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Sailboat holidays & skippered tours

The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.

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4.8

Super!

Squid Festival: let's close the season on a 15m boat with a flourish! - 2 boats in company

Italy: Tuscany

3 days - 2 nights

2 departures available

October - November

€280

Per person

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5.0

Super!

From Milos to Mykonos by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September

€1,000

€750

Per person

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5.0

Super!

Croisière de rêve sous voiles dans les îles de la société 14 Jours

Pacific Ocean: French Polynesia

13 days - 13 nights

One departure available

October - November

€2,090

Per person

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4.8

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€300

Per person

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4.8

Super!

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€600

Per person

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4.9

Super!

Four days in the Aeolian Islands from Capo D'Orlando

Italy: Aeolian Islands

4 days - 4 nights

One departure available

September

€400

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

5 departures available

September - October

Starting from

€370

Per person

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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

€453

€430

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

3 departures available

September - October

€650

Per person

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4.8

Super!

Squid Festival: let's close the season on a high note! - on board a 17mt boat

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€280

Per person

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4.9

Super!

NEW YEAR's Eve between sea and land in Norway: chasing the Northern Lights - COTTAGE + SAILBOAT

North Sea: Norway

11 days - 11 nights

One departure available

December - January

€1,300

Per person

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5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

2 departures available

September

Starting from

€1,000

€750

Per person

Why book a holiday with Sailsquare?

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

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

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 - Sailboat holidays & skippered tours

19069 reviews

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Gulf of Poets and Cinque Terre

09/7/2026

Davide A.

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IT

3 wonderful days! Giorgio and Francesca pampered us! Lunches in wonderful coves, even a BBQ on board! In the evening dinner in a small bay, we couldn't ask for anything better. We saw all the places of the 5 terre, Porto Venere, the graces... Too bad there wasn't much wind but the boat is really beautiful and very comfortable! Thank you and hope to see you soon! Highly recommended experience!

Summer 2026 - Catamaran week in the Pontine Islands

09/7/2026

Beatrice Chiara V.

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IT

Beautiful itinerary, skipper Marco showed great professionalism, availability and attention to our needs. He made us discover enchanting coves. Special note of merit to Giulia, our hostess who spoiled us with delicious dishes and great sympathy throughout the week. In short, a holiday ten and praise. To be repeated.
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Amazing Pontine Islands on a sailing boat

09/7/2026

CARLO V.

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IT

Congratulations to the Skipper who proved to be professional and allowed us to visit numerous places even in a few days. The boat has very small spaces that compensate for its real use, which is to sail.

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

09/7/2026

Salvatore Giuseppe Antonio S.

-

IT

Beautiful holiday with Gianfranco captain skipper always available and company for a wonderful tour of the islands in the name of relaxation, snorkeling and fun. Recommended for everyone

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