Cool Destinations
Top Sicily activities
Top Sicily landmarks
Beyond Sicily
Sicily trip ideas
  • Tours by category
  • Tours by accessibility
  • Tours by feature
  • Tours by the numbers
  • Top Sicily landmark tours
  • Tours in nearby places
  • Explore Italy tours
  • Sicily travel guides
  • Sicily travel calendar
Language $Currency
Login / Sign up
Bookings
Bookings
Cool Rewards Rewards
$0.00
Cool Rewards Rewards
$0.00
Wishlists
Wishlists
Profile
Help Center
Language
Log out
Start your search
Change your search
Place or activity
Select Dates

Top Sicily Sailing Trips

24 Results
Sort by:
Featured
Filter
Languages Clear
Time of Day Clear
22
13
3
Duration Clear
0
16
18
0
0
Price Clear
$0 $500+
Rating Clear
20
23
23
Specials Clear
23
6
0
10
1
Features Clear
2
6
18
0
23
2
Accessibility Clear
0
8
23
Families Clear
13
10
8

Sicily Tours

Attractions

Guides

Calendar

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 …More

4.9 (142)

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 (142)
from
$134
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 …More

Likely to Sell Out
Likely to Sell Out
Taormina, Italy
4.8 (114)

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 (114)
from
$82
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 …More

4.6 (60)

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 (60)
from
$80
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 …More

4.8 (67)

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 (67)
from
$64
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. …More

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
$82
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 …More

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
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 …More

5.0 (29)

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 (29)
from
$1,345
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 …More

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
$57
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. …More

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
$69
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 …More

5.0 (69)

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 (69)
from
$92
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 …More

4.8 (57)

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 (57)
from
$82
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 …More

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
$128
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 …More

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
$385
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. …More

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
$1,286
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 …More

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
$615
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 …More

Likely to Sell Out
Likely to Sell Out
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
$1,345
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 …More

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
$1,401
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. …More

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
$701
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 …More

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
$76
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. …More

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
$906

Frequently Asked Questions

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

Recent tour reviews
Best experience - don't miss
New York City
Private Sail Boat Tour to Favignana and Levanzo from Trapani
Roam17949093101, Sep 2026
Best experience - don't miss
Excellent experience - definitely worth the money and time - do not miss- Federico was extremely informative about the islands and the best suggestion for lunch. He had a lot of patience with me as I was a little hesitate to get in the water. I would book this tour over and over. The islands are beautiful and he shows you how much they are
Read more
Sail, Swim, and See the the Volcano
New York City
Catania: Sail Cyclops Coast by Boat and Enjoy a Sicilian Aperitif
johncV7260LN, Sep 2026
Sail, Swim, and See the the Volcano
Such a great experience! The EtnaTribe crew were so friendly and accommodating. Unfortunately we sailed on a day that did not have much wind, so we motored to the destination and enjoyed a swim in the sea as we watched Mount Etna spew grey smoke into the air. My son mastered standing on the paddle board while we all swam in the lovely salt water sea. Afterward, during the return, we dined on delicious olives, sausage and bruschette and sipped prosecco. Beautiful boat and crew. Top 5 experience.
Read more
Great dolphin tour
New York City
Dolphin Watching & Conservation – Dolphins in the Gulf of Catania
Madeleine_M, Sep 2026
Great dolphin tour
Great tour with very friendly guides. We saw dolphins and flying fish. The guides were respectful towards the animals, keeping some distance, but the dolphins were curious and came closer to the boat. I can highly recommend this experience.
Read more
Fabulous sunset Sail
New York City
Sailing Tour Taormina Bay
Kimberly_A, Sep 2026
Fabulous sunset Sail
The trip was absolutely fabulous and our skipper was very knowledgeable about the boat and the waters. She was also very knowledgeable about information in the area. I would highly recommend this trip.
Read more
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
FANTASTIC EXPERIENCE
New York City
Catania boat tour along the coast with aperitif and snorkeling
I2443VCgiovannaa, Sep 2026
FANTASTIC EXPERIENCE
Compliments to Gioacchino, a professional skipper who is attentive and thoughtful toward his guests. To Sofia, the assistant skipper, who is equally competent, helpful, and engaging. Thanks guys, those from elementary school!!
Read more
Boat trip with swimming in natural pools
New York City
Egadi Sail Boat Tour to Favignana and Levanzo from Trapani
alessandrosG1498CL, Sep 2026
Boat trip with swimming in natural pools
Fantastic day, Marcello was excellent, both in his explanations and in trying to dock for swimming in the best spots. Everything perfect, including the aperitif
Read more
Top notch
New York City
Catania: Sail Cyclops Coast by Boat and Enjoy a Sicilian Aperitif
camillerJ4830LO, Sep 2026
Top notch
Superb crossing with Jennifer and the skipper! Highly recommended 😊
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
Recommended
New York City
Egadi Sail Boat Tour to Favignana and Levanzo from Trapani
alessandrodE6594GZ, Sep 2026
Recommended
Marcello was fantastic, even though the weather wasn't the best, he was really good at guiding and advising us on alternatives to Levanzo and Marettimo.
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
A dream
New York City
Private Sail Boat Tour to Favignana and Levanzo from Trapani
alessandrodE4226DI, Sep 2026
A dream
Boat trip with my girlfriend.. Fabulous tour! A unique experience! First time for us on a sailboat, it was a dream. A thank you to Captain Marcello, very professional and extremely friendly. But above all, compliments on the cleanliness of the boat, everything kept with precision and obsessive order. Furthermore, you have complete freedom to move around all areas of the boat, always following the appropriate recommendations. Heartfelt thanks!
Read more
A beautiful gift
New York City
Boat tour in Palermo east – Excursion with aperitif
R4962RKmariag, Sep 2026
A beautiful gift
A beautiful experience! Vincenzo is very kind, he conveys his love for the sea and his boat Clara and his deep knowledge of these coasts! He was very helpful and flexible, he even took us a little further than planned to see the sunset :) Clara is a little gem that he clearly takes excellent care of. We are very happy to have given ourselves this gift!
Read more
Fantastic boat trip
New York City
Boat tour in Palermo east – Excursion with aperitif
778giuliof, Sep 2026
Fantastic boat trip
I recommend everyone to go on at least one excursion a month with the wonderful captains, Vincenzo and Paolo. Even fantastic, prepared and competent. They give you a carefree, relaxing and engaging day. Discovering marine nature and more, we had a lot of fun, very good aperitif on the boat. Money well spent!!!!
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
Sicily Tours
Attractions
Guides
Calendar
View more