Sicily Yacht Charter Itineraries

Back to Italy

Sicily to Sicily
Charter Itinerary

12 Days Charter Itinerary
Embark on a spectacular sailing journey around Sicily, the largest island in the Mediterranean and a treasure trove of history, natural beauty, and vibrant culture. From ancient Greek temples and Baroque towns to smoking volcanoes and crystalline bays, Sicily offers endless discoveries along its coastline. This curated itinerary takes you full circle, allowing you to explore the island’s rich past, lively markets, secluded anchorages, and charming harbors — one unforgettable port at a time. Whether you’re sailing solo, with family, or chartering with a crew, this voyage will immerse you in the authentic rhythm of Sicilian life by sea.
Make the best of your Sicily yacht trip with our Sicily to Sicily yacht charter itinerary.
Day 1

Palermo

Begin your journey in Sicily’s vibrant capital. Dock at Marina Villa Igiea or Cala Marina, then spend the day exploring the Palermo Cathedral, Teatro Massimo, and the bustling Ballarò Market. Don’t miss a street food tasting — arancine, panelle, and cannoli await.
Day 2

Cefalù

Sail east along the northern coast to Cefalù, a charming medieval town backed by rocky cliffs. Visit the majestic Cefalù Cathedral, a UNESCO World Heritage Site, and climb La Rocca for panoramic views. Swim off the sandy beach before enjoying fresh seafood along the harbor.
Day 3

Capo d’Orlando

Cruise toward Capo d’Orlando, a relaxed seaside town and a jumping-off point for the Aeolian Islands. Stroll along the waterfront promenade, visit local boutiques, or enjoy sunset dining with views of distant islands like Vulcano and Lipari.
Day 4

Milazzo

Head to Milazzo, a gateway to the northeast and the Aeolian archipelago. Tour the Castello di Milazzo, perched above the old town, or relax in secluded coves near the Piscina di Venere. This is a great stop to stock up before a wilder stretch of coast.
Day 5

Taormina

Sail to Giardini Naxos, the marina closest to glamorous Taormina. Spend the day exploring the Greek Theatre, medieval streets, and scenic viewpoints of this clifftop town. Cool off with a dip at Isola Bella, one of Sicily’s most photographed beaches.
Day 6

Syracuse

Cruise south to the ancient port of Syracuse, a city steeped in history. Dock near Ortigia Island, and visit the Ear of Dionysius, Temple of Apollo, and Piazza Duomo. Enjoy a romantic dinner in Ortigia’s lantern-lit alleys.
Day 7

Marzamemi

Sail to the picturesque fishing village of Marzamemi, known for its tuna fishing heritage and charming stone piazzas. Wander through artisan shops, swim in quiet bays, and enjoy a long, slow lunch of seafood pasta and Sicilian wine by the sea.
Day 8

Porto Palo di Capo Passero

Begin your westward return by heading to Porto Palo di Capo Passero. This is a quieter town, ideal for relaxing onboard, swimming in turquoise waters, and enjoying the rustic charm of southern Sicily.
Day 9

Agrigento

Sail toward San Leone, the coastal gateway to Agrigento. Take a short taxi inland to explore the Valley of the Temples, one of the most iconic archaeological sites in the Mediterranean. Watch the sun set behind the ancient ruins before returning to your boat.
Day 10

Mazara del Vallo

Cruise along the southern coast to Mazara del Vallo, a town with Arab-Norman influences and a strong fishing tradition. Visit the Dancing Satyr Museum, stroll through the Kasbah district, and sample local couscous with fresh catch from the sea.
Day 11

Favignana

Make a detour to Favignana in the Egadi Islands for snorkeling and a peaceful day off the grid.
Day 12

Palermo

Complete your Sicilian loop by sailing back to Palermo. Celebrate the end of your journey with a farewell dinner in the lively Vucciria district or at a rooftop restaurant overlooking the city’s twinkling skyline.

