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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!

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

Italy: Tuscany

7 days - 7 nights

2 departures available

September - October

€650

Per person

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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

One departure available

September

€260

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

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4.9

Super!

Sail to the edge of the world among the wonders of the North (cottage + sailboat)

North Sea: Norway

7 days - 7 nights

One departure available

October

€1,200

Per person

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4.9

Super!

Sailing holiday among the wonders of the Cyclades from Athens

Greece: Cyclades

6 days - 7 nights

One departure available

September - October

€835

Per person

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5.0

Super!

Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

Italy: Tuscany

2 days - 2 nights

One departure available

October

€250

€238

Per person

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4.8

Super!

Experience the sea in October!

Italy: Tuscany

2 days - 2 nights

4 departures available

October

€200

Per person

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5.0

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

€690

Per person

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4.3

New

Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September - October

€890

Per person

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5.0

Let's discover Portofino, Santa Margherita and Sestri Levante together

Italy: Liguria

2 days - 2 nights

5 departures available

October - November

Starting from

€380

Per person

Why book a holiday with Sailsquare?

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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

19122 reviews

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We have known the Aeolian Islands for 20 years, live them with us!

09/13/2026

MATTIA B.

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IT

Wonderful week! Pasquale Domenico Ambrogio, a spectacular character with a great moral extension

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

09/13/2026

Elisa V.

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IT

Super experience! Sleeping in the roadstead is exciting... swimming in the sea immediately after breakfast is priceless! Sunrise and sunset... too! Josuah was super, he shared with us all aspects of the boat and fishing, we shared pleasant and fun moments of adventure and relaxation. Thank you Josuah for this wonderful experience and congratulations on your [hidden]... a very cozy boat! We recommend it to everyone!
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Whale watching cruise with WWF guide between Northern Sardinia and South Corsica

09/13/2026

Matteo F.

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IT

A crazy week of sailing, wind and dream beaches. Thanks to the skipper Paolo, the sailor Dario and the biologist Elisa for making it even more special. I will not easily forget the crossing of the Strait of Bonifacio with the rough seas and the sighting of dolphins 🐬

Sailing holiday in the archipelago of La Maddalena and Costa Smeralda

09/13/2026

Polyanne M.

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ES

A very disappointing experience and very different from what we expected from the contracted itinerary. We chose this one-week sailing trip precisely to get to know some of the most spectacular coves and landscapes of the La Maddalena archipelago and the south of Corsica. The itinerary included areas such as Caprera, Spargi, Budelli, Santa Maria, Lavezzi, Cavallo and Bonifacio, and our expectation was to sail, discover coves and enjoy those landscapes of turquoise blue water, light sand and large granite formations so characteristic of this area. However, by the end of the week we felt that we saw very little of all that this route had to offer. We passed through some places and were in Budelli, specifically in the Spiaggia del Cavaliere area, as well as other points and ports along the route, but many of the places that had made us choose this trip were left out. What disappointed us the most was that throughout the week we practically did not live the experience we imagined of anchoring the sailboat in front of a spectacular cove with turquoise blue waters. Nor did we get to enjoy those small coves surrounded by huge granite rocks that are one of the most representative images of the archipelago. We fully understand that on a boat trip wind, sea state and safety can force you to modify the itinerary, and we would never expect a skipper to sail when conditions were unsafe. But it is one thing to adapt a route for safety and another to end a week with the feeling of having spent too much time between ports and unspecial anchorages, leaving a huge part of the places that motivated our choice unknown. We had pending places such as Cala Corsara in Spargi, Cala Coticcio in Caprera, Lavezzi, Bonifacio and other coves along the route, in addition to a good part of that navigation between beaches and crystal clear waters that we expected to experience. After a week, our feeling was: we were in one of the most famous and beautiful archipelagos in the Mediterranean, but we could hardly get to know what makes it really special. And that, considering the price and the expectations created by the itinerary, was a huge disappointment. But the most difficult part of this experience was not only everything we missed. It was the constant feeling of helplessness for not being able to participate in decisions about our own journey. At no time did we feel that we could really choose, propose alternatives or give an opinion on how to make the most of the days. Every time we tried to ask about another cove, another anchorage or a different possibility, we had the feeling that any proposal ended up being redirected towards the option that the skipper Frederico considered most convenient. There came a time when we practically stopped asking and remained silent, because we felt that it didn't matter what we said. That dynamic generated a lot of anxiety and anguish during a vacation that we had hired precisely to enjoy, disconnect and experience something special with the family. We fully understand and respect that the final word on boating safety rests with the skipper. We do not question that. What we missed very much was communication, alternatives and the willingness to seek, within the possible conditions, options that also responded to what we wanted to know. Our perception for a good part of the trip was that the decisions ended up systematically favoring the easiest option for the skipper, instead of trying to build with us the best possible experience within the circumstances of each day. And that feeling ended up deeply affecting our experience. We were in an extraordinary place, had invested a lot of money and had a week to enjoy it, but we ended up feeling like voiceless passengers on our own journey.

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