Top Italy Sailing Trips

Q: What are the best options for Italy Sailing Trips?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Italy Sailing Trips are: Five Star Private Cruise Relax SailYacht La Maddalena Islands Sorrento Coast : Sailing Cruise with Swim, Brunch & Prosecco Half-Day Private Tour by Catamaran in Polignano a Mare Venice Sailing Cruise to northern lagoon Private Boat Tour or Inflatable Boat Departures Sorrento, Positano, Capri

Q: What are the best kid-friendly options for Italy Sailing Trips Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Italy Sailing Trips are: Cagliari boat tour: 4 swim stops, snorkeling & Sardinian aperitif Half-Day Sailing Excursion Sailing Boat Tour Locations in the Gulf of Cagliari Aperitif at sunset on a sailboat Day trips to the Egadi Islands: Favignana and Levanzo View all kid-friendly Tours →

Q: Which Italy Sailing Trips have Instant Confirmation?

Italy Sailing Trips with Instant Confirmation include: Private Gondola Tour Cagliari boat tour: 4 swim stops, snorkeling & Sardinian aperitif Plemmirio Sailing Tour from Ortigia with Snorkeling Sailing Boat Tour Locations in the Gulf of Cagliari Aperitif at sunset on a sailboat View all Tours with Instant Confirmation →

Q: Which Italy Sailing Trips have Free Cancellation?

Italy Sailing Trips with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include: Private Gondola Tour Cagliari boat tour: 4 swim stops, snorkeling & Sardinian aperitif Half-Day Sailing Excursion Plemmirio Sailing Tour from Ortigia with Snorkeling Sailing Boat Tour Locations in the Gulf of Cagliari View all Tours with Free Cancellation →

Q: I need a ride! Which Italy Sailing Trips have Hotel Pickup?

No problem. These Italy Sailing Trips include Hotel Pickup: Boat tour of the Amalfi Coast with Aperitif Private Sailing Boat Tour to the Tonnara of Scopello Two Days Tour Including Boat-ride in Polignano Exclusive Private Sailboat Tour on the Amalfi Coast Private Sailing Boat Trip with Educational Wine Tasting View all Tours with Hotel Pickup →

Q: Got any more Italy trip ideas?

We sure do. Check out our curated lists of hand-picked Italy Tours. Top 10 Italy 2026 Senior-friendly tours Italy The best tours and activities for culture lovers in Italy Top Day Trips from Italy Things to do in Italy this summer View all Italy Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Italy?

Based on our sales data over the past year, the most popular styles of tours and activities in Italy are: Italy Luxury & Special Occasions Italy Luxury Tours Italy Tours & Sightseeing Italy Cultural & Theme Tours Italy Walking & Biking Tours View all tour styles in Italy →

Sailing Experience on Lake Como with Private Skipper

The lake center of Lake Como is unique for its natural beauty and for the sumptuous ancient villas that overlook it, observing all this from …More

Lake Como, Italy

4.9 (96)

Sailing Experience on Lake Como with Private Skipper

The lake center of Lake Como is unique for its natural beauty and for the sumptuous ancient villas that overlook it, observing all this from...

3 hours Free Cancellation

4.9 (96)

from
$855

Private Guided Sailing Boat Tour on Lake Como with Aperitif

Sailing aboard a one-hundred-year-old boat in the romantic and stunning scenery of Lake Como. They both have a story to tell. The ideal situation for …More

Lake Como, Italy

5.0 (5)

Private Guided Sailing Boat Tour on Lake Como with Aperitif

Sailing aboard a one-hundred-year-old boat in the romantic and stunning scenery of Lake Como. They both have a story to tell. The ideal situation for...

2 hours Free Cancellation

5.0 (5)

from
$856

Private tour of the Conero Riviera on a sailing boat

The private experience to discover the Conero Riviera and its wonders! We start from the tourist port of Ancona, sail along the most beautiful coves …More

Ancona, Italy

5.0 (2)

Private tour of the Conero Riviera on a sailing boat

The private experience to discover the Conero Riviera and its wonders! We start from the tourist port of Ancona, sail along the most beautiful coves...

8 hours Free Cancellation

5.0 (2)

from
$861

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
$883

Tropea, Exclusive Sailing Cruise. 4h with Aperitif. MiRo’

A dream sailing experience on a 15m Grand Large boat between Tropea and Capo Vaticano! Set sail with us for a half-day adventure to discover …More

Tropea, Italy

5.0 (42)

Tropea, Exclusive Sailing Cruise. 4h with Aperitif. MiRo’

A dream sailing experience on a 15m Grand Large boat between Tropea and Capo Vaticano! Set sail with us for a half-day adventure to discover...

4 hours

5.0 (42)

from
$1,027

Sailing aboard a one-hundred-year-old boat in the romantic and stunning scenery of Lake Como. They both have a story to tell. The ideal situation for …More

Lake Como, Italy

5.0 (1)

Private Guided Sailing Boat Tour on Lake Como with Aperitif

Sailing aboard a one-hundred-year-old boat in the romantic and stunning scenery of Lake Como. They both have a story to tell. The ideal situation for...

3 hours Free Cancellation

5.0 (1)

from
$1,130

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

8-Hour Private Sailing Boat Tour of Catania and Brucoli

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....

