Charter a sailing boat in Sicily

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Top trending boats in Sicily

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Listings are ranked based on a score that is recalculated every 24 hours using multiple criteria. Learn more

Explore Mondello, Malflorio, and Capo Gallo in Half a Day

Marina Adorno, Palermo, Italy

4.9

(6)

From

$661

/ day

+100 boats available

How we rank results

Listings are ranked based on a score that is recalculated every 24 hours using multiple criteria. Learn more

Milazzo

4.7

(9)

LOUISE @la_barca_di_canapa per una nautica più sostenibile

4 people · 4 cabins · 4 berths · 13 m

Booked 2 times in the last 24h

From

$626

/ day

Rental Catamaran LAGOON Lagoon 450 Capo d'Orlando

Capo d'Orlando

4.9

(6)

Lagoon 450 F

10 people · 4 cabins · 8 berths · 14 m

Full-Day Sailing Experience – Zingaro Nature Reserve & Scopello Rocks

Marina di Castellammare del Golfo, Trapani, Italy

Full-Day Sailing Experience – Zingaro Nature Reserve & Scopello Rocks

Skipper included

Superowners

Sailboat

8 hours · For groups of up to 11 people

Fuel included

Flexible cancellation

From

$1,183

Instant Booking

Sailing Experience from Castellammare – Scopello Faraglioni

Marina di Castellammare del Golfo, Trapani, Italy

Sailing Experience from Castellammare – Scopello Faraglioni

Skipper included

Superowners

Sailboat

4 hours · For groups of up to 11 people

Fuel included

Flexible cancellation

From

$828

Instant Booking

Rental Sailboat Beneteau Oceanis Clipper 423 Marsala

Marsala

4.9

(15)

Beneteau Oceanis clipper 423

10 people · 4 cabins · 10 berths · 13 m

From

$406

/ day

Rental Sailboat DUFOUR 56 Exclusive Capo d'Orlando

Capo d'Orlando

Sailboat DUFOUR 56 Exclusive 17m

(2017)

Skipper mandatory

Sailboat

16 people · 4 cabins · 8 berths · 17 m

Porto Arenella, Palermo, Italy

4.8

(37)

Sailing excursion

Owner as skipper

Superowners

Sailboat

4 hours · For groups of up to 7 people

From

$355

Sunset Aperitif at Villa Igiea - Four Hours Sailing along the Palermo Coast

Marina di Villa Igiea, Palermo, Italy

5.0

(3)

Sunset Aperitif at Villa Igiea - Four Hours Sailing along the Palermo Coast

Skipper included

Superowners

Sailboat

3 hours · For groups of up to 18 people

Fuel included

From

$1,526

Instant Booking

Rental Sailboat Hanse Hanse 575 Sailboat Milazzo

Milazzo

3.7

(6)

Hanse 575

(2017)

Skipper optional

Sailboat

10 people · 4 cabins · 8 berths · 17 m

From

$1,183

/ day

Rental Sailboat Jeanneau Sun Odyssey 440 Capo d'Orlando

Capo d'Orlando

4.5

(2)

Jeanneau Sun Odyssey 440

(2020)

Skipper optional

Sailboat

10 people · 4 cabins · 10 berths · 13.4 m

Special offer

Sailing Day Trip from Catania · Acitrezza's Faraglioni Rocks and Ulysses' Cave

Port of Catania, Catania, Italy

New

Sailing Day Trip from Catania · Acitrezza's Faraglioni Rocks and Ulysses' Cave

Skipper included

Sailboat

8 hours · For groups of up to 12 people

Fuel included

Flexible cancellation

From

$1,148

Randello Nature Reserve and Montalbano Lighthouse — Catamaran Tour

Scoglitti, Italy

4.9

(4)

Randello Nature Reserve and Montalbano Lighthouse — Catamaran Tour

Owner as skipper

Superowners

Catamaran

8 hours · For groups of up to 12 people

Fuel included

Flexible cancellation

From

$1,183

Instant Booking

Rental Sailboat BENETEAU OCEANIS 45 Capo d'Orlando

Capo d'Orlando

5.0

(2)

Sailboat BENETEAU OCEANIS 45 14m

10 people · 4 cabins · 10 berths · 14 m

Booked 5 times in the last 24h

From

$422

/ day

Rental Sailboat Comar Comet 383 Tonnarella

Tonnarella

4.8

(6)

Comet 383 - Charternautica

6 people · 3 cabins · 8 berths · 11.8 m

Booked 4 times in the last 24h

From

$457

/ day

Sunset/night on the Ragusa coast — 4 hours from Scoglitti

Scoglitti, Italy

4.9

(4)

