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2005 - 2025
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Top trending Sailboats in Tuscany
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+100 sailboats available
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Rental Sailboat Jeanneau Sun Odyssey 51 Portoferraio
Rental Sailboat Jeanneau Sun Odyssey 51 Portoferraio

Portoferraio

5.0(6)

Dufour335GL (1993)

  • Skipper mandatory
  • Sailboat
  • Super owner
8 people · 3 cabins · 8 berths · 15 m
  • Fuel included

From 
$725 / day

Rental Sailboat IW Varvet IW40 Piombino
Rental Sailboat IW Varvet IW40 Piombino

Piombino

4.5(13)

IW Varvet IW40 (1979)

  • Skipper mandatory
  • Sailboat
8 people · 2 cabins · 6 berths · 12 m

From 
$337 / day

Rental Sailboat Hallberg Rassy Hallberg rassy 42E Porto Ercole
Rental Sailboat Hallberg Rassy Hallberg rassy 42E Porto Ercole

Porto Ercole

5.0(14)

Sailboat Hallberg Rassy Hallberg rassy 42E 13.00m (1990)

  • Skipper optional
  • Sailboat
  • Super owner
6 people · 2 cabins · 6 berths · 13 m

From 
$665 / day

Rental Sailboat Dufour 385 Grand Large Marina di Grosseto
Rental Sailboat Dufour 385 Grand Large Marina di Grosseto

Marina di Grosseto

4.9(8)

Sailboat Dufour 385 Grand Large 11.76m (2010)

  • Skipper mandatory
  • Sailboat
  • Super owner
5 people · 2 cabins · 4 berths · 11.8 m
  • Fuel included

From 
$484 / day

Rental Sailboat Hanse 411 Marina di Grosseto
Rental Sailboat Hanse 411 Marina di Grosseto

Marina di Grosseto

5.0(5)

Sailboat Hanse 411 12.65m (2003)

  • Skipper mandatory
  • Sailboat
  • Super owner
8 people · 3 cabins · 6 berths · 12.7 m

From 
$519 / day

Rental Sailboat  Hanse 460 - 4 cabine - 2 bagni - 8 posti letto Castiglioncello
Rental Sailboat  Hanse 460 - 4 cabine - 2 bagni - 8 posti letto Castiglioncello

Castiglioncello

New

Sailboat Hanse 460 - 4 cabine - 2 bagni - 8 posti letto 14.00m (2025)

  • Skipper optional
  • Sailboat
8 people · 4 cabins · 8 berths · 14 m

From 
$432 / day

Rental Sailboat Dufour 445 grand large Monte Argentario
Rental Sailboat Dufour 445 grand large Monte Argentario

Monte Argentario

4.6(19)

Sailboat Dufour 445 grand large 13.35m (2012)

  • Skipper mandatory
  • Sailboat
  • Super owner
10 people · 4 cabins · 6 berths · 13.4 m

From 
$492 / day

Rental Sailboat Jeanneau Sun Odyssey 380 San Vincenzo
Rental Sailboat Jeanneau Sun Odyssey 380 San Vincenzo
Special offer

San Vincenzo

4.9(2)

Sailboat Jeanneau Sun Odyssey 380 11.75m (2023)

  • Without captain
  • Sailboat
  • Super owner
6 people · 3 cabins · 6 berths · 11.8 m

From 
$380 / day

Rental Sailboat Beneteau Oceanis 411 Marina di Carrara
Rental Sailboat Beneteau Oceanis 411 Marina di Carrara

Marina di Carrara

4.6(22)

Sailboat Beneteau Oceanis 411 12.71m (2005)

  • Skipper mandatory
  • Sailboat
  • Super owner
10 people · 3 cabins · 8 berths · 12.7 m

From 
$516 / day

Rental Sailboat Jeanneau Sun Odyssey 43ds Portoferraio
Rental Sailboat Jeanneau Sun Odyssey 43ds Portoferraio
Special offer

Portoferraio

New

Sailing Elba with Two Boats: Where Magic Meets the Anchorage (2002)

  • Skipper mandatory
  • Sailboat
4 people · 3 cabins · 6 berths · 13.2 m

From 
$690 / day

Rental Sailboat Jeanneau Sun Odyssey 410 San Vincenzo
Rental Sailboat Jeanneau Sun Odyssey 410 San Vincenzo
Special offer

San Vincenzo

4.8(1)

Sailboat Jeanneau Sun Odyssey 410 12.35m (2021)

