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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 72 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

5 departures available

August - September

Starting from

€1,041

€989

Per person

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4.7

Weekend Elba o Capraia

Italy: Tuscany

3 days - 2 nights

One departure available

May

€340

€306

Per person

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4.8

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

9 departures available

June - August

Starting from

€395

€356

Per person

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4.8

Long weekend on Elba: 4 days of sun and sailing

Italy: Tuscany

3 days - 3 nights

7 departures available

July - September

Starting from

€410

€369

Per person

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5.0

Week end Elbani

Italy: Tuscany

3 days - 2 nights

7 departures available

May - June

Starting from

€251

Per person

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4.8

Educational Sailing Cruise: from Cagliari to Marina di Pisa

Italy: Tuscany

7 days - 7 nights

One departure available

September

€750

Per person

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4.4

Magnificent weekend of sailing on the island of Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

May - July

€250

Per person

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4.8

Weekend on the Island of Elba

Italy: Tuscany

3 days - 2 nights

3 departures available

April - June

Starting from

€260

€234

Per person

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4.8

Midweek special on the island of Elba, 2 nights

Italy: Tuscany

3 days - 2 nights

2 departures available

September

€260

€234

Per person

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4.8

Special May - Weekend on Elba

Italy: Tuscany

3 days - 2 nights

2 departures available

May

€220

€198

Per person

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4.9

Four days exclusively on Elba between aperitifs and sailing

Italy: Tuscany

4 days - 3 nights

12 departures available

April - October

Starting from

€250

Per person

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4.7

Trekking & Sailing to discover Capraia

Italy: Tuscany

3 days - 2 nights

One departure available

May

€299

€269

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 Tuscany

3508 reviews

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Midweek special on the island of Elba, 2 nights

01/24/2026

Sara M.

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Italy

I left with my brother: there were 7 of us, plus Marco. It was our first boat experience and we couldn't ask for anything better! Marco was extremely kind, helpful and attentive to every detail. The combination of the boat excursion and the trekking on the island was simply fantastic, everything impeccably organized. In addition, there was also the opportunity to enjoy free time in total relaxation. I absolutely recommend this experience with Marco!
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Experience the Befana as you have never seen it before... by boat!

01/14/2026

federico b.

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Italy

Beautiful 4 relaxing days despite the adverse weather, the legendary Francesco solved with trips to beautiful and really interesting places, excellent crew immediately close-knit.
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Weekend on Elba "Only for four" for maximum comfort

11/25/2025

D. D.

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Italy

Great weekend! Impeccable welcome on Friday evening, really much appreciated. Very professional and prepared skipper (also the other crew members) - experienced hands-on in the challenging (but fun) crossing. I learned a lot (main objective - achieved). I hope to have the chance of another experience together soon.
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Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/10/2025

giulia f.

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Italy

I participated in the weekend on a sailing boat organized for the Squid Festival and I couldn't ask for anything better! It was a wonderful experience, between sea, wind and excellent company. The crew was great: nice people and with a great desire to have fun. The skipper is super professional, but also helpful and attentive to let us experience sailing in a relaxed and fun way. I can't wait to get back on board for the next adventure! ⚓️🐙✨ Giulia, Eva and Martina

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