Under sail · SAILING TOURS WITH DRINKS IN ITALY

Sailing Tours with Drinks in Italy: 9 Worth the Sea Air

9 sailing trips  ·  seats from $56 each

A sail that suits a couple rarely suits a stag party. Below, 9 sailing tours with drinks in Italy with the detail that tells them apart: boat, crew size, food and drink, swim time.

Catania: Sail Tour of Cyclops Coast with Sicilian Aperitif - The volcanic coast toward Aci Trezza
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Catania: Sail Tour of Cyclops Coast with Sicilian Aperitif

1.Catania: Sail Tour of Cyclops Coast with Sicilian Aperitif

★★★★★★★★★★4.7 · 548 reviews · 4 hours · from $69Top of the fleet

Sail from Catania to Aci Trezza with an English or Italian speaking skipper and guide. You’ll see Aci Castello, swim and snorkel near the Cyclopean Isles, try a SUP, and enjoy Prosecco with Sicilian bites. Guides such as Sergio, Jennifer, Lulu, and Gabriele are known for warm hosting and clear local explanations.

“Sergio and Jennifer made our trip special. They were both super helpful, and great in explaining all aspects of our sailing trip up the coastline. They were kind and helpful and we couldn’t have asked for a better sailing experience. We would thoroughly recommend a sailing experience with these two lovely people. Gordon & Rachel Potter”

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Cagliari Sailing Boat Tour with Snorkeling and Drink - Starting at Marina Piccola beside Poetto Beach
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Cagliari Sailing Boat Tour with Snorkeling and Drink

2.Cagliari Sailing Boat Tour with Snorkeling and Drink

★★★★★★★★★★4.9 · 454 reviews · 3 hours · from $56Lowest fare aboard

Join skipper Maurizio for a three-hour sailing trip from Marina Piccola beside Poetto Beach. With no more than eight people aboard, you’ll cruise past Devil’s Saddle, swim in clear coves, snorkel among small fish, and enjoy a soft drink. The route changes with the wind, so expect a real sailing experience rather than a fixed boat ride.

“This was an excellent boat trip! The captain was informative, interactive and funny. The stops we made along the way were beautiful and amazing places to swim. The boat was great and he makes sure it is not overcrowded. I would highly recommend this tour!”

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Alghero: Sunset Sailing Aperitif Experience - Sailing toward Maddalenetta
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Alghero: Sunset Sailing Aperitif Experience

3.Alghero: Sunset Sailing Aperitif Experience

★★★★★★★★★★4.9 · 367 reviews · 2 hours · from $65

Join Andrea aboard a small sailboat from Alghero Port for a two-hour sunset cruise. Sail across the bay, stop near Maddalenetta for swimming and snorkeling, then enjoy Sardinian snacks, wine, beer, soft drinks, and Andrea’s homemade spritz with music and views of Capo Caccia.

“It would be great if smoking wasn’t allowed but I suppose that’s a cultural thing.”

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Sailing day trip on Tall Ship Andrea Jensen with Lunch and Wine - Cruising along Sardinia’s Coral Riviera
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Sailing day trip on Tall Ship Andrea Jensen with Lunch and Wine

4.Sailing day trip on Tall Ship Andrea Jensen with Lunch and Wine

★★★★★★★★★★5.0 · 360 reviews · 7 hours (approx.) · from $169Best loved

Spend about seven hours sailing from Alghero with Colin and Rachel aboard the traditional wooden Andrea Jensen. See Capo Caccia’s cliffs, swim and snorkel in a secluded bay, enjoy a freshly prepared two-course lunch with wine and beer, then sail back beneath the ship’s red sails.

“We spent a absolutely superb day on this very lovable boat. The crew were a pleasure to be with and as English speaking owners made the day that little easier. The food and drink which was excellent were offered without hesitation. The company of limited numbers on board added to the free spirit of the day. Colin, Rachel and Constance their little helper. Thank you for a wonderful day. David & Amanda 27 Aug 2020”

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Cagliari: Sailing Tour with 4 Stops, Snorkeling and Prosecco - Cala Mosca is your first chance to get in the water
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Cagliari: Sailing Tour with 4 Stops, Snorkeling and Prosecco

5.Cagliari: Sailing Tour with 4 Stops, Snorkeling and Prosecco

★★★★★★★★★★4.8 · 341 reviews · from $61

Join Alma Sailing Charter for a three-hour sail from Cagliari toward the Devil’s Saddle. Swim and snorkel at Cala Mosca, Cala Fighera, and Sella del Diavolo, with gear, floats, a bathroom, and a fresh-water shower provided. Alma, Patrick, Paolo, Laura, or other crew members may share local stories in English, Italian, or French.

