- Breaux Bay Craft 37m Luxury Crewed Motor Yacht
- Length: 37 m
- Year: 1979 (2020 refit)
- Cabins: 4
- Berths: 8
- From $69000 to $75000 per week
BOATBOOKINGS SAYS:
"Embark on an adventure of a lifetime with ARIADNE, the luxurious yacht equipped with the latest water toys for non-stop excitement in the Bahamas."
- 3 cabins Bareboat Sailing Yacht
- Length: 46 m
- Year: 2011
- Cabins: 3
- Berths: 6
- From $4399 per week
