Homepage cover
sailsquare logo

Sailboat yacht sailing holidays & tours in Ionian Islands

Discover more than 12 opportunities to get on board a Sailboat adventure in Ionian Islands. A unique experience with a local skipper, starting at €350 a week.

cover image
avatar image

4.8

Super!

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

Greece: Ionian Islands

7 days - 7 nights

10 departures available

May - July

Starting from

€650

€585

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

29 departures available

March - October

Starting from

€460

Per person

cover image
avatar image

5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

31 departures available

March - October

Starting from

€460

Per person

cover image
avatar image

4.4

Sailing from the magnificent Peloponnese to beautiful Zakynthos and Kefalonia

Greece: Ionian Islands

6 days - 7 nights

One departure available

July - August

€660

Per person

cover image
avatar image

4.4

Sailing in the footsteps of Ulysses: Kefalonia, Ithaca and Lefkada

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€660

Per person

cover image
avatar image

4.3

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

17 departures available

May - October

Starting from

€845

€761

Per person - min 2 pax

cover image
avatar image

5.0

Ionian Islands by Sailing: Trekking, Snorkeling and Sea Adventure

Greece: Ionian Islands

6 days - 6 nights

3 departures available

January - December

€500

Per person

cover image
avatar image

4.4

Preveza, Antipaxos, Paxos and Corfu: between extraordinary landscapes and sea

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€690

Per person

cover image
avatar image

4.3

Gone with the Wind, Corfu and the Poseidon Islands

Greece: Ionian Islands

6 days - 7 nights

3 departures available

September

€630

Per person

cover image
avatar image

4.4

From Greece to Italy, sailing between Corfu, Santa Maria di Leuca, Gallipoli and Crotone

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€660

Per person

cover image
avatar image

4.3

In the Sea of Ulysses among the most beautiful islands on Bavaria 50 with hostess

Greece: Ionian Islands

6 days - 7 nights

8 departures available

July - August

Starting from

€750

€638

Per person

cover image
avatar image

5.0

Exclusive sailing week among the wonders of Ionian Greece

Greece: Ionian Islands

6 days - 7 nights

One departure available

October

€1,200

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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 yacht sailing holidays & tours in Ionian Islands

850 reviews

avatar placeholder

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

10/19/2025

Jean-Loup N.

-

Switzerland

Hello! We had a wonderful time with Andrea and Marta around the islands of Corfu, Paxos, and Antipaxos, discovering their hidden gems. The boat was spotless and spacious (we were five on board); everything was perfectly taken care of, and all I had to do was relax on the deck. As is often the case in the Mediterranean, sailing conditions aren’t always ideal, and our skipper preferred using the motor rather than the sails — which made the trip smooth and relaxing as we cruised from one beautiful anchorage to another. A special note for fans of the Netflix series Maestro in Blue: you might even come across the filming set — or the director and crew — during your cruise! Thank you again, Andrea and Marta! Cheers!
avatar placeholder

Pack your suitcase and we'll take care of the rest!! Stewards on board!

10/15/2025

Elena L.

-

Germany

Everything was simply perfect! The crew was incredibly flexible and accommodated all of our individual requests. We felt comfortable, well looked after, and completely safe at all times. The food was excellent and always freshly prepared for us. An all-around wonderful experience that we would repeat anytime. Highly recommended!
avatar placeholder

Pack your suitcase and we'll take care of the rest!! Stewards on board!

10/7/2025

Sharron G.

-

United Kingdom

We were the last group to sail this year & enjoyed reading the other reviews as everyone had such positive feedback. We weren’t disappointed and although the weather wasn’t kind to us we couldn’t have had a better experience. Alessandro is an amazing skipper, he’s young but he’s been sailing forever & certainly knows his way around his boat and the waters & islands we sailed around. He made you feel safe & well looked after. Carlo couldn’t do enough for us all & his food & hospitality were excellent, making us laugh as we tried to speak Italian. We couldn’t believe how he was able to serve up the dishes from the tiny galley kitchen. Something different every day and he even caught a tuna & that was served up for lunch, you don’t get fresher than that. We couldn’t have had a better adventure with better crew. Thank you Alessandro & Carlo! PO5 will return xxxxx
avatar placeholder

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

10/6/2025

Corinne W.

-

Switzerland

It was very nice and beautyful, when the sun was shining.☀️We had a good time and the crew was very nice, helpful. And kind. Thank you!

Customer Support

nightLifeGeneralInfo

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!

search

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