header cover
sailsquare logo

Private yacht sailing holidays with skipper in the Aeolian Islands

Discover the magic of sailing holidays in the Aeolian Islands! Hire a whole boat: a new way of traveling with your loved one, your friends or your family. Find your dream adventure among thousands of holidays from the Mediterranean to the Caribbeans.

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

October - November

€583

Per person

cover image
avatar image

4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

24 departures available

May - October

Starting from

€600

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

One departure available

October - November

€475

Per person

cover image
avatar image

3.0

7 islands in comfort and convenience

Italy: Aeolian Islands

6 days - 6 nights

One departure available

November

€600

Per person

cover image
avatar image

4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

18 departures available

May - October

Starting from

€680

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

15 departures available

July - October

Starting from

€590

Per person

cover image
avatar image

4.6

Aeolian Islands: wellness, taste, fun with fabulous cook on board

Italy: Aeolian Islands

7 days - 7 nights

8 departures available

July - August

Starting from

€910

€865

Per person - min 2 pax

cover image
avatar image

5.0

EOLIE IN RELAX - Boat with 3 cabins and 3 bathrooms

Italy: Aeolian Islands

6 days - 7 nights

One departure available

October - November

€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

14 departures available

April - October

Starting from

€400

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

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 - Private yacht sailing holidays with skipper in the Aeolian Islands

469 reviews

avatar placeholder

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

10/20/2025

Marco F.

-

Italy

Pasquale is a profound lover and connoisseur of the Aeolian Islands. Beyond the experience at sea, it also suggests excursions and places to visit on land
avatar image

Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

09/29/2025

Stella H.

-

France

Fantastic destination. Great sized catamaran. Food provided by our hostess was good. There are a few of issues that need highlighting: 1. The size of the boat and its starting point changed after I booked online. 2. I had asked if a single supplement applied to my booking as (at the point of booking) the boat/catamaran only had 4 berths. I was told there wasn’t a supplement. We were assigned a larger boat and I was allotted a single cabin - the same size as for the hostess/chef. 3. I did not receive a confirmation by email of what I had booked (so had no evidence of what I was to expect when I arrived). I was in a cabin suitable for a child and had to share a bathroom. There was no WiFi available. I had no exterior window. The fan in my room only worked by connecting 2 loose wires (like hotwiring a car!). The sockets in my room worked intermittently. 4. The skipper was extremely competent in his professional work. However, his English was not good enough to be listed as a second language. In addition, he could have been more regular about informing ALL the passengers at the same time about the itinerary for the day (which differed significantly in order from that on the website). Informing us whilst we were eating would have been the perfect time. 5. On the day of departure we were asked to meet 2 hours earlier than arranged but the cleaners had not finished their work and we left 2 hours behind schedule. This we were sitting around for 4 hours unnecessarily. Better communication might have avoided this. 6. The wording for the itinerary is not clear regarding the transfer from an airport. I feel it needs to be explicit that this isn’t included. 7. The skipper was in a hurry to return to port on the night before last and omitted a final swim stop. He left the boat before the others.
avatar placeholder

Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

09/28/2025

Sara D.

-

Italy

Beyond expectations...
avatar image

Let's discover the Aeolian Islands together by sailing

09/28/2025

Alessandro N.

-

Italy

Very positive experiences, well organized and well managed. Amazing location

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