Sicily Yachts for Charter

Exclusive Selection
Discover the perfect fleet of yachts for your Sicily yacht charter itinerary. Whether you are looking for a sleek sailing yacht to cruise in the utmost silence or a luxurious motor yacht, our team of charter brokers curated the ultimate selection. 
Sunreef 80 Sail

GREYB

23.99m

I

Sunreef

I

2022
From €77,000 p/w
8 Guests
in 4 Cabins
Mediterranean
& N/A

KNEAD IT

25.3m

I

Pearl

I

2024
From €70,000 p/w
10 Guests
in 5 Cabins
Palma de Mallorca, Spain
& Palma de Mallorca, Spain

ZOZO

26.78m

I

Azimut

I

2023
From €75,000 p/w
10 Guests
in 5 Cabins
West Mediterranean
& N/A

Cornelia

34m

I

RMK Marine

I

2006
From €70,000 p/w
9 Guests
in 4 Cabins
Mediterranean
& N/A

SEALEN B

34.2m

I

Royal Huisman

I

2000 (2023)
From €59,000 p/w
8 Guests
in 4 Cabins
Mediterranean
& N/A

ROBUSTO

34.2m

I

Custom Line

I

2009
From €82,000 p/w
10 Guests
in 5 Cabins
Mediterranean
& Mediterranean

SERENO

35m

I

Benetti

I

2002
From €110,000 p/w
11 Guests
in 5 Cabins
West Mediterranean
& West Mediterranean

S7

39.3m

I

Tansu

I

2016 (2020)
From €126,000 p/w
12 Guests
in 5 Cabins
Caribbean
& Bahamas / Caribbean

Thumper

40.05m

I

Sunseeker

I

2014
From €168,000 p/w
12 Guests
in 5 Cabins
Mediterranean
& N/A

Silver Wind

43.63m

I

ISA Yachts

I

2014 / 2018
From €165,000 p/w
11 Guests
Mediterranean
& N/A

MAXIMILIAN MMIV

45.02m

I

Sunrise

I

2009 (2018)
From €180,000 p/w
11 Guests
in 5 Cabins
Mediterranean
& Mediterranean

Te Manu

49.38m

I

Codecasa

I

1998 / 2019
From €196,000 p/w
12 Guests
Mediterranean
& Caribbean

EMERALD

50.4m

I

Feadship

I

1990 (2023)
From €210,000 p/w
12 Guests
in 6 Cabins
Mediterranean
& N/A

R.M.F

52m

I

Sanlorenzo

I

2022
From €294,000 p/w
10 Guests
in 5 Cabins
Mediterranean
& Mediterranean

NITA K II

52.12m

I

Amels

I

2004 (2023)
From €250,000 p/w
12 Guests
Mediterranean
& Bahamas

AFTER YOU

55m

I

Heesen

I

2011 (2022)
From €330,000 p/w
12 Guests
in 6 Cabins
Mediterranean
& N/A

The Wellesley

56.20m

I

Oceanco

I

1993 / 2016
From €230,000 p/w
12 Guests
in 6 Cabins
Mediterranean
& N/A
Katina yacht for charter

Katina

60m

I

Brodosplit BSO d.o.o.

