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

5.0

Super!

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

Croatia: Split Archipelago

7 days - 7 nights

One departure available

September

€1,100

Per person

cover image
avatar image

5.0

Super!

A week from Palmarola to Ventotene, passing through Ponza

Italy: Pontine Islands

7 days - 7 nights

One departure available

September

€795

Per person

cover image
avatar image

5.0

Super!

Paros-Naxos and Small Cyclades

Greece: Cyclades

5 days - 5 nights

One departure available

September

€900

Per person

cover image
avatar image

4.9

Super!

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

Italy: Tuscany

2 days - 2 nights

One departure available

September

€280

Per person

cover image
avatar image

5.0

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

September - October

€1,080

Per person

cover image
avatar image

4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

3 departures available

October

Starting from

€294

Per person

cover image
avatar image

5.0

Super!

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Italy: Lake Garda

1 day - 0 nights

3 departures available

September - October

€99

Per person

cover image
avatar image

5.0

Super!

Weekend of fun and relaxation on a sailing boat on the island of Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€250

Per person

cover image
avatar image

4.9

Super!

Sailing adventure in Norway: chasing the Northern Lights

North Sea: Norway

7 days - 7 nights

2 departures available

January - December

€1,200

Per person

cover image
avatar image

4.9

Super!

Traveling and Dreaming in the Gulf of Poets - All inclusive

Italy: Liguria

2 days - 2 nights

One departure available

May

€360

Per person

cover image
avatar image

5.0

Super!

Weekend Garda Lake 

Italy: Lake Garda

2 days - 2 nights

One departure available

October

€179

Per person

cover image
avatar image

4.8

Super!

Weekend sailing in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

September

€290

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

17438 reviews

avatar placeholder

Sailing holiday on the Côte d'Azur: discover the charm of the French Riviera

09/15/2025

Vittoria R.

-

Italy

Although the weather was not the best, the experience was overall positive between the excellent company we were lucky enough to find and the evocative places visited. Our skipper Manuel stood out for his friendliness, patience and attention to everyone's needs, We had a lot of fun!
avatar placeholder

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

09/15/2025

Patrik D.

-

Germany

The one week on the boat "[hidden]" with Skipper Paolo and Sailor Vitorrio was absolutly amazing and passed way too fast. Paolo is a really good skipper who knows the best spots, best bays and best restaurants all while explaining and teaching you about sailing. Vitorrio is a superb sailor, always helpfull and upbeat, excellent cook and perfect apnea buddy. The north coast of Sardegna and southcoast of Corsica hold pristine beaches, amazing sunsets and delicious food and life on board feels like class trip with only the best things of it. Can recommend it sincerly to everybody, no matter age or origin, just go and do it and see for yourself!
avatar placeholder

Gulf of Poets and Cinque Terre

09/15/2025

Mariangela C.

-

Italy

A perfect sailing weekend! Giorgio and Francesca made us feel at home right away, they wisely modified the itinerary based on the sea conditions, allowing us to fully enjoy the experience. Top boat! To be repeated
avatar placeholder

Weekend Elba o Capraia

09/15/2025

Valentina N.

-

Italy

Very prepared skipper, fun crew so overall an excellent experience definitely to be repeated.

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