Skippered Charter Vacations

View the Skippered opportunities below or click here to charter an entire boat, skippered and/or crewed, in your desired location.
  • St Lucia to Grenada Adventure Sailing Vacation

    2019, Fri Nov 22 2:00pm - Sun Dec 01
    Category Type
    Skippered Charter Vacation,
    Mile/Resume Building Adventure
    Operated by Start Location
    Saint Lucia, Rodney Bay
    Our Caribbean adventure sailing vacation includes the incredible islands of St Lucia, St Vincent & The Grenadines and Grenada. This is a great way for those of you travelling solo, as couples or small groups to enjoy the luxury of a yacht charte... Learn more
  • Category Type
    Skippered Charter Vacation
    Operated by Start Location
    Grenada, Port Louis, Saint George's
    Our Caribbean adventure sailing trip takes in the incredible islands of Grenada, Ronde Island, Carriacou, Sandy, Union and Happy Island, Petit St Vincent, Tobago Cays, Mayreau, Bequia and St Vincent! This is a great way for those of you travellin... Learn more
  • New Year Caribbean Sailing Holiday

    2019, Sun Dec 29 2:00pm - Sun Jan 05
    Category Type
    Skippered Charter Vacation,
    Sailing Training Adventure
    Operated by Start Location
    Saint Vincent And The Grenadines, Blue Lagoon, Saint George
    Are you wanting to celebrate this new year in style? How about bringing in 2020 with sand between your toes and with a rum cocktail in your hand! Here is an overview of our New Year Caribbean sailing holiday, which includes sailing around the incredibl... Learn more
  • By The Cabin Charter from St Vincent to Grenada

    2020, Fri Jan 10 2:00pm - Sun Jan 19
    Category Type
    Skippered Charter Vacation,
    Sailing Training Adventure
    Operated by Start Location
    Saint Vincent And The Grenadines, Blue Lagoon, Saint George
    Click 'Learn More' to get a detailed outline of our by-the-cabin yacht charter from St Vincent via the Grenadines to Grenada. It is the perfect sailing trip for solo travellers, couples and small groups looking to relax in paradise and also get som... Learn more
  • Virgin Islands Shared Cabin Charter

    2020, Fri Mar 20 2:00pm - Fri Mar 27
    Category Type
    Skippered Charter Vacation,
    Sailing Training Adventure
    Operated by Start Location
    Virgin Islands (US), Red Hook, Saint Thomas
    Join our shared cabin charter as we sail around stunning islands in the US and British Virgin Island. If you are travelling solo, as a couple or a small group and you love to sail, this is a great way to enjoy the US and the British Virgin Islands... Learn more
  • BVI Cabin Charter including Anegada

    2020, Sun Apr 19 2:00pm - Sun Apr 26
    Category Type
    Skippered Charter Vacation,
    Sailing Training Adventure
    Operated by Start Location
    Virgin Islands (British), Trellis Bay, Tortola
    Our BVI Cabin Charter itinerary is the perfect sailing destination for single travellers looking for a sailing adventure. And it is the sailing trip if you are looking for hands-on sailing experience with an RYA sailing instructor, an all-inclusive men... Learn more
  • Adventure Sailing Trip from Antigua to St Lucia

    2020, Fri May 15 2:00pm - Sun May 24
    Category Type
    Skippered Charter Vacation,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    Operated by Start Location
    Antigua And Barbuda, Jolly Harbour, Saint John
    Our sailing adventure trip includes the incredible islands of Antigua, Guadeloupe, Dominica, Martinique and St Lucia. This is a great way for those of you travelling solo, as couples and small groups to enjoy the delights of a private yacht charte... Learn more
  • Sailing Adventure Holiday from St Lucia to Grenada

    2020, Fri May 29 2:00pm - Sun Jun 07
    Category Type
    Skippered Charter Vacation,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    Operated by Start Location
    Saint Lucia, Rodney Bay, Gros Inlet
    This sailing adventure holiday takes in the incredible islands of St Lucia, St Vincent & The Grenadines and Grenada. This is a great way for those of you travelling solo, as couples and small groups to enjoy a private cabin charter and get hands-o... Learn more
  • Cabin Charter Sailing in St Vincent & The Grenadines

    2020, Fri Jun 26 2:00pm - Sun Jul 05
    Category Type
    Skippered Charter Vacation,
    Sailing Training Adventure
    Operated by Start Location
    Saint Vincent And The Grenadines, Blue Lagoon, Saint George
    Would you like to sail with us on a cabin charter in the Grenadines, otherwise known as paradise! We will sail around the incredible islands of St Vincent, Petit Nevis, Mustique, Mayreau, Tobago Cays, Petit Tabac, Mopion Island, Petit St Vincent... Learn more