Of course, there are ever-popular options like Santorini in the Southern Cyclades, but by opting to sail around the islands rather than stay on one, you can avoid the crowds a little bit more by combining the most famous islands, with more remote escapes. I have started planning my own sailing trip around Greece for next year, you can see how I’m putting it together here.
A pool of water with a person in at the bottom of a Canyon in Dominica
Here are some of my favourite destinations I’ve ever visited, and a few dream trips too, all of which are best explored with the freedom of sailing the oceans.
Some of my favourite islands I visited include Hvar, the island of the rich and famous where I enjoyed great scuba-diving, and Korcula, a laid-back escape where the medieval walled city is known as ‘Little Dubrovnik’.

The island of Korcula, Croatia


Fiji is one of those perfect places to kick back and relax, and while I based myself in Nadi and enjoyed plenty of day-trips to the Fijian islands, taking a bigger trip sailing on a Yacht would have been much easier than coming back and forth.

Cruise the Croatian Coastline

Some of the most outer-post islands of Europe are the Azores, an archipelago of islands that belong to Portugal.
There are countless options for sailing expeditions across The Americas, from icy escapes in the far south and north to tropical sailings around the Caribbean, here are a few picks to inspire you.
An absolute dream of mine is to explore Madagascar, to see the lemurs, witness the baobab trees that tower into the sky, and admire the colourful chameleons.

Island hopping around Greece

A beautiful red pagoda temple, part of the Shikoku Pilgrimage through Kochi
Batabou Beach in Dominica from the road
The stunning Yasawa Islands, an archipelago of volcanic islands with amazing sandbars and snorkelling options would be my suggested starting point, and I hope when I return to Fiji I’ll have the chance to visit these gorgeous spots.

Pico Azores
Views of Pico Island, Azores

Sail around the volcanic Azores of Portugal

A king penguin colony at Volunteer Point
Highlights include dolphin and whale watching from the yacht, hiking up the highest mountain in Portugal on Pico, visiting lush green expired volcanic craters and lakes with waterfalls in Flores or hiking through the bright blue Hydrangeas that cover all of Sao Miguel.

Three Dolphins jumping out of the water in Dominica
Playful Dolphins

The Americas

While the waters are known to be choppy in the winter months, a yacht charter around the main nine islands in the summer months is a delight, and as the ferry and flight options are already quite expensive to move around the islands, it can almost be more cost-effective to visit in this manner. If you want to spend a fair bit of time on the islands though, then you will do better to pick a smaller cluster of islands to visit, than them all.

Go wild for wildlife amongst the Galapagos Islands

Raja Ampat
Not quite Antarctica, but the penguin filled the Falkland Islands provide an incredible, and remote, wildlife-focused escape.
You can’t mention a sailing charter around the continent without considering a yacht tour around the Galapagos Islands, a truly incredible experience and right at the top of my bucket list.

Discover Dominica, the nature island of the Caribbean

Pico Azores
I absolutely loved Mauritius and getting to know more about this fantastic nation. Not only are the beaches sublime, but there is an abundance of other reasons to visit Mauritius – from cultural and religious attractions to markets of delicious snacks and tumbling waterfalls.
The coastline of Sado Island

A king penguin colony at Volunteer Point
A king penguin colony on the Falkland Islands

Meet all the penguins across the Falkland Islands

I absolutely fell in love with Dominica, the land of mountains, rainforest and waterfalls – and one of the least touched by tourism in the Caribbean.
There are more than 700 islands to explore on a Croatia island yacht trip, made even more appealing by the fact that a lot of the most popular cities to visit are directly on the coast, such as Split or Zadar. Interestingly, Dubrovnik is also actually separated from the rest of the country by a tiny strop of Bosnia and Herzegovina’s coastline.
I adored my time in the Falkland Islands, where vast remote islands are inhabited by penguins and sheep, rather than people. The capital city of Stanley is the starting point for most trips, and of course, there are larger ships that can be taken to other destinations such as the South Georgia islands, or even to Antarctica.


You can’t consider a yacht trip to Europe and not think of Greece, where some 6000 islands await.

A typical beach in Mauritius

Take a catamaran cruise around Mauritius

A standard 14-day itinerary will loop around the outer islands, such as Weddell or Carcass Island with penguin sightings, or West Point Island, where an incredible array of albatross colonies await.
A catamaran sailing trip around Mauritius will give you a chance to see various parts of the island, enjoy the crystal clear waters to snorkel in. Certain sailings may also offer the chance to visit other closeby islands such as Réunion or Rodrigues.

Explore the islands of Madagascar

When I visited Raja Ampat some eight years ago I felt like the luckiest man in the world, this pristine paradise truly felt like being in a desktop screensaver.
There are countless options for exploring the Pacific islands – whether that’s the wildlife-filled isles of Australia or the more remote outposts.

Asia & Pacific

Smaller live-aboard sailing yachts are a much wiser option. The scuba-diving here is an absolute dream, and by being on a live-aboard you’ll be able to enjoy the most amazing scuba daily, whilst also seeing amazing sights like remote islands or the famed viewpoint at Pianemo.

Raja Ampat
Raja Ampat: Welcome to the real life screensaver

Visit a real-life paradise in Raja Ampat

Ever since I backpacked across Croatia, from Dubrovnik all the way up to Slovenia, I’ve promised myself one day I will return to sail along the coast.
Sado Island, for example, is an old gold mining outpost, where you can now visit these historic mines and see where much of the nation’s wealth comes from. There are plenty of other things to enjoy here, from rare birdlife to traditional tub boat rides in the harbour.
Three Dolphins jumping out of the water in Dominica

Jump around Japan’s unforgettable islands

Further south, Shikoku is one of the main islands of Japan, which includes four different provinces. Here you’ll find a huge pilgrimage route of over 80 Buddhist temples, amazingly clear waters and inland rivers, and also some surprising water-focused activities, like the unique deep-sea therapy spas in Kochi, a region that I absolutely fell in love with.
A beautiful blue and green bay in Corfu
In the summer months I don’t believe you can do any better than exploring the islands of Europe, from UNESCO vineyards in Portugal to the never-ending sandy coastline of Croatia, here are my top three!

Private island Fiji
Private Islands in Fiji

Flit around the many islands of Fiji

Since I was a child I’ve been obsessed with the oceans and boats, and in awe of the great expanses of water that seem so never-ending. The idea of exploring the islands of the world by yacht has become even more appealing since my best friend started working in the industry, even though she tells me it’s a far cry from the life ‘Below Deck’ would have you believe.
Taking a sailing adventure to Japan offers you the chance to see a completely different side of the country. While a city-trip to Tokyo might be all about high-speed and modern sightings, the islands offer a much more traditional experience.
While cruise ships do call at Dominica, it tends to be a less popular port of call and due to the rugged landscape of the island most day-trips offered to the larger ships focus on one part of the nation. By visiting on a small yacht charter you’ll have more options and freedom to visit the top sights of the island – such as Canyoning or hiking along never-ending trails with rare bird sightings. Of course, you also have amazing scuba-diving and whale spotting from the boat.

Similar Posts