Luxury Gay Group Trip: Caribbean Cruise vacations

Gay Group Trip: Caribbean Cruise

Trip Summary:
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From

8 days

From

$ pp

At a glance

? Our group trips are a great chance to travel with others. We also recommend adding in a few extra nights tailor-made to ensure you build the perfect itinerary.

Join a gay group trip and sail around the most beautiful islands of The Carribean. Enjoy some tropical designer shopping at Gustavia and sail around the beautiful bays of St. Martin. You’ll sail the reefs of Prickly Pear Cays, scuba dive in the crystal clear waters and even try some fishing – best of luck.

The Carribean is one of the most beautiful parts of the world. With this gay sailing cruise, sailing from island to island over eight days is an ideal way to discover it. This is, incidentally, a clothing optional cruise.

More Information


The Caribbean presents a complex landscape for LGBTQ+ travelers, with each island offering a different level of acceptance and legal protections. While many Caribbean nations have historically had conservative attitudes towards LGBTQ+ issues, there has been a growing shift toward greater acceptance and inclusivity, particularly in more tourist-focused areas. Some countries have made significant strides in LGBTQ+ rights, with laws decriminalizing same-sex sexual activity and legalizing same-sex marriage, while others remain more restrictive.

Destinations like Puerto Rico, Aruba, and Barbados have gained reputations for being more LGBTQ+ friendly, with vibrant gay scenes, inclusive resorts, and popular Pride events that attract visitors from around the world. Puerto Rico, as a U.S. territory, offers legal protections for LGBTQ+ individuals, including marriage equality, making it one of the most welcoming destinations in the region. The Dominican Republic, known for its stunning beaches and luxury resorts, has a growing LGBTQ+ tourism industry, especially in places like Punta Cana, where same-sex couples can enjoy an inclusive environment.

However, many other Caribbean islands, while they may offer beautiful landscapes and unique cultural experiences, still have laws that criminalize same-sex sexual activity or lack legal protections for LGBTQ+ individuals. Social acceptance varies widely, and LGBTQ+ travelers should exercise caution in more conservative areas, particularly outside major tourist centers.

Despite these challenges, the Caribbean remains a popular travel destination, with some islands offering safe and inclusive spaces where LGBTQ+ individuals can enjoy the region’s natural beauty, luxury resorts, and rich cultural experiences. As awareness grows and advocacy continues, many Caribbean nations are slowly moving toward greater acceptance, making the region an exciting and evolving destination for LGBTQ+ travelers seeking both adventure and relaxation.

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In detail

? Don't forget that most of our itineraries can be totally customized. Our expert team will be able to talk you through all the options.

Day 1: St. Martin

Our Caribbean cruise begins in St. Martin. It’s only an hour from the airport to the yacht. Boarding begins at 5:30 pm.

Day 1: St. Martin

Day 2: St. Barth's

After breakfast we’ll sail to St. Barth’s and anchor for lunch at the tiny island of Ile Fourchue – the only inhabitants are goats!

We’ll spend the evening in the bay of Gustavia town and have dinner there.

Day 2: St. Barth's

Day 3: St. Barth

St. Barth is distinguished by white sand beaches and excellent shops – leave some space in your case if you love designer swag. Browsing around Gucchi in a tropical setting is quite an experience.

We’ll sail to Anse du Colombier in the afternoon and scuba dive for rays and sea turtles. You can join a pre-sunset hike through tropical vegetation to the north of the island.

We’ll have a BBQ in the evening.

Day 3: St. Barth

Day 4: Grand Casse

This morning we’ll sail to Grand Casse, an idyllic bay with plenty of bars and restaurants. Once a week there is a local market and Carnaval.

Day 4: Grand Casse

Day 5: Anguilla

On our way to Anguilla we’ll anchor at Road Bay. Here you’ll find crystal clear water to swim in and excellent local seafood at the restaurant, The Pumphouse.

Day 5: Anguilla

Day 6: Prickly Pear Cays

We’ll sail through the reefs on our way to Prickly Pear Cays. It’s an ideal spot for scuba diving! We’ll anchor at Sandy Island and spend the night at Crocus Bay. Tonight we’ll dine at the celebrated restaurant, D’Avida.

Day 6: Prickly Pear Cays

Day 7: Saint Martin

On our last day we’ll sail past Anguilla to Saint Martin. We’ll get a chance to try some fishing – see if you can catch a tuna. We’ll spend the night in Anse Marcel.

Day 7: Saint Martin

Day 8: Departure

After breakfast, we’ll sail to the Marina at Marigot. Say goodbye to your fellow sailors and head to your next destination.

Day 8: Departure

Why book with us?

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We want to ensure you have the best experience with us so we’ll keep working on your itinerary until perfect. You will have your own personal dedicated member of our team who will help build a trip that is bespoke to you.


Call our travel experts on +44 (0)20 7157 1570

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