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: Alghero - Sailboat trip with lunch on board, 4 hours by Boat from Castellammare del Golfo to Zingaro and Scopello Day trips to the Egadi Islands: Favignana and Levanzo Sailing Boat Tour Locations in the Gulf of Cagliari Lake Como SMALL GROUP Boat Tour Aperitivo & Prosecco Included

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 →

Private Traditional Sailboat Tour of the Conero Riviera

Why choose the DonMar? Because no other boat in Numana can offer the same tailor-made and authentic sailing experience, without sacrificing comforts, like cushy seats …More

Ancona, Italy

5.0 (19)

Private Traditional Sailboat Tour of the Conero Riviera

Why choose the DonMar? Because no other boat in Numana can offer the same tailor-made and authentic sailing experience, without sacrificing comforts, like cushy seats...

3 hours 30 minutes Free Cancellation

5.0 (19)

from
$88

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

4.9 (74)

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

4.9 (74)

from
$90

Tour of the island of Ischia in schooner

If you want to live an exciting, unique and unrepeatable experience, come with us on the boats "Joya" and "Manida", vintage sailing ships, completely renovated …More

Isola d'Ischia, Italy

4.9 (60)

Tour of the island of Ischia in schooner

If you want to live an exciting, unique and unrepeatable experience, come with us on the boats "Joya" and "Manida", vintage sailing ships, completely renovated...

7 hours Free Cancellation

4.9 (60)

from
$92

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
$97

Positano Boat Tour with Swimming & Photography from Amalfi

Sail between Amalfi & Positano by local into breathtaking Coast views. Get professional photo shoots, Jump water from Boat, enjoy swimming far from crowds. …More

Amalfi, Italy

5.0 (1)

Positano Boat Tour with Swimming & Photography from Amalfi

Sail between Amalfi & Positano by local into breathtaking Coast views. Get professional photo shoots, Jump water from Boat, enjoy swimming far from crowds....

3 hours Free Cancellation

5.0 (1)

from
$98

La Maddalena Archipelago Sailing Tour with Lunch from Palau

The best itinerary. This is real sail trip. If you are interested in sailing experience we can give you the opportunity to learn the basic. …More

Palau, Italy

4.8 (132)

La Maddalena Archipelago Sailing Tour with Lunch from Palau

The best itinerary. This is real sail trip. If you are interested in sailing experience we can give you the opportunity to learn the basic....

7 hours Free Cancellation

4.8 (132)

from
$103

Sailing Cruise in Maddalena Archipelago from Maddalena

The best itinerary. Multi-Language crew (English, Spanish, Italian, Dutch, French, German). This is real sail trip. Between stop point we go under sails. If you …More

La Maddalena, Italy

4.8 (87)

Sailing Cruise in Maddalena Archipelago from Maddalena

The best itinerary. Multi-Language crew (English, Spanish, Italian, Dutch, French, German). This is real sail trip. Between stop point we go under sails. If you...

7 hours Free Cancellation

4.8 (87)

from
$103

An elegant Bavaria 33 Cruiser for sailing excursions (day trips, sunset aperitifs) and customized boat events (dinners, team building, birthday parties) based in Gallipoli. We …More

Lecce, Italy

4.6 (14)

Sailing boat excursion in Salento

An elegant Bavaria 33 Cruiser for sailing excursions (day trips, sunset aperitifs) and customized boat events (dinners, team building, birthday parties) based in Gallipoli. We...

7 hours Free Cancellation

4.6 (14)

from
$108

Asinara: Sailing trip in the park of Asinara

Asinara sailing school - Excursions Asinara is an operator authorized by the Asinara national park. departure at 9.30am return at 5.00pm During the day there …More

5.0 (38)

Asinara: Sailing trip in the park of Asinara

Asinara sailing school - Excursions Asinara is an operator authorized by the Asinara national park. departure at 9.30am return at 5.00pm During the day there...

8 hours Free Cancellation

5.0 (38)

from
$114

Sailing tour Archipelago of La Maddalena from Palau

Spend a whole day on a sailboat discovering the La Maddalena Archipelago, departing from Palau, accompanied by an expert skipper, you will sail among pristine …More

5.0 (728)

Sailing tour Archipelago of La Maddalena from Palau

Spend a whole day on a sailboat discovering the La Maddalena Archipelago, departing from Palau, accompanied by an expert skipper, you will sail among pristine...

