14 Sunset Sailing Cruises in Italy to Get on the Water

1.Sunset Sailing Aperitif Experience

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

Join Andrea aboard a small sailboat from Alghero Port for a two-hour sunset cruise. Sail toward Maddalenetta, swim or snorkel in clear water, then enjoy local wine, beer, spritz, soft drinks, snacks, music, and views of Capo Caccia. The boat carries a limited number of people, making this a friendly, social evening rather than a crowded harbor trip.

“Fantastic host, absolutely wonderful views. You have to do this if you visit Alghero”

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2.Spritz and Sunset Sailing Tour

★★★★★★★★★★4.8 · 141 reviews · 3 hours · from $77

Spend three hours on a small sailing boat from Catania with skipper Bruno, cruising past the Ulysses’ Grotte and Aci Castello. Swim or snorkel in clear coastal water, learn a little about sailing and local legends, then enjoy Sicilian snacks, wine, beer, or an Aperol Spritz as the sun drops.

“Such a wonderful experience on the boat with Bruno! He taught Us so much about the area and the history as well as providing great food and drinks”

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3.Sunset sailing on lake Como with Private Skipper

★★★★★★★★★★5.0 · 88 reviews · 2 hours (approx.) · from $713 whole boat, up to 9Top rated

Set out from Bellagio at 6 p.m. on a private 38-foot sailing yacht with a skipper such as Federico or Marco. Cruise past villas, coves, and lakeside towns while enjoying Prosecco, Italian aperitivo snacks, and local stories. The route can change with wind, waves, and boat traffic, and the boat returns to Bellagio after two hours.

“We loved the opportunity to see the lake shore from the water. There was no wind, so we motored only, but the leisurely pace, the beautiful weather, and the views were amazing. Our captain gave us a nice tour, sharing names of places and some stories of what we were seeing on the shoreline. He is a skilled sailor and made us feel very welcome and pampered.”

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4.Sunset Apéritif on a 15m sailing boat

★★★★★★★★★★5.0 · 79 reviews · 2 hours · from $59Best value

Join Davide and Camilla for a two-hour sunset sail from Alghero, limited to 10 people. You’ll pass the old town walls, anchor near Maddalenetta Island, and enjoy Sardinian snacks, wine, beer, Spritz, swimming, snorkeling, or paddleboarding from a spacious 15-meter boat.

“Super schöner Trip, leckere Snacks und feine Drinks 👌🏼🥂 Als es richtig dunkel wurde, wurde es wirklich wunderschön - vielen Dank 🫶🏼”

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5.Guided Sunset Sailing Trip with Aperitif & Prosecco

★★★★★★★★★★4.7 · 67 reviews · from $768 whole boat, up to 10

Set out from Catania Nautical Club for three hours along Sicily’s volcanic coast. Your skipper and host team, including crew members such as Giulia, Sergio, Carlo, or Julia, guide you toward the Ulysses Caves, with a swimming stop, sunset views, local appetizers, and prosecco. The listing identifies the experience as a private group tour.

“Great day on the sea watching dolphins and sunset while sipping Prosecco”

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6.Sunset and Aperitif on a Sailing Boat in Alghero

★★★★★★★★★★4.5 · 24 reviews · 2 hours (approx.) · from $66

Set out from Alghero with a small group and follow the medieval sea walls toward Isolotto della Maddalena. You can swim at sunset, then enjoy local wine, snacks, and music aboard a 1978 motor-sailer. Captains such as Alessandro, Andreas, and Alejandro shape the mood, which can range from relaxed to full party.

“We were on one of two boats going out that evening. Our captain was Alessandro and we had a great time. He is a fantastic host and of the two boats we were definitely on the party boat. He had the whole boat dancing. The sunset was spectacular as was the trip out and back. As he was the only crew, the sail was not used, but it was still a great trip.”

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7.2-hour sunset tour by sailboat with aperitif.

★★★★★★★★★★5.0 · 19 reviews · 2 hours (approx.) · from $60

Join Lidia and Sergio of Sapore di vela for a two-hour sunset sail from Alghero. You’ll glide beneath the old Spanish walls, pause near Maddalenetta for an optional night swim, enjoy local wine and small bites, and return to port in darkness with a six-language proximity audio guide.

“It was a very personal experience, we were the only two passengers and we felt like we were part of the family. Hospitality and welcome was wonderful, very knowledgeable and informative. The boat was very special.”

