Sailing Trips in Italy

Sailing Trips in Italy with a Professional Skipper and Host

Joining a sailing trip in Italy is a wonderful way to explore one of the Mediterranean’s most beautiful island regions. With an experienced skipper on board, no sailing experience is required — you can simply relax while the crew takes care of navigation, daily planning, and life on board.

These small-group sailing trips take you through the breathtaking waters of the La Maddalena Archipelago, a protected marine paradise known for its turquoise bays, granite islands, and secluded beaches. Guided by a knowledgeable skipper and welcoming host, your sailing trip in Italy blends relaxation, island exploration, and the unforgettable atmosphere of life at sea.

Discover Italy on a Small-Group Sailing Trip

now this - Off northern Sardinia’s Costa Smeralda lies Italy’s sailing paradise – the Maddalena archipelago. Here you can snorkel in crystalline waters, enjoy Italian cuisine, discover hidden beaches and quaint ports, but most of all, experience the joys of sailing. A week-long holiday in Italy that’s unlike any other.

On a sailing trip with a skipper and a host, you can enjoy every minute of your sailing holiday, without having to worry about doing any sailing, cooking or planning. An all-inclusive holiday includes breakfast and lunch, a drinks package, accommodation aboard the boat, port fees and other sailing costs. On top of this, every day you will be given a guided tour of new destinations and islands off northern Sardinia and as far as southern Corsica.

What does a typical day on board look like?

MORNING

Waking up on a yacht during a sailing trip in Greece is a peaceful way to begin the day. Start with a refreshing morning swim in the clear Mediterranean water or enjoy a quiet cup of coffee on deck as the harbor slowly comes to life. Soon after, a generous breakfast is served on board and shared together in the cockpit — the perfect start before another day of sailing and island exploration.

MID-MORNING

After breakfast, the skipper gathers everyone briefly to outline the day’s sailing route and highlights along the way. Then it’s time to set sail. If you’re curious about sailing, you’re welcome to get involved — from helping raise the sails to learning a bit about navigation — while those who prefer can simply relax on deck and enjoy the sunshine. As the yacht glides between islands, there’s plenty of time to unwind and take in the beauty of the Greek sea.

LUNCHTIME

As lunch approaches, we stop in a quiet, peaceful bay where we put down anchor for a few hours and enjoy a lunch prepared with local ingredients. There will also be plenty of time for sunbathing, swimming and enjoying your surroundings. Perhaps you’ll take the dinghy out to explore the nearest beach?

AFTERNOON

After lunch, we sail on to one of Greece’s beautiful harbours, towns or villages, where you will spend the night. Some light snacks are served on arrival and the skipper will tell you more about the day’s destination.

Our Destinations

Join our sailing trips in some of the world’s most beautiful cruising regions. During the summer season, explore iconic Mediterranean and Baltic destinations such as Croatia, Greece, Italy, and Sweden. When autumn and winter arrive in Europe, our sailing journeys continue in the warm waters of the Caribbean.

Whichever destination you choose, the experience remains the same — a carefully designed, all-inclusive sailing trip where the crew takes care of the sailing, planning, and onboard hospitality. All you need to do is relax, enjoy the journey, and discover new places at sea.

Your questions answered

Our sailing trips are designed to be simple and mostly all-inclusive, allowing you to relax and fully enjoy the experience at sea. Each sailing trip with a professional skipper and host includes:

A qualified and certified skipper with strong local knowledge and extensive sailing experience
A dedicated host who prepares breakfast and lunch on board, along with a drinks package during the trip
Accommodation in a double cabin on the yacht
Bed linen and towels
Boat-related costs such as port fees, LPG, and diesel

Many sailing trips also include return flights from selected departure airports as well as return transfers between the airport and the marina.

The only additional costs during the trip are typically evening meals ashore and any personal spending for shopping or other purchases during the journey.

During your sailing trip, the crew ensures everything runs smoothly so you can fully relax and enjoy the experience at sea. The host takes care of meals on board, preparing and serving breakfast and lunch while creating a welcoming and social atmosphere for everyone on board.

Our sailing trips include breakfast, lunch, and a drinks package with water, soft drinks, and wine or beer served with meals. In the evenings, the yacht typically docks in a harbor town or island village where guests enjoy dinner ashore and explore the local restaurants and cafés.

