Sailing Trips
Embark on a sailing adventure along the Dalmatian coastline, island hop Greece, journey along the Turkish Riviera, or soak up the sun from your yacht moored off the beautiful beaches of Thailand. Enjoy water activities from kayaking to paddle boarding, discover incredible ports, swim straight off your sailing boat, and kick back for sundowners on the deck on one of our 97 sailing trips around Asia, Europe and the Caribbean.
Top Selling Sailing Trips
27 Days London to London
Operated By:
Topdeck From
$5,413
Save
$240
8 Days Phuket to Phuket
Operated By:
Contiki From
$1,190
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$49
8 Days Split to Dubrovnik
Operated By:
Busabout From
$1,103
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$68
8 Days Split to Split
Operated By:
Contiki From
$1,774
Save
$78
14 Days Bangkok to Phuket
Operated By:
Busabout From
$2,063
Save
$86
View all 97 Sailing Trips
Discover
Popular sailing experiences and highlights around the world
Kayak Halong Bay
Paddle between the towering karsts of Halong Bay, marvelling at this wonderland of secluded bays, intriguing cave systems, floating villages and limestone pillars.
Dive into the Adriatic
The azure water beckons as you pull up for swim stops between exploring the historic ports and natural wonders of Croatia on a sailing trip along the Dalmatian coast.
Caribbean Sunsets
Watch the sun set on a day of snorkelling the clear waters of the Caribbean. A daily delight on your Cuban sailing adventure through the Canarreos Archipelago.
Treasures of Thailand
Discover iconic beaches and hidden gems only accessible by boat as you call the waters off Thailand home. Swim in the turquoise water by day and, should you choose, sleep on the deck under the stars by night.
Aegean Vistas
Island hop through the Greek Islands strolling the charming coastal villages and dining in local tavernas. Take in sweeping views from whitewashed terraces as a puzzle of blue and white fit together perfectly before you.
How We Work
Choose from 97 sailing and island hopping trips with Global Journeys
Over 350,000 departures on sale right now
We partner with only the best Operators
Multi-award winning over 9 years
No booking fees. Your own dedicated travel advisor
Pick your dream tour, cruise or river cruise, select your departure and fill out our short enquiry form.
You'll be assigned your own dedicated Global Journeys travel advisor to help you with your holiday.
Book online, in-store or over the phone, pack your bags & enjoy your journey!
Brochures Featuring Sailing Trips
97 Sailing holidays sourced from 22 Operator brochures
Recent Reviews
What our clients are saying about their sailing and island hopping adventures
“Beautiful, Stunning and highly recommend!”
Stacey - New Zealand Jul 2016
I loved that this tour was chilled and relaxed! We had 16 people on our tour (two big boats with 8 people on each) so we weren't cramped at all, had plenty of space. The waters were beautiful, crystal clear and nothing like I'd ever seen before!! We spent half the time swimming and the other half eating :D I would seriously pay the price again just to have our onboard chef (Mustafa!) cook for me again, it's that good!!! The fishing villages were cute although empty of tourists, I felt sorry for the
...read more souvenir shops trying to sell their merchandise. Inside the rooms are really hot to sleep in so most of us slept up top on the deck, but with the warm weather and beautiful scenery it was a plus. Highlight was paragliding over Blue Lagoon - absolutely breathtaking I highly recommend!
“The Greek islands are very beautiful”
Jennifer Yip - Australia May 2013
This tour was great fun. The tour manager was really nice and friendly and everyone in the group was also really fun and always up for a good time. The cruise was very relaxing and all the ports we visited were great. The buffet meals were all pretty decent and for 80 euros, it was a great deal for unlimited drinks over the 4 days on the cruise. The optional activities were also very fun and interesting. The Greek islands are very beautiful. Would definitely recommend this to single travelers or
...read more even pairs or groups between ages 18-30! 
