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

4.7

Flotilla Marmaglia Sun & Fun - Croatia

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

€1,180

€1,080

Per person

cover image
avatar image

4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

8 departures available

July - September

Starting from

€700

Per person

cover image
avatar image

4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

2 departures available

August

€1,290

€1,190

Per person

cover image
avatar image

4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

11 departures available

July - October

Starting from

€590

Per person

cover image
avatar image

4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€1,260

€1,070

Per person

cover image
avatar image

4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

8 departures available

July - September

Starting from

€600

€570

Per person

cover image
avatar image

4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

11 departures available

July - October

Starting from

€1,200

€1,080

Per person

cover image
avatar image

4.7

Midweek sailing trip in the Gulf of Naples

Italy: Naples & Amalfi Coast

3 days - 3 nights

One departure available

July

€390

Per person

cover image
avatar image

4.7

Marmaglia mini-flotilla: discovering the Kornati Islands

Croatia: Kornati Islands

7 days - 7 nights

One departure available

August

€1,140

€950

Per person

cover image
avatar image

4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

4 departures available

July - September

Starting from

€795

Per person

cover image
avatar image

4.6

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

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

€1,110

€999

Per person

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

11 departures available

July - October

Starting from

€570

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

17938 reviews

Sail in Menorca with a cook on board!

07/3/2026

Véronique S.

Everything was perfect! Very neat and very clean boat! Delicious Maussi's food and Alex the skipper very attentive and professional. You feel like part of a family. I recommend 100%.
avatar image

Four days in the Pontine Islands, just a stone's throw from Rome

07/3/2026

Simone G.

-

IT

I spent fantastic days with Antonio: a true lover of the sea who knows what he is doing. Take it easy with him: he steers the boat safely and stress-free, always with a steady hand and a lot of experience. He knows perfectly the best places to anchor, the most hidden coves and the tricks of the weather, so every stop becomes a small treasure. Antonio is nice, helpful and knows how to put everyone at ease, even those who are at their first experience on a boat and, very importantly, he turned out to be an excellent cook!
avatar image

From Mykonos to Milos

07/2/2026

Maximiliano S.

-

AR

Great experience, we traveled 2 couples and we are very grateful for all the attention provided by Andrea, we sailed through all the cyclades and she made us enjoy and share great moments and know places. Unique and incredible and having fun with our travel companions Elena, Patrick and Toni, who were very funny. A sublime experience.

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

07/2/2026

Luigi C.

-

IT

Good evening, the all-inclusive writing is misleading as it is not clear from the program that to go down to Positano and Capri there are other costs to be divided among the participants.

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