603

experiences

4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€690

€621

Per person

5.0

Super!

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

10 departures available

June - August

Starting from

€390

€351

Per person

4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

9 departures available

June - October

€650

Per person

4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

6 departures available

July - October

€260

Per person

4.9

Super!

Weekend in the Gulf of Alassio and Gallinara Island

Italy: Liguria

2 days - 2 nights

8 departures available

June - August

Starting from

€250

Per person

New

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

3 departures available

June - July

Starting from

€300

€270

Per person

4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

5 departures available

July - August

Starting from

€900

Per person

4.9

Super!

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

Italy: Tuscany

2 days - 2 nights

3 departures available

June - September

€280

Per person

4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

5 departures available

July - September

Starting from

€400

€360

Per person

5.0

Super!

Sail in Menorca with a cook on board!

Spain: The Balearic Islands

5 days - 5 nights

3 departures available

June - August

Starting from

€950

€808

Per person

4.9

Super!

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

Italy: Tuscany

6 days - 6 nights

11 departures available

June - September

Starting from

€980

Per person

4.9

Super!

Fast Sailing Experience between Authentic Islands and Good Food

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

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

17765 reviews

Three-Day Sailing Tour to the Pontine Islands

06/13/2026

Giorgio T.

the trip to palmarola is wonderful, and the skipper Antonio was very professional, we had a great time,

Magical Bridge to the Pontine Islands

06/12/2026

Federica G.

Fantastic experience! Amazing group and fabulous skippers. Special mention for the Super Costy who spoiled and pampered us for all 4 days!

Summer is made for the Aeolian Islands! Weekly cruise

06/11/2026

Patrizia R.

Very comfortable boat. For the first time I found a skipper who lent himself to the purchase of a galley without waste and in any case complete and integrated by specific requests of the crew. The skipper also prepared tasty meals on board, including typical dishes of the Aeolian culinary tradition. On board we enjoyed a relaxed and very pleasant atmosphere and the stops took place, weather permitting, in the most iconic places of the Aeolian archipelago. It is an experience that I certainly recommend. Patricia

June 2 - cetacean watching expedition in the Pelagos Sanctuary with WWF guide

06/10/2026

Guido F.

Beautiful experience. The enthusiasm and ability to involve biologists is remarkable. The only pity we never sailed.

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!