The Caribbean

Gay Group Trip: Caribbean Explorer

8 days£
Group Trip

Join a gay sailing trip and spend eight days exploring the Caribbean. Our trip will begin in Sint Maarten and we’ll venture on to St. Barts, St Kitts, Anguilla and beyond. We’ll be sailing in style on a 156-foot sailboat. You’ll be joined by two trip leaders, and a crew of ten including chefs, the captain and twenty-four fellow travellers. Breakfasts, lunches, dinners, snacks and drinks are all included.

This is the best way to discover the charms of the Caribbean. You’ll spend a week island-hopping around some of the Caribbean’s most beautiful destinations, including islands, beaches, little towns and ports. There’ll be plenty of ways to keep yourself occupied on the ship in the warm February sun.

Call our travel experts on

+44 (0)20 7157 1570
Request More Information
Departing on
  • 12th February 2022 Saturday
  • 19th February 2022 Saturday
The Caribbean LGBT Rights

Group Trip Breakdown

Sint Maarten

Day 1: Sint Maarten

Our Caribbean sailing adventure begins in the Dutch outpost of Sint Maarten. We’ll gather together for a debrief on the adventures to come at 4pm. You can opt to spend a couple of extra days on the island before the trip formally begins.

The Caribbean

Day 2: Sailing

Today we’ll explore Simpson Bay and maybe even try some local rum. We’ll then hop on board the 156-foot vessel and begin our exploration of the Caribbean. This really is the best way to explore the Caribbean islands.


Days 3-7: St Barts, St Kitts & Nevis, Anguilla, Tintamarre

We’ll have seven days to explore many of the most beautiful ports, caves and beaches in the Caribbean. The exact itinerary may change in line with sea conditions, and this will be at the discretion of the captain. Either way, we’ll have the ship to ourselves for the week and we’ll be island-hopping around one of the most beautiful parts of the world.

Enjoy the sun, swim in the turquoise waters and unwind on deck. As well as swim shorts, you could bring a nice outfit or two if you’d like to have dinner on land. On the ship, we’ll have the large social deck and the indoor dining area on the upper deck. The lower deck is where you’ll find the cabins – each one has a porthole and private cabin.


Day 8: Departure

On the final day, we’ll sail back to Sint Maarten and say our goodbyes. You’ll be transferred to the airport for your return flight.

Sounds good? Call our travel experts:

+44 (0)20 7157 1570
Make an Enquiry

    Make an Enquiry

    Call the team now for a chat on +44 (0)20 7157 1570.
    Tap to Call

    All personal data is processed in accordance with our Privacy Policy and you can opt-out at any time.

    We plant trees with EcologiDid You Know? We plant trees for every booking!

    For every booking made with we commit to planting at least 100 trees to help reduce the impact of travel on future generations. Trees are planted in the name of our clients via our parter Ecologi. It's the least we can do to give back.

    Read more about Ecologi and how they are helping to reduce the world's carbon footprint.