Sailboat Tours & Trips in Caribbean

Find a Sailboat trip that explores Caribbean. There are 8 tours to choose from, that range in length from 7 days up to 10 days. The most popular month for these tours is April, which has the most tour departures.

8 Sailboat trips through Caribbean with 20 reviews

  1. Sailing Cuba Tour
    8 days
     • 4 Cities
     • Sailing

    Sailing Cuba

    4.5 (14 reviews)Delicious Meals
    "Philippa was attentive caring knowledgeable and showed neverendng energy in doing..."
    Visiting 
    Cuba
    Group Size: 
    Max 16
    Tour Operator: 
    G Adventures
    Age Range: 
    16 to 99 year olds
    Travel Style: 
    Sailboat, Discovery
    From $ 1,583
    US $1,187
    -25% OFF
    You save: $396
    See Trip
  2. Sailing the British Virgin Islands – Tortola to Tortola Tour
    7 days
     • 4 Cities
     • Sailing

    Sailing the British Virgin Islands – Tortola to Tortola

    3.6 (5 reviews)Economical
    "Yes... we knew we were going to have to buy food for meals but the way in which this..."
    Visiting 
    Virgin Island, British
    Ocean: 
    Atlantic
    Group Size: 
    Max 8
    Tour Operator: 
    G Adventures
    Age Range: 
    16 to 99 year olds
    Travel Style: 
    Sailboat, Discovery, Christmas & New Year +1 more
    From $ 1,699
    US $1,274
    -25% OFF
    You save: $425
    See Trip
  3. Adventure Sailing Charter from St Lucia to Grenada Tour
    10 days
     • 13 Cities
     • Sailing

    Adventure Sailing Charter from St Lucia to Grenada

    Visiting 
    Saint Lucia, Saint Vincent and the Grenadines, Grenada
    Ocean: 
    Atlantic
    Group Size: 
    Max 6
    Tour Operator: 
    BlueFoot Travel
    Age Range: 
    30 to 65 year olds
    Travel Style: 
    Sailboat
    From
    US $2,725
    See Trip
  4. Adventure Sailing Trip in Grenada & The Grenadines Tour
    10 days
     • 11 Cities
     • Sailing

    Adventure Sailing Trip in Grenada & The Grenadines

    Visiting 
    Grenada, Saint Vincent and the Grenadines
    Ocean: 
    Atlantic
    Group Size: 
    Max 6
    Tour Operator: 
    BlueFoot Travel
    Age Range: 
    30 to 65 year olds
    Travel Style: 
    Sailboat
    From
    US $2,725
    See Trip
  5. Sailing Cuba - South Coast Explorer Tour
    8 days
     • 6 Cities
     • Sailing

    Sailing Cuba - South Coast Explorer

    5.0 (1 review)
    "This was an amazing trip. I loved every minute of it! Lovely balance of beach, sailing..."
    Visiting 
    Cuba
    Country Region: 
    Central Cuba
    Group Size: 
    Max 16
    Tour Operator: 
    G Adventures
    Age Range: 
    16 to 99 year olds
    Travel Style: 
    Sailboat, Discovery, Christmas & New Year +1 more
    From $ 1,583
    US $1,029
    -35% OFF
    You save: $554
    See Trip
  6. Cabin Charter Sailing Adventure in St Vincent & The Grenadines Tour
    10 days
     • 11 Cities
     • Sailing

    Cabin Charter Sailing Adventure in St Vincent & The Grenadines

    Visiting 
    Saint Vincent and the Grenadines
    Ocean: 
    Atlantic
    Group Size: 
    Max 6
    Tour Operator: 
    BlueFoot Travel
    Age Range: 
    30 to 65 year olds
    Travel Style: 
    Sailboat
    From
    US $2,725
    See Trip
  7. Cabin Charter Sailing Holiday in the Virgin Islands Tour
    8 days
     • 9 Cities
     • Sailing

    Cabin Charter Sailing Holiday in the Virgin Islands

    Visiting 
    Virgin Islands, U.S., Virgin Island, British
    Ocean: 
    Atlantic
    Group Size: 
    Max 6
    Tour Operator: 
    BlueFoot Travel
    Age Range: 
    30 to 65 year olds
    Travel Style: 
    Sailboat
    From
    US $2,498
    See Trip
  8. Cabin Charter Sailing Adventure in the BVI Tour
    8 days
     • 8 Cities
     • Sailing

    Cabin Charter Sailing Adventure in the BVI

    Visiting 
    Virgin Island, British
    Ocean: 
    Atlantic
    Group Size: 
    Max 6
    Tour Operator: 
    BlueFoot Travel
    Age Range: 
    30 to 65 year olds
    Travel Style: 
    Sailboat
    From
    US $2,498
    See Trip

Sailboat Tours & Trips in Caribbean Reviews

  • "One of the best, most relaxing weeks of my life sailing in paradise! Amazing beaches,..."
    Sailing Cuba
  • "Great to see a fantastic place getting itself back to normality without the crowds."
    Sailing the British Virgin Islands – Tortola to Tortola
  • "This was an amazing trip. I loved every minute of it! Lovely balance of beach, sailing..."
    Sailing Cuba - South Coast Explorer