I

2015
From €245,000 p/w
12 Guests
in 6 Cabins
Mediterranean
& Caribbean

The Langley

62.21m

I

Aegean Yachts

I

2009
From €150,000 p/w
12 Guests
in 6 Cabins
Mediterranean
& N/A

GOLDEN HORIZON

162m

I

Brodogradevna Industrija Split

I

2021
From €910,000 p/w
274 Guests
Flexible
& Flexible

BOOM

17m

I

Lagoon

I

2018
From €15,400 p/w
10 Guests
in 5 Cabins
Eastern Mediterranean
& N/A

ADEA

18.3m

I

Sunreef Yachts

I

2017
From €26,000 p/w
8 Guests
in 4 Cabins
Western Mediterranean
& Western Mediterranean

LA FREGATE

19.5m

I

Lagoon

I

2017
From €35,500 p/w
8 Guests
in 4 Cabins
Western Mediterranean
& N/A

SOUL

20.15m

I

Azimut

I

2022
From €34,000 p/w
6 Guests
in 3 Cabins
Western Mediterranean
& Western Mediterranean

ADEONA

20.36m

I

Fountaine Pajot

I

2021
From €38,000 p/w
8 Guests
Mediterranean
& Leeward Islands

ALL FOR YOU

20.42m

I

Princess

I

2024
From €27,000 p/w
6 Guests
in 3 Cabins
Italy
& Italy

FORZA

20.46m

I

Sunseeker

I

2022
From €27,600 p/w
7 Guests
in 3 Cabins
N/A
& Mediterranean

FIVE II

20.5m

I

Sunseeker

I

2022
From €33,000 p/w
6 Guests
in 3 Cabins
Western Mediterranean
& Western Mediterranean

ALIKA

21.07m

I

Oyster Yachts

I

2016
From €33,000 p/w
6 Guests
Mediterranean
& Windward Islands

SHAWLIFE

21.25m

I

Princess

I

2016
From €30,000 p/w
8 Guests
in 4 Cabins
Mediterranean
& Mediterranean

SPIRIT OF RIO

21.32m

I

Princess

I

2021
From €39,000 p/w
8 Guests
in 4 Cabins
South of France
& N/A

MX5

21.4m

I

Pershing

I

2016
From €45,000 p/w
6 Guests
in 4 Cabins
Balearics
& N/A

MALOLO

21.7m

I

Sunseeker

I

2014
From €35,000 p/w
8 Guests
in 3 Cabins
Eastern Mediterranean
& N/A

LEGENDARY

22.26m

I

Pershing

I

2008 (2024)
From €41,300 p/w
7 Guests
in 3 Cabins
Balearics
& Balearics

WILJIM V

22.31m

I

Princess

I

2022
From €38,000 p/w
8 Guests
in 4 Cabins
Mediterranean
& Mediterranean

VABOSA

22.64m

I

Azimut

I

2018
From €36,000 p/w
8 Guests
in 4 Cabins
French Riviera & Italy
& N/A

YOLO

22.7m

I

Sunreef Yachts

I

2022
From €56,000 p/w
8 Guests
in 4 Cabins
Balearics
& Windward Islands

SUMMER BREEZE

23m

I

Pearl Yachts

I

2014 (2020)
From €37,000 p/w
8 Guests
in 4 Cabins
Western Mediterranean
& Western Mediterranean

LA GATTA

23.28m

I

Lagoon

I

2019
From €59,000 p/w
8 Guests
in 4 Cabins
Balearic Islands
& N/A

BLACK PEARL II

23.6m

I

Baltic Yachts

I

2008
From €32,000 p/w
6 Guests
in 3 Cabins
Balearic Islands
& Windward Islands

KOMODO

23.6m

I

Azimut

I

2018
From €50,000 p/w
8 Guests
in 3 Cabins
Balearic Islands, Canary Islands,
& n/a

JOY

23.8m

I

Lagoon

I

2018
From €50,000 p/w
8 Guests
in 4 Cabins
Western Mediterranean
& N/A

FOREVER ROSANNA

24m

I

AZIMUT

I

2010
Price on Request
9 Guests
Western Mediterranean
& Western Mediterranean

MINDFULNESS

24m

I

Advanced Yachts

I

2021
From €34,000 p/w
6 Guests
in 3 Cabins
West Mediterranean
& N/A

ULTIM

24m

I

Leopard

I

2006 (2020)
From €30,000 p/w
6 Guests
in 3 Cabins
Mediterranean
& Caribbean

RIVIERA

24m

I

ALALUNGA

I

2009
Price on Request
9 Guests
Western Mediterranean
& Western Mediterranean

MANTA

24m

I

Sunreef

I

2021
From €77,000 p/w
10 Guests
in 5 Cabins
Mediterranean
& N/A

MARTITA

24.3m

I

Palumbo

I

2022
From €45,000 p/w
8 Guests
in 4 Cabins
West Mediterranean
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