7 to 8 hours Free Cancellation

5.0 (728)

from
$114

Sailing excursion in the Asinara National Park

Spend an unforgettable day aboard a sailing boat along the coasts of the Asinara National Park in northwestern Sardinia. An experience of absolute relaxation and …More

4.9 (16)

Sailing excursion in the Asinara National Park

Spend an unforgettable day aboard a sailing boat along the coasts of the Asinara National Park in northwestern Sardinia. An experience of absolute relaxation and...

7 hours 30 minutes

4.9 (16)

from
$114

Catamaran excursions in the Asinara island National park

The excursion and mainly marine of about 8 hours in the Asinara National Park is based on the visit of bays where you can swim …More

4.9 (143)

Catamaran excursions in the Asinara island National park

The excursion and mainly marine of about 8 hours in the Asinara National Park is based on the visit of bays where you can swim...

8 hours Free Cancellation

4.9 (143)

from
$115

Catamaran Tour from La Caletta near Olbia – Experience Sardinia’s Coast

Sailing from La Caletta : Relax away from mass tourism Experience the breathtaking east coast of Sardinia around La Caletta and Berchida. Discover freedom on …More

5.0 (38)

Catamaran Tour from La Caletta near Olbia – Experience Sardinia’s Coast

Sailing from La Caletta : Relax away from mass tourism Experience the breathtaking east coast of Sardinia around La Caletta and Berchida. Discover freedom on...

8 hours Free Cancellation

5.0 (38)

from
$124

Monomaran Tour to La Maddalena Archipelago from Palau

Every day we leave aboard a spacious and comfortable 16 meter sailing unit, called “Monomarano” for its exceptional characteristics of liveability and comfort on board …More

5.0 (188)

Monomaran Tour to La Maddalena Archipelago from Palau

Every day we leave aboard a spacious and comfortable 16 meter sailing unit, called “Monomarano” for its exceptional characteristics of liveability and comfort on board...

7 hours 30 minutes Free Cancellation

5.0 (188)

from
$124

Magdalene Archipelago Sailing Tour | From Santa Teresa

Spend a whole day discovering the magnificent La Maddalena Archipelago aboard an elegant 16-meter Beneteau Cyclades 50.5 sailboat, departing from Santa Teresa di Gallura at …More

Olbia, Italy

5.0 (565)

Magdalene Archipelago Sailing Tour | From Santa Teresa

Spend a whole day discovering the magnificent La Maddalena Archipelago aboard an elegant 16-meter Beneteau Cyclades 50.5 sailboat, departing from Santa Teresa di Gallura at...

7 to 8 hours Free Cancellation

5.0 (565)

from
$125

Sailing boat tour to Tavolara and Dolphins from Gulf of Aranci

Discover the Tavolara and Molara Marine Protected Area with a 7-8 hour sailing excursion, departing daily from the port of Golfo Aranci. You will navigate …More

5.0 (7)

Sailing boat tour to Tavolara and Dolphins from Gulf of Aranci

Discover the Tavolara and Molara Marine Protected Area with a 7-8 hour sailing excursion, departing daily from the port of Golfo Aranci. You will navigate...

7 hours 30 minutes Free Cancellation

5.0 (7)

from
$125

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
$126

Bari sailing cruise in search of dolphins

It is not the usual tour but a riot of emotions. Those who wish can participate in the maneuvers on board and in driving the …More

Bari, Italy

4.8 (20)

Bari sailing cruise in search of dolphins

It is not the usual tour but a riot of emotions. Those who wish can participate in the maneuvers on board and in driving the...

3 hours 30 minutes Free Cancellation

4.8 (20)

from
$126

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 (143)

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 (143)

from
$131

One day excursion on a sailing boat in the Gulf of Alghero

"Treat yourself to unforgettable moments in the marvelous setting of the Gulf of Alghero, admiring the coast and the cliffs with all their imposing beauty. …More

4.9 (106)

One day excursion on a sailing boat in the Gulf of Alghero

"Treat yourself to unforgettable moments in the marvelous setting of the Gulf of Alghero, admiring the coast and the cliffs with all their imposing beauty....

8 hours Free Cancellation

4.9 (106)

from
$132