header cover
sailsquare logo

Sailboat yacht sailing holidays & tours in Aeolian Islands

Discover more than 14 opportunities to get on board a Sailboat adventure in Aeolian Islands. A unique experience with a local skipper, starting at €350 a week.

cover image
avatar image

4.8

Super!

Let's discover the Aeolian Islands together in Vela

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€690

Per person

cover image
avatar image

5.0

Super!

We have known the Aeolian Islands for 20 years. - Live them with us.

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

October - November

€583

Per person

cover image
avatar image

5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September

€689

Per person

cover image
avatar image

5.0

Super!

Island of Vulcano (Aeolian Islands) in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

2 days - 1 night

One departure available

September

€265

€239

Per person

cover image
avatar image

4.5

The hidden jewels of the Aeolian Islands sailing from Palermo

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

September - November

Starting from

€475

€451

Per person

cover image
avatar image

3.0

7 islands in comfort and convenience

Italy: Aeolian Islands

6 days - 6 nights

6 departures available

September - November

Starting from

€600

Per person

cover image
avatar image

4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

September - October

Starting from

€625

Per person

cover image
avatar image

4.9

Between seas and volcanoes, fall in love with the Aeolian Islands

Italy: Aeolian Islands

5 days - 4 nights

3 departures available

September - October

€590

Per person

cover image
avatar image

5.0

EOLIE IN RELAX - Boat with 3 cabins and 3 bathrooms

Italy: Aeolian Islands

6 days - 7 nights

6 departures available

September - November

Starting from

€433

Per person

cover image
avatar image

5.0

Sea, sailing and relaxation in the beautiful Aeolian archipelago

Italy: Aeolian Islands

4 days - 4 nights

4 departures available

September - October

€600

Per person

cover image
avatar image

4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

One departure available

November

€650

€585

Per person

cover image
avatar image

5.0

We circumnavigate the Aeolian Islands starting from Vulcano

Italy: Aeolian Islands

6 days - 6 nights

4 departures available

September - October

Starting from

€550

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 Aeolian Islands

1804 reviews

avatar placeholder

A week in the Aeolian Islands - 6 islands in seven days

09/15/2025

Ilaria I.

-

Italy

Top experience! Nicola, the skipper, is nice and super reliable, he took us to magnificent places, he was understanding to put up with us all, always available even with the kitchen, but never intrusive, and proposed an itinerary based on the weather that allowed us to see 6 islands, and allowing those who wanted to disembark on land and take turns in the village, or stay on the boat for those who, like me, prefer to enjoy the beauty of the roadstead. Very beautiful and spacious boat, as much as a sailboat can be, equipped with many small modernity and comforts. Even the group that was created with the other participants was beautiful and cohesive, leaving everyone their own freedoms. The journey to reach the Aeolian Islands and to return, starting from Livorno, was not the easiest and most direct, but it was really worth it, so don't be discouraged but leave and choose Nicola, a man of the sea and experience, and you will feel "safe". What to add if not one I hope "see you soon!" Thank you Nicola and your [hidden]!
avatar image

A week in the Aeolian Islands - 6 islands in seven days

09/14/2025

Philippe H.

-

Belgium

Discovery of the Aeolian Islands with a friendly crew. Simple comfort and in line with our expectations. Cruise for lovers of the sea and extraordinary volcanic landscapes.
avatar placeholder

Let's discover the Aeolian Islands together in Vela

09/13/2025

Antoine D.

-

Canada

Very nice week aboard Mario's sailboat. The extraordinary landscapes and crystal clear water were there. Swimming every day, visiting the islands, each more charming than the next, and nights under the stars lulled to the rhythm of the waves. I recommend!
avatar placeholder

Magical Aeolian Islands

09/13/2025

Giulia T.

-

Italy

We did the tour of the Aeolian Islands in the last week of August and we got on very well with Francesco. Super professional and a great commander. It was truly a wonderful experience. Not to mention the islands. Wonderful!

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