369

experiences

4.8

Super!

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

Italy: Tuscany

7 days - 7 nights

26 departures available

April - October

Starting from

€500

Per person

5.0

Super!

Zakynthos and the Strofades Islands: a unique route in Ionian Greece

Greece: Ionian Islands

6 days - 6 nights

7 departures available

June - July

Starting from

€850

Per person

4.8

Super!

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

Per person

4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

5 departures available

July - August

Starting from

€900

Per person

4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

8 departures available

May - September

Starting from

€220

Per person

5.0

Super!

June 2nd long weekend in the Tuscan Archipelago with PROFESSIONAL CHEF SKIPPER

Italy: Tuscany

4 days - 4 nights

One departure available

May - June

€500

€475

Per person

4.9

Super!

A day of sailing in the Gulf of Trieste

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

One departure available

May

€99

Per person

5.0

Super!

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

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

Per person

4.9

Super!

VelaTrek weekend on the Island of Elba All-inclusive - 2 boats

Italy: Tuscany

3 days - 2 nights

2 departures available

May - September

€390

€351

Per person

4.9

Super!

Long weekend sailing in Istria between nature and history

Croatia: Istrian peninsula

3 days - 3 nights

One departure available

April - May

€360

Per person

5.0

Super!

Chioggia to Corfu

Greece: Ionian Islands

8 days - 7 nights

One departure available

May

€550

Per person

5.0

Super!

Aeolian Islands and Egadi Islands in a week with chef on board

Italy: Aegadian islands

7 days - 7 nights

One departure available

July - August

€950

Per person

Why book a holiday with Sailsquare?

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

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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

17616 reviews

Cape Horn and Patagonia Glaciers Expedition 15 days/14 nights

01/31/2026

Francesco C.

Italy

A dream that has become reality! Passing Cape Horn under sail cannot be described. The expedition both from a sailing and naturalistic point of view was fantastic. Laurent is a very good skipper from all points of view, the emotions in crossing certain landscapes are incredible. The on-board company is just as pleasant. However, the difference is made by Laurent: prepared, reliable, calm, helpful and much more. An experience that I recommend to all sailors! Thank you Laurent !!

Midweek special on the island of Elba, 2 nights

01/24/2026

Sara M.

Italy

I left with my brother: there were 7 of us, plus Marco. It was our first boat experience and we couldn't ask for anything better! Marco was extremely kind, helpful and attentive to every detail. The combination of the boat excursion and the trekking on the island was simply fantastic, everything impeccably organized. In addition, there was also the opportunity to enjoy free time in total relaxation. I absolutely recommend this experience with Marco!

Wellness Adventure Retreat

01/14/2026

Donna S.

Canada

We had an amazing time on board. Great food. Lots of activities. We got to see sharks, dolphins, and many types of tropical fish. Luca was a great host. The boat was beautiful and very clean. The location was absolutely stunning!

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

01/14/2026

Sophie P.

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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