  • Without captain
  • Sailboat
  • Super owner
6 people · 3 cabins · 6 berths · 12.4 m

From 
$415 / day

Rental Sailboat Jeanneau Sun odyssei 43 Elba
Rental Sailboat Jeanneau Sun odyssei 43 Elba

Elba

4.7(35)

Sailboat Jeanneau Sun odyssei 43 13.32m (2004)

  • Skipper optional
  • Sailboat
  • Super owner
10 people · 3 cabins · 4 berths · 13.3 m

From 
$432 / day

Rental Sailboat Delphia Delphia 40 Marina di Grosseto
Rental Sailboat Delphia Delphia 40 Marina di Grosseto

Marina di Grosseto

5.0(1)

Sailboat Delphia Delphia 40 12.00m (2007)

  • Skipper mandatory
  • Sailboat
4 people · 3 cabins · 4 berths · 12 m

From 
$829 / day

Rental Sailboat Dufour Dufour 410 Grand Large Marina di Grosseto
Rental Sailboat Dufour Dufour 410 Grand Large Marina di Grosseto

Marina di Grosseto

5.0(38)

Bavaria 34 Cruiser (2014)

  • Skipper mandatory
  • Sailboat
  • Super owner
6 people · 3 cabins · 4 berths · 12 m
Rental Sailboat BENETEAU OCEANIS 510 Viareggio
Rental Sailboat BENETEAU OCEANIS 510 Viareggio

Viareggio

4.8(23)

Sailboat BENETEAU OCEANIS 510 15.50m (1992)

  • Skipper optional
  • Sailboat
  • Super owner
10 people · 4 cabins · 10 berths · 15.5 m

From 
$699 / day

Our client reviews
4.9 / 5
Score calculated based on 663066 reviews
See all reviews

Boats Reviews

Reviews are displayed in chronological order
Lauren
Date of the review 10/11/25 · Date of the rental 9/11/25
We had a great trip however due to weather conditions we stayed in one spot for 8 hours, when asked if we could venture to another place later in the day, the captain said no which we totally understand due to safety, however on the trip back waters were calm and many boats on the water. Separately, our captain was very kind and helpful but tended to sit and stare the whole day which was slightly uncomfortable. Recommend having them move to a different part of the boat when possible to allow for some privacy.
Fanny
Date of the review 9/1/25 · Date of the rental 8/26/25
Fabulous! Thank you so much to Barbara and Gianluca for hosting us on their lovely cosy sailboat. Friendliness, efficiency, discretion, and very attentive to security, we had a wonderful time on board and the beach our captain chose was perfect. Recommend 100%!
Alessandro - Settemari
Date of the review 8/26/25 · Date of the rental 8/25/25
Very nice and respectful guy, everything worked great. Till next time, take care
Azzurra
Date of the review 7/29/25 · Date of the rental 7/19/25
if we can have client like Joao, we would'nt need to check the boat in & out!!! recommended client!!

Rent a sailboat in Tuscany with Click&Boat

Tuscany is a region waiting to be discovered: the centre of Etruscan civilisation, the cradle of the Renaissance and the patron of some of the most beautiful landscapes in Italy. Organise your next vacation to discover its history and long traditions, and take a relaxing break and enjoy the beautiful blue sea.

The ideal solution? To rent a sailing boat in Tuscany with Click&Boat, to set sail in complete safety!

Discover all the offers available on the platform and find the perfect sailing boat for your trip. Would you like help in planning? Send a free request for a quote, an expert consultant will then assist you with your project and help you organize all the details.

Don't have a driver's license but don't want to miss out on your dream trip? Hire a sailing boat with captain in Tuscany and count on the experience of a professional sailor to navigate the most fascinating routes of the region, in total safety. Sail without worries and have a relaxing cruise with family or friends: it will be an unforgettable trip!


Still haven't got your ideas in order and looking for inspiration? Check out the various offers available at different destinations at Click&Boat:

What is the price of Sailboat charters in Tuscany?

Sailboat charters can cost from $117.00 to $3,850.00 per day in Tuscany. The factors that affect the price are diverse, such as the date of sailing, duration of sailing, and capacity of the boat among others.


Rent a sailboat in Tuscany: the ideal way to explore the surroundings


Looking for an unforgettable and exciting trip? Rent a sailboat in Tuscany and let yourself be captivated by the charm of its natural landscape.

