Sailing Tours & Trips in Italy
Get ready to hoist the sails on a sailing adventure of Italy. Whether you are island hopping or gliding along the coast, with 15 sailing holidays lasting from 3 days up to 26 days, we have made finding the right sailboat tour a breeze! Click here to see all sailing vacations.
15 Sailing trips in Italy with 47 reviews
SailingAmalfi Coast Sailing Adventure
"Great guide who couldn’t do enough for us. We arrived as strangers and left as..."
- Destinations
- Procida, Ischia, Sorrento, Pompeii, Naples, Amalfi, Capri
- Age Range
- 15 to 99 year olds
- Country Region
- Amalfi Coast, South Italy, Campania+1 more
- Travel Style
- Active Adventure, Group, Fully Guided, Explorer+2 more
- Operated in
- English
- Operator
- Intrepid Travel
-15%- Tour length
- 7 days
- Price per day
- $274
- From $2,255
- US$1,917
- +$87 local payments
You save: $338
SailingSail Italy: Procida to Amalfi
- Destinations
- Procida, Ischia, Sorrento, Pompeii, Naples, Amalfi
- Age Range
- 15 to 99 year olds
- Country Region
- Amalfi Coast, South Italy, Campania+1 more
- Travel Style
- Active Adventure, Group, Fully Guided, Explorer+2 more
- Operated in
- English
- Operator
- Intrepid Travel
-15%- Tour length
- 4 days
- Price per day
- $246
- From $1,155
- US$982
- +$43 local payments
You save: $173
SailingAeolian Islands Cruise in Gulet 2023
- Destinations
- Milazzo, Stromboli, Panarea Island, Lipari, Filicudi Island, Salina, Vulcano
- Age Range
- 12 to 90 year olds
- Country Region
- South Italy
- Travel Style
- Group
- Operated in
- English
- Operator
- Dimensione Sicilia - Dimsi Incoming Operator Srl
- Tour length
- 8 days
- Price per day
- $177
- From
- US$1,418
- +$340 local payments
SailingNew Gulet Cruise among Aeolian Islands, Sicily
- Destinations
- Milazzo, Stromboli, Panarea Island, Lipari, Filicudi Island, Salina, Vulcano
- Age Range
- 18 to 90 year olds
- Country Region
- South Italy
- Travel Style
- Active Adventure, Gulet, Private, Group, Partially Guided, Explorer+3 more
- Operated in
- English, Italian
- Operator
- Soleto Travel
- Tour length
- 8 days
- Price per day
- $249
- From
- US$1,995
Amalfi Coast Dream - Small-Group Tour
- Destinations
- Rome, Naples, Pompeii, Sorrento, Capri, Anacapri
- Age Range
- 12 to 99 year olds
- Country Region
- Amalfi Coast, South Italy, Campania+1 more
- Travel Style
- Private, Group, Partially Guided, Sailing, Historical+3 more
- Operated in
- English
- Operator
- Omega Tours
- Tour length
- 4 days
- Price per day
- $277
- From
- US$1,108
Naples 2 The Amalfi Coast Long Weekend
- Destinations
- Naples, Amalfi, Capri, Anacapri, Positano, Sorrento, Pompeii
- Age Range
- 18 to 30 year olds
- Country Region
- Amalfi Coast, South Italy, Campania+1 more
- Travel Style
- Group, Fully Guided, Sailing, Coach / Bus+2 more
- Operated in
- English
- Operator
- Bus2alps
- Tour length
- 5 days
- Price per day
- $110
- From
- US$549
Venice & the Jewels of Veneto (2024) (Venice to Venice, 2024)
- Destinations
- Venice, Island of Mazzorbo, Burano, Chioggia
- Age Range
- 16 to 100 year olds
- Ship
- S.S. La Venezia
- Country Region
- Northern Italy, Veneto, Prosecco+1 more
- Travel Style
- Group, Fully Guided, Sailing, Historical+2 more
- Operated in
- English
- Operator
- Uniworld Boutique River Cruise Collection
-10%- Tour length
- 8 days
- Price per day
- $371
- From $3,299
- US$2,969
- +$250 upfront costs
You save: $329Highlights of Southern Italy - Crotone (Start Civitavecchia (Rome), End Dubrovnik)
- Destinations
