



The end of the summer season: what better time to enjoy the calm sea, the empty beaches, and the mild climateof Elba and Capraia?
September is the perfect month to take a little more time off before the new year begins: a sailing vacation is just what you need! We’ll sail among the islands of Tuscany, cruising along the whale-watching route aboard a comfortable sailboat. One of the most popular sailing trips in the Tyrrhenian Sea is now even more comfortable, making it perfect for those who aren’t fond of long crossings. During these 5 days on a boat with a skipper, you’ll make your first stop south ofElba Island, beginning your exploration of the Cetacean Sanctuary: with the wind in your hair, the open sea, and dolphins playing at the bow of our boat—it will be a deeply moving moment that will stay with you until you spotCapraia Island and the coastof Elba. Spending a week sailing in Tuscany will let you discover just how many wonders these islands hide right around the corner—without having to take flights or travel thousands of kilometers. Choose an organized sailing vacation and get ready to breathe in the adventure to the fullest.
WHERE ARE WE GOING?
Program
First day
We’re setting sail: Elba
The itinerary for a sailing vacation always depends on the direction and strength of the wind and sea, but, generally speaking, here’s what we’ll be doing during this sailing vacation in Tuscany. Meet at the boarding port by 10 a.m. We’ll have just enough time to stock the galley and set off forElba, where—depending on the wind direction—we’ll celebrate with our first swim near Lido di Capoliveri , Procchio, or Marciana Marina, and spend the night at anchor. Over the next few days, with a little luck, we’ll spot some cetaceans as we sail throughthe Tuscan Archipelago.
Second day
The Wonderful Island of Capraia
If the weather permits, we can continue our voyage toward the island of Capraia, a wild gem of the Tuscan Archipelago. As we sail, those who are more active can assist the skipper with the maneuvers, learning the secrets of sailing, while those who prefer to relax can enjoywhale watching in the heart of the Cetacean Sanctuary.
Upon arrival, a refreshing dip awaits us in Capraia’s pristine coves, where nature takes center stage. The day concludes with dinner ashore, featuring the authentic flavors of Tuscan cuisine and the unique atmosphere of this wild and fascinating island. A day that combines adventure, camaraderie, and the best the sea has to offer!
Third day
The Gentle Seas of the Tuscan Archipelago
We set sail once moreand let the wind carry us toward Procchio and Sant’Andrea, two of the most charming towns in the northern part of Elba Island. After a couple of days at sea, this is the perfect day to slow down and enjoy the crystal-clear waters among pristine coves. This is the heart of slow tourism,the outdoor lifestyle, and experiences in touch with nature— all increasingly sought after for summer vacations. The day ends with a night at anchor, far from lights and noise, under an incredibly starry sky: one of the most evocative moments of the entire trip, perfect for those seeking sustainable travel, wild seas, and authentic experiences.
Fourth day
Portoferraio and Porto Azzurro
The sailing vacation with skipper continues with a stop to visit Portoferraio, the historical and cultural heart of Elba Island, where you can breathe in the authentic atmosphere of an ancient fishing village. We continue towards the beautiful Bay of Porto Azzurro, surrounded by green hills and crystal clear waters, ideal for an afternoon of diving and snorkeling on Elba. Before ending the day, we go ashore for some shopping in the characteristic shops and finish off with a typical Tuscan dinner, enjoying the genuine flavors and views that make this island an unforgettable destination.
Fifth day
Disembarkation
We’re coming to the end of these five days of sustainable sailing among the islands of Tuscany. Thanks to the sailboat and our skipper, we’ve explored the wild bays of the Tuscan Archipelago, shared authentic experiences with the new friends we met on board, and—perhaps—even spotted a few dolphins along the way. Now it’s truly time to say goodbye, with the hope of returning to the boat as soon as possible for another week or weekend of sailing in good company. See you on the next sailing vacation with Jonas!
Transportation to the boarding location, sheets and towels, any tourist tax where applicable, and anything not listed under “Includes.”
Please note that provisions, marina fees, and fuel are not included, as they depend on the group’s arrangements and are handled on-site through a shared fund; they typically amount to about €30–40 per person per day.
Punta Ala or other ports along the Tuscan coast. You will be aboard a 16-meter sailboat with 3 cabins and 2 bathrooms. Very large and spacious owner's cabin in the bow and two cabins with separate beds in the stern.
Participants: boat for 6 people.
To promote sustainable travel, choose the TRAIN! The boarding ports are also accessible by public transportation.
You may only enter the port to load or unload, but there is a free public parking lot not far from the port where you can usually find a spot without any trouble.
Do you need more information?

The soundtrack to this Jonas experience
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Everyone experiences travel in their own way: whether riding a bike, sailing a boat, exploring on foot, or riding a horse.