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: Sailing Experience to Capo Caccia from Alghero Private La Maddalena Archipelago Tour by Sailing Boat from Palau unique aperitif experience at sunset on a catamaran 3 - Day Sailing Experience : Learn & Explore Capri and Amalfi Coast Two Days Tour Including Boat-ride in Polignano

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 →

Small Group Sailing Tour in Amalfi Coast with Aperitif

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 (86)

Small Group Sailing Tour in Amalfi Coast with Aperitif

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...

180 to 210 minutes Free Cancellation

5.0 (86)

from
$218

Sorrento Coast : Sailing Cruise with Swim, Brunch & Prosecco

You will sail in the splendid waters of Sorrento, Capri or Procida. The route will be dictated by the wind that will accompany us blowing …More

Pompeii, Italy

5.0 (4)

Sorrento Coast : Sailing Cruise with Swim, Brunch & Prosecco

You will sail in the splendid waters of Sorrento, Capri or Procida. The route will be dictated by the wind that will accompany us blowing...

7 hours Free Cancellation

5.0 (4)

from
$228

Sailing boat tour in the La Maddalena archipelago

In our tour we try to stop in the less crowded beaches and in the more reserved bays seeing magnificent places with new boats. …More

5.0 (24)

Sailing boat tour in the La Maddalena archipelago

In our tour we try to stop in the less crowded beaches and in the more reserved bays seeing magnificent places with new boats....

7 hours Free Cancellation

5.0 (24)

from
$230

Lake Como SMALL GROUP Boat Tour Aperitivo & Prosecco Included

Forget noisy speedboats! Sail Lake Como with Ricky, a friendly local skipper. Enjoy great chats, Prosecco and aperitivo, soak up the Italian slow life and …More

Lake Como, Italy

5.0 (51)

Lake Como SMALL GROUP Boat Tour Aperitivo & Prosecco Included

Forget noisy speedboats! Sail Lake Como with Ricky, a friendly local skipper. Enjoy great chats, Prosecco and aperitivo, soak up the Italian slow life and...

4 hours Free Cancellation

5.0 (51)

from
$240

Day trip on a sailing catamaran in Sardinia

The special thing about a catamaran is the generous amount of space. Whether comfortably on the trampoline nets or together with the skipper on the …More

Olbia, Italy

5.0 (60)

Day trip on a sailing catamaran in Sardinia

The special thing about a catamaran is the generous amount of space. Whether comfortably on the trampoline nets or together with the skipper on the...

9 to 10 hours Free Cancellation

5.0 (60)

from
$241

Two Days Tour Including Boat-ride in Polignano

hello!! this tour is FANTASTIC.. includes: pick up drop off, accomodation 1 night, sightseeing tour of Polignano a Mare and BOAT-ride tour !! ENJOY!! (please …More

Bari, Italy

5.0 (2)

Two Days Tour Including Boat-ride in Polignano

hello!! this tour is FANTASTIC.. includes: pick up drop off, accomodation 1 night, sightseeing tour of Polignano a Mare and BOAT-ride tour !! ENJOY!! (please...

2 days Hotel pickup offered Free Cancellation

5.0 (2)

from
$251

4h Tour on Lake Como - Small Group Catamaran Tour from Tremezzo

Hop aboard the first catamaran on Lake Como and enjoy an unforgettable experience! Once on board, enjoy the living area at the stern and a …More

Lake Como, Italy

4.9 (108)

4h Tour on Lake Como - Small Group Catamaran Tour from Tremezzo

Hop aboard the first catamaran on Lake Como and enjoy an unforgettable experience! Once on board, enjoy the living area at the stern and a...

4 hours Free Cancellation

4.9 (108)

from
$257

Exclusive Capri Boat Tour from Naples or Sorrento

Start on a magical journey as a local guide welcomes you at the Naples or Sorrento port and cross over to Capri on a fast …More

Sorrento, Italy

5.0 (8)

Exclusive Capri Boat Tour from Naples or Sorrento

Start on a magical journey as a local guide welcomes you at the Naples or Sorrento port and cross over to Capri on a fast...

6 hours Free Cancellation

5.0 (8)

from
$358

Exclusive dinner on a Taormina sailing boat

Make a special occasion such as a birthday or an anniversary unique, or simply surprise your sweetheart with a romantic dinner on board, departing from …More

5.0 (1)

Exclusive dinner on a Taormina sailing boat

Make a special occasion such as a birthday or an anniversary unique, or simply surprise your sweetheart with a romantic dinner on board, departing from...

3 hours Free Cancellation

5.0 (1)

from
$379

Shared Five Star Cruise Relax SailYacht La Maddalena Islands

Discover the marine paradise of the archipelago of La Maddalena on a sailing boat with the convenient departure from the port of Cannigione. Hop aboard …More

La Maddalena, Italy

5.0 (56)

Shared Five Star Cruise Relax SailYacht La Maddalena Islands

Discover the marine paradise of the archipelago of La Maddalena on a sailing boat with the convenient departure from the port of Cannigione. Hop aboard...

