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Yacht island hopping: Which destination does it best?

With the new year’s bitter weather showing no sign of stopping, our thoughts have already turned to our next sunny escape. This summer, we’re upping our holiday game with a yacht island hopping adventure. We know what you’re thinking – travelling between so many destinations often means slumming it on sweaty ferries or being held captive to cruise liner itineraries, somewhat ruining the vacation vibe. But not so when you have your own private boat to get you from A to B.

One boat that has been giving us some serious inspiration for this is the 34.2m HAPPY DAYS yacht, seemingly built for island hopping holidays. With a large garage filled with all the yacht toys you could dream of, a sunny, spacious decor and an alfresco Jacuzzi, we can’t think of a better way to travel.

If you are lucky enough to afford a yacht, the next thing to