130

experiences

5.0

New

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€250

Per person

4.0

European Mile Builder - Leg 6: Malta to Gibraltar

Spain: Andalusia

9 days - 9 nights

One departure available

October - November

€550

Per person

4.1

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

37 departures available

January - December

Starting from

€275

€248

Per person

4.7

Squid Festival 2026! - Capraia Isola

Italy: Tuscany

2 days - 2 nights

One departure available

October - November

€250

Per person

4.8

LET'S GO TO TOTANI - Festival in Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€375

Per person

5.0

Weekend in Tuscany between Argentario and Giglio Island

Italy: Tuscany

3 days - 2 nights

3 departures available

October - November

€280

Per person

5.0

Let's discover Portofino, Santa Margherita and Sestri Levante together

Italy: Liguria

2 days - 2 nights

3 departures available

October - November

Starting from

€430

Per person

4.5

Wild Corsica: The Magic of a Boat Trip

France: Corsica

7 days - 7 nights

4 departures available

July - August

Starting from

€1,000

Per person

4.9

E-bike & Sailing Experience with wine tasting on Elba - 2 boats

Italy: Tuscany

3 days - 2 nights

One departure available

October

€250

€238

Per person

4.0

European Mile Builder - Leg 2: Gibraltar to Las Palmas

Atlantic islands: Canary Islands

6 days - 6 nights

One departure available

November

€660

Per person

5.0

2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

Italy: Sicily

2 days - 1 night

3 departures available

October

€215

Per person

4.4

From Martinique to Guadeloupe riding the trade winds

Caribbean: Guadeloupe

10 days - 10 nights

One departure available

February

€1,250

€1,125

Per person

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Reviews - Sailboat holidays & skippered tours

19273 reviews

The Saronic Islands sailing, skippered and on-board kitchen

10/14/2026

Kaija H.

Annalisa and Emanuel hosted a very nice and safe sailing trip in their boat involving everyone. Despite the changed route plans due to bad weather the previous week, they were able to replan us a nice trip in the Cyclades Islands. We visited beautiful natural bays, enjoyed sailing, swimming, snorkling, sun bathing, fishing, ancient historical places and delicious fresh home-cooked food. Annalisa and Emanuel are the best and most patient hosts I have ever had!

Sailing and Trekking in the Aeolian Islands

10/14/2026

Massimo G.

A week in full relaxation in the Aeolian Islands.Mario is a professional and helpful skipper with his customers, putting them immediately at ease, For your holiday in this archipelago I highly recommend to contact him .... MARIO

Barcolana Weekend: experience the largest regatta in the world

10/13/2026

Francesco S.

Ilaria in a nutshell Great skipper Great cook Super nice

The fantastic Saronic Islands and the surroundings of Athens

10/13/2026

Alexander S.

We had an exciting and memorable week on board with Alessandro. We were lucky to enjoy boat trips every day and especially loved sharing his delicious pasta meals. We quickly embraced his Italian spontaneity, with new destinations and ideas along the way, making the experience all the more adventurous and unique. A wonderful week for those who enjoy a relaxed, authentic Italian sailing experience!

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