Top Italy Sailing Trips

Q: Which Italy Sailing Trips have Instant Confirmation?

Italy Sailing Trips with Instant Confirmation include: A private day on a sailing boat in the archipelago of La Maddalena Capri Island Private Boat Tour Experience Boat Tour to Amalfi Coast, Capri, Ischia & Procida Daily Sailing Tour in Palermo with lunch. Private Boat 4h Scopello and Gypsy from Castellammare del Golfo View all Tours with Instant Confirmation →

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

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

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

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

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

Sunset Jazz Catamaran Cruise with Aperitivo and Live Saxophone

Every evening our luxury catamaran turns into a jazz boat. Enjoy the most magical sunset with a live saxophonist and a true Venetian Aperitivo. Pure …More

Venice, Italy

4.9 (296)

Sunset Jazz Catamaran Cruise with Aperitivo and Live Saxophone

Every evening our luxury catamaran turns into a jazz boat. Enjoy the most magical sunset with a live saxophonist and a true Venetian Aperitivo. Pure...

1 hour 30 minutes Free Cancellation

4.9 (296)

from
$91

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

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
$87

Discover the bays around the coast of Taormina with our sailing tour from Giardini Naxos. Enjoy the experience on board of our sailboat with a …More

Taormina, Italy

4.8 (116)

Sailing Tour Taormina Bay

Discover the bays around the coast of Taormina with our sailing tour from Giardini Naxos. Enjoy the experience on board of our sailboat with a...

3 hours Free Cancellation

4.8 (116)

from
$80

4 hours by Boat from Castellammare del Golfo to Zingaro and Scopello

The skipper guided by the daily wind, will decide the most suitable route in order to ensure the most favorable and attractive conditions for guests. …More

4.8 (56)

4 hours by Boat from Castellammare del Golfo to Zingaro and Scopello

The skipper guided by the daily wind, will decide the most suitable route in order to ensure the most favorable and attractive conditions for guests....

4 hours Free Cancellation

4.8 (56)

from
$80

Catamaran tour stops bathing and snorkeling toast with prosecco

The tour lasts three hours and departs from Portus Karalis, the Marina in the center of Cagliari a few steps from the cruise terminal, you …More

Cagliari, Italy

4.9 (192)

Catamaran tour stops bathing and snorkeling toast with prosecco

The tour lasts three hours and departs from Portus Karalis, the Marina in the center of Cagliari a few steps from the cruise terminal, you...

3 hours Free Cancellation

4.9 (192)

from
$80

Sunset tour on a sailing boat with aperitif

If you choose us for the sunset tour you will live an exclusive 2-hour experience that will set you apart from any other vacationer in …More

Alghero, Italy

5.0 (39)

Sunset tour on a sailing boat with aperitif

If you choose us for the sunset tour you will live an exclusive 2-hour experience that will set you apart from any other vacationer in...

2 hours Free Cancellation

5.0 (39)

from
$80

Dolphin Watching & Conservation - Dolphins in the Gulf of Catania

We are the only ones to carry out eco-tourist activity of observation of cetaceans in the Gulf of Catania, respecting the international code of good …More

4.8 (59)

Dolphin Watching & Conservation - Dolphins in the Gulf of Catania

We are the only ones to carry out eco-tourist activity of observation of cetaceans in the Gulf of Catania, respecting the international code of good...

3 hours Free Cancellation

4.8 (59)

from
$79

Catania boat tour along the coast with aperitif and snorkeling

Rely on us to live a unique experience along the lava coast of Catania aboard a comfortable sailboat. You can admire Etna and the city …More

4.6 (64)

Catania boat tour along the coast with aperitif and snorkeling

Rely on us to live a unique experience along the lava coast of Catania aboard a comfortable sailboat. You can admire Etna and the city...

4 hours Free Cancellation

4.6 (64)

from
$79

Unique and romantic sunset experience on a sailing boat with a view of Mount Etna and the Catania coast. Together with our staff you can …More

4.3 (6)

Sailing tour at sunset in catania

Unique and romantic sunset experience on a sailing boat with a view of Mount Etna and the Catania coast. Together with our staff you can...

3 hours Free Cancellation

4.3 (6)

from
$75

unique aperitif experience at sunset on a catamaran

Evening excursion with aperitif at sunset. The evening outing with aperitif at sunset is a 2-hour excursion that allows you to discover a part of …More

4.9 (11)

unique aperitif experience at sunset on a catamaran

Evening excursion with aperitif at sunset. The evening outing with aperitif at sunset is a 2-hour excursion that allows you to discover a part of...

2 hours Free Cancellation

4.9 (11)

from
$68

Experience the magic of the Devil's Saddle from the sea Boat tour in Cagliari, emotion, relaxation and nature. Discover one of the most fascinating places …More

5.0 (23)

Sailing excursion Gulf of Cagliari

Experience the magic of the Devil's Saddle from the sea Boat tour in Cagliari, emotion, relaxation and nature. Discover one of the most fascinating places...

3 hours Free Cancellation

5.0 (23)

from
$68

Unmissable sailing tour in the exclusive Devil's Saddle

Enjoy a three-hour boat trip from Marina di Sant’Elmo al Poetto. Relax, swim, admire the beautiful scenery and explore the island on a group or …More

5.0 (9)

Unmissable sailing tour in the exclusive Devil's Saddle

Enjoy a three-hour boat trip from Marina di Sant’Elmo al Poetto. Relax, swim, admire the beautiful scenery and explore the island on a group or...

3 hours Free Cancellation

5.0 (9)

from
$68

Cagliari boat tour: 4 swim stops, snorkeling & Sardinian aperitif

Discover the Gulf of Cagliari from a unique perspective! Set sail with us on board an authentic wooden gozzo and live an unforgettable experience between …More

Cagliari, Italy

4.8 (372)

Cagliari boat tour: 4 swim stops, snorkeling & Sardinian aperitif

Discover the Gulf of Cagliari from a unique perspective! Set sail with us on board an authentic wooden gozzo and live an unforgettable experience between...

3 hours Free Cancellation

4.8 (372)

from
$67

Catania: Boat Trip with Aperitif, Prosecco and Snorkeling

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

5.0 (7)

Catania: Boat Trip with Aperitif, Prosecco and Snorkeling

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....

5 hours Free Cancellation

5.0 (7)

from
$67

Day trips to the Egadi Islands: Favignana and Levanzo

tour of the Egadi Islands is a unique experience for several reasons: The Egadi Islands—including Favignana and Levanzo—offer spectacular natural scenery and crystal-clear waters. A …More

4.8 (44)

Day trips to the Egadi Islands: Favignana and Levanzo

tour of the Egadi Islands is a unique experience for several reasons: The Egadi Islands—including Favignana and Levanzo—offer spectacular natural scenery and crystal-clear waters. A...

8 hours Free Cancellation

4.8 (44)

from
$63