Italy

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Sailing Holidays in Italy

Discover one of the most fascinating countries in the world on a yacht charter in Italy! Breathtaking coastal views, historical and cultural landmarks, and the vibrant people make this country the perfect place for your sailing holidays. Italy welcomes you with myriad boating destinations. Go sailing by boat rental in Sicily and cruise around Stromboli volcano, or relax on Cala Rossa beach. Explore the Amalfi Coast and the Gulf of Naples by a yacht charter in Italy: Capri, Positano, or Marina Corricella. Go sailing in Italy by boat charter in Sardinia or yacht rental in Tuscany or head for the sunny Cinque Terre and visit Monte Argentario, or the Elba island. No matter what part of “The Belpaese” you will choose for your sailing adventure on Sailo boat charter in Italy, you’re guaranteed to have a summer to remember!

SMS

Our Favorite Itineraries in Italy

1

Amalfi Coast

Sail along the Amalfi Coast, Bay of Naples, and Capri
- Day 1
  
  Positano
  
  Stop 1
  - Next stop
  - Positano
    
    Departure: 5:00 pm
    
    Start your Italy adventure in the city of Positano at the center of the Amalfi Coast. Arrive earlier and spend the day in the city, or have a late start with just the evening cruise.
- Day 1
  
  Amalfi
  
  Stop 2
  - Previous stop
    
    Next stop
  - Amalfi
    
    Arrival: 6:00 pm; Departure: 8:00 pm
    
    Take yourself out on a sunset sail to experience the unique beauty this coast is famous for by sailing to the small city of Amalfi. Have dinner on the boat or disembark to try one of Amalfi's numerous restaurants lining the water. Choose to stay for a relaxing evening or return after dinner to experience the exciting nightlife back in Positano.
- Day 1-2
  
  Positano
  
  Stop 3
  - Previous stop
    
    Next stop
  - Positano
    
    Arrival: 9:00 pm; Departure: 11:00 am
    
    Back on dry land, Positano is rich with shopping, dining, and cultural sites to explore. The next morning is also a great opportunity to visit one of the many beaches or hike along the cliffside.
- Day 2
  
  Nerano
  
  Stop 4
  - Previous stop
    
    Next stop
  - Nerano
    
    Arrival: 12:30 pm; Departure: 2:30 pm
    
    On your way around the coast, Nerano is a lesser-known but equally as beautiful stop. Take a short diversion from the sail to Sorrento and explore one of Nerano's many gourmet restaurants for a late lunch or explore the olive groves.
- Day 2-3
  
  Sorrento
  
  Stop 5
  - Previous stop
    
    Next stop
  - Sorrento
    
    Arrival: 4:00 pm; Departure: 11:00 am
    
    Next stop is Sorrento. Here you can find the best views of the Bay of Naples and also spot Mt. Vesuvius in the distance. Have a beautiful evening at any of the areas excellent restaurants while observing this unique view. As the birthplace of Limoncello liqueur, start the evening with a chilled glass and start exploring the busy streets filled with lively bars for a fun night out.
- Day 3-4
  
  Ischia
  
  Stop 6
  - Previous stop
    
    Next stop
  - Ischia
    
    Arrival: 3:00 pm; Departure: 9:00 am
    
    Spend the afternoon at one of Ischia's beaches or spas. For a more active experience, venture into the commercial center for some light shopping or historic quarter to witness castles frozen in time. Take a detour on your way over and sail around Procida, the smallest and least touristy islands in the Bay of Naples.
- Day 4-5
  
  Capri
  
  Stop 7
  - Previous stop
    
    Next stop
  - Capri
    
    Arrival: 11:30 am; Departure: 10:00 am
    
    Capri is the final new destination along this trip, and it will be one you won't want to leave. This alluring island is picturesque and plentiful, so spend the day indulging in one of Capri's many attractions. Sail around the length of the island for beautiful views, and stop along the way for swimming, snorkeling, and potentially a short trip to the famous grottos. The island itself offers a range of dining and shopping options to keep you occupied far past a day's time.
- Day 5
  
  Positano
  
  Stop 8
  - Previous stop
  - Positano
    
    Arrival: 1:00 pm
    
    While the journey is over, the sail back to Positano from Capri has one final parting gift. Experience the unforgettable views of the Amalfi Coast one extra time before the trip ends. Choose to leave after a leisurely breakfast or some extra beach time in Capri, or leave early and spend the day back in Positano.
2

