Charter a Yacht in Annapolis and Chesapeake Bay

Visit the gorgeous buildings in Annapolis and 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 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 continuing maintaining traditional lifestyles. In the northern part of the Bay, you can stop in Baltimore, Annapolis, Georgetown and Chestertown. The sailing around Chesapeake Bay is all “line of sight” with the breeziest times of 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 bareboat charter yachts from Annapolis, or contact us if you would like some further details.

See our Chesapeake sailing itinerary

Displaying: Your Search Results in Annapolis MD
Lipari 41 - 3 Cabins - Annapolis
Lipari 41
    3 Cabins - Annapolis
  • 3 Cabins Bareboat Catamaran
  • Length: 11.95 m
  • Year: 2013
  • Cabins: 3
  • Berths: 6
  • From $4700 to $6800 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11.95 m (40' 7")
  • Year: 2013
From $4700 to $6800
per week

BOATBOOKINGS SAYS:
"An ocean going catamaran, at ease in all sea conditions."

Orana 44 - 3 + 1 Cabins - Annapolis
Orana 44
    3 + 1 Cabins - Annapolis
  • 3 + 1 Cabins Charter Yacht
  • Length: 11.76 m
  • Year: 2011
  • Cabins: 4
  • Berths: 7
  • From $5595 per week
Details Enquire
  • Berths: 7
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11.76 m (40' )
  • Year: 2011
From $5595
per week

Jeanneau 379 - 3 Cabins - Annapolis
Jeanneau 379
    3 Cabins - Annapolis
  • 3 Cabins Charter Yacht
  • Length: 11.28 m
  • Year:
  • Cabins: 3
  • Berths: 6
  • Enquire for prices
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 11.28 m (38' )
  • Year:
Enquire for prices

Sun Odyssey 469 - 2014 - 3 Cabins
Sun Odyssey 469
    2014 - 3 Cabins
  • 2014 Bareboat Sailing Yacht
  • Length: 14.005 m
  • Year: 2014
  • Cabins: 3
  • Berths: 8
  • Enquire for prices
Details Enquire
  • Berths: 8
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 14.005 m (47' 8")
  • Year: 2014
Enquire for prices

Jeanneau 53 - 3 Cabins - Annapolis
Jeanneau 53
    3 Cabins - Annapolis
  • 3 Cabins Charter Yacht
  • Length: 16.06 m
  • Year:
  • Cabins: 3
  • Berths: 6
  • Enquire for prices
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 16.06 m (54' 9")
  • Year:
Enquire for prices

BOATBOOKINGS SAYS:
"A great sailing boat for all the family!"

REFLECTION
REFLECTION
  • Bareboat Sailing Yacht
  • Length: 13.35 m
  • Year: 2013
  • Cabins: 2
  • Berths: 6
  • From $5580 to $6200 per week
Details Enquire
  • Berths: 6
  • Cabins: 2
  • Crew: Bareboat
  • Type: Sail
  • Length: 13.35 m (45' 3")
  • Year: 2013
From $5580 to $6200
per week

BOATBOOKINGS SAYS:
"Pure Sailing Pleasure!"

Jeanneau 44DS - 3 Cabins - Annapolis
Jeanneau 44DS
    3 Cabins - Annapolis
  • 3 Cabins Bareboat Sailing Yacht
  • Length: 13.75 m
  • Year: 2013
  • Cabins: 3
  • Berths: 6
  • From $5580 to $6200 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 13.75 m (46' 7")
  • Year: 2013
From $5580 to $6200
per week

BOATBOOKINGS SAYS:
"Pure Sailing Pleasure!"

Sun Odyssey 379 (2013) - 2 Cabins - Annapolis
Sun Odyssey 379 (2013)
    2 Cabins - Annapolis
  • 2 Cabins Charter Yacht
  • Length: 11.34 m
  • Year: 2013
  • Cabins: 2
  • Berths: 6
  • Enquire for prices
Details Enquire
  • Berths: 6
  • Cabins: 2
  • Crew: Bareboat
  • Type: Sail
  • Length: 11.34 m (38' 6")
  • Year: 2013
Enquire for prices

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

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

Beneteau 393 - 3 Cabins - Annapolis
Beneteau 393
    3 Cabins - Annapolis
  • 3 Cabins Bareboat Sailing Yacht
  • Length: 11.94 m
  • Year: 2005
  • Cabins: 3
  • Berths: 6
  • From $2395 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 11.94 m (40' 6")
  • Year: 2005
From $2395
per week

BOATBOOKINGS SAYS:
"Spacious and efficient bluewater cruiser, perfect for extended charters."

Lagoon 400 - 3 Cabins - Annapolis
Lagoon 400
    3 Cabins - Annapolis
  • 3 Cabins Bareboat Catamaran
  • Length: 11.97 m
  • Year:
  • Cabins: 3
  • Berths: 8
  • Enquire for prices
Details Enquire
  • Berths: 8
  • Cabins: 3
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11.97 m (40' 9")
  • Year:
Enquire for prices

Leopard 40 - 4 Cabins - Annapolis
Leopard 40
    4 Cabins - Annapolis
  • 4 Cabins Charter Catamaran
  • Length: 12.2 m
  • Year: 2005
  • Cabins: 4
  • Berths: 8
  • Enquire for prices
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 12.2 m (41' 8")
  • Year: 2005
Enquire for prices

Jeanneau 409 - 2 Cabins - Annapolis
Jeanneau 409
    2 Cabins - Annapolis
  • 2 Cabins Bareboat Sailboat
  • 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"

WING GULL
WING GULL
  • Bareboat Sailboat
  • Length: 12.34 m
  • Year: 2013
  • Cabins: 3
  • Berths: 6
  • From $4725 to $5200 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 12.34 m (41' 10")
  • Year: 2013
From $4725 to $5200
per week

BOATBOOKINGS SAYS:
"A delight to sail"

Jeanneau 45i - 3 Cabins - Annapolis
Jeanneau 45i
    3 Cabins - Annapolis
  • 3 Cabins Charter Yacht
  • Length: 13.23 m
  • Year: 2007
  • Cabins: 3
  • Berths: 6
  • From $2399 to $3899 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 13.23 m (45' 3")
  • Year: 2007
From $2399 to $3899
per week

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