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Private yacht sailing holidays with skipper in Tuscany

Discover the magic of sailing holidays in the Aeolian Islands! Get onboard with a local skipper and live a unique adventure with your crew: learn to sail, explore incredible places, recharge your batteries and experience the local culture & gastronomy.

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

2 departures available

August - September

Starting from

€793

€714

Per person

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4.9

Taste of the sea between the island of Capraia and Northern Corsica

Italy: Tuscany

7 days - 7 nights

One departure available

July

€700

Per person

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5.0

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

6 departures available

July - September

Starting from

€293

€264

Per person

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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

4 departures available

July - September

Starting from

€1,041

€989

Per person

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4.9

Super!

Midweek on Elba, from Monday to Thursday

Italy: Tuscany

3 days - 3 nights

One departure available

July

€395

€375

Per person

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4.9

Super!

Sailing week in the Tuscan Archipelago

Italy: Tuscany

7 days - 6 nights

4 departures available

August - September

Starting from

€700

€665

Per person

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4.8

Midweek special on the island of Elba, 2 nights

Italy: Tuscany

3 days - 2 nights

7 departures available

July - October

Starting from

€260

€247

Per person

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4.7

Whale watching cruise with WWF guide between Tuscany and Northern Corse

Italy: Tuscany

6 days - 7 nights

7 departures available

July - September

Starting from

€1,041

€989

Per person

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5.0

Weekend of sailing and relaxation on Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

July

€250

Per person

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4.9

Super!

Weekend on Elba Island

Italy: Tuscany

3 days - 2 nights

One departure available

July

€290

Per person

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5.0

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

2 departures available

July - August

Starting from

€430

Per person

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4.9

Super!

Long weekend on Elba: 4 days of sun and sailing

Italy: Tuscany

3 days - 3 nights

One departure available

September

€380

€342

Per person

Why book a holiday with Sailsquare?

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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 - Private yacht sailing holidays with skipper in Tuscany

409 reviews

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A weekend in the most beautiful coves of Elba

07/1/2025

Lucia F.

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Italy

Un Weekend Indimenticabile all'Isola d'Elba: Sole, Mare e Ottima Compagnia! Ho appena trascorso un weekend in barca all'Isola d'Elba con il capitano Marco e Carmen, e non potrei essere più entusiasta! È stata un'esperienza semplicemente perfetta sotto ogni punto di vista, e la consiglio vivamente a chiunque cerchi una fuga dalla routine all'insegna del relax e del divertimento. Innanzitutto, il meteo è stato impeccabile: sole splendente e un mare calmo e cristallino ci hanno accompagnato per tutte e tre le giornate, permettendoci di goderci appieno ogni bagno e ogni caletta nascosta. Le condizioni erano ideali per la navigazione, rendendo ogni spostamento un vero piacere, abbiamo anche fatto una bellissima veleggiata al rientro al porto di Piombino. Ma ciò che ha reso questo weekend davvero speciale sono state le persone a bordo. Si è creata subito un'atmosfera di allegria, chiacchiere e momenti di puro svago. E non posso non menzionare il nostro capitano Marco, un vero professionista! Non solo era estremamente competente e sicuro nella conduzione della barca, ma anche simpatico e alla mano, ovviamente vale lo stesso anche per Carmen, che ci ha subito messo a nostro agio appena arrivati. La conoscenza del luogo, da parte di Marco, ci ha permesso di scoprire angoli incantevoli e meno battuti, e la sua disponibilità ha reso ogni richiesta un'opportunità per imparare qualcosa di nuovo o semplicemente per apprezzare ancora di più il viaggio. In sintesi, questo weekend all'Isola d'Elba è stato un mix perfetto di natura mozzafiato, relax totale e ottima compagnia. Consigliato!!
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6 days of Elba, Capraia and Corsica

06/30/2025

Stefano M.

