header cover
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!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

8 departures available

August - October

Starting from

€570

Per person

cover image
avatar image

5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

August - October

Starting from

€690

Per person

cover image
avatar image

4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

3 departures available

August - September

Starting from

€1,041

Per person

cover image
avatar image

5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€1,100

Per person

cover image
avatar image

5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

3 departures available

August - September

Starting from

€1,150

€1,035

Per person

cover image
avatar image

5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

11 departures available

August - October

Starting from

€570

Per person

cover image
avatar image

4.7

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

Italy: Tuscany

6 days - 7 nights

2 departures available

July - August

Starting from

€1,052

€999

Per person

cover image
avatar image

5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

3 departures available

August - September

Starting from

€950

Per person

cover image
avatar image

4.4

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

France: French Riviera and Porquerolles

6 days - 7 nights

8 departures available

July - September

Starting from

€730

€657

Per person

cover image
avatar image

4.8

Super!

Sailing among the Islands of Ulysses. Stewardess on board

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€800

Per person

cover image
avatar image

5.0

Super!

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

2 departures available

July

Starting from

€300

€270

Per person

cover image
avatar image

4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

8 departures available

July - October

Starting from

€230

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

18086 reviews

Long weekend among the queens of the archipelago - Elba and Capraia

07/15/2026

Giovanni P.

-

IT

Great experience!! Edoardo top, beautiful boat, scary sea!!

Amazing Pontine Islands on a sailboat with private bathrooms

07/15/2026

Teodora Raffaella B.

-

IT

Beautiful holiday Skipper Top company 6 out of 8 gorgeous, another couple from Naples no, they smoked too much and were noisy and screaming,

Cast off for a week at sea, a thousand ways to experience it!

07/15/2026

Michael J.

-

DE

Our one-week sailing trip through the Saronic Gulf deserved a definitive 5-star rating for its perfect blend of adventure and incredible food. We explored the car-free streets of Hydra and swam in the crystal-clear, secluded bays of Dokos. Captain Alexandre amazed us, especially with a rich, authentic Bolognese that tasted like it simmered for hours. Our stops in Spetses and Poros offered beautiful views, but the true highlight was dining right on deck. Captain Alexandre's perfectly creamy risotto easily rivaled any high-end restaurant we found onshore. Each night ended with stargazing and the gentle rocking of the yacht under the Greek sky. This five-star combination of spectacular island views and gourmet sailing cuisine made for an unforgettable journey.

Corfu between bays, taverns and myths.

07/15/2026

Chrystel O.

-

FR

Wonderful experience ! Nice and friendly people on board. Beautiful landscapes. Would definitely book again with this crew anywhere :)

Customer Support

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!

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