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Top Sicily Sailing Trips

26 Results
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Sicily Tours

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Egadi Sail Boat Tour to Favignana and Levanzo from Trapani
4.9 (140)

Egadi Sail Boat Tour to Favignana and Levanzo from Trapani

Our skipper will guide you to discover the Egadi Islands, following the wind’s breath. Live a unique experience between secret caves, inaccessible bays and uncountable...

8 hours • Free Cancellation
4.9 (140)
from
$135
4 hours by Boat from Castellammare del Golfo to Zingaro and Scopello
Likely to Sell Out
Likely to Sell Out
4.8 (56)

4 hours by Boat from Castellammare del Golfo to Zingaro and Scopello

The skipper guided by the daily wind, will decide the most suitable route in order to ensure the most favorable and attractive conditions for guests....

4 hours • Free Cancellation
4.8 (56)
from
$83
Catania: Sail Cyclops Coast by Boat and Enjoy a Sicilian Aperitif
4.8 (65)

Catania: Sail Cyclops Coast by Boat and Enjoy a Sicilian Aperitif

Live a memorable sailing cruise! Choose between a morning tour or a magical sail with the warm, romantic colors of sunset. Discover the stunning beauty...

4 hours • Free Cancellation
4.8 (65)
from
$65
Private Sail Boat Tour to Favignana and Levanzo from Trapani
5.0 (27)

Private Sail Boat Tour to Favignana and Levanzo from Trapani

Our skipper will guide you to discover the Egadi Islands, following the wind’s breath. Live a unique experience between secret caves, inaccessible bays and uncountable...

8 hours • Free Cancellation
5.0 (27)
from
$1,352
Sailing Tour Taormina Bay
Taormina, Italy
4.8 (113)

Sailing Tour Taormina Bay

Discover the bays around the coast of Taormina with our sailing tour from Giardini Naxos. Enjoy the experience on board of our sailboat with a...

3 hours • Free Cancellation
4.8 (113)
from
$82
4 Hours Catamaran Tour to the Scala dei Turchi
5.0 (33)

4 Hours Catamaran Tour to the Scala dei Turchi

Our activity is eco-friendly (weather and sea conditions permitting we will sail). Possibility to swim, snorkel and stand up paddle. Our skippers are licensed and...

4 hours • Free Cancellation
5.0 (33)
from
$76
Plemmirio Sailing Tour from Ortigia with Snorkeling
Likely to Sell Out
Likely to Sell Out
5.0 (69)

Plemmirio Sailing Tour from Ortigia with Snorkeling

With us you will live a unique experience in the Plemmirio Marine Protected Area starting from the beautiful setting of Ortigia and snorkeling accompanied by...

2 hours 30 minutes • Free Cancellation
5.0 (69)
from
$65
Catania boat tour along the coast with aperitif and snorkeling
4.6 (58)

Catania boat tour along the coast with aperitif and snorkeling

Rely on us to live a unique experience along the lava coast of Catania aboard a comfortable sailboat. You can admire Etna and the city...

4 hours • Free Cancellation
4.6 (58)
from
$81
Boat tour in Palermo east - Excursion with aperitif
5.0 (66)

Boat tour in Palermo east - Excursion with aperitif

Enjoy the real Sicily!!! Between sea, relaxation and healthy fun along the wonderful coast of Mongerbino. Depart from the picturesque fishing village of Porticello to...

5 hours • Free Cancellation
5.0 (66)
from
$93
Catania: Boat Trip with Aperitif, Prosecco and Snorkeling
Likely to Sell Out
Likely to Sell Out
5.0 (7)

Catania: Boat Trip with Aperitif, Prosecco and Snorkeling

Embark on a unique and exciting adventure among the Sicilian waves. Depart from the port of Catania until you reach the coast of Aci Trezza....

5 hours • Free Cancellation
5.0 (7)
from
$70
Dolphin Watching & Conservation - Dolphins in the Gulf of Catania
4.8 (56)

Dolphin Watching & Conservation - Dolphins in the Gulf of Catania

We are the only ones to carry out eco-tourist activity of observation of cetaceans in the Gulf of Catania, respecting the international code of good...

3 hours • Free Cancellation
4.8 (56)
from
$83
Daily Egadi Tour: Favignana and Levanzo in Rubber Dinghy
5.0 (59)

Daily Egadi Tour: Favignana and Levanzo in Rubber Dinghy

The Tour is a unique experience that gives the opportunity to visit the most beautiful coves of the island of Favignana and Levanzo. Live to...