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Switzerland

Vacanza stupenda da tutti i punti di vista! Itinerario ben strutturato, con spostamenti non troppo lunghi, ma allo stesso tempo sufficienti per godersi il viaggio a vela, e tappe incantevoli nei luoghi più suggestivi dell'isola d'Elba. Antony è uno skipper preparato e con molta esperienza, ma soprattutto è una bella persona. Ci siamo trovati subito in sintonia, e la convivenza in barca è stata semplice. e piacevole. Antony non si è limitato a condurre la barca, ma si è dedicato a noi al 100%: ci ha intrattenuti, soprattutto i ragazzi, coinvolgendoci nella conduzione della barca, intrattenendoci durante il giorno con bagni, nuotate con maschera, visita di grotte, sci d'acqua con il tender, stand-up paddle; e di sera con giochi e chiacchierate. Inoltre è un ottimo cuoco, ogni giorno è stata un'esperienza culinaria diversa con piatti da tutto il mondo, e ha saputo adattarsi alle nostre esigenze senza problemi (cucina senza glutine per celiachia). La barca era abbastanza spaziosa per il nostro gruppo di 2 adulti e 4 ragazzi (3 cabine, ognuna con il suo bagno), ma ci sta tranquillamente una settima persona nello spazio comune. I costi extra sono stati mantenuti al minimo, nonostante alcuni viaggi fatti a motore per mancanza di vento. Ci sentiamo assolutamente di consigliare una vacanza con Antony. Noi torneremo sicuramente!
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A weekend in the most beautiful coves of Elba

06/30/2025

Alessandro m.

Sulla [hidden] Risate e Divertimento sono assicurati! Carmen e Marco ci hanno accolto sulla propria barca come Fossimo di Famiglia. Marco , lo skipper, sì mostrato un ottimo segugio di mare capace di farti vivere delle splendide Emozioni in totale sicurezza! Abbiamo Circumnavigato l' Isola d' Elba partendo da Piombino sostando nei punti più suggestivi e Caratteristici e dormendo in Mare quando possibile. Pulizia e Disponibilità ai massimi livelli. La [hidden] è davvero una bella Barca. Nel Ringraziare Marco e Carmen per il bel Weekend trascorso consiglio sicuramente questa esperienza a tutti coloro che hanno voglia di Scoprire le Meraviglie dell' Elba con il vento in Poppa!
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Elba and the Tuscan archipelago on board a catamaran

06/30/2025

Stefania B.

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Italy

Come prima esperienza di vacanza in barca da sola posso dire che è andata alla grande. Grazie a un tempo favorevole abbiamo raggiunto la Corsica (fantastica) e vissuto tutta la settimana in barca, senza mettere mai piede a terra: quello che volevo. Barca comodissima con spazio per tutti ! Pranzi e cene stellati (in tutti i sensi). Il capitano [hidden] esperto e disponibile, ha condiviso ogni decisione con il gruppo . Cris, suo fidato braccio destro, sempre operativo e paziente a tutte le varie nostre richieste. Esperienza che consiglio vivamente. TORNERÒ SICURAMENTE

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Why rent a sailing boat with skipper in Tuscany

  • Sailing in Tuscany for those who live in northern Italy is really convenient: a few hours of travel by car or train and you are immediately on a boat, ready to sail for a weekend, a bridge or a real summer holiday. Sailing boats for hire in Tuscany depart from one of the many ports in the province of Livorno, from Castiglioncello to Piombino, or further south at Punta Ala and Talamone.
  • If the starting point is easy to reach, the itineraries and destinations can be the most diverse, which is why chartering a sailing boat with skipper in Tuscany is an excellent solution! You're spoilt for choice: Elba, Giglio and Capraia are within easy reach, but if you get the hang of it, you can reach the Corsica or sail around all the smaller islands of the Tuscan Archipelago.
  • The favourable season for renting a sailing boat in Tuscany is quite wide: in summer temperatures are excellent and you rarely suffer from scorching heat, especially on a boat. But even in spring and autumn you can make the most of a sailing holiday, with the cooler weather and brilliant colours of a less harsh sun.
  • Not just sailing! Never before has it been so easy as in Tuscany to combine a sailing holiday with other activities, such as trekking and visits to the islands of the archipelago, dinners in delightful little restaurants and birdwatching... while waiting to spot a dolphin!

Hire a sailing boat in Tuscany and build a tailor-made holiday!

You can rent a sailing boat in Tuscany with a skipper and set the pace of your holiday by the sea: you can enjoy total relaxation with itineraries along the coast, discovering the Argentario and the Island of Elba, even with your children; or you can choose more challenging routes, dedicating a greater number of hours to sailing to reach more distant destinations and test your skills as sea wolves. The choice is yours!

