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Yacht sailing holidays & skippered tours in Guadeloupe

Discover hundreds of sailing holidays in Guadeloupe. Book a place on board and enjoy a unique experience with a local skipper with a local skipper at attractive prices.

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Yacht sailing holidays & skippered tours in Guadeloupe

36 reviews

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Unforgettable Mini Flotilla in the Caribbean - Dominica and Guadeloupe

01/26/2026

Giulia V.

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Italy

Andrea and Federico are true professionals and always kind and very nice, capable and cheerful sailors, nautical experts and entertainers. Beautiful holiday, fun and in complete safety!
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New Year's Eve 2026 discovering the Lesser Antilles by catamaran

01/15/2026

Deborah C.

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Italy

Super-comfortable catamaran Itinerary definitely improvable Good organization Good skipper
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Come and discover Guadeloupe and its archipelago: a paradise on the water

01/14/2026

Sophie P.

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Canada

An unforgettable sailing trip in Guadeloupe and the islands 🌴 We discovered Les Saintes, Marie-Galante and had a huge crush on Petite-Terre 💙 Sabrina and Patrick are incredibly welcoming and friendly. We spent a week on their sailboat, in a friendly and soothing atmosphere between tarot games and chili lovers and underwater excursions. 🌶️🃏 🐠 Patrick and Sabine are excellent skippers, very professional and reassuring. . This trip allowed us to really rest and recharge. An experience that I recommend without hesitation ✨ Sophie and Louis
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Come and discover Guadeloupe and its archipelago: a paradise on the water

12/24/2025

Manfred B.

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Austria

It was a great week with Sabine and Patrick! They are very flexible and strive to accommodate every request! Every day a new adventure! Sailing, shore excursions, snorkeling......, - there is something for everyone

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Guides & tips


Caribbean

From Cuba to the Grenadines, via the fascinating Bahamas and the green Antilles: Martinique, Dominica and Guadeloupe. Either way, a dream trip to tropical islands.
Guide to the Caribbean by catamaran

Grenadines

Une constellation d'îles immergées dans une mer cristalline allant du vert au bleu profond : les fonds marins limpides cachent un trésor qui n'est pas seulement celui des pirates..
Guide to the Grenadines by catamaran

When to go in the Caribbean

What are the best times to go to the Caribbean? What climate will I find?
Caribbean weather and climate guide

Guadeloupe: the best travel ideas

Other travel ideas

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