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 Mar...
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...
- Hargrave 101 Luxury Crewed Motor Yacht
- Length: 30.78 m
- Year: 2010 (2018 Refit)
- Cabins: 4
- Berths: 8
- 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 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!"
- 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 to $5775 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!"
- Bareboat Sailing Yacht
- Length: 17.8 m
- Year: 2017
- Cabins: 4
- Berths: 6
- From 7700 to 7700 per week
BOATBOOKINGS SAYS:
"A Jeanneau 58 suitable for family charters in the Chesapeake Bay!"
- 3 Cabins Bareboat Catamaran
- Length: 11.7 m
- Year: 2019
- Cabins: 3
- Berths: 6
- From $5387 per week
BOATBOOKINGS SAYS:
"Hop aboard for an amazing experience sailing the Chesapeake Bay in a 2019 Fountaine Pajot Lucia 40!"
- 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 to $4270 per week
BOATBOOKINGS SAYS:
"The Jeanneau Sun Odyssey 419 is the perfect boat for sailing the Chesapeake Bay!"
- 2 Cabins Bareboat Sailing Yacht
- Length: 12.34 m
- Year: 2020
- Cabins: 2
- Berths: 4
- From $3738 per week
BOATBOOKINGS SAYS:
"Sailing out of Annapolis has never been so stylish!"
- 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:
"A brand new 4 cabin catamaran."
- 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"
- 3 cabins Bareboat Sailing Yacht
- Length: 46 m
- Year: 2011
- Cabins: 3
- Berths: 6
- From $4399 per week