Your host and skipper are always happy to share their favorite recommendations, helping you discover the best places to dine and experience authentic local cuisine along the way.

Staying on a yacht during a sailing trip is a comfortable and unique experience. While life on board offers many of the conveniences of home, yachts operate with limited space, water, and electricity, so guests are encouraged to use resources thoughtfully — for example by keeping showers shorter when the yacht is anchored or moored.

Guests stay in a private cabin aboard a sailing yacht or catamaran, depending on the trip. Each cabin accommodates two people, so solo travelers typically share a cabin with another guest. Depending on the yacht model, cabins may feature either double beds or bunk beds.

All yachts are equipped with comfortable sleeping areas, a kitchen (galley), bathrooms with showers and toilets, and several spaces to relax and socialize, including the cockpit, the foredeck, and the interior saloon.

While sailing, phones and small devices can be charged through 12V power outlets. When the yacht is docked in a marina with shore power, 220V outlets are also available. Some yachts are equipped with generators, allowing the use of 220V power even when not connected to shore electricity.

In many destinations, marina facilities also provide additional showers and toilets that guests can use during the trip.

When Is the Best Time to Go Sailing in Italy?

The sailing season for our sailing trips in Italy runs from June to September. During this time, we explore the stunning waters of the La Maddalena Archipelago in northern Sardinia — a spectacular sailing region known for its sheltered bays, steady winds, and beautiful island landscapes. We typically pause trips during the busiest Italian holiday period from mid-July to mid-August, when boat traffic and prices reach their peak.

June is ideal for travelers who prefer warm but comfortable temperatures around 25–30°C, lush Mediterranean scenery, and calmer sailing conditions. The sea is refreshing and the islands are still relatively peaceful.

July and August bring the height of the Mediterranean summer, with temperatures often exceeding 30°C. Harbors and island villages are lively during this period, especially around the famous Italian holiday Ferragosto in mid-August.

In September, the atmosphere becomes more relaxed again. The sea remains warm, the weather is pleasant, and both visitor numbers and prices begin to ease — making it a wonderful time to enjoy sailing trips in Italy at a more tranquil pace.

We sail with these yachts

Lagoon 42

Experience the Italian archipelagoes in the most enjoyable way. The catamaran Lagoon 42 is a favourite for those who love large sundecks and smooth sailing. The air con and generator make for a more comfortable stay during even the hottest summer months.

Number of guests
Four large and spacious cabins with double beds and also a private toilet. Room for 8 guests and 2 crew members

Highlights
Most sociable option if you’re more into mingling than sailing.

Which routes do we sail in Italy?

Our sailing trips in Italy depart from Cala dei Sardi, located on the northeast coast of Sardinia, just north of Olbia. From this beautiful marina, the journey begins into one of the Mediterranean’s most breathtaking sailing regions.

Throughout the week, the skipper plans the sailing route based on wind and weather conditions while also taking the group’s preferences into account. On a typical sailing trip, there is time to explore several islands and coastal towns, often including highlights such as La Maddalena, Caprera, and Spargi within the stunning La Maddalena Archipelago. If conditions allow, the itinerary may even include a scenic sail across the strait to southern Corsica, adding another beautiful destination to the adventure.

What our clients say

"Boon was incredible to work with. I used them to broker a yacht in the Philippines and it was one of the best trips of my life….and I am a frequent traveler with high expectations. Polina is a seasoned professional and responded to all of my requests and questions in lightning speed. The contracting process was painless. It’s rare to receive this level of concierge service these days. HIGHLY RECOMMEND!"

Amber Z.

"Kaarel and Polina were incredibly helpful throughout the whole process. I would definitely book a charter yacht through them again."

Sophie D.

"We had the most amazing experience! Everything went perfectly smoothly from start to finish. The team was incredibly helpful, kind, and genuinely on our side — something that’s rare to find, especially when dealing with the often tricky world of boat rentals. Thanks to Boon Yacht OÜ, we enjoyed the most beautiful trip on a yacht in Croatia, completely stress-free. Their professionalism and personal touch made all the difference. We can’t wait to book our next adventure through them again — highly recommended! ⛵✨"

Epp S.

"We had an amazing experience with Kaarel and Polina providing great ideas and support for our charter"

Meelis K.

Sailing Trips in Italy

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