342

experiences

4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

4 departures available

September - October

Starting from

€600

€540

Per person

4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

3 departures available

August - September

Starting from

€312

Per person

5.0

Wellness, sun, sea and adventure: a weekend full of sailing!

Italy: Tuscany

3 days - 2 nights

One departure available

September

€230

Per person

4.5

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

2 departures available

August

Starting from

€850

Per person

4.8

Discovering the Aeolian Islands Between Nature, Relaxation and Fun

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

August - September

Starting from

€845

Per person

5.0

Super!

A sailing story between Favignana, Levanzo and Marettimo

Italy: Aegadian islands

7 days - 7 nights

3 departures available

August - September

Starting from

€640

Per person

4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

4 departures available

August - October

Starting from

€860

Per person

5.0

Super!

Kefalonia to Corfu

Greece: Ionian Islands

6 days - 6 nights

One departure available

August - September

€900

Per person

4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

2 departures available

August

€990

Per person

4.9

Super!

Sail to the edge of the world among the wonders of the North (cottage + sailboat)

North Sea: Norway

7 days - 7 nights

One departure available

October

€1,200

Per person

4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€280

Per person

4.9

Super!

Rhodes Kalymnos South Dodecanese on magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,200

Per person - min 2 pax

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Reviews - Sailboat holidays & skippered tours

18359 reviews

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

08/4/2026

Sarah L.

This trip was way above my expectations. Matteo is a terrific skipper, everything was perfectly planned, the itinerary was great and well balanced between different bays to enjoy the sea, and some places where we could visit small beautiful towns. We had a lovely time with the others as well, we all became friends quite quickly through Matteo’s sense of community, the week was a delight. Thank you again for this unexpected experience, I am very grateful.

Face to face with the Archipelago(s)

08/4/2026

Noemi V.

Overall very positive experience. The weather conditions also allowed us to unfurl the sails. The skipper accompanied us with great professionalism and unparalleled sympathy. Thank you Frankie! Hoping to replicate!

Sailing in Tigullio: Half-Day Experience from Rapallo

08/4/2026

LUCA ADRIANO B.

Well organized sailing excursion. We bathed, without haste, in two beautiful places.. Captain and crew treated us well with lots of focaccia and pizza for a snack!

The Island of Elba, to make you live a special experience!

08/4/2026

Silvia P.

Beautiful boat experience, attention to guests is above everything. Skipper friendly person, always attentive, from the first moment of meeting. His pastes are good, in particular the garlic, oil and chilli, to take your breath away... with a good glass of wine, then, everything tastier!! ... and a good master of knots ... Seriously, great holiday!

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