8 hours Free Cancellation

from
$1,130

A sailing boat tour to discover Palermo, Capo Zafferano, Arco Azzurro and the coast of Palermo. During the boat trip, you will learn about the …More

5.0 (1)

Full-day Boat tour Palermo

A sailing boat tour to discover Palermo, Capo Zafferano, Arco Azzurro and the coast of Palermo. During the boat trip, you will learn about the...

7 hours Free Cancellation

5.0 (1)

from
$1,134

Private Catamaran Sailing (boat tour) La Caletta-Olbia Sardinia

Catamaran Cruise from La Caletta : Santa Lucia, Capo Comino & Berchida Come aboard the Discovery and experience the East Coast from a new perspective. …More

5.0 (7)

Private Catamaran Sailing (boat tour) La Caletta-Olbia Sardinia

Catamaran Cruise from La Caletta : Santa Lucia, Capo Comino & Berchida Come aboard the Discovery and experience the East Coast from a new perspective....

8 hours Free Cancellation

5.0 (7)

from
$1,140

Enjoy a day of sailing along the coast of Rimini in the direction of Cattolica, there will be a refreshing break in the waters of …More

Rimini, Italy

Day on the boat in Rimini

Enjoy a day of sailing along the coast of Rimini in the direction of Cattolica, there will be a refreshing break in the waters of...

4 hours Free Cancellation

from
$1,141

3 - Day Sailing Experience : Learn & Explore Capri and Amalfi Coast

Set sail on an unforgettable journey along Italy’s most breathtaking coastline. From the enchanting Sorrento Coast, the adventure unfolds over three magical days of sea, …More

Pompeii, Italy

5.0 (4)

3 - Day Sailing Experience : Learn & Explore Capri and Amalfi Coast

Set sail on an unforgettable journey along Italy’s most breathtaking coastline. From the enchanting Sorrento Coast, the adventure unfolds over three magical days of sea,...

3 days

5.0 (4)

from
$1,263

Our private tour along the north-west coast of Sardinia offers a unique and unforgettable experience, exploring hidden gems such as Capo Galera, Cala Dragunara and …More

Alghero, Italy

5.0 (5)

Private sailing experience in Alghero

Our private tour along the north-west coast of Sardinia offers a unique and unforgettable experience, exploring hidden gems such as Capo Galera, Cala Dragunara and...

7 hours 30 minutes Free Cancellation

5.0 (5)

from
$1,284

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

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
$1,312

Lake Como: 4-Hour Private Catamaran Tour with Aperitif

A private cruise aboard the only catamaran on Lake Como, even during sunset—a one-of-a-kind experience to share with your partner. Come aboard to admire some …More

Lake Como, Italy

5.0 (7)

Lake Como: 4-Hour Private Catamaran Tour with Aperitif

A private cruise aboard the only catamaran on Lake Como, even during sunset—a one-of-a-kind experience to share with your partner. Come aboard to admire some...

4 hours Free Cancellation

5.0 (7)

from
$1,362

Amalfi Skip the Crowds Private Chill Experience on a Sail Yacht

You will have an unforgettable, breathtaking point of view of the Amalfi Coast, away from city traffic. You could just relax and live a daydream …More

Capri, Italy

5.0 (33)

Amalfi Skip the Crowds Private Chill Experience on a Sail Yacht

You will have an unforgettable, breathtaking point of view of the Amalfi Coast, away from city traffic. You could just relax and live a daydream...

270 to 390 minutes Free Cancellation

5.0 (33)

from
$1,378

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
$1,378

Departing from Tropea, the tour includes a visit to the enchanting White Grotto, then continue past Formicoli and the beautiful Bay of Riaci, before reaching …More

Tropea, Italy

5.0 (6)

Private tour on sailing boat

Departing from Tropea, the tour includes a visit to the enchanting White Grotto, then continue past Formicoli and the beautiful Bay of Riaci, before reaching...

4 hours Free Cancellation

5.0 (6)

from
$1,378

Private Sailing Boat Trip with Educational Wine Tasting

What makes such a boat trip unique is that you get to enjoy the amazing view of Naples from the sea while sailing in the …More

Naples, Italy

Private Sailing Boat Trip with Educational Wine Tasting

What makes such a boat trip unique is that you get to enjoy the amazing view of Naples from the sea while sailing in the...

6 to 7 hours Hotel pickup offered Free Cancellation

from
$1,378

Private La Maddalena Archipelago Tour by Sailing Boat from Palau

Discovering the La Maddalena Archipelago with a private sailboat tour. The most exclusive and authentic way to discover the wonders of Sardinia and the La …More

5.0 (14)

Private La Maddalena Archipelago Tour by Sailing Boat from Palau

Discovering the La Maddalena Archipelago with a private sailboat tour. The most exclusive and authentic way to discover the wonders of Sardinia and the La...

7 hours

5.0 (14)

from
$1,481

Boat Tour to Amalfi Coast, Capri, Ischia & Procida

Amalfi Tour Campania organizes customized itineraries to discover Naples and the beautiful Amalfi Coast, as well as unforgettable boat tours to the most fascinating islands …More

Pompeii, Italy

5.0 (2)

Boat Tour to Amalfi Coast, Capri, Ischia & Procida

Amalfi Tour Campania organizes customized itineraries to discover Naples and the beautiful Amalfi Coast, as well as unforgettable boat tours to the most fascinating islands...

7 to 8 hours Free Cancellation

5.0 (2)

from
$1,703