118

experiences

5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

3 departures available

August

Starting from

€849

Per person

5.0

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

Italy: Tuscany

3 days - 2 nights

3 departures available

July - September

Starting from

€230

Per person

5.0

Tuscany and Corsica: sailing sun adventure good food energy and well-being

Italy: Tuscany

3 days - 3 nights

3 departures available

June - September

Starting from

€350

Per person

4.7

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

42 departures available

January - December

Starting from

€275

€261

Per person

5.0

Super!

Tuscan Archipelago: night and day sailing

Italy: Tuscany

4 days - 3 nights

One departure available

August

€320

€272

Per person

4.9

Super!

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

Italy: Tuscany

7 days - 6 nights

8 departures available

August - September

Starting from

€650

Per person

4.9

Super!

VelaTrek weekend on the Island of Elba All-inclusive - 2 boats

Italy: Tuscany

3 days - 2 nights

One departure available

September

€390

€351

Per person

4.9

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

5 departures available

May - June

Starting from

€350

€315

Per person

5.0

Super!

A day of sun and swimming

Italy: Tuscany

1 day - 0 nights

One departure available

June

€70

Per person

4.9

Super!

Discovering the Island of Elba: 3 days of sea, wind and sun

Italy: Tuscany

3 days - 3 nights

3 departures available

May - June

Starting from

€400

€360

Per person

4.9

Super!

On holiday with Dad to discover Elba and Capraia

Italy: Tuscany

4 days - 4 nights

3 departures available

June

€400

Per person

4.9

Super!

Weekend of relaxation and fun to discover the Island of Elba

Italy: Tuscany

3 days - 2 nights

5 departures available

May - September

Starting from

€299

Per person

Why book a holiday with Sailsquare?

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Reviews - Sailboat yacht sailing holidays & tours in Tuscany

3530 reviews

May 1st long weekend between Elba and Capraia - 2 boats in company

05/6/2026

Massimo A.

Italy

Matteo is the most knowledgeable person on sailing I have ever met, and his boat has a comfort far superior to normal charters, having 18 meters in length. Perfect organization and reliability. The tour of Elba is easy but wonderful

May Day between Elba and Capraia

05/6/2026

Silvia V.

Italy

Very competent skipper, with a choice of stages always careful and well thought out to avoid possible inconveniences and please everyone. Thanks to the good weather and the favorable wind, it was the perfect combination of sailing and moments of relaxation and conviviality."

May Day between Elba and Capraia

05/5/2026

Eugenia C.

Italy

We had a good time, company as unlikely as it is fun. Fantastic weather, beautiful sea

May 1st long weekend between Elba and Capraia - 2 boats in company

05/4/2026

simone m.

Italy

Matteo is super fantastic, professional to the max with a pinch of irony that puts all his guests at ease!!

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