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 to 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
See all our trips: Sailing vacations in Scotland
Read more: Scotland travel guide

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 to September
Our top selling trip: Amalfi Coast sailing vacation, Italy
See all our trips: Amalfi coast vacations
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 to 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 to 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. Spitsbergen, Arctic



Step on board a beautiful sailing boat for an Arctic adventure around the islands of the Svalbard archipelago in the far north of Norway. This is a sailing vacation to occupy all your senses with access to dramatic fjords, guided wildlife walks and on-board talks with polar experts – plus the ever-present chance of seeing a polar bear peek over the horizon.

When to go: May to July
Our top selling trip: Arctic sailing voyage in North Spitsbergen
See all our trips: Spitsbergen cruising vacations
Read more: Spitsbergen micro cruising travel guide

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 to 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 to September
Our top selling trip: Whale & dolphin research in Ligurian Sea, Italy
See all our trips: Marine conservation vacations
Read more: Marine conservation travel guide

9. Turquoise Coast, Turkey


Families can explore Turkey’s idyllic Turquoise Coast on a traditional gulet on a trip designed for parents and kids (and grandparents too of course). Shore excursions range from gentle hikes to mud baths, ancient ruins and sandy beaches, while kids will love jumping off the side of the wooden gulet, and the thrill of sleeping on deck beneath the stars.

When to go: July to August
Our top selling trip: Family sailing vacation in Turkey
See all our trips: Gulet cruising vacations and Family sailing vacations
Read more: Gulet cruising travel guide

10. Bay of Biscay, Spain


Wax your wooden leg and prep your eye patch: this isn’t just any old tall ship sailing trip, but a chance to sail between two famous pirate festivals on the English coast, with swashbuckling adventures in the Channel Islands in between. You’ll have a great crew on hand – both your fellow greenhorns and an experienced crew who’ll teach you the ropes, plus you get the chance to take hold of the ship’s wheel and climb the rigging.

When to go: mid-May
Our top selling trip: Tall ship sailing pirate festivals
See all our trips: Tall ship vacations
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
Arctic sailing voyages, North Spitsbergen

Arctic sailing voyages, North Spitsbergen

Spitsbergen tall-ship wildlife and natural history sailing

From 3045 8 Days ex flights
Greek Island cruising vacation

Greek Island cruising vacation

Discover a side of Greece riddled with myth and magic.

From US $4955 9 Days ex flights
Sailing vacation in the Aegean Sea

Sailing vacation in the Aegean Sea

Uninhabited islands in a 6 person boat

From £572 7 Days ex flights
Dubrovnik to Hvar sailing vacation

Dubrovnik to Hvar sailing vacation

Active sailing adventure around Croatian Islands

From 990 5 Days ex flights
Greece sailing holiday for families

Greece sailing vacation for families

Sailing trip for families/friends in Greek islands

From 5450 8 Days ex flights
Family yacht charter sailing vacation in Greece

Family yacht charter sailing vacation in Greece

Private sailing with fun games, reliving mythical tales

From 2100 8 Days ex flights
Skye and the Small Isles sailing vacation

Skye and the Small Isles sailing vacation

Sail Scotland's Small Isles and visit spectacular Skye

From £1520 9 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 £730 7 Days ex flights
Cyclades sailing & walking vacation in Greece

Cyclades sailing & walking vacation in Greece

Combine a sailing & hiking adventure around the Cyclades

From £726 7 Days ex flights
Photo credits: [Page banner: Markos Mant] [intro photo: graywolf] [Amalfi Coast, Italy: xwildflowerx] [Spitsbergen, Arctic: Aqua-Firma]