header cover
logo

Log in

Summer best deals

cover image
avatar image

4.8

Ionian Greece on a sailboat made entirely of wood

Greece: Ionian Islands

,

From May 30 to Jun 5

4 spots
available

€500

€450

Per person

cover image
avatar image

4.8

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

,

From May 30 to Jun 6

8 spots
available

€640

€576

Per person

cover image
avatar image
Sailing the Small Cyclades with Hostess

Greece: Cyclades

,

From May 30 to Jun 6

6 spots
available

€1,320

€1,188

Per person

cover image
avatar image

4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

,

From May 30 to Jun 6

8 spots
available

€850

€765

Per person

cover image
avatar image

4.5

Premium

DALMATIAN Paradise - Catamaran cruise with hostess FULL BOARD

Croatia: Split Archipelago

,

From May 30 to Jun 6

12 spots
available

€1,520

€1,292

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

,

From May 30 to Jun 6

Rebekah and Suzanne

have already booked

€1,300

€975

Per person

cover image
avatar image

5.0

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

,

From May 30 to Jun 6

6 spots
available

€550

€495

Per person

cover image
avatar image

New

Egadi mon amour: seven days to fall in love, be amazed and relax.

Italy: Aegadian islands

,

From May 30 to Jun 6

8 spots
available

€600

€540

Per person

cover image
avatar image

4.6

Enjoy: in the blue of the Aeolian Islands

Italy: Aeolian Islands

,

From May 30 to Jun 5

7 spots
available

€630

€567

Per person

cover image
avatar image

4.5

Premium

GUADELOUPE Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Guadeloupe

,

From May 30 to Jun 6

12 spots
available

€1,385

€1,247

Per person - min 2 pax

cover image
avatar image

4.5

Premium

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

,

From May 30 to Jun 6

12 spots
available

€1,540

€1,386

Per person - min 2 pax

cover image
avatar image

4.5

Premium

ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Saint Martin

,

From May 30 to Jun 6

12 spots
available

€1,385

€1,247

Per person - min 2 pax

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Sailsquare

Travellers

Providers

Follow us on

FB IconIG IconYT Icon

Secure payments

MastercardVisaGoogle PayApple Pay

Top Destinations

Top Travel Ideas

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964