Sicily · SAILING

15 Sailing Trips in Sicily to Build a Day Around

36 tours  ·  from $48 a head

Every trip has one free day too few. These 15 sailing trips justify the slot, priced and timed so you can decide in minutes and get back to the fun part.

Lampedusa: Yacht excursion, swimming stops and typical lunch - Tabaccara Bay before the crowds
Cruises & Boat Tours, Lunch Experiences, Sailing, Tour Reviews, Tours

Lampedusa: Yacht excursion, swimming stops and typical lunch

1.Lampedusa: Yacht excursion, swimming stops and typical lunch

★★★★★★★★★★5.0 · 195 reviews · 7 hours · from $101Our pick

Spend seven hours circling Lampedusa by yacht, with turquoise swim stops, cave visits, island stories, and a generous fresh-fish lunch.

“Bellissima gita in Barca con l’equipaggio della Sciatumia, il comandante ci ha fatto sentire fin da subito a nostro agio e ha sempre coinvolto tutti i partecipanti dell,escursione. Il mangiare é stato strepitoso e oltre le aspettative. Gita e equipaggio consigliatissimo.”

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Catania: Spritz and Sunset Sailing Tour - Sailing the Route of Ulysses
Boat Tours in Catania, Catania Tours, Cruises & Boat Tours, Evening Experiences, Evening Tours in Catania, Sailing, Sailing Trips in Catania, Tour Reviews, Tours

Catania: Spritz and Sunset Sailing Tour

2.Spritz and Sunset Sailing Tour

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

Sail Catania’s coast at sunset with Bruno, swim near the Ulysses Grotte, and enjoy Sicilian snacks, wine, beer, and Aperol Spritz.

“The Sunset cruise was great. We sailed, north and returned to outside the Harbour and had nibbles and wine. We had the option to swim or sail.”

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Half Day Sailing Tour Taormina Bay - Swim stops near Isola Bella
Boat Tours in Taormina, Cruises & Boat Tours, Sailing, Taormina Tours, Tour Reviews, Tours

Half Day Sailing Tour Taormina Bay

3.Half Day Sailing Tour Taormina Bay

★★★★★★★★★★4.5 · 134 reviews · 3 to 4 hours (approx.) · from $95

Sail from Giardini Naxos along Taormina Bay, swim near Isola Bella, snorkel, and enjoy Sicilian snacks and white wine with a small group.

“This tip was incredible! The views were beautiful and the water was perfect! Before you go they give you clear instructions on how to arrive and where to park if needed. My trip was almost canceled due to the weather so they kept in touch the entire time! Once I arrived, shortly after I was greeted by my captain Lulu. She was very warm, inviting, and knowledgeable about the islands. Best boat guide I have ever had! The sailboat was also very well kept with a lot of space and I felt very safe the entire time! The food was also very good and there was a way to have…”

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Full Day Sailing Tour Catania-Acitrezza - An hour in Acitrezza and the Cyclopean Islands
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Full Day Sailing Tour Catania-Acitrezza

4.Full Day Sailing Tour Catania-Acitrezza

★★★★★★★★★★5.0 · 114 reviews · 8 hours (approx.) · from $119

Sail from Catania to Acitrezza for lava cliffs, Acicastello, snorkeling, a fish lunch, Sicilian wine, and a small-group day at sea.

“This was not a good experience. I will skip petty complaints and focus on safety concerns. At the conclusion of our tour the motor on our sailboat failed. We were headed back to port and there was not enough wind to get us there. The captain phoned someone, but it was in Italian, we could not understand. We hoped someone was on their way to tow us in, but we sat for 3 hours waiting. The captain brought out a very old 3.5hp Johnson kicker motor, but it did not run. Finally, my 13 year old sun flagged down a small fishing boat who reluctantly gave us a tow. Mechanical…”

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Cefalù: Mini Yacht with Snorkel Stops, Caves and Aperitif - Starting at Cafè Eolo in Cefalù’s port
Boat Tours in Cefalù, Cefalù Tours, Cruises & Boat Tours, Sailing, Tour Reviews

Cefalù: Mini Yacht with Snorkel Stops, Caves and Aperitif

Catania: Coastline Sailing Trip with Aperitif and Prosecco - Meeting the skippers and getting underway
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Catania: Coastline Sailing Trip with Aperitif and Prosecco

Sailing to Cyclops Islands Group Tour - Aci Trezza and the rocks of the Cyclops
Cruises & Boat Tours, Sailing, Tour Reviews, Tours

Sailing to Cyclops Islands Group Tour

7.Sailing to Cyclops Islands Group Tour

★★★★★★★★★★5.0 · 77 reviews · from $138

Sail from Catania to the Cyclops Islands with lunch, drinks, swimming, volcanic coast views, and a small group capped at 10 people.

