header cover
sailsquare logo

Log in

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.

cover image
avatar image

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

cover image
avatar image

4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

2 departures available

September

€400

Per person

cover image
avatar image

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

cover image
avatar image

4.7

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

Italy: Tuscany

6 days - 6 nights

6 departures available

June - August

Starting from

€1,052

€999

Per person

cover image
avatar image

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

cover image
avatar image

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

cover image
avatar image

5.0

Super!

Weekend del Garda

Italy: Lake Garda

2 days - 2 nights

One departure available

April - May

€179

Per person

cover image
avatar image

4.8

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

6 days - 7 nights

12 departures available

May - September

Starting from

€583

€525

Per person

cover image
avatar image

4.9

Super!

June 2nd long weekend sailing through the Istrian seaside villages (from Lignano)

Croatia: Istrian peninsula

4 days - 4 nights

One departure available

May - June

€460

Per person

cover image
avatar image

4.9

Super!

Sailing course for beginners

Italy: Liguria

2 days - 1 night

6 departures available

January - March

€270

Per person

cover image
avatar image

5.0

Super!

Sail in Sardinia! - Cook on board

Italy: Northern Sardinia

5 days - 5 nights

5 departures available

June - July

€1,000

€850

Per person

cover image
avatar image

5.0

Super!

The awakening of the lake

Italy: Lake Garda

1 day - 0 nights

7 departures available

June - August

Starting from

€69

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

17623 reviews

avatar placeholder

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!
avatar placeholder

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
avatar image

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.
avatar placeholder

Dream New Year's Eve sailing in Thailand

01/14/2026

Marina G.

-

Italy

Gianluca is a delightful person attentive to the well-being of customers. Clean boat with everything you need. Very centered galley. Let's wait for another itinerary to do with Gianluca!

Customer Support

nightLifeGeneralInfo

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!

search

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!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964