8 hours

5.0 (56)

from
$397

Enjoy a private 30-minute gondola ride complete with prosecco and a rose, creating the perfect setting for a romantic proposal with your loved one. This …More

Venice, Italy

5.0 (1)

Proposal Gondola Ride in Venice

Enjoy a private 30-minute gondola ride complete with prosecco and a rose, creating the perfect setting for a romantic proposal with your loved one. This...

30 minutes Free Cancellation

5.0 (1)

from
$404

Venice Sailing Cruise to northern lagoon

The Venice lagoon is one of the most important lagoon landscapes in Europe. Traveling by boat is the best way to observe the unique environment up close. …More

Venice, Italy

5.0 (2)

Venice Sailing Cruise to northern lagoon

The Venice lagoon is one of the most important lagoon landscapes in Europe. Traveling by boat is the best way to observe the unique environment up close....

4 to 5 hours

5.0 (2)

from
$552

Private Boat Tour or Inflatable Boat Departures Sorrento, Positano, Capri

Booking these tours will be an unforgettable experience because only by sea can you admire the most beautiful coasts and landscapes that unfortunately cannot be …More

Pompeii, Italy

5.0 (2)

Private Boat Tour or Inflatable Boat Departures Sorrento, Positano, Capri

Booking these tours will be an unforgettable experience because only by sea can you admire the most beautiful coasts and landscapes that unfortunately cannot be...

8 hours 30 minutes Free Cancellation

5.0 (2)

from
$574

Sunset Sailing Lake Como with Private Skipper

Experience lake Como from a new perspective! Visit the most amazing coves, villas and towns of Lake Como on board of a 38ft sailing yacht. …More

Lake Como, Italy

4.9 (84)

Sunset Sailing Lake Como with Private Skipper

Experience lake Como from a new perspective! Visit the most amazing coves, villas and towns of Lake Como on board of a 38ft sailing yacht....

2 hours Free Cancellation

4.9 (84)

from
$672

See the coast of Cefalù from another perspective, sail on a sailboat, swim in our sea and avoid the very crowded beaches. …More

4.8 (5)

Sailing tour in Cefalù

See the coast of Cefalù from another perspective, sail on a sailboat, swim in our sea and avoid the very crowded beaches....

3 hours Free Cancellation

4.8 (5)

from
$689

Sailing tour in Syracuse and guided snorkeling - Private

Discover the coast of Syracuse with an exclusive private sailing tour. Sail through crystal clear waters and breathtaking cliffs, exploring the enchanting Plemmirio Marine Protected …More

5.0 (3)

Sailing tour in Syracuse and guided snorkeling - Private

Discover the coast of Syracuse with an exclusive private sailing tour. Sail through crystal clear waters and breathtaking cliffs, exploring the enchanting Plemmirio Marine Protected...

4 hours Free Cancellation

5.0 (3)

from
$746

Half-Day Private Tour by Catamaran in Polignano a Mare

The catamaran experience is unique and it is worth experiencing it and admiring the city of Polignano dal Mare, it is not the classic boat …More

Bari, Italy

5.0 (2)

Half-Day Private Tour by Catamaran in Polignano a Mare

The catamaran experience is unique and it is worth experiencing it and admiring the city of Polignano dal Mare, it is not the classic boat...

3 hours 30 minutes Free Cancellation

5.0 (2)

from
$749

Activities on the Amalfi coast with a sailing boat

the sailing boat tour allows you to appreciate the beauty of the Amalfi coast, experience the thrill of sailing, immerse yourself in the crystalline waters …More

Salerno, Italy

5.0 (4)

Activities on the Amalfi coast with a sailing boat

the sailing boat tour allows you to appreciate the beauty of the Amalfi coast, experience the thrill of sailing, immerse yourself in the crystalline waters...

8 hours 30 minutes Free Cancellation

5.0 (4)

from
$799

Exclusive Private Sailboat Tour on the Amalfi Coast

A Private tour where the flexibility and availability of the staff will make the experience even more exclusive. In addition to the enchanting places to …More

Salerno, Italy

5.0 (13)

Exclusive Private Sailboat Tour on the Amalfi Coast

A Private tour where the flexibility and availability of the staff will make the experience even more exclusive. In addition to the enchanting places to...

8 hours Hotel pickup offered Free Cancellation

5.0 (13)

from
$804

Private sailing trip along Capri and the Sorrento Coast

Embark on an unforgettable journey along the stunning Sorrentine Peninsula with this exclusive boat tour. Your adventure begins at Marina di Cassano in Sant'Agnello, where …More

Sorrento, Italy

5.0 (5)

Private sailing trip along Capri and the Sorrento Coast

Embark on an unforgettable journey along the stunning Sorrentine Peninsula with this exclusive boat tour. Your adventure begins at Marina di Cassano in Sant'Agnello, where...

9 hours Free Cancellation

5.0 (5)

from
$825