experiences

4.8

Super!

Come and discover Guadeloupe and its archipelago: a paradise on the water

Caribbean: Guadeloupe

6 days - 6 nights

5 departures available

February - December

€730

Per person

4.8

Super!

Come and discover Guadeloupe and its archipelago: a paradise on the water

Caribbean: Guadeloupe

7 days - 7 nights

10 departures available

January - December

€850

Per person

4.9

Beaches and entertainment: sailing between Curaçao and Bonaire

Caribbean: ABC Islands: Aruba, Bonnaire, Curaçao

7 days - 7 nights

7 departures available

June - August

€450

Per person

5.0

12 days of sailing from Martinique to Guadeloupe

Caribbean: Guadeloupe

11 days - 11 nights

One departure available

January - February

Starting from

€1,795

Per person - min 2 pax

5.0

Paradise on a sailing boat with All Inclusive

Caribbean: San Blas Islands - Panama

7 days - 7 nights

One departure available

July

€1,750

Per person

5.0

12 days/11 nights around Grenada and the Grenadines

Caribbean: Grenada

11 days - 11 nights

2 departures available

November - December

€1,795

Per person - min 2 pax

5.0

San Blas Islands - All Inclusive

Caribbean: San Blas Islands - Panama

7 days - 7 nights

3 departures available

July - August

€1,167

Per person

5.0

San Blas Islands: Private Boat for 2 Persons - All Inclusive

Caribbean: San Blas Islands - Panama

7 days - 7 nights

12 departures available

January - December

Starting from

€1,625

Per person

A dream trip for 2 people in the wilderness - All inclusive

Caribbean: San Blas Islands - Panama

6 days - 6 nights

16 departures available

August - November

Starting from

€1,350

Per person

5.0

Sailing and Wild Life in San Blas between traditions and turquoise waters

Caribbean: San Blas Islands - Panama

7 days - 7 nights

6 departures available

August - September

Starting from

€1,500

€1,350

Per person

5.0

12 day Cruising/Sailing Experience around St. Martin and St. Barth's

Caribbean: Saint Martin

11 days - 11 nights

3 departures available

March - April

€1,795

Per person - min 2 pax

Explore San Blas paradise

Caribbean: San Blas Islands - Panama

4 days - 4 nights

10 departures available

July - September

€200

Per person

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

Reviews - Monohull yacht sailing holidays & tours in the Caribbean

109 reviews

12 day Cruising/Sailing Experience around St. Martin and St. Barth's

04/17/2025

Basiel B.

United States

We had a fantastic trip sailing around St. Martin, St. Barth and St. Kitts & Nevis with Rob and Jackie, who were super relaxed and made us feel 200% welcome. The boat is beautiful and very well taken care of, a perfect intro to real-deal sailing. Rob is an excellent skipper mindful of safety (& comfort), and Jackie spoils you with her cooking. Snorkeling gear an paddle board available for aquatic leisure. Cannot recommend them more for a relaxing trip around the Caribbean!

Sailing adventure through the Caribbean: St Vincent & the Grenadines

02/8/2025

mara v.

Italy

Avventura a bordo di un ketch meravigliosa, lo skipper Hernan una persona di assoluta professionalità ,competenza e dotato di grandissima esperienza nel mondo della navigazione ci ha portato alla scoperta di fantastici scorci di paradiso nei caraibi. E' stata una bella esperienza sotto ogni punto di vista. Prezzo molto competitivo del viaggio e barca dotata di tutto. Sicuramente mi affiderei nuovamente allo skipper Hernan per un'altra avventura a bordo di Palawan

New Year's Eve under the Caribbean sun

01/14/2025

Gaetano F.

Era da tempo che volevo fare un veleggiata fino alle Grenadine. Sono complessivamente alquanti soddisfatto della vacanza, nonostante un po' di tensione tra un membro dell'equipaggio ed il capitano

New Year's Eve Flotilla: Relaxation and Fun in Guadeloupe - FIXED PRICE FLIGHT FROM PARIS

01/7/2025

Laura B.

France

let yourself go… in every adventure and fun ☀️🥂⛵️🪩👯 always perfect with marmaglia ♥️

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