“Excellent captain and first mate, one of the best ways to see Catania, learn some Sicilian history, and take a dip in the Mediterranean Sea”

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Giardini Naxos: Dolphin Catamaran Sunset Tour with Aperetif - Cruising past Capo Taormina and the sea caves
Boat Tours in Taormina, Cruises & Boat Tours, Dolphin Watching, Dolphin Watching in Taormina, Evening Experiences, Evening Tours in Taormina, Sailing, Taormina Tours, Tour Reviews, Tours

Giardini Naxos: Dolphin Catamaran Sunset Tour with Aperetif

Catania: Guided Sunset Sailing Trip with Aperitif & Prosecco - Sailing beside the Etna Coast
Boat Tours in Catania, Catania Tours, Cruises & Boat Tours, Evening Experiences, Evening Tours in Catania, Guided, Sailing, Sailing Trips in Catania, Tour Reviews

Catania: Guided Sunset Sailing Trip with Aperitif & Prosecco

Discovering Cefalù's Coastline Activity on a Mini Catamaran - Three Hours Along the Cefalù Coast
Boat Tours in Cefalù, Cefalù Tours, Cruises & Boat Tours, Sailing, Tour Reviews

Discovering Cefalù’s Coastline Activity on a Mini Catamaran

Favignana e Levanzo: tour condiviso Yacht Shalimar IV - Meeting at Trapani port before 9:30 a.m.
Boat Tours in Trapani, Cruises & Boat Tours, Egadi Islands Tours, Sailing, Tour Reviews, Tours, Trapani Tours

Favignana e Levanzo: tour condiviso Yacht Shalimar IV

Catania: Coastline Sailing Trip 6hr with Aperitif and Lunch - Seeing Catania from the water
Boat Tours in Catania, Catania Tours, Cruises & Boat Tours, Lunch Experiences, Sailing, Sailing Trips in Catania, Tour Reviews

Catania: Coastline Sailing Trip 6hr with Aperitif and Lunch

12.Coastline Sailing Trip 6hr with Aperitif and Lunch

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

Sail Catania’s volcanic coast to Aci Castello and the Cyclops Islands with swimming, prosecco, pasta lunch, and a friendly sailing crew.

“We had a wonderful and very relaxing day sailing the Catania coastline. Ivan provided a lot of information on the history of Catania and Giulia prepared us a wonderful lunch. We are very happy that we chose to do this activity during our stay in Catania and we recommend it to all looking for a fun activity. Thank you once again to Ivan and Giulia for a great experience. Grazie Mille!!”

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Full Day Sailing Boat Tour to the Egadi Islands - Favignana’s coves and two hours near shore
Cruises & Boat Tours, Egadi Islands Tours, Full-Day, Sailing, Tour Reviews, Tours

Full Day Sailing Boat Tour to the Egadi Islands

13.Full Day Sailing Boat Tour to the Egadi Islands

★★★★★★★★★★5.0 · 58 reviews · from $104

Sail from Trapani to Favignana and Levanzo on a small-group boat tour with swimming, snorkeling, quiet coves, and flexible routes.

“Exceptional day and experience! Passionated people who are going to bring you to fantastic places where no one can go. Our best day of our trip in Sicily! Grazie per tutto!”

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Private Sailing Tour to Cyclops Islands from Catania - Swimming at Ulysses’ Caves
Cruises & Boat Tours, Private, Sailing, Tour Reviews, Tours

Private Sailing Tour to Cyclops Islands from Catania

14.Private Sailing Tour to Cyclops Islands from Catania

★★★★★★★★★★5.0 · 45 reviews

Review of Catania’s private Cyclops Islands sailing tour, with Etna views, Ulysses’ Caves, Sicilian lunch, swimming, and practical booking advice.

“This was one of the best days of our week long trip to Sicily. So much fun! Gianluca and Carlo were amazing - showed us some beautiful places along the coast, shared interesting stories, made us lunch, poured us prosecco, made us laugh - it Read more”

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7-Hour Private Yacht Tour on the Island of Pantelleria - Arco dell’Elefante and the island’s coves
Cruises & Boat Tours, Private, Sailing, Tour Reviews, Tours

7-Hour Private Yacht Tour on the Island of Pantelleria

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