8 hours • Free Cancellation
5.0 (59)
from
$129
Sailing tour in Syracuse and guided snorkeling - Private
Likely to Sell Out
Likely to Sell Out
5.0 (2)

Sailing tour in Syracuse and guided snorkeling - Private

Discover the coast of Syracuse with an exclusive private sailing tour. Sail through crystal clear waters and breathtaking cliffs, exploring the enchanting Plemmirio Marine Protected...

4 hours • Free Cancellation
5.0 (2)
from
$623
Exclusive dinner on a Taormina sailing boat
Likely to Sell Out
Likely to Sell Out
5.0 (1)

Exclusive dinner on a Taormina sailing boat

Make a special occasion such as a birthday or an anniversary unique, or simply surprise your sweetheart with a romantic dinner on board, departing from...

3 hours • Free Cancellation
5.0 (1)
from
$390
Ortigia and Plemmirio on a sailing boat
Likely to Sell Out
Likely to Sell Out
5.0 (1)

Ortigia and Plemmirio on a sailing boat

Do you want to live a unique experience that you can tell and remember forever? Take part in the "Ortigia and Plemmirio in a sailing boat" experience....

4 hours • Free Cancellation
5.0 (1)
from
$1,300
Daily Sailing Tour in Palermo with lunch.
5.0 (11)

Daily Sailing Tour in Palermo with lunch.

Guests can live a unique experience and admire our wonderful coast. Once in the clear sea of the Gulf of Mondello, near the Capo Gallo...

7 hours • Free Cancellation
5.0 (11)
from
$1,411
Private Boat 4h Scopello and Gypsy from Castellammare del Golfo
5.0 (1)

Private Boat 4h Scopello and Gypsy from Castellammare del Golfo

The skipper, guided by the daily wind, will decide the most suitable route in order to ensure guests the most favorable and captivating conditions. Stops...

4 hours • Free Cancellation
5.0 (1)
from
$1,353
Sailing tour in Cefalù
4.8 (5)

Sailing tour in Cefalù

See the coast of Cefalù from another perspective, sail on a sailboat, swim in our sea and avoid the very crowded beaches....

3 hours • Free Cancellation
4.8 (5)
from
$709
Sailing tour at sunset in catania
4.3 (6)

Sailing tour at sunset in catania

Unique and romantic sunset experience on a sailing boat with a view of Mount Etna and the Catania coast. Together with our staff you can...

3 hours • Free Cancellation
4.3 (6)
from
$77
Ragusa coast: Private Sailing tour
4.0 (2)

Ragusa coast: Private Sailing tour

Spend a relaxing day sailing with your group of no more than 8 guests with this private sailing tour from Ragusa....

