Gay Sailing Holidays in Croatia, Greece, Italy, Caribbean & Thailand
What to Expect on a Pride Sailing Week
Pride Sailing Holidays creates small-group gay sailing holidays designed for connection, freedom and unforgettable Mediterranean experiences. Whether you’re joining as a solo traveller, couple or group of friends, our hosted gay sailing trips combine stunning island itineraries, inclusive community, and professionally crewed yachts.
We specialise in cabin charters and private yacht charters across Croatia, Greece, Italy and Thailand. Each week blends relaxed daytime sailing, crystal-clear swim stops, vibrant port towns, and curated social experiences — from sunset drinks in Mykonos to beach parties in Hvar.
Our Pride sailing holidays are designed to balance social energy with space to unwind.
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• Daily sailing between iconic Mediterranean islands
• Swim stops in secluded bays
• Hosted dinners and optional nightlife experiences
• Time to explore historic towns and beach clubs
• Professional skipper and dedicated crew
• Small group atmosphere (typically 8–12 guests per yacht)
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You can book a private cabin on a shared yacht or charter an entire yacht with your group.
A Safe, Inclusive and Social Environment
We understand that feeling safe and welcome matters. Pride Sailing Holidays is built around community and inclusivity. Our trips attract a diverse mix of guests from around the world, and our itineraries are selected to offer both celebration and comfort.
Whether you’re looking for a high-energy week in Mykonos or a more relaxed island-hopping experience in Croatia, we create a space where you can be yourself — fully and confidently.
Destinations
Explore our most popular LGBTQ+ sailing destinations:
• Gay Sailing Croatia (Split to Dubrovnik)
• Gay Sailing Greece (Ionian & Mykonos)
• Gay Sailing Italy (Sicily & Sardinia)
• Thailand Island Sailing
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Our sailing holidays typically include:
• Accommodation in a private or shared cabin
• Professional gay/gay friendly skipper and host
• Yacht fuel and marina fees (as specified per itinerary)
• Bed linen
• Structured weekly itinerary
Full details are listed on each departure page.