Top 10 sailing vacations


not just any old life on the ocean waves

We only promote sailing vacations that leave coastlines, marine life and island communities exactly as you found them and if you're searching for ideas, away from the wake of tourist cruise ships, right here is where you set sail. Ancient odysseys in the southeast Aegean; lochs and lighthouses in the Scottish Hebrides; and Caribbean coral cays in Cuba's Canarreos, our top 10 sailing trips will have you shipshape in an instant, so grab a sundowner, settle into your hammock and read on.

1. Greek Aegean


Clear blue skies juxtaposed against white painted windmills make sailing in Greece an absolutely legendary prospect. The Greek Cyclades, from Santorini to Syros, promise epic Aegean adventures packed with sensational sunsets, crystal clear coves and sand dusted seaside tavernas.

When to go: May - September
Our top selling trip: Cyclades Islands sailing vacation, Greece
See all our trips: Sailing vacations in the Cyclades
Read more: Cyclades travel guide

2. Greater Clyde, Scotland


Join Captain Jock aboard his stylish sailing yacht ‘Yemaya’ to explore the magnificent River Clyde, and islands such as Arran and Bute. The days are kept free as a bird, so that you can walk, visit distilleries, tour castles and gardens, golf or kayak, returning for sundowners on deck in the evening before meals of locally caught seafood and meat from Scotland’s great ‘natural larder’. And do bring binoculars: on a typical six-day cruise you might encounter eagles, dolphins, seals, otters or basking sharks.

When to go: May to September
Our top selling trip: River Clyde Sailing Vacation

3. Amalfi Coast, Italy


Italy's Amalfi Coast has long attracted sailors searching for shimmering shorelines around the islands of Capri, Procida and Ischia. Leave the glitz and glamour for the paparazzi as you sail into an infinite blue Bay of Naples before anchoring for limoncello aperitifs and freshly fried calamari at sunset.

When to go: May – September
Our top selling trip: Amalfi Coast sailing vacation, Italy
Read more: Amalfi Coast travel guide

4. Aegean Sea, Greece


Situated between Santorini and Mykonos, the Small Cyclades offer some superb sailing. The buzzing nightlife on the larger islands of Ios and Naxos combines with traditional tavernas and archeological sites on Amorgos to create a flexible and varied sailing itinerary.

When to go: May - September
Our top selling trip: Greek Islands sailing vacation, Santorini to Mykonos
See all our trips: Sailing vacations in Greece
Read more: Greek Islands travel guide

5. Croatia


Sailing around Croatia's Elaphiti Archipelago, as you make the voyage north from Dubrovnik to Split, puts a whole new perspective on the islands' pristine pine forests and salt water lakes. Discover the Dalmatian Coast where Mljet, Korcula, Hvar and Brac supply sublime scenic shelter for sailors.

When to go: May - September
Our top selling trip: Croatia sailing vacation, Dubrovnik to Split
See all our trips: Sailing vacations in Croatia
Read more: Croatia travel guide

6. Turkey, Aegean



Step on board a traditional luxury gulet for an Aegean adventure around the islands of Turkey and Greece. This is a sailing vacation to occupy all your senses with access to ancient sites, secluded coves and lesser-visited islands fusing wonderfully well with 5-star standards.

When to go: April - October
Our top selling trip: Luxury gulet cruise in the Aegean
See all our trips: Gulet cruising vacations in Turkey

7. Hebrides, Scotland


Whisky galore and wildlife aplenty make Scotland's Hebrides a real joy, with the chance to set sail on a traditional tall ship about as atmospheric an experience as you could wish for. Explore sea lochs and open estuaries overlooked by castles and lighthouses on wild and woolly headlands.

When to go: May - August
Our top selling trip: Whisky and wildlife sailing vacation in Scotland
See all our trips: Sailing vacations in Scotland and Inner Hebrides vacations
Read more: Scotland travel guide

8. Ligurian Sea, Italy


The Ligurian Sea stretches from Tuscany to the French Riviera and provides a safe haven for fin whales, striped dolphins and numerous other marine mammals. Known as the Pelagos Sanctuary, this area offers outstanding opportunities for volunteers interested in sailing and watching cetaceans.

When to go: May - September
Our top selling trip: Whale & dolphin research in Ligurian Sea, Italy
Read more: Marine conservation travel guide

9. Dodecanese Islands, Greece


Sailing between the Greek Dodecanese and the southwest of Turkey is an effortlessly calm experience. Waterfronts are lined with characterful tavernas offering opportunities to compare and contrast cultural cuisine before setting sail on a luxury gulet in search of yet more Aegean idylls.

When to go: April - September
Our top selling trip: Luxury gulet cruise in the Aegean
See all our trips: Gulet cruising vacations

10. Bay of Biscay, Spain


You get the chance to take hold of the ship’s wheel and climb the rigging on a tall ship sailing voyage. And this isn’t any old sailing – you’ll be exploring the Bay of Biscay in Northern Spain, where mild, shallow waters provide shipside swim spots and the potential for whale and dolphin sightings. You’ll have a great crew on hand – both your fellow greenhorns and an experienced crew who’ll teach you the ropes.

When to go: mid-May
Our top selling trip: Bay of Biscay tall ship sailing vacation
Read more: Tall ship vacations travel guide




Written by Chris Owen
Sailing in Croatia

Sailing in Croatia

A multi-activity adventure sailing cruise in Croatia

From 580 4 Days ex flights
Luxury gulet cruise in the Aegean 2023

Luxury gulet cruise in the Aegean 2023

5 star services while cruising the Greek Islands in luxury

From £1250 8 Days ex flights
Sailing and biking Cyclades vacation, Greece

Sailing and biking Cyclades vacation, Greece

Self guided or guided (upon request) tour in the Cyclades

From 1500 8 Days ex flights
Dubrovnik to Hvar sailing vacation

Dubrovnik to Hvar sailing vacation

Active sailing adventure around Croatian Islands

From 920 5 Days ex flights
Sailing vacation in Greece, Mykonos to Santorini

Sailing vacation in Greece, Mykonos to Santorini

The boat, the beach and inviting Greek villages

From US $1775 8 Days ex flights
Tall ship sailing holiday, Bay of Biscay

Tall ship sailing vacation, Bay of Biscay

Explore bay of Biscay by tall ship

From 490 14 Days ex flights
Yoga and sailing retreat in Greece

Yoga and sailing retreat in Greece

-A week of relaxation and yoga while sailing the Ionian sea!

From £850 7 Days ex flights
Greek Islands sailing vacation, Santorini to Mykonos

Greek Islands sailing vacation, Santorini to Mykonos

Sapphire waters, whitewashed villages & history laden ruins

From US $1775 8 Days ex flights
Liveaboard diving and sailing vacation in Greece

Liveaboard diving and sailing vacation in Greece

Combine a sailing and diving adventure in the Greek islands

From £719 7 Days ex flights
Arctic sailing voyages, North Spitsbergen

Arctic sailing voyages, North Spitsbergen

Spitsbergen tall-ship wildlife and natural history sailing

From 2790 8 Days ex flights
Photo credits: [Page banner: Markos Mant] [intro photo: graywolf] [Amalfi Coast, Italy: xwildflowerx] [Turkey, Aegean: Joselu Blanco]