Enjoy the glories of Tuscany in a totally new way, with a three-day sailing trip

Tuscany is rightly famed for its glorious countryside, the inspiration for some of the world’s greatest artists for millennia.


Departures available between May and September, guaranteed for a minimum of two guests.

Tour begins and ends at Grosseto railway station.

Day one: check-in and Punta Ala


On the first day of your tour, your guide will collect you in the early afternoon from Grosseto railway station. You will be driven to Scarlino harbor and introduced to your new home afloat, which will host you for the next two nights. Before setting off, an experienced local skipper will show you around the boat, ensuring you feel entirely at ease, and will also offer you an all-important safety briefing.

Aperitivos and dinner in the beautiful village of Punta Ala or Castiglione della Pescaia will be followed by your first night on board. Punta Ala lies approximately two hours’ journey south-west of Florence; it’s a well-kept secret amongst Italians and is particularly favored by wealthy visitors from all over the world. The famous Tuscan hills, many topped by the fortified houses so unique to the region, roll down to the azure sea; in the distance, you can see the island of Elba, which is famous as the scene of the Emperor Napoleon’s first incarceration.

Punta Ala is justifiably famed for its striking marina, where hundreds of sailing vessels gather; the vision of a forest of masts standing out against a stunning Mediterranean sunset will linger long in the memory. In the summer months, the marina comes to life, with a plethora of bars, restaurants, coffee shops and nightspots for visitors to enjoy.

Day two: Isola d’Elba and wine tasting


After breakfast, we will cast off and set sail for the island of Elba. Along the way, we will pause a few times to enjoy the amazing seascape and perhaps indulge in a little swimming – which should give you an appetite for a classic Tuscan lunch, taken on board.

Elba is Italy’s third-largest island (after Sardinia and Sicily) and forms part of the National Park of the Tuscan Archipelago, the largest marine park anywhere in Europe.

Renowned for housing Emperor Napoleon in his brief 1814 exile, the story of Elba stretches back into prehistory; the Ligurian Ilvata tribe named the island Ilva after themselves. The Etruscans, and later the Romans, were quick to inhabit the island, valuing it for its mud baths and rich mineral deposits.

The island is steeped in history, and you will have the opportunity to marvel at the discoveries of archaeologists in its museums before going on to visit striking fortresses and military installations, such as Castello del Volterraio, as well as stunning 19th-century Napoleonic buildings such as the Palazzina del Mulini.

Beyond the works of humans on the island, Elba is justifiably celebrated for its clear blue seas and stunning beaches. Even in an area as beautiful as Tuscany, it stands out as a jewel in the crown, a location that rivals – and beats – any paradise island in the world.

After some more chances to swim in the limpid waters, we will sail on to Porto Azzurro, our home for the evening. Here, you can visit a local winery for a wine tasting, and then take your new knowledge of local wines down to the bars, restaurants and night spots of this lovely village.

Once a small fishing village that grew up around the base of the local fort, Porto Azzurro clusters around the recently renovated Piazza Matteotti, which overlooks the marina and offers a fine view of the comings and goings of the beautiful yachts as well as the local fishing fleet. A multitude of superb restaurants awaits your pleasure, many built on stilts over the sea, while in the village, as well as many shops selling local crafts, you should not miss the 18th century Parish Church of the Madonna del Carmine and the Sacro Cuore di Maria Oratory.

If you time your visit right, you may get to join in one of the town’s celebrated festivals; on July 25th the local patron saint (St James) is celebrated with the Festa del Pescatore (Fishermen’s Festival), when the whole town turns out en fete to eat, drink and attend religious ceremonies. On September 8th, the feast day of Madonna del Monserrato is marked with equal enthusiasm, with a religious procession and numerous celebratory events.

Day three: Lunch on board and return to Grosseto

After breakfast, we will set sail for Scarlino harbor, taking the opportunity to visit some of the smaller islands we pass along the way. After another delicious lunch on board, you can enjoy the final leg of your trip as we sail back to Scarlino, arriving late afternoon, from where you will be driven back to Grosseto station.

Your captain

Riccardo is a qualified BLSD instructor, an experienced mountaineer, trekker and free climber who exchanged the mountains for the sea nearly thirty years ago, drawn by the lure of Italy’s sparkling waters. You couldn’t be in safer hands: as well as possessing unrivalled sailing expertise, Riccardo is a qualified first aider, including defibrillator use. He teaches expert sailing courses for the Italian Sailing Federation and is a member of the examination board for nautical licenses at the Port of Piombino.

Your vessel

You will set sail aboard a luxury blue water cruiser, specially designed for long trips, stability and safety. This is an oceangoing yacht that can handle any weather or sea conditions in comfort.

The yacht boasts a central cockpit that not only offers a comfortable command post, but also allows for a spacious sundeck in the bow. The yacht is equipped with every latest high-tech navigation aid and communication device to ensure the safety and security of its guests.

Below deck, you will find luxurious handcrafted mahogany interiors rivaling any shore-bound hotel, and fully functioning heating and air conditioning guarantee your comfort in all conditions.


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