Sunset/night on the Ragusa coast — 4 hours from Scoglitti

Owner as skipper

Superowners

Catamaran

4 hours · For groups of up to 12 people

Fuel included

Flexible cancellation

From

$828

Instant Booking

…

Our client reviews

4.9 / 5

Score calculated based on 745880 reviews

See all reviews

Destination Reviews

Reviews are displayed in chronological order

B

Brenna

Date of the review 8/20/26 · Date of the rental 8/19/26

Very beautiful area - there were specific regulations regarding where you can anchor the boat
A

Antonio

Date of the review 8/5/26 · Date of the rental 8/2/26

We had an amazing half-day boat charter in Cefalù for our group of 10. The boat was clean, comfortable, and the views of the coastline were absolutely beautiful. Gabriele and his mate, Christian, were outstanding hosts—friendly, professional, and made sure everyone had a great time from start to finish. They went above and beyond to make the trip relaxing and enjoyable. If you’re visiting Cefalù and looking for a memorable experience on the water, I highly recommend booking with them. It was one of the highlights of our trip!
Drew

Date of the review 7/12/26 · Date of the rental 7/5/26

We chartered out of Sicily with GruppoTOC/EnjoyMe and visited some stunning spots along the Sicilian coast. The crew, Lorenzo (captain) and Luciana (stewardess), knew exactly where to take us and made every stop feel special. Crystal clear water, beautiful scenery, and a pace that felt relaxed and unrushed. What I loved most was how personal the whole experience felt. Lorenzo navigated flawlessly and Luciana made sure we were taken care of the entire time. They both went above and beyond in a way you don't always get on a charter. For other renters: do the full day, not a half day. Bring sunscreen, and let the crew guide you on the route. They know the best spots. And if you can book with GruppoTOC/EnjoyMe specifically, do it. This was actually the day I proposed to my partner, and the crew helped make it absolutely perfect. Could not recommend more highly.
A

Ali

Date of the review 9/1/25 · Date of the rental 8/25/25

I would highly recommend renting your boat from here :) Staff are amazing
A

Anastasia

Date of the review 8/13/25 · Date of the rental 8/8/25

An unforgettable day in Marzamemi! The Giorgi 46 was in excellent condition, comfortable, spacious, and perfect for exploring the beautiful Sicilian coast. Alfonso, our skipper, was truly exceptional – professional, knowledgeable, and incredibly friendly. He made us feel at ease from the first moment, sharing fascinating local stories and taking us to stunning hidden spots we would never have found on our own. Everything was perfectly organised, from departure to return, with great attention to detail and safety. The whole experience was relaxed, luxurious, and full of memorable moments. Highly recommended for anyone visiting Sicily – we will definitely book again!
J

Jessica

Date of the review 7/20/25 · Date of the rental 7/17/25

We went down to Scopolo and then stoped at multiple beaches located on the coast of the nature reserve - it was beautiful!
A

Andrea

Date of the review 7/1/24 · Date of the rental 6/30/24

Natural and historical place full of night life, very close to Palermo Capital City, just in the middle between Cefalu' and Palermo, one hour from airport, quiet location for any age I would say, good food.Really recommended
R

Raymond

Date of the review 10/5/22 · Date of the rental 10/3/22

The inner city is very beautifull with great beutifull buildings, squares full of people. Nicely lit. Great restaurants.

Boats Reviews

Reviews are displayed in chronological order

V

Valerie

Date of the review 9/13/26 · Date of the rental 9/8/26

Amazing time! There were 9 adults and we had plenty of room. Salvo I was very friendly and accommodating. We will definitely rent from him again when we return to Sicily!
Simon

Date of the review 8/26/26 · Date of the rental 8/26/26

Very nice Experience, easy comunication and great introduction to the boat, felt very safe in the whole process.
Alessandro

Date of the review 7/5/26 · Date of the rental 7/5/26

Jo and her friends and family were wonderful guests. They were friendly, respectful, and a pleasure to have on board. They treated the yacht with great care and created a relaxed, positive atmosphere throughout the trip. Communication was smooth from start to finish, and we would be delighted to welcome them back anytime. Highly recommended to any host!
K

Kathy

Date of the review 5/29/26 · Date of the rental 5/29/26

We had such a great time on Giuseppe’s boat! Our family of 10 (7 adults and 3 kids ages10,7,2) took a 4 hour cruise, stopped to swim and cruise along the coast. We brought lunch and drinks - it was perfect! We would highly recommend! It was a lovely relaxing day on the water. Grazie Giuseppe!!!
C

Cory

Date of the review 10/7/25 · Date of the rental 10/1/25

Had so much fun on Mirko’s boat! Even though the weather wasn’t great the day we went, we still had a very enjoyable time lounging on the sundeck on the boat infront of Maniace Castle and around Ortigia. Mirko was very helpful and checked on us multiple times to make sure we were doing well. Would highly recommend!
T