Elba Island

Reaching and discovering the coasts of Elba on a sailing boat replaces a seaside holiday with the relaxation and comfort that are often so difficult to achieve in summer, especially if you are on a vacation with children, busy looking for parking, beaches that are not too crowded, shade and cool drinks.

You will have everything you need when you want it on your charter boat: crystal clear waters at any time of day, diving and snorkelling, snacks and naps when you feel like it... and, of course, you will be able to explore new places, beaches and old towns every day.

The coasts of the island of Elba are a constant discovery: the sea varies from blue to green and frames granite cliffs, white pebble beaches or sandy beaches, coloured like the minerals in which the island is rich.
There are many harbours and tourist ports where you can stock up on food and wine delicacies; among the places we recommend you include in your sailing itinerary on the island of Elba are the villages of Portoferraio, Porto Azzurro, Rio Marina and the beaches of Capo Bianco, Marina di Campo and Sansone.

Tuscan Archipelago National Park: seagulls, dolphins, butterflies and a dream seabed

The Tuscan Archipelago National Park, created in 1996, is one of the Italian parks with the strongest integration between land (22%) and sea (78%) and the greatest number of islands, significantly distant and different from each other, rich in endemic species to be safeguarded.
A real dream for nature lovers who, by hiring a skippered sailing boat, can discover a unique biodiversity in total freedom, just a stone's throw from home.

After Elba, the largest islands in the archipelago are Giglio and Capraia, both of which are popular with divers and snorkelers because of their clear waters and wealth of life: try to spot the now rare seahorse among the Posidonia leaves, and keep your eyes peeled for grouper, bream, sea bream and amberjack burrows in the rocky recesses

The Cetacean Sanctuary between northern Italy and France also stretches around the islands of the Tuscan Archipelago, and it is not uncommon in the summer months to spot dolphins and fin whales; but looking up will also give you satisfaction: Corsican Gulls, Peregrine Falcons, Berta and Kestrels fly here.

Gorgona to the north and Giannina to the south. Gorgona to the north and Giannutri to the south are the two wild and mysterious islands that enclose the park area and can become a final destination for your personalised sailing itinerary.

Along the Tuscan coast

For a sailing cruise of a few days or for a family holiday, sailing along the beautiful Tuscan coast gives you a taste of the unique views and sea life.
To the north, you start with a fascinating stretch of coastline over 150 kilometres long that is not easy to explore by land except on horseback: the Maremma, full of coves and long stretches of sandy coastline protected by pine forests.

More southerly, renting a skippered sailing boat can help you discover the Argentario promontory at your own pace, with its sheer cliffs and crags, contrasting with the Orbetello lagoon, a WWF Oasis, and the long beaches of Feniglia and Giannella. The exclusive Capalbio coastline is only a breath away!

From Tuscany around the Tyrrhenian Sea: setting sail

If you're ready to cast off for good, chartering a sailboat from Tuscany allows you to go wherever you want... to Corsica for example. From the island of Elba or Capraia you can set sail, usually towards Cap Corse, always with the best possible advice from your skipper, of course.

Not able to organise a sailing boat rental in Tuscany? Try to look for a boat for rent in Sardinia, in Croatia, or a boat in Turkey. Tuscany is waiting for you at the next opportunity!

How to rent a sailing boat with skipper in Tuscany

  • Letting a whole boat guarantees you total freedom. Many of our proposals for sailing holidays in Tuscany can be exclusive! Choose the right period of time with the filters on the page and enter the holiday that fascinates you most: by moving the cursor to "whole boat" (below the price) you will get an idea of the cost for the charter and what it includes. This is how you start to organise your exclusive holiday, whether with family or friends.
  • Sailsquare allows you to contact the skipper directly in order to receive all the information you need and to define every useful detail for the rental of the sailboat.
  • Time is money! Book early (at least 2-4 months) and you will find great prices and early-booking discounts. If you're not planning to leave during the peak season, the bargain is assured and the choice of boats or catamarans for exclusive charter is certainly wider.
  • The sailboat rental with skipper enables you to experience a carefree holiday. Depending on your wishes and the weather conditions, the professional skipper will make the best decisions every day: itinerary, shore excursions, best swimming spots and moorings. All that's left for you to do is enjoy a relaxing and carefree sailing holiday.
  • If you have any questions about the sailboat and catamaran skippered charter service, or would like more information, please read our frequently asked questions page, or contact us!

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