193

experiences

4.9

Super!

Giglio Island - Festival of Grapes and Open Cellars

Italy: Tuscany

3 days - 3 nights

One departure available

September

€280

Per person

4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

5 departures available

September - October

Starting from

€230

Per person

4.9

Super!

Three days of adventure in the Aeolian Islands

Italy: Aeolian Islands

3 days - 3 nights

One departure available

September

€400

Per person

4.9

Super!

Cyclades from Milos to Milos

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

5.0

Super!

Weekend between Ponza and Palmarola Comfortable - max 4 people

Italy: Pontine Islands

2 days - 2 nights

One departure available

September

€440

€396

Per person

5.0

Super!

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

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

€760

Per person

4.8

Super!

All Inclusive Tour: Capri, Amalfi, Cetara, e Sorrento

Italy: Naples & Amalfi Coast

5 days - 5 nights

One departure available

September

€1,150

Per person

4.8

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

One departure available

September

€980

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

September

€1,000

€750

Per person

5.0

Super!

Croisière de rêve sous voiles dans les îles de la société 14 Jours

Pacific Ocean: French Polynesia

13 days - 13 nights

One departure available

October - November

€2,090

Per person

4.8

Super!

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€600

Per person

4.9

Super!

Four days in the Aeolian Islands from Capo D'Orlando

Italy: Aeolian Islands

4 days - 4 nights

One departure available

September

€400

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

18993 reviews

Flotilla Smeralda: La Maddalena Archipelago with Velasquez - MEN'S SEATS ONLY

09/1/2026

Chiara F.

A memorable holiday, shared with special people and sea lovers. We saw beautiful corners, alternating evenings in port and at anchor. The organizer, the best!

La Dolce Vita on a sailboat: discovering the Côte d'Azur

09/1/2026

Lidia E.

A wonderful week, between great wind and great fun, flown away really too quickly! Andrea is a trained, safe skipper and excellent company. He was available to explain the maneuvers, to let us practice and to always give us new notions and ideas about navigation, with a lot of patience. The boat, comfortable and spacious, allowed us to enjoy the sea to the fullest. The company took care of the rest: a truly unique, pleasant group united by a beautiful desire for wind and learning. The atmosphere of availability and sharing that was created among everyone was also very nice. In short, a special and truly stimulating holiday!

Holiday in the Aeolian Islands: comfort, adventure and music! - Cook on board

09/1/2026

Salvatore S.

We had a pleasant week. We were treated with attention. Excellent food and nice company.

The Mediterranean Flotilla: Capri, Ischia, Procida and the Pontine Islands - ONLY MEN SEATS

09/1/2026

Monica F.

Fantastic experience, we went around the islands with unforgettable nights at anchor, many dives and aperitifs at sunset. Personally, I found the right compromise between fun and moments of relaxation. A special thanks to the skipper of our boat who was always attentive, competent and available to our requests.

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 20 3514 4220

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!