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

4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€716

Per person

cover image
avatar image

5.0

Super!

From Skiathos to Athens

Greece: Sporades

7 days - 7 nights

One departure available

September

€620

Per person

cover image
avatar image

5.0

Super!

Lose yourself in the magic of the Southern Ionian Islands

Greece: Ionian Islands

7 days - 6 nights

One departure available

August

€1,100

Per person

cover image
avatar image

4.9

Super!

Giglio Island - Festival of Grapes and Open Cellars

Italy: Tuscany

3 days - 3 nights

One departure available

September

€280

Per person

cover image
avatar image

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

cover image
avatar image

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

cover image
avatar image

4.9

Super!

Cyclades from Milos to Milos

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

cover image
avatar image

5.0

Super!

Sailing Holiday with a Hostess Among the Wonders of Northern Sardinia

Italy: Northern Sardinia

6 days - 6 nights

2 departures available

August - September

€1,600

Per person

cover image
avatar image

4.6

Gargano National Park and Marine Protected Area of the Tremiti Islands

Italy: Puglia

4 days - 5 nights

2 departures available

August

€640

Per person

cover image
avatar image

4.9

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

Italy: Tuscany

7 days - 6 nights

2 departures available

August - September

Starting from

€650

Per person

cover image
avatar image

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

Per person

cover image
avatar image

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

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

18523 reviews

avatar image

Different flotilla in Ionian Greece: nature, new friends and fun

08/16/2026

Paolo N.

-

IT

A wonderful experience, but with several critical issues to improve Overall it was certainly a wonderful experience, which allowed us to experience the sea, meet new people and share really pleasant moments. Precisely for this reason, however, I believe it is important to underline some major organizational shortcomings that have negatively affected a part of the trip and which, in my opinion, should absolutely be improved. The first concerns the complete disorganization of the evenings on land. We expected that, since it was a real flotilla made up of 5 boats, reservations would be planned and organized in advance in the clubs, so that we could all be together and experience the evenings as a single group. Instead, we often found ourselves having to organize ourselves, losing precisely that group and flotilla dimension that we expected from the trip. The excursions were also unclear and not always well organized. We would have liked to have had more opportunities to reach particularly beautiful sea areas and, above all, to live some organized experiences to enjoy the sunset from the sea, which on a sailing trip should represent one of the most beautiful moments. Another critical issue was the lack of music on the individual boats, despite the fact that we had been told that the system was working. Considering the type of trip and the spirit of the holiday, having the possibility to put music on board was an element that we expected and that would contribute a lot to the atmosphere. We also had the problem of the rowing tender, due to the engine not working. It is understandable that technical problems may occur, but it would have been important to find an alternative solution quickly, especially considering the need to move smoothly from the boat to land. Finally, and perhaps this is the thing I regretted the most, the final evening was completely unorganized. On a group trip and especially in a flotilla of 5 boats, I would have expected a final moment organized to be all together, celebrate the end of the trip and say goodbye. The lack of a real final goodbye was, in my opinion, a serious lack: after a week shared together, it would have been the least to expect a moment dedicated to closing the experience all together. In conclusion, there is certainly the memory of a beautiful experience and a holiday that could have been really fantastic, but precisely for this reason I believe that these aspects must be taken seriously into consideration. With more organization of activities, evenings and group moments, the trip could have reached a much higher level.
avatar image

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

08/16/2026

federica c.

-

CH

A unique experience, with professionals capable of transmitting knowledge, passion and actively involving. Wonderful places, perfect organization, pleasant group. Ready for more experiences 🫠

Five days in Croatia with skipper, instructor and cook

08/16/2026

Silvia P.

-

IT

It was our first time sailing and we didn't know what to expect. But, thanks to Flavio, everything was perfect! Safe, helpful, with a contagious passion for the sea and excellent skills in the kitchen! The group of people on board made it even more special! Sea, sailing, good food and nice people. What more could you want? Silvia and Fede

A sailing holiday: discovering the Pontine Islands

08/16/2026

Mariagrazia T.

-

IT

Location beyond expectations and the skipper Mattia really special and attentive. To be redone!

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