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8.sunset on a sailing boat with aperitif

★★★★★★★★★★4.8 · 14 reviews · 2 - 3 hours · from $91

Set sail from Alghero with skipper Sergio aboard a 13-meter Beneteau sailboat. You’ll cruise toward La Maddalenetta Island, watch the sunset near Capo Caccia, enjoy local wine and an aperitif, and may swim from the boat after dark. The trip lasts 2 to 3 hours and carries up to 10 passengers.

“La gita in barca al tramonto con il signor Sergio è stata un’esperienza davvero unica. Siamo partiti alle 19,30, una mia amica, io, mio figlio di 11 anni, i figli della mia amica e tre ragazze spagnole che non conoscevamo. Il signor Sergio ci ha messo subito a nostro agio facendoci accomodare in barca. Una volta salpati ci ha fatto la storia delle mura di Alghero facendocele ammirare da lontano, e ha fatto ascoltare alle ragazze spagnole nella loro lingua la spiegazione fatta a noi. Dopo un po’ ci siamo ancorati in una bellissima insenatura e i ragazzi hanno fatto il bagno al tramonto tuffandosi a più riprese dalla barca,…”

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9.Cannero Riviera: Sunset Sailing Lago Maggiore

★★★★★★★★★★5.0 · 12 reviews · 2 hours · from $93

Join skipper Adrian for a two-hour sunset sail from Cannero Riviera to the Castelli di Cannero and along the lakeside promenade. Drinks and snacks are included, and Adrian may let you take the helm when conditions allow. English, German, and Italian are spoken. His friendly dogs, Eva and Libby, may also come aboard.

“Absolut genialer Trip mit Adrian und seinen 2 Hunden. Es war ein unvergessliches Abenteuer,das ich jedem empfehlen kann. Wir kommen nächstes Jahr wieder. Vielen Dank”

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10.Sunset aperitif on a sailing boat in Alghero

★★★★★★★★★★5.0 · 8 reviews · 2 hours (approx.) · from $66

Spend about two hours sailing from Alghero’s RainbowMolo, with the old city glowing at sunset. Stop at La Maddalenetta for a swim, SUP, or snorkeling, then enjoy snacks, soft drinks, and local wine prepared by the skipper. The small group holds no more than 12 people, and Andrea may be at the helm.

“Wow! The sunset and spot were fantastic, the whole was surpassed by Andrea.”

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11.sunset sailing tour from Fertilia

★★★★★★★★★★5.0 · 7 reviews · 2 hours · from $77

Join a small-group sunset sail from Fertilia with up to eight people aboard a 9.2-meter cabin boat. Your skipper, named David or Davide in booking details, takes you toward Porto Conte, Capo Galera, or Lazzaretto for a swim and Sardinian aperitif. The two-hour trip includes fuel, insurance, a bathroom, shower, and swim ladder.

“very Nice people. Forgeous tour. Great Sardinian food and wines.”

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12.Asinara & La Pelosa Sunset Private Sailing Tour

★★★★★★★★★★4.5 · 6 reviews · from $357 whole boat, up to 4

Sail from Stintino with skipper Maurizio or another Italian- or English-speaking skipper, stopping at La Pelosa and the Asinara marine reserve. Swim in clear water, enjoy Sardinian cold cuts, cheeses, bruschette, salmon, and Akenta wine, then return about an hour after sunset. The small group is limited to four people.

“The peace, jump into the water, sunset with enough to eat and drink on the sailing ship, Italian speaking, friendly, sporty 😉skipper”

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13.Sailing at Sunset on Lake Como: How to escape from daily routine

★★★★★★★★★★5.0 · 5 reviews · 3 hours (approx.) · from $296

Spend about three hours on a sailboat with skipper Mauro and assistant Isabella, sailing north from the Malgrate area toward Lecco and Abbadia Lariana. You will stop for a swim and shared aperitivo with Prosecco, food, and sunset views of Monte Resegone. The boat holds no more than six people.

“We had a wonderful experience and highly recommend this tour. Both Isabella and Mauro were very knowledgeable and friendly. The food was fantastic for the whole family. This would be a great experience for adults and families. They even helped arrange transportation to and from our hotel and were so accommodating.”

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14.Sunset Sailing Tour with Sicilian Aperitif

★★★★★★★★★★4.5 · 2 reviews · 4 hours · from $69

Set sail from Catania with an English or Italian crew for four hours along the lava coast toward Aci Trezza. Swim and snorkel near Ulysses’ Cave, use the SUP, then enjoy cheeses, olives, salami, local bread, and Sicilian sparkling wine as the sun drops behind Mount Etna.

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