370

experiences

5.0

Super!

Sail around Menorca! - Cook on board

Spain: The Balearic Islands

5 days - 5 nights

4 departures available

June - August

Starting from

€900

€765

Per person

5.0

Super!

Corfù Paxos Antipaxos

Greece: Ionian Islands

6 days - 6 nights

2 departures available

September

€900

Per person

5.0

Super!

Sailing from Menorca to Sardinia

Spain: The Balearic Islands

5 days - 5 nights

One departure available

June

€700

€595

Per person

4.9

Super!

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

3 departures available

July - August

Starting from

€410

€328

Per person

5.0

Super!

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

Greece: Cyclades

6 days - 6 nights

One departure available

August

€1,150

Per person

5.0

Super!

North-east Sardinia and south Corsica on a beautiful 16m boat with HOSTESS

Italy: Northern Sardinia

7 days - 7 nights

9 departures available

June - August

Starting from

€1,470

€1,397

Per person

4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

2 departures available

September

€400

Per person

4.8

Super!

Magical weekend in the Aeolian Islands

Italy: Aeolian Islands

4 days - 3 nights

One departure available

April - May

€360

Per person

4.8

Super!

The gems of the Amalfi Coast: Capri Light Blue, Positano Blue Sky, Amalfi Dreaming History

Italy: Naples & Amalfi Coast

4 days - 3 nights

3 departures available

April - July

Starting from

€320

Per person

5.0

Super!

Ibiza & Formentera All inclusive week with Cook

Spain: The Balearic Islands

6 days - 6 nights

3 departures available

May - September

Starting from

€750

€675

Per person

5.0

Super!

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

19 departures available

June - October

€1,250

Per person

5.0

Super!

Weekend del Garda

Italy: Lake Garda

2 days - 2 nights

One departure available

April - May

€179

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

17615 reviews

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

Experience the Befana as you have never seen it before... by boat!

01/14/2026

federico b.

Italy

Beautiful 4 relaxing days despite the adverse weather, the legendary Francesco solved with trips to beautiful and really interesting places, excellent crew immediately close-knit.

Customer Support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Call us at

+44 2035144220

Read our

Contact & Support

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!