Sailboat Charters Chesapeake Bay. Sailing Yacht Charter Chesapeake Bay

14 sailboats in Chesapeake Bay available: rent a high quality sailboat, book your sailing vacation online now on YACHTICO.com North Atlantic Ocean Travel Advice
Filter summary: Location Chesapeake Bay boat type Sailing boat

Available yacht charter boats in Chesapeake Bay within the next six months:

  • Sailing yacht Hunter 33 available for charter in Port Annapolis Marina

    Sailing yacht Hunter 33 available for charter in Port Annapolis Marina

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2009 - Cabins: 2 - Berths: 4
    Bareboat charter
    Max 4 persons
    The price is calculated for 7 day charter and 4 passengers
    • Hunter 33[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Best Price Instant Confirmation
    from 2.816 per week
    from $ 3,126 per week
    View Details
  • Sailing yacht Dufour 382 Grand Large for rent in Annapolis

    Sailing yacht Dufour 382 Grand Large for rent in Annapolis

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2017 - Cabins: 2 - Berths: 4
    Bareboat charter
    Max 4 persons
    The price is calculated for 7 day charter and 4 passengers
    • Dufour 382 Grand Large[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Best Price Instant Confirmation
    from 4.284 per week
    from $ 4,755 per week
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  • Sailing yacht Sun Odyssey 45DS for rent in Port Annapolis Marina

    Sailing yacht Sun Odyssey 45DS for rent in Port Annapolis Marina

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2008 - Cabins: 2 - Berths: 4
    Bareboat charter
    Max 4 persons
    The price is calculated for 7 day charter and 4 passengers
    • Sun Odyssey 45DS[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Best Price Instant Confirmation
    from 4.243 per week
    from $ 4,709 per week
    View Details
  • Sail boat Jeanneau 53 available for charter in Annapolis

    Sail boat Jeanneau 53 available for charter in Annapolis

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2011 - Cabins: 3 - Berths: 6
    Bareboat charter
    Max 6 persons
    The price is calculated for 7 day charter and 6 passengers
    • Jeanneau 53[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Best Price Instant Confirmation
    from 5.399 per week
    from $ 5,992 per week
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  • Yacht Sun Odyssey 409 for rent in Annapolis

    Yacht Sun Odyssey 409 for rent in Annapolis

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2012 - Cabins: 3 - Berths: 6
    Bareboat charter
    Max 6 persons
    The price is calculated for 7 day charter and 6 passengers
    • Sun Odyssey 409[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Best Price Instant Confirmation
    from 4.174 per week
    from $ 4,633 per week
    View Details
  • Sailing yacht Dufour 460 Grand Large for charter in Port Annapolis Marina

    Sailing yacht Dufour 460 Grand Large for charter in Port Annapolis Marina

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2017 - Cabins: 3 - Berths: 6
    Bareboat charter
    Max 6 persons
    The price is calculated for 7 day charter and 6 passengers
    • Dufour 460 Grand Large[Yacht Price incl. Taxes]
    • Dinghy engine
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Best Price Instant Confirmation
    from 5.263 per week
    from $ 5,842 per week
    View Details
  • Sailing yacht Sun Odyssey 50DS available for charter in Annapolis

    Sailing yacht Sun Odyssey 50DS available for charter in Annapolis

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2011 - Cabins: 3 - Berths: 6
    Bareboat charter
    Max 6 persons
    The price is calculated for 7 day charter and 6 passengers
    • Sun Odyssey 50DS[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Confirmed in 24h
    from 5.080 per week
    from $ 5,638 per week
    View Details
  • Yacht Sun Odyssey 409 for rent in Annapolis

    Yacht Sun Odyssey 409 for rent in Annapolis

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2013 - Cabins: 3 - Berths: 6
    Bareboat charter
    Max 6 persons
    The price is calculated for 7 day charter and 6 passengers
    • Sun Odyssey 409[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Maryland Amusement Tax
    • VAT or sales tax
    Confirmed in 24h
    from 4.034 per week
    from $ 4,479 per week
    View Details
  • Sailing yacht Sun Odyssey 409 available for charter in Port Annapolis Marina

    Sailing yacht Sun Odyssey 409 available for charter in Port Annapolis Marina

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2012 - Cabins: 2 - Berths: 4
    Bareboat charter
    Max 4 persons
    The price is calculated for 7 day charter and 4 passengers
    • Sun Odyssey 409[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Confirmed in 24h
    from 3.702 per week
    from $ 4,109 per week
    View Details
  • Sailing yacht Sun Odyssey 44 DS for rent in Annapolis

    Sailing yacht Sun Odyssey 44 DS for rent in Annapolis

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2013 - Cabins: 2 - Berths: 4
    Bareboat charter
    Max 4 persons
    The price is calculated for 7 day charter and 4 passengers
    • Sun Odyssey 44 DS[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Confirmed in 24h
    from 4.040 per week
    from $ 4,484 per week
    View Details
  • Sail boat Sun Odyssey 469 for charter in Annapolis

    Sail boat Sun Odyssey 469 for charter in Annapolis

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2014 - Cabins: 3 - Berths: 6
    Bareboat charter
    Max 6 persons
    The price is calculated for 7 day charter and 6 passengers
    • Sun Odyssey 469[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Maryland Amusement Tax
    • VAT or sales tax
    Confirmed in 24h
    from 4.940 per week
    from $ 5,484 per week
    View Details
  • Yacht Oceanis 34 for rent in Port Annapolis Marina

    Yacht Oceanis 34 for rent in Port Annapolis Marina

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2011 - Cabins: 2 - Berths: 4
    Bareboat charter
    Max 4 persons
    The price is calculated for 7 day charter and 4 passengers
    • Oceanis 34[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Confirmed in 24h
    from 3.001 per week
    from $ 3,330 per week
    View Details
  • Sailing yacht Oceanis 45 available for charter in Port Annapolis Marina

    Sailing yacht Oceanis 45 available for charter in Port Annapolis Marina

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2013 - Cabins: 3 - Berths: 6
    Bareboat charter
    Max 6 persons
    The price is calculated for 7 day charter and 6 passengers
    • Oceanis 45[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Confirmed in 24h
    from 4.380 per week
    from $ 4,861 per week
    View Details
  • Sailing boat Dufour 460 Grand Large for rent in Port Annapolis Marina

    Sailing boat Dufour 460 Grand Large for rent in Port Annapolis Marina

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2017 - Cabins: 3 - Berths: 6
    Bareboat charter
    Max 6 persons
    The price is calculated for 7 day charter and 6 passengers
    • Dufour 460 Grand Large[Yacht Price incl. Taxes]
    • Dinghy engine
    • Yacht Insurance
    • Towels
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Confirmed in 24h
    from 5.353 per week
    from $ 5,942 per week
    View Details
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This yacht is available with skipper/crew only.You are able to charter and drive this boat yourself. A skipper can be booked as an additional extra if required.The maximum number of guests this boat can accommodate.