Toni

Date of the review 9/25/25 · Date of the rental 9/25/25

It was a really nice boat. 27 knot down the coast! Nice. Everything was fine. Boat was clean and 100% as mentioned. Nice and kind people. White Club is a nice start and landing point. Harbour is big enough to drive without heavy Maneuvering.
P

Paul

Date of the review 9/21/25 · Date of the rental 9/18/25

Marina Yacht was flexible with my arrival / return time (we were running late) and had everything we needed for an amazing rental: cooler, snorkeling equipment, ice, etc. The speakers on the boat did not work and we had a small hiccup with the engine overheating on the way out of the marina, but it recovered quickly. We did lose the top to the cooler due to the wind, so if they give you a cooler with an unsecure top, make sure to secure it to avoid a charge. Also, the bottom of the sea in that area is rocky with some large rocks that can easily steal your anchor (we lost ours in San Vito) which will cost you 70 Euro - so try to find a sandy spot to anchor.
A

Annalyse

Date of the review 9/16/25 · Date of the rental 9/16/25

we had the most amazing boat tour today with Francesco and Pasquale! They took us all along the stunning Taormina coast, showing us the most beautiful spots and sharing their local knowledge with so much passion. The water was crystal clear, the views were breathtaking, and the whole experience felt so relaxed and fun. Francesco and Pasquale were incredibly kind, welcoming, and made the day unforgettable. Truly one of the highlights of our trip, we can’t recommend them enough! Lots of love from the Australian crew 🇦🇺💕

Frequently Asked Questions about Sicily

What is the price of renting a sailboat for a day in Sicily?

The average price of renting a sailboat for the day in Sicily is $1,027. A few factors can determine the cost of the rental, such as the time of year, how old the boat is, and the boat equipment. Depending on these factors, the price of renting a sailboat can range from $348 and $3,248.

What is the typical daily cost of hiring a skipper in Sicily?

The cost of hiring a skipper can differ based on the boat's destination and owner. In Sicily, the typical rate of a skipper is $100 per day.

How many sailboats are available for rental in Sicily?

Currently, there are approximately 565 sailboats available for rental in Sicily. The number may change depending on the season.

How much does a sailboat charter cost in Sicily in the high season versus the low season?

The average price of chartering a sailboat in Sicily in the high season is approximately $1,160 per day, while they are around $447 per day in the low season.

What are the most sought-after sailboat brands in Sicily?

In Sicily you will find a wide variety of sailboats from Beneteau or Jeanneau.

Rent a sailboat near Sicily

In Sicily, privately owned boats are available for rental. See other boats in the area.

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Rent another type of boat in Sicily

If you want to rent something different from the sailboat in Sicily?
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Charter a sailing boat in Sicily

Explore Mondello, Malflorio, and Capo Gallo in Half a Day

From $1,597

Full-day boat trip: Taormina and the east coast of Sicily

From $3,313

Sailboat Jeanneau Sun Odissey 45 14m

From $661 / day

LOUISE @la_barca_di_canapa per una nautica più sostenibile

From $626 / day

Lagoon 450 F

Full-Day Sailing Experience – Zingaro Nature Reserve & Scopello Rocks

From $1,183

Sailing Experience from Castellammare – Scopello Faraglioni

From $828

Beneteau Oceanis clipper 423

From $406 / day

Sailboat DUFOUR 56 Exclusive 17m

Sailing excursion

From $355

Sunset Aperitif at Villa Igiea - Four Hours Sailing along the Palermo Coast

From $1,526

Hanse 575

From $1,183 / day

Jeanneau Sun Odyssey 440

Sailing Day Trip from Catania · Acitrezza's Faraglioni Rocks and Ulysses' Cave

From $1,148

Randello Nature Reserve and Montalbano Lighthouse — Catamaran Tour

From $1,183

Sailboat BENETEAU OCEANIS 45 14m

From $422 / day

Comet 383 - Charternautica

From $457 / day

Sunset/night on the Ragusa coast — 4 hours from Scoglitti

From $828

Destination Reviews Reviews are published without prior moderation. Learn more

Boats Reviews Reviews are published without prior moderation. Learn more

Frequently Asked Questions about Sicily

What is the price of renting a sailboat for a day in Sicily?

What is the typical daily cost of hiring a skipper in Sicily?

How many sailboats are available for rental in Sicily?

How much does a sailboat charter cost in Sicily in the high season versus the low season?

What are the most sought-after sailboat brands in Sicily?

Rent a sailboat near Sicily

Rent another type of boat in Sicily

From

$1,597

From

$3,313

From

$661

/ day

From

$626

/ day

From

$1,183

From

$828

From

$406

/ day

From

$355

From

$1,526

From

$1,183

/ day

From

$1,148

From

$1,183

From

$422

/ day

From

$457

/ day

From

$828

Destination Reviews

Boats Reviews