Sailing Tours & Trips
Hoist the sails, it's time for an adventure on the high seas! Bring your pirate fantasies to life island-hopping through the Caribbean, or with a dreamy island getaway in Greece. Whether you're setting sail on an exclusive private yacht in the Mediterranean or joining a group trip meandering through the wildlife-rich Galapagos Islands - the world is your oyster on a sailing adventure!
250+ Sailing trips with 4,224 reviews
Croatia Sailing Adventure
"As a first time solo traveller Ivan made me feel very welcome. He is very friendly..."
- Destinations
- Split, Hvar Island, Pomena, Dubrovnik, Korcula Island, Makarska
- Age Range
- 18 to 39 year olds
- Regions
- Dalmatia, Adriatic, Croatian Islands+1 more
- Travel Style
- Beach, Group, Fully Guided, Explorer+1 more
- Operated in
- English
- Operator
- TruTravels
-20%- Tour length
- 8 days
- Price per day
- $182
- From $1,815
- US$1,452
You save: $363More information
Sailing Greece - Mykonos to Santorini
"This was a great sailing adventure partly because of our wonderful skipper Dov. He..."
- Destinations
- Mykonos, Naxos, Paros, Antiparos, Ios, Sifnos, Folegandros, Santorini
- Age Range
- 16 to 70 year olds
- Ship
- G Adventures Sailing Yacht
- Regions
- Athens Santorini & Mykonos, Greek Islands, Aegean Islands, Cyclades Greece+3 more
- Travel Style
- Beach, Group, Fully Guided, Explorer+1 more
- Operated in
- English
- Operator
- G Adventures
-15%- Tour length
- 8 days
- Price per day
- $170
- From $1,599
- US$1,359
You save: $239More information
Sailing Thailand - Phuket to Phuket
"This week sailing in the Thailand islands was amazing. The crew took us from one..."
- Destinations
- Phuket, Phang Nga Bay, Ko Phi Phi, Ko Racha Yai, Koh Yao Yai
- Age Range
- 16 to 90 year olds
- Country Region
- Southern Thailand
- Travel Style
- Group, Fully Guided, Explorer, Christmas & New Year+2 more
- Operated in
- English
- Operator
- G Adventures
-15%- Tour length
- 7 days
- Price per day
- $225
- From $1,849
- US$1,572
You save: $277More information
CROATIA SAIL - Split to Split (The Dalmatian Voyager)
479 reviewsAWARD WINNER"AMAZING! The trip was a fantastic way to explore Croatia and meet new friends. The..."
- Destinations
- Split, Makarska, Mljet Island, Dubrovnik, Korcula Island, Hvar Island, Omis
- Age Range
- 22 to 40 year olds
- Regions
- Dalmatia, Adriatic, Croatian Islands+1 more
- Travel Style
- Active Adventure, Group, Fully Guided, Explorer+2 more
- Operated in
- English
- Operator
- Koda Sail
- Tour length
- 8 days
- Price per day
- $189
- From
- US$1,513
- +$77 local payments
More informationSail Dubrovnik to Split-Above Deck
"It was one of the best tours we have been on. Loads of fun with lots of swimming..."
- Destinations
- Dubrovnik, Mljet Island, Korcula Island, Hvar Island, Makarska, Omis, Split
- Age Range
- 18 to 40 year olds
- Regions
- Dalmatia, Adriatic, Croatian Islands+1 more
- Travel Style
- Group, Fully Guided, Explorer+1 more
- Operated in
- English
- Operator
- Travel Talk
-35%- Tour length
- 8 days
- Price per day
- $114
- From $1,399
- US$909
You save: $489More informationSail Split to Dubrovnik Above Deck
"I loved the islands. The boat was cool and the captain and other crew were fantastic...."
- Destinations
- Split, Omis, Makarska, Hvar Island, Korcula Island, Mljet Island, Dubrovnik
- Age Range
- 18 to 40 year olds
- Regions
- Dalmatia, Adriatic, Croatian Islands+1 more
- Travel Style
- Group, Fully Guided, Explorer+1 more
- Operated in
- English
- Operator
- Travel Talk
-45%- Tour length
- 8 days
- Price per day
- $96
- From $1,399
- US$769
You save: $629More informationPearls of Adriatic cruise
"I wish to thank the crew and local guides for a great time we had on this cruise!..."
- Destinations
- Trogir, Split, Hvar Island, Mljet Island, Dubrovnik, Korcula Island, Brac
- Age Range
- 18 to 75 year olds
- Regions
- Dalmatia, Adriatic, Croatian Islands+1 more
- Travel Style
- Boat, Group, Partially Guided+1 more
- Operated in
- English, German
- Operator
- Perfecta Travel
- Tour length
- 8 days
- Price per day
- $91
- From
- US$726
- +$38 local payments
More informationPearl of the Adriatic Montenegro Cruise
"We just arrived home from our 7 day sailing trip with 16 of our closest friends and..."
