header cover
sailsquare logo

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

4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

18 departures available

May - October

Starting from

€680

Per person

cover image
avatar image

4.5

Your holiday in the paradisiacal sea of Ibiza & Formentera

Spain: The Balearic Islands

6 days - 6 nights

14 departures available

June - September

Starting from

€790

Per person

cover image
avatar image

4.9

Between seas and volcanoes, fall in love with the Aeolian Islands

Italy: Aeolian Islands

5 days - 4 nights

15 departures available

July - October

Starting from

€590

Per person

cover image
avatar image

4.9

Four days exclusively on Elba between aperitifs and sailing

Italy: Tuscany

4 days - 3 nights

12 departures available

April - October

Starting from

€250

Per person

cover image
avatar image
Mystic Shores: Exploring the Canaries

Atlantic islands: Canary Islands

7 days - 7 nights

9 departures available

January - December

€900

€630

Per person

cover image
avatar image
Sardinia Race... tour of Sardinia in a squadron... NoStop!

Italy: Southern Sardinia

5 days - 4 nights

One departure available

May - June

€800

Per person

cover image
avatar image

4.6

Aeolian Islands: wellness, taste, fun with fabulous cook on board

Italy: Aeolian Islands

7 days - 7 nights

8 departures available

July - August

Starting from

€910

€865

Per person - min 2 pax

cover image
avatar image
Arctic New Year: Sailing, Trekking, and Aurora adventures in Norway

North Sea: Norway

14 days - 14 nights

One departure available

December - January

€999

Per person

cover image
avatar image

5.0

12 days of sailing from Martinique to Guadeloupe

Caribbean: Guadeloupe

11 days - 11 nights

One departure available

January - February

Starting from

€1,795

Per person - min 2 pax

cover image
avatar image

4.0

Sagra del totano a Capraia 2025

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€390

Per person

cover image
avatar image
A terrace overlooking the sea: a day to discover the Gulf of Naples

Italy: Naples & Amalfi Coast

1 day - 0 nights

6 departures available

October

€110

Per person

cover image
avatar image

4.3

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

17 departures available

May - October

Starting from

€845

Per person - min 2 pax

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

17604 reviews

avatar placeholder

North-East Sardinia and South Corsica on a sailing boat with gourmet cuisine

10/25/2025

Teresa B.

-

Germany

We were very lucky to spend 7 days with Bledar on his sailboat around Sardinia and Corsica and it was unforgettable! Every day, Bledar surprised us with new, freshly prepared culinary highlights - fresh, creative and prepared with a lot of love. He took care of us touchingly, left nothing to be desired and led us to the most beautiful bays, islands and snorkeling spots. We got to know wonderful people and thanks to his warm nature, everything felt like a vacation with friends. This week was the perfect mix of relaxation, adventure and enjoyment. It was the best holiday we have ever had. Thank you, dear Bledar, for this magical time! ❤️⛵️ Tuttepossible!
avatar image

IBIZA and FORMENTERA - ALL INCLUSIVE - on 18m ketch with skipper

10/25/2025

Sara C.

-

Italy

A week of relaxation, laughter, new friendships, baths, good food, karaoke, and slow life marked by the movements of the sea. Filippo is an expert, sunny captain, attentive to every need, super cook and master of the grill! His dog Nao is an adorable companion for travel and adventures in sup and cycling. The natural beauty of Ibiza and Formentera in October offers breathtaking views between rocky cliffs and blue sea, white sandy beaches and crystal clear water, perfect weather for exploring Formentera by bike and visiting its lighthouses overlooking the sea and well-kept villages. [hidden] comfortable, solid and spacious boat has given us beautiful sailing crossings.
avatar placeholder

Barcolana weekend in Trieste and surroundings.

10/24/2025

Marilisa V.

-

Italy

Marino skipper of great experience and sympathy; Super event and experience just as much!
avatar image

Weekend in Capraia, the island with timeless sunsets

10/22/2025

Don D.

-

Italy

Great weekend !! Sailing until the last breath, all with a good skipper and also crew

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