Top 10 sailing holidays
As a keen sailor myself, I’m biased, but I think going by boat is one of the best ways to holiday. You can stop and swim, you can go and see what’s round the next headland and, yes, you can read an entire book from a hammock strung under the boom. I know that sailing isn’t for everyone – if it was, there’d be no need for resorts and cruise ships. But since you’re here, let me persuade over to the sunny side with our top 10 best sailing trips. Some are adventurous offshore expeditions, others are lazy island-hopping trips. All endeavour to leave coastlines as you find them, and contribute income to island communities.
1. Croatia
It’s not just where you go – the lovely Elaphiti Islands, just beyond Dubrovnik – but how you go that makes sailing in Croatia so special. A locally owned and crewed vessel will give you fantastic insight into the small islands in this area of the Dalmatian Coast. A catamaran gives you more space for sun-lounging – and stand-up paddleboard and kayak storage, too. Not that they’ll be kept in storage long.
When to go: April to October
Our top selling trip: Sailing in Croatia
See all our trips: Sailing holidays in Croatia
Read more: Sailing in Croatia travel guide
When to go: April to October
Our top selling trip: Sailing in Croatia
See all our trips: Sailing holidays in Croatia
Read more: Sailing in Croatia travel guide
2. Spitsbergen
Step aboard 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 holiday to occupy all your senses – the feel of the cold air, the sound of a thousand seabirds or the crack of the ice – and the smell of a walrus colony! Access dramatic fjords, guided wildlife walks and on-board talks with polar experts, and feel the excitement of 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 holidays
Read more: Spitsbergen micro cruising
3. Greece with the family
Forget a private pool when the sea is this blue: Greece’s lovely Ionian Islands are a playground for families on sailing boats. In summer, the seas are calm, sheltered as they are between the islands, and there are very few long distances to cover, meaning more time for swimming. Watch your kids’ confidence grow in and out of the water – until they’re swinging off a bowline and jumping off the side.When to go: May to September
Our top selling trip: Greece sailing holiday for families
See all our trips: Greece sailing holidays
Read more: Sailing in Greece travel guide
4. Dhoni sailing in the Maldives
Traditional dhonis were originally used as fishing boats in the Maldives, catching up with tuna shoals, their speciality. Now, the speciality is relaxation. Hop from atoll to atoll, and when you’re done with the sunbathing, there are frequent stops at great reefs for snorkel exploration. Evening entertainment comes from inhabited, not uninhabited islands: go ashore to watch a dance performance and be hosted by a Maldivian community.
When to go: August to May
Our top selling trip: Maldives holidays, dhoni cruise
See all our trips: Maldives small ship cruising holidays
Read more: Maldives small ship cruising
When to go: August to May
Our top selling trip: Maldives holidays, dhoni cruise
See all our trips: Maldives small ship cruising holidays
Read more: Maldives small ship cruising
5. Cruising the Scottish islands
The wild headlands of the Inner Hebrides bubble off the west coast of the Scottish mainland. From a distance, they look bare and rugged, but close up they are full of life: not just white-tailed eagles, but golden eagles; not just dolphins, but pods of orca and even basking sharks and large whales. So, this isn’t just a sailing trip, but one with wildlife watching, fishing and exploring, too.When to go: April to September
Our top selling trip: Skye and the Small Isles sailing holiday
See all our trips: Sailing holidays in Scotland
Read more: Small ship cruising in Scotland guide
6. Luxury Aegean cruising
Those glamorous, swaggering ships you see anchored off the Turkish coast, varnished to the hilt with lovely long bowsprits? They’re gulets – originally used as sponge-diving vessels, but now almost entirely repurposed for tourism. Some carry hordes of day trippers to popular beaches, but others are destined for calmer schedules, hopping down the aptly named Turquoise Coast: just you, the view and a local crew.When to go: April to October
Our top selling trip: Turquoise coast luxury gulet cruise, Turkey
See all our trips: Gulet cruising holidays
Read more: Luxury cruising in the Aegean
7. Liveaboard diving holiday in Greece
A wonderful way to appreciate the Greek waters from both above and below the surface: spend a week diving and sailing around the Cyclades. Living on board your sailing boat you’ll have fantastic access to dive sites both famous and closely guarded secrets. There’s perhaps no easier way to be dive-ready every morning than spending the night a few hundred metres off the site at anchor.
When to go: April to November
Our top selling trip: Liveaboard diving and sailing holiday in Greece
See all our trips: Greece sailing holidays
Read more: Sailing in Greece travel guide
When to go: April to November
Our top selling trip: Liveaboard diving and sailing holiday in Greece
See all our trips: Greece sailing holidays
Read more: Sailing in Greece travel guide
8. Amalfi Coast and Bay of Naples
One of the most beautiful parts of Italy, the hillside towns along the Amalfi Coast get plenty of visitors – but might be best admired from the quiet of the water. That’s where our sailing holiday comes in. In summer there’s stable weather, gentle wind, and you can escape the heat at the cool, high-altitude crater of Mount Vesuvius, or by simply taking a dip in the sea.When to go: May to September
Our top selling trip: Amalfi Coast sailing holiday
See all our trips: Amalfi Coast holidays
Read more: Amalfi Coast sailing guide
9. Whale watching in Norway
When one billion herring migrate through the fjords of Northern Norway, humpbacks, orcas and even fin whales crash the party. And you can crash it, too: to watch their different, elaborate hunting tactics play out, and to look out for the Northern Lights: dinner and a show, indeed. The excitement takes place in winter: low season for tourism in the area, but high season for herring, their hunters, and the aurora.When to go: November to January
Our top selling trip: Whale watching sailing holiday, Norway
See all our trips: Norway sailing holidays
Read more: Killer whale watching in Norway
10. South Atlantic
Sailing is a fantastic way to have a real adventure without necessarily needing real experience – so you – yes you – could sail across the Atlantic with just a week of training (or less) under your belt to become a competent crew member. Sleep in shifts, work in watches, learn to navigate by the stars, and make extraordinary connections; on the way across the South Atlantic you stop at Saint Helena, one of the most remote island communities in the world.
When to go: November to January
Our top selling trip: Sail across the South Atlantic Ocean
See all our trips: Offshore sailing holidays
Read more: Sailing expeditions guide
When to go: November to January
Our top selling trip: Sail across the South Atlantic Ocean
See all our trips: Offshore sailing holidays
Read more: Sailing expeditions guide
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