header cover
sailsquare logo

Sailboat yacht sailing holidays & tours in Ionian Islands

Discover more than 25 opportunities to get on board a Sailboat adventure in Ionian Islands. A unique experience with a local skipper, starting at €350 a week.

25

experiences

cover image
avatar image

4.8

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Duration:

7 days - 7 nights

Greece:

Ionian Islands

avatar image
avatar image
avatar image

68 travellers

Starting from

€650

€722

Per person

cover image
avatar image

5.0

Super!

Corfu and the Ionian Islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

avatar image
avatar placeholder

2 travellers

€711

€790

Per person

cover image
avatar image

5.0

Sailing WellEssere in Ionian Greece

Duration:

7 days - 7 nights

Greece:

Ionian Islands

avatar image
avatar placeholder
avatar placeholder

6 travellers

Starting from

€1,215

€1,350

Per person

cover image
avatar image

4.4

In the Sea of Ulysses among the most beautiful islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

avatar image
avatar placeholder
avatar placeholder

4 travellers

Starting from

€675

€750

Per person

cover image
avatar image

4.9

Super!

Sailing Cruise in the Ionian Islands

Duration:

7 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

€665

€700

Per person

cover image
avatar image

3.7

Adventure around Lefkada, Khefalonia, Ithaca and Zakynthos

Duration:

6 days - 6 nights

Greece:

Ionian Islands

avatar placeholder
avatar placeholder
avatar placeholder

4 travellers

Starting from

€522

€549

Per person

cover image
avatar image

4.9

Flotilla in Ionian Greece (sailboats with gennaker)

Duration:

6 days - 7 nights

Greece:

Ionian Islands

avatar placeholder
avatar placeholder

2 travellers

€1,150

Per person

cover image
avatar image

4.3

Weekend a Corfù

Duration:

3 days - 3 nights

Greece:

Ionian Islands

Give this experience a try!

€390

Per person

cover image
avatar image
YogaSail, Yoga Retreat on board a sailboat in the Ionian Islands

Duration:

7 days - 7 nights

Greece:

Ionian Islands

avatar placeholder
avatar placeholder
avatar placeholder

9 travellers

€850

Per person

cover image
avatar image

4.9

One-way flotilla in Ionian Greece from Zakynthos to Lefkas

Duration:

6 days - 7 nights

Greece:

Ionian Islands

avatar placeholder
avatar placeholder
avatar placeholder

7 travellers

€1,050

Per person

cover image
avatar image

5.0

Corfù Paxos Antipaxos

Duration:

6 days - 6 nights

Greece:

Ionian Islands

avatar placeholder
avatar placeholder
avatar placeholder

12 travellers

Starting from

€900

Per person

cover image
avatar image

4.9

Corfu to Kalamata by magnificent 15-meter boat

Duration:

10 days - 10 nights

Greece:

Ionian Islands

Give this experience a try!

€700

Per person - min 2 pax

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

780 reviews

avatar placeholder

Gone with the Wind: Corfu and the Ionian Islands

04/1/2025

jenna C.

-

Canada

I was so excited to go sailing in Greece. This dream unfortunately took a quick turn into a nightmare. The captain didn’t take us to any of the sites listed on the itinerary. We stayed close to the original port the whole trip. We would ask him each day to go to one of the listed places and he would just ignore the suggestions. He would also blame it each day on the weather yet we had beautiful weather the whole trip, minus the first day. The boat itself was constantly breaking down. We had a broke toilet which was not a plus. But the worst part of the trip was when the captain used the outside shower in front of myself and a few of the other girls on the boat. He proceeded to take his swim shorts off deliberately flashing his private parts to us. All the lady’s became super uncomfortable on the boat afterwards. It was super inappropriate. Would highly recommended spending your money elsewhere. Was a horrific experience.
avatar placeholder

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

03/23/2025

Matt V.

-

United States

Absolutely phenomenal sailing adventure with Alessandro and Andrea! From the moment we stepped aboard in Corfu with our three children (ages 7, 10 and 12), we knew we were in expert hands. They crafted the perfect itinerary, taking us to the stunning islands of Paxos and beyond, revealing the hidden gems of Greece. Our days were filled with unforgettable experiences: hiking to ancient temples, swimming and snorkeling in pristine bays, collecting sea shells, exploring historic castles, and wandering through charming seaside towns. The boat was incredibly comfortable, making our nights as enjoyable as our days. The meals onboard were all excellent as well and the accomodations were clean and cozy. Alessandro and Andrea's hospitality was truly exceptional. They are not only skilled sailors, but also passionate guides, sharing their love for Greece with us. They even played Uno with our kids every afternoon. Their knowledge and enthusiasm made this vacation one of the best we've ever had. Thank you, Alessandro and Andrea, for showing us the most beautiful side of Greece! You are simply the best! 5 stars without a doubt.
avatar placeholder

The alternative to the catamaran in the Ionian Islands

10/15/2024

Belinda B.

-

Australia

Best live aboard sailing trip I have done. The boat was exceptionally comfortable and everything clean and in ship shape ! The skipper was great at helping us learn the ropes to participate in the sailing if we wanted to. I loved having the SUP and snorkel sets on board to use when we moored in beautiful bays. It was terrific to catch fresh fish to eat along the way too. Thanks so much to Manuele for making my first trip to Greek Is such a wonderful experience.
avatar placeholder

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

10/7/2024

Lorenza G.

La barca è molto accogliente e ben tenuta. Lo skipper molto competente, disponibile e rassicurante. Abbiamo navigato a vela e fatto bellissimi bagni nonostante il meteo non sia stato dei migliori. Esperienza da consigliare.

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

MastercardVisaAmerican ExpressApple pay

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