“It’s a short but absolutely lovely excursion. Alma and Patrick were amazing guides, Alma is so knowledgeable with the whole area and is very funny. The swimming spots were very nice and they can provide you with a mask and noodles for free. Beer and snacks can be bought on board too! If you’re looking for a quick adventure out on the waters of Cagliari I’d recommend them very highly!! Thank you both!”

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Catania: Coastline Sailing Trip with Aperitif and Prosecco - Seeing Catania’s volcanic coast from the sea
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Catania: Coastline Sailing Trip with Aperitif and Prosecco

6.Catania: Coastline Sailing Trip with Aperitif and Prosecco

★★★★★★★★★★4.9 · 87 reviews

Join a private sailing trip from Club Nautico in Catania for three hours along Sicily’s volcanic coast. Your skipper and hostess, such as Ivan and Giulia, share views of Mount Etna, beaches, cliffs, and the Cyclops coast. Swim in the Ionian Sea, then enjoy Sicilian appetizers and Prosecco before returning to the club.

“Was a bit unlucky with the weather but the trip was decent and the guides Ben an gulia were excellent with us and made the trip well worth it”

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Catania: Guided Sunset Sailing Trip with Aperitif & Prosecco - Sailing beside Sicily’s volcanic coast
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Catania: Guided Sunset Sailing Trip with Aperitif & Prosecco

7.Catania: Guided Sunset Sailing Trip with Aperitif & Prosecco

★★★★★★★★★★4.7 · 67 reviews

Set sail from Catania Nautical Club for three hours along Sicily’s volcanic coast. Your skipper and host, possibly Giulia, Sergio, Carlo, Benjamin, or Ivan, guide you toward Ulysses Caves for a short swim, followed by local appetizers and prosecco as the sky changes color. English and Italian tours are available.

“It was AWESOME. Julia rocks :) Could be improved: Better appetizers!”

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Catania: Coastline Sailing Trip 6hr with Aperitif and Lunch - Seeing Catania’s volcanic coast from the sea
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Catania: Coastline Sailing Trip 6hr with Aperitif and Lunch

8.Catania: Coastline Sailing Trip 6hr with Aperitif and Lunch

★★★★★★★★★★4.8 · 60 reviews · from $134

Spend six hours aboard a 43 to 49-foot sailing boat from Club Nautico Catania. Skippers such as Ivan, Benjamin, Gianluca, and Petri guide you along Ulysses’ coast, while the hostess serves prosecco, aperitif, and pasta cooked onboard. Swim near the Ulysses Caves, Aci Castello, and the Cyclops Islands.

“Both the captain and first mate were very nice. It was relaxing to be on the ocean.”

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Lake Como Sailing Boat Group Tour Aperitivo & Prosecco Included - The aperitivo, drinks, and onboard rhythm
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Lake Como Sailing Boat Group Tour Aperitivo & Prosecco Included

9.Lake Como Sailing Boat Group Tour Aperitivo & Prosecco Included

★★★★★★★★★★5.0 · 34 reviews · 4 hours (approx.) · from $234

Spend about four hours sailing Lake Como’s central Golden Triangle with skipper Ricky and, on some departures, assistant Nadia. Expect villa and village views, local aperitivo, Prosecco, beer, soft drinks, and possibly a swim stop. The boat carries no more than six people, making this a personal alternative to a large sightseeing cruise.

“This sailing tour was truly the highlight of our week in Italy! From start to finish, everything was seamless and so much fun. Ricky was an absolutely excellent host — warm, knowledgeable, and incredibly skilled. His expertise and easygoing personality made us feel completely comfortable while he shared fascinating stories and insights about Lake Como and its surroundings. The aperitivo on board was such a special touch — sipping prosecco and enjoying the views as we sailed past stunning villas and charming towns was pure magic. The entire experience felt relaxed, personal, and beautifully organized. If you’re visiting Lake Como, don’t miss this tour! It’s the perfect blend of adventure,…”

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Other ways to get on the water

Sunset Sailing CruisesCatamaran Sailing TripsSailing and Snorkeling TripsPrivate Sailing ChartersIsland Hopping Sailing TripsTall Ship and Schooner Sailing
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