Top 10 sailing holidays


not just any old life on the ocean waves

We only promote sailing holidays 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 holiday, Greece
See all our trips: Sailing holidays in the Cyclades
Read more: Cyclades travel guide

2. Mergui Archipelago, Myanmar


Sail alongside nomadic seafarers (the Moken), between out of reach anchorages and lush green volcanic slopes, as the untouched islands of Myanmar’s Mergui Archipelago (also known as Myeik) bring every exotic seafaring fantasy bounding to the bow. Zip via Zodiac in search of coral, waterfalls and Southeast Asia’s best kept secret beaches.

When to go: November - April
Our top selling trip: Burma sailing holiday, the Mergui Archipelago
See all our trips: Sailing holidays in Myanmar
Read more: Small ship cruising in Myanmar 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 – September
Our top selling trip: Amalfi Coast sailing holiday, 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 holiday, Santorini to Mykonos
See all our trips: Sailing holidays 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 holiday, Dubrovnik to Split
See all our trips: Sailing holidays in Croatia
Read more: Croatia travel guide

6. Cuba


Combine Caribbean culture and historic heritage with captivating coral reefs and sunken shipwrecks in Cuba. Set sail around the Canarreos archipelago and Cayo Largo where sensational scenes, above and below the water, make a Cuba sailing holiday an absolute pleasure for sailors and divers alike.

When to go: December - May
Our top selling trip: Cuba sailing holiday, Canarreos Archipelago and Cayo Largo
See all our trips: Sailing holidays in Cuba

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 holiday in Scotland
See all our trips: Sailing holidays in Scotland and Inner Hebrides holidays
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 holidays

10. The Bahamas


Sumptuously sandwiched between Miami and northern Cuba, the Bahamas boast a bounty of beautiful beaches, coral cays and underwater grottos, perfect for sailors looking to sample life on an Atlantic wave and enjoy a spot of snorkelling, kayaking or SUP boarding before a fried fish supper.

When to go: February - May
Our top selling trip: Bahamas Windjammer sailing holiday
Hello.
If you'd like to chat about sailing or need help finding a holiday to suit you we're very happy to help.
Rosy & team

01273 823 700
Written by Chris Owen
Sailing in Croatia

Sailing in Croatia

A multi-activity adventure sailing cruise

From €580 4 Days ex flights
Burma sailing holiday, the Mergui archipelago

Burma sailing holiday, the Mergui archipelago

Adventurous exploration of the Myeik Archipelago in Burma

From £1775 9 Days ex flights
Sailing holiday in the Aegean Sea

Sailing holiday in the Aegean Sea

Unique sailing adventure off the beaten track in Greece

From £520 7 Days ex flights
Cyclades sailing & walking holiday in Greece

Cyclades sailing & walking holiday in Greece

Combine a sailing & hiking adventure around the Cyclades

From £685 7 Days ex flights
Wildlife sailing holiday in Scotland

Wildlife sailing holiday in Scotland

Extraordinary wildlife above and below the waves

From £750 6 Days ex flights
Greek Islands sailing holiday, Santorini to Mykonos

Greek Islands sailing holiday, Santorini to Mykonos

Sapphire waters, whitewashed villages & history laden ruins

From £999 8 Days ex flights
Whisky and wildlife sailing holiday in Scotland

Whisky and wildlife sailing holiday in Scotland

Malt Whisky and Wildlife Cruise to Mull, Jura and Islay

From £1200 9 Days ex flights
Whale & dolphin research in Ligurian Sea, Italy

Whale & dolphin research in Ligurian Sea, Italy

Whale and dolphin conservation trip

From €795 6 Days ex flights
Sailing holiday in Greece, Mykonos to Santorini

Sailing holiday in Greece, Mykonos to Santorini

The boat, the beach and inviting Greek villages

From £999 8 Days ex flights
Virgin Islands cruise holiday

Virgin Islands cruise holiday

Romantic Virgin Islands sailing holiday for 1 loving couple

From US $7700 7 Days ex flights
Photo credits: [Page banner: Christian Joudrey] [intro photo: graywolf] [Amalfi Coast, Italy: xwildflowerx] [Cuba: Alessandro Caproni]
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