Tuscany has a 397 km long coastline overlooking the Ligurian and Tyrrhenian seas, where long stretches of sand alternate with stretches of wild and varied vegetation.

Browse through the many proposals of sailing boats in Tuscany for rent on Click&Boat and choose the most suitable port to start your sailing project: from the famous base of Punta Ala to those of Livorno, Marina di Salivoli and Piombino, which are generally more popular for trips to the island of Elba and other islands of the Tuscan archipelago.

Other popular ports in the area are Viareggio, from where you can easily reach the Cinque Terre National Park, San Vincenzo and Talamone, the latter being ideal for sailing towards the Argentario Promontory.

If you are in the southern part of the region, you can look for sailing boats for hire in Castiglioncello, Porto Santo Stefano or Porto Ercole and sail in peace and quiet in the surroundings.


Tuscany, culture and good food


Tuscany, the land of poets and artists, the centre with views of the stunning landscape, is undoubtedly one of the most fascinating regions in Italy.

  • Is there anything better than hiring a sailing boat with Click&Boat and taking the opportunity to discover the region from two different perspectives, from the heart of the cities and from the view of the open sea? By alternating between sailing and shore leave, you can get to know the history of the villages of Siena, Volterra and San Gimignano up close, discover the narrow streets of Lucca and go in search of Florence's cultural heritage.
  • Many palaces and museums are waiting to enchant you with their magical stories and memories of the successful artists who have left their mark on them. Dante, Petrarch and Macchiavelli, or even Botticelli, Leonardo Da Vinci and Michelangelo, but the list goes on and on.
  • If that's not enough, let yourself be won over by the aromas and flavours of Tuscan gastronomy, dishes and products so delicious they seduce even the most refined palate: from the Chianti wines to the wines of Val d'Orcia, from steaks based on Cinta Senese to the many dishes whose protagonist is the region's truffle.
  • Have you done the whole tour? Then set sail for an incredible boat trip to the island of Elba, the island of Giglio and the other islands of the Tuscan archipelago.
  • Hire a sailboat in Tuscany with Click&Boat and organize your next trip to discover one of the most beautiful regions of Italy: between the colors of the sea, the scents and the flavors of the cuisine, this place will conquer you from the first moment!


When is the best time to go to Tuscany?


You have found all the information you need to rent your sailing yacht, and now you want to know when to go?


When is the best time to go? The best time to go to Tuscany is from the end of April to the end of September, but if the climate is pleasant, you can already have sunny days in early April, ideal for sailing in peace and quiet.

The hottest months are on average July and August, but it is also possible to find refreshingly clear waters in June and September.

When November comes, the season usually changes, with cooler days and a high probability of rain. The weather tends to stay the same at least until March, when spring arrives and makes it possible to go boating again with quite warm sunny days.


Sailing vacations in Tuscany: how to do it?


Is a sailing vacation in Tuscany your dream trip? Then you are sure to be satisfied! But how do you organize your rental on Click&Boat, the world's leading boat rental platform?

If you already have a clear idea of the port of departure, you can enter it in the search field at the top of the page, otherwise, you can leave the Tuscany region specified. Enter the start and end dates of the rental, if you want a captain on board and then refine your search using the filters on the left: number of cabins, budget, boat length, yard, boats on promotion and much more.

Another option is to click "Ask for a quote" at the bottom of our homepage, fill out the details of your dream vacation and we will send you a few options!

Frequently Asked Questions about Tuscany

What is the price of renting a sailboat for a day in Tuscany?

The average price of renting a sailboat for the day in Tuscany is $546. A few factors can determine the cost of the rental, such as the time of year, how old the boat is, and the boat equipment. Depending on these factors, the price of renting a sailboat can range from $36 and $1,142.

What is the typical daily cost of hiring a skipper in Tuscany?

The cost of hiring a skipper can differ based on the boat's destination and owner. In Tuscany, the typical rate of a skipper is $250 per day.

How many sailboats are available for rental in Tuscany?

Currently, there are approximately 184 sailboats available for rental in Tuscany. The number may change depending on the season.

How much does a sailboat charter cost in Tuscany in the high season versus the low season?

The average price of chartering a sailboat in Tuscany in the high season is approximately $727 per day, while they are around $426 per day in the low season.

What are the most sought-after sailboat brands in Tuscany?

In Tuscany you will find a wide variety of sailboats from Beneteau or Jeanneau.

Rent another type of boat in Tuscany

If you want to rent something different from the sailboat in Tuscany?
Check out other boats on our website