4 hours
4.0 (2)
from
$915

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Sailboat Cruise
New York City
Sailing Tour Taormina Bay
Philip_A, Sep 2026
Sailboat Cruise
What a great time. Lulu our captain was awesome. She pointed out lots of sites and was very knowledgeable. She was also very flexible with our time. Allowed us to swim a little longer in one location than the other. Great way to start your day
Read more
Wonderful boat day
New York City
4 hours by Boat from Castellammare del Golfo to Zingaro and Scopello
DiMcFree, Sep 2026
Wonderful boat day
It was a wonderful boat ride. The sea is gorgeous. The boat is lovely and it was not too crowded. A very enjoyable for our trip.
Read more
A dolphin trip that totally respects the dolphins
New York City
Dolphin Watching & Conservation – Dolphins in the Gulf of Catania
colinsD6334CB, Sep 2026
A dolphin trip that totally respects the dolphins
Fantastic trip with Carlo and the skipper. They totally respect that this is the dolphin’s natural home and we are the guests privileged to view them. We got to see plenty of dolphins and even received a little display at the end where they seemed to be saying thank you and bye! Lovely to be out on the water and view Aci Castello and Aci Trezza from the sea. Recommended
Read more
Relaxing boat tour in Sicily
New York City
Catania: Sail Cyclops Coast by Boat and Enjoy a Sicilian Aperitif
E3843BGjamess, Sep 2026
Relaxing boat tour in Sicily
A wonderfully relaxing boat tour with beautiful scenery and a very friendly, knowledgeable guide. We learned so much about the area while simply enjoying the amazing Sicilian coastline — highly recommended!
Read more
Excellent
New York City
Catania: Sail Cyclops Coast by Boat and Enjoy a Sicilian Aperitif
Dmytro007, Sep 2026
Excellent
It was a great tour, thanks to Gabriel and Gabriella, tour, swimming and prosecco were excellent!
Read more
Great experience
New York City
Catania boat tour along the coast with aperitif and snorkeling
G8091JIclareb, Sep 2026
Great experience
Fabulous morning beautiful swimming- lovely crew.
Read more
Unique and unforgettable experience
New York City
Dolphin Watching & Conservation – Dolphins in the Gulf of Catania
R1247ZJdanielb, Sep 2026
Unique and unforgettable experience
A wonderful and unforgettable experience! 🐬Carlo was a great guide – very likable, competent, and passionate about his work. He took a lot of time to explain everything to us and provided a lot of interesting information about the dolphins and the region.We saw various sea creatures during the tour. The guide and skipper take the topic of marine conservation very seriously and also retrieved larger pieces of trash from the sea along the way and brought them back to shore.Towards the end of the tour, we were very lucky and discovered a large group of dolphins. We were able to watch them for quite a while – a truly special moment and a perfect end to the tour!We enjoyed the tour very much and would do it again anytime. A clear recommendation for everyone looking for a special experience in Catania.
Read more
Sun and sea adventure
New York City
Boat tour in Palermo east – Excursion with aperitif
tanyaw912, Sep 2026
Sun and sea adventure
Really fun morning in the Med. We enjoyed very much the tour and the company. Boat was well equipped with snorkels and floats. We were super pleased that we booked, it was one of the highlights of of our holiday. Great host and beautiful scenery 👌 The boat, Clara, was very easy to get in and out. We felt very safe and had the company of another fun family of multiple ages.
Read more
Wonderful day on a sailboat in the Egadi Islands
New York City
Egadi Sail Boat Tour to Favignana and Levanzo from Trapani
510lucav, Sep 2026
Wonderful day on a sailboat in the Egadi Islands
Beautiful sailboat trip with swims in the fantastic waters of Favignana and Levanzo and a pleasant stop in Favignana. Professional skipper and generous with useful tips.
Read more
Beautiful sites and stunning fish!
New York City
Boat tour in Palermo east – Excursion with aperitif
jonathansL7153JX, Aug 2026
Beautiful sites and stunning fish!
We had a really great boat tour and snorkel! The black coral were beautiful and our captain, Vincenzo, was the friendliest guy in the world. So knowledgeable and he shared many great stories.
Read more
An experience not to be missed
New York City
Catania boat tour along the coast with aperitif and snorkeling
deboracU3661UN, Aug 2026
An experience not to be missed
Nice experience. Giorgio and Sofia M. were truly exceptional.
Read more
Great Afternoon On The Water
New York City
Sailing Tour Taormina Bay
Happiness479044, Aug 2026
Great Afternoon On The Water
We had an amazing afternoon on the water near Naxos and Taormina. Lulu is very nice. She is very knowledgeable about the area and had lots of interesting facts to share. We swam at a couple of spots and had lunch and wine on the boat. I would definitely recommend this sailing tour.
Read more
Chilled girls afternoon
New York City
4 Hours Catamaran Tour to the Scala dei Turchi
melissabX3166HP, Aug 2026
Chilled girls afternoon
Super friendly guides, lovely experience, very relaxed and plenty of snacks and drinks - a great experience. We found the meeting place a bit hard to find but very responsive and talked is in!
Read more
A great experience
New York City
Plemmirio Sailing Tour from Ortigia with Snorkeling
T1086FZsabinew, Aug 2026
A great experience
Totally great 4 hours - Roberto accompanied us while snorkeling and showed us. the diversity of the underwater world and dove with us into several caves ♥️ Sebastian our captain was also very nice! Explanations, stories, and small talk led to an unforgettable day! Thank you - Grazie 🙏
Read more
Wonderful Favignana
New York City
Private Sail Boat Tour to Favignana and Levanzo from Trapani
emanuelebP9127BB, Aug 2026
Wonderful Favignana
Skipper Marcello was professional and helpful, a splendid day.
Read more
Great experience in Riserva dello Zingaro
New York City
4 hours by Boat from Castellammare del Golfo to Zingaro and Scopello
X3206HDchiarab, Aug 2026
Great experience in Riserva dello Zingaro
Beautiful places and enough time to swim and explore, amazing Tonnara di Scopello
Read more
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