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 99 sailing trips around Asia, Europe and the Caribbean.

Top Selling Sailing Trips

27 Days London to London
Operated By: Topdeck
From
$5,759
Save
$240
8 Days Phuket to Phuket
Operated By: Contiki
From
$1,202
Save
$37
4 Days Amalfi to Procida
Operated By: Intrepid
From
$1,071
Save
$27
8 Days Split to Dubrovnik
Operated By: Busabout
From
$1,103
Save
$46
6 Days Santa Cruz Island to Baltra Island
Operated By: Exodus
From
$4,271
Save
$192
8 Days Split to Split
Operated By: Contiki
From
$1,270
Save
$248
View all 99 Sailing Trips

Discover

Popular sailing experiences and highlights around the world

Kayak Halong Bay
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
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
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
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
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 99 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
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Brochures Featuring Sailing Trips

99 Sailing holidays sourced from 28 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

“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