- Civitavecchia, Sorrento, Amalfi, Giardini Naxos, Crotone, Otranto, Monopoli, Dubrovnik+1 more
- Age Range
- 12 to 90 year olds
- Ship
- Emerald Sakara
- Country Region
- South Italy
- Travel Style
- Active Adventure, Beach, Group, Fully Guided+1 more
- Operated in
- English
- Operator
- Emerald Cruises
Deal- Tour length
- 8 days
- Price per day
- $660
- From
- US$5,280
Coastal Gems of Italy & Croatia - Vis Island, Croatia
- Destinations
- Venice, Vis, Dubrovnik, Otranto, Crotone, Giardini Naxos, Sorrento, Civitavecchia, Rome+1 more
- Age Range
- 12 to 90 year olds
- Ship
- Emerald Sakara
- Travel Style
- Group, Fully Guided, Explorer+1 more
- Operated in
- English
- Operator
- Emerald Cruises
Deal- Tour length
- 8 days
- Price per day
- $728
- From
- US$5,820
Taste of Italy & Italian Treasures - a land & cruise journey
- Destinations
- Venice, Rapallo, Florence, Rome, Ponza, Capri, Amalfi, Lipari, Giardini Naxos, Taormina, Gozo, Valletta+3 more
- Age Range
- 12 to 99 year olds
- Ship
- Scenic Eclipse
- Travel Style
- Group, Fully Guided, In-depth Cultural+1 more
- Operated in
- English
- Operator
- Scenic Luxury Cruises & Tours
- Tour length
- 17 days
- Price per day
- $836
- From
- US$14,218
Ultimate Italy (Small Groups, Venice Simplon- Orient- Express, 12 Days)
- Destinations
- Italy, Vatican City (Holy See), France
- Age Range
- 5 to 99 year olds
- Travel Style
- Family, Group, Fully Guided, Sailing, Historical+3 more
- Operated in
- English
- Operator
- Luxury Gold
- Tour length
- 12 days
- Price per day
- $1,194
- From
- US$14,325
Italian Treasures
- Destinations
- Civitavecchia, Rome, Ponza, Capri, Amalfi, Positano, Ravello, Salerno, Lipari, Giardini Naxos, Taormina, Gozo, Mgarr, Valletta+5 more
- Age Range
- 12 to 99 year olds
- Ship
- Scenic Eclipse
- Country Region
- South Italy
- Travel Style
- Group, Fully Guided, Sailing+1 more
- Operated in
- English
- Operator
- Scenic Luxury Cruises & Tours
Deal- Tour length
- 9 days
- Price per day
- $1,033
- From
- US$9,295
- Sailing
Sail Italy: Amalfi to Procida
"Had a Great time sailing along the Beautiful Amalfi Coast & Islands with a Fun Bunch..."
- Destinations
- Amalfi, Capri, Procida
- Age Range
- 15 to 99 year olds
- Country Region
- Amalfi Coast, South Italy, Campania+1 more
- Travel Style
- Group, Fully Guided, In-depth Cultural+1 more
- Operated in
- English
- Operator
- Intrepid Travel
-35%- Tour length
- 4 days
- Price per day
- $191
- From $1,175
- US$764
- +$43 local payments
You save: $411 Ionian Sea Adventure - Gythio, Greece
- Destinations
- Athens, Gytheio, Cephalonia, Catania, Naples, Civitavecchia, Rome
- Age Range
- 12 to 90 year olds
- Ship
- Emerald Azzurra
- Travel Style
- Group, Fully Guided, Explorer+1 more
- Operated in
- English
- Operator
- Emerald Cruises
Deal- Tour length
- 8 days
- Price per day
- $744
- From
- US$5,950
- Sailing
Sailing along the beautiful Amalfi Coast
- Destinations
- Agropoli, Capri, Ischia, Sorrento, Positano
- Age Range
- 20 to 40 year olds
- Country Region
- Amalfi Coast, South Italy, Campania+1 more
- Travel Style
- Private, Group, Partially Guided+1 more
- Operated in
- Only: German
- Operator
- sailwithus
- Tour length
- 8 days
- Price per day
- $100
- From
- US$802
Italy Sailing Tour Reviews
"I just returned and can't say enough good things about the trip. Quarters on the..."
Amalfi Coast Sailing Adventure"The boat was in great condition. The Bavaria 51 was a delight to sail. Very stable,..."
Sail Italy: Amalfi to Procida
Sailing Tours
- Sailboat (5)
Islands
- Sicily (5)
Regions in Italy
- South Italy (28)
- Amalfi Coast (10)