- Destinations
- Tivat, Kotor, Budva, Sveti Stefan, Luštica, Herceg Novi, Perast
- Age Range
- 16 to 99 year olds
- Boat
- Gulet Sadri Usta
- Country Region
- Adriatic
- Travel Style
- Gulet, Private, Partially Guided, Explorer+2 more
- Operated in
- English
- Operator
- DM Yachting
-5%- Tour length
- 8 days
- Price per day
- $248
- From $2,091
- US$1,987
- +$110 local payments
You save: $104More informationAmalfi Coast Sailing Adventure
"This was pretty insane. It's a great (and cheap) way to see a stretch of coast that..."
- 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
- +$88 local payments
You save: $338More informationMed Sailing in Croatia (from Split to Dubrovnik)
"had a week with them in croatia and was great. Geoff was really attentive and helped..."
- Destinations
- Split, Brac, Hvar Island, Vis, Korcula Island, Pomena, Mljet Island, Dubrovnik
- Age Range
- 18 to 80 year olds
- Regions
- Dalmatia, Adriatic, Croatian Islands+1 more
- Travel Style
- Group, Fully Guided
- Operated in
- English
- Operator
- Med Sailing Holidays
- Tour length
- 8 days
- Price per day
- $308
- From
- US$2,466
More informationPearls of Adriatic Deluxe cruise
"we were on deluxe cruise by Perfecta Travel last summer and it was magical experience..."
- Destinations
- Trogir, Split, Hvar Island, Mljet Island, Dubrovnik, Korcula Island, Brac
- Age Range
- 18 to 75 year olds
- Regions
- Dalmatia, Adriatic, Croatian Islands+1 more
- Travel Style
- Boat, Group, Fully Guided
- Operated in
- English, German
- Operator
- Perfecta Travel
- Tour length
- 8 days
- Price per day
- $104
- From
- US$831
- +$38 local payments
More informationMed Sailing in Greece - Ionian Sea
"So let me preface this by saying I have not gone on a sail yet and with Corona happening,..."
- Destinations
- Lefkada, Meganisi, Ithaca, Sami, Fiskardo, Lefkas, Kalamos
- Age Range
- 18 to 80 year olds
- Islands
- Greek Islands, Ionian Islands+1 more
- Travel Style
- Group, Partially Guided
- Operated in
- English
- Operator
- Med Sailing Holidays
- Tour length
- 8 days
- Price per day
- $438
- From
- US$3,500
More informationWestern Cyclades & Santorini Sailing Week
"Great skipper excellent choice of islands"
- Destinations
- Paros, Ios, Santorini, Folegandros, Kimolos, Milos, Sifnos
- Age Range
- 6 to 75 year olds
- Islands
- Greek Islands, Aegean Islands, Cyclades Greece+2 more
- Travel Style
- Active Adventure, Family, Private, Group, Fully Guided, Explorer+3 more
- Operated in
- English
- Operator
- YachtHop
- Tour length
- 7 days
- Price per day
- $311
- From
- US$2,179
More informationSailing Yoga Practice & SUP in Cyclades Greece.
- Destinations
- Kea, Kythnos, Syros, Tinos, Andros, Karystos
- Age Range
- 18 to 70 year olds
- Regions
- Athens Santorini & Mykonos, Greek Islands, Aegean Islands, Cyclades Greece+3 more
- Travel Style
- Active Adventure, Beach, Private, Fully Guided+1 more
- Operated in
- English
- Operator
- Med Sun Yachts (PC)
- Tour length
- 7 days
- Price per day
- $124
- From
- US$870
More informationSail 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
- +$44 local payments
You save: $173More information
Sailing Tours & Trips Reviews
"I had an amazing week on the boat. Ivan was a great tour guide, he felt like a friend..."
Croatia Sailing Adventure"Our guide Dov was great...very personnel and helpful"
Sailing Greece - Mykonos to Santorini"Overall great experience Loved being on the water and we got very lucky with the..."
Sailing Thailand - Phuket to Phuket"Amazing tour, couldn’t rate it highly enough. I was a solo female traveller and..."
CROATIA SAIL - Split to Split (The Dalmatian Voyager)"Croatia is beautiful. The boat has no actually sails. The rooms were small. The food..."
Sail Dubrovnik to Split-Above Deck"I attended this trip during the first week of the season travelling on the pirate..."
Sail Split to Dubrovnik Above Deck
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