Sardinia

Sail the northwest shores of Sardinia and see the famous Costa Smeralda
- Day 1
  
  Porto Cervo
  
  Stop 1
  - Next stop
  - Porto Cervo
    
    Departure: 10:00 am
    
    Start your adventure in the luxurious city of Porto Cervo! Once one of the most exclusive areas of the world, treat yourself to exquisite shopping, great food, and pristine beaches. Come a night early to experience the lively nightlife and maybe even spot a celebrity. There are many events held here throughout the summer, see if there are any you can attend while passing through!
- Day 1-2
  
  La Maddalena Island
  
  Stop 2
  - Previous stop
    
    Next stop
  - La Maddalena Island
    
    Arrival: 12:00 pm Departure: 3:00 pm (following
    
    The first stop is the beautiful and quaint La Maddalena. Explore the untouched surrounding islands and beaches, each different from the next. Spend the day swimming, relaxing, and enjoying the peace. Bring food from Porto Cervo and enjoy a private picnic on the beach, or try one of the quiet cafes scattered among the islands.
- Day 2
  
  Arzachena
  
  Stop 3
  - Previous stop
    
    Next stop
  - Arzachena
    
    Arrival: 4:30 pm Departure: 6:30 pm
    
    Spend the afternoon venturing farther inland to the city of Arzachena. Take a more adventurous path and explore the fantastically preserved ancient ruins still standing in the city. On a different note, visit the local vineyard for a special tasting of Sardinian wines. Either way, Arzachena is a refreshing change of scenery before returning to the beautiful beaches of the coast.
- Day 2-3
  
  Porto Cervo
  
  Stop 4
  - Previous stop
    
    Next stop
  - Porto Cervo
    
    Arrival: 8:00 pm Departure: 12:00 pm
    
    Return to spend the night in the familiar city of Porto Cervo. Enjoy a sunset sail coming from Arzachena. Experience the nightlife in one of Porto Cervo's comfortable and upbeat bars, or relax after the long day of exploration. Spend the morning lounging on the beach or swimming in the shallow waters.
- Day 3
  
  Porto Rotondo
  
  Stop 5
  - Previous stop
    
    Next stop
  - Porto Rotondo
    
    Arrival: 2:00 pm Departure: 6:00 pm
    
    Take a quick break from the beaches and sail farther south to the town of Porto Rotondo. Here you will find an assortment of shops to browse from, many featuring handmade jewelry, crafts, and art. Try one of the area's restaurants for lunch and stroll around the harbor before returning to your boat.
- Day 3-4
  
  Costa Smeralda
  
  Stop 6
  - Previous stop
    
    Next stop
  - Costa Smeralda
    
    Arrival: 7:00 pm Departure: 10:00 am
    
    Costa Smeralda runs south along the coast from Porto Cervo and brings all the glamorous charm along with it. The coast is lined similarly with beaches, resorts, shopping, and the best restaurants. Stop at one of the many marinas and sample the splendor of Costa Smeralda for the night on your way back north to Porto Cervo.
- Day 4
  
  Porto Cervo
  
  Stop 7
  - Previous stop
  - Porto Cervo
    
    Arrival: 11:00 am
    
    The sail back to Porto Cervo is enriched with the constant panorama of crisp sand beaches and crystal blue water. Stop again along the way for a quick swim, snorkel, or excursion to the beaches back along the Costa Smeralda.
3

Yacht Charter in Italy - Medieval Architecture

Sailing in Italy to enchanting medieval port cities
- Starting point
  
  Cecina
  
  Starting point
  - Next stop
  - Cecina
    
    Starting Port
    
    Hoist the sails from your Sailo yacht charter in Italy and come along for the ride as we admire medieval cities and architecture from some of the most charming coastal cities in Italy.
- Day 1
  
  Massa and Carrara
  
  Stop 1
  - Previous stop
    
    Next stop
  - Massa and Carrara
    
    46 NM from last port
    
    For the first stop during your sailing holidays in Italy, make way for the province of Massa-Carrara. Visit the cathedral in the coastal city of Carrara and admire the intricacies carved into the marble towering above your head. To fulfill your castle daydreams, head to the Malaspina castle nestled on a hill over the city. Dating back to the 12th century, spending a day exploring this fortress will give you a first-hand taste of medieval architecture.
- Day 2
  
  Livorno
  
  Stop 2
  - Previous stop
    
    Next stop
  - Livorno
    
    30 NM from last port
    
    Known as a port city for centuries, Livorno is rich in multicultural heritage from around the globe. Dock your yacht charter in Italy in Tuscany’s third largest city for a delightful cultural experience. Take a small boat through the canals nicknamed “Little Venice” and be sure to stop at a local restaurant for some of the best seafood on the coast!
- Day 3
  
  Piombino
  
  Stop 3
  - Previous stop
    
    Next stop
  - Piombino
    
    37 NM from last port
    
    For the next stop during your sailing holidays in Italy, head to Piombino! Nestled between the Ligurian Sea and the Tyrrhenian Sea this coastal paradise is a must as you’re sailing in Italy. Venture up to Piazza Bovio for a stunning view of the seaside. Be sure to bring your camera to snap a memory of the panoramic coastline!
- Day 4
  
  Porto Santo Stefano
  
  Stop 4
  - Previous stop
    
    Next stop
  - Porto Santo Stefano
    
    39 NM from last port
    
    For the next stop sailing in Italy, we head to Porto Santo Stefano. A bustling port city, dock your Sailo yacht and explore the charming historic district by foot. For a taste of Spanish architecture, make way to the Spanish fortress hovering above the city. Built in the 17th century during Spanish rule and in impeccable condition, wander through the fortress and be transported to another time and place.
- Day 5
  
  Grosseto
  
  Stop 5
  - Previous stop
    
    Next stop
  - Grosseto
    
    47 NM from last port
    
    For an authentic Tuscan experience, drive your Sailo yacht charter in Italy to the picturesque Grosseto. Not often frequented by tourists, a visit to this charming port town will offer you a genuine Italian experience. Stroll through the historic center and stop in a local restaurant to chat up the owner in broken English and hand gestures. Some of the best recommendations come from conversations with locals!
- Ending point
  
  Cecina
  
  Ending point
  - Previous stop
  - Cecina
    
    44 NM from last port
    
    We hope you had a “fantastico” adventure with us on your Sailo yacht charter in Italy! Set sail back to Cecina for an end to a wonderful adventure.
4

Yacht Charter in Italy - Tuscan Coast

Sailing in Italy to secluded ports
- Starting point
  
  Cecina
  
  Starting point
  - Next stop
  - Cecina
    
    Starting Port
    
    Step aboard a Sailo yacht charter in Italy for a journey on crystal clear waters through southern Tuscany!
- Day 1
  
  Piombino
  
  Stop 1
  - Previous stop
    
    Next stop
  - Piombino
    
    21 NM from last port
    
    For the first stop during your vacation sailing in Italy, head to the naval town of Piombino. A small seaside village, you can easily walk the city in one day to admire medieval architecture. For a stunning view of the coast, walk up the sea cliff to Piazza Bovio where you can snap pictures of Montecristo or Corsica islands!
- Day 2
  
  Punta Ala
  
  Stop 2
  - Previous stop
    
    Next stop
  - Punta Ala
    
    13 NM from last port
    
    A secret seaside town, Punta Ala is the idyllic port for those seeking tranquil sailing holidays in Italy. With rolling green hills contrasted by turquoise seas, you will find it easy to sit back, relax and enjoy the sunset with a cocktail in hand. We recommend stopping by La Vela for a seaside panoramic dinner. Translating to sail, La Vela’s contemporary architecture lives up to it’s namesake.
- Day 3
  
  Castiglione Della Pescaia
  
  Stop 3
  - Previous stop
    
    Next stop
  - Castiglione Della Pescaia
    
    7 NM from last port
    
    For the next stop on your Sailo boat charter in Italy, hoist the sails and head to Castiglione Della Pescaia. Known for its environmentally sustainable beaches, Castiglione Della Pescaia is the perfect spot to take the dinghy to shore and spend a day sunbathing on the beach. With some of the clearest water in Italy, bring along snorkel gear to see what you can find below the water’s surface!
- Day 4
  
  Follonica
  
  Stop 4
  - Previous stop
    
    Next stop
  - Follonica
    
    21 NM from last port
    
    Known as the “Miami of the Maremma,” Fallonica will be the next stop on your yacht charter in Italy. Don’t be fooled by the high rises along the shore, this seaside town still offers plenty of tranquility. Surrounded by natural parks and beautiful beaches, you will spend the day in sunny bliss!
- Day 5
  
  San Vincenzo
  
  Stop 5
  - Previous stop
    
    Next stop
  - San Vincenzo
    
    25 NM from last port
    
    Nearing the end of your trip sailing in Italy, head to the picturesque San Vincenzo. Enjoy an afternoon sail and come to dock in the safe harbor. With restaurants offering local, fresh produce and delightful wines to sip during sunset, this off-the-beaten path marina will not disappoint.
- Ending point
  
  Cecina
  
  Ending point
  - Previous stop
  - Cecina
    
    12 NM from last port
    
    While we are sad you have to depart your Sailo boat charter in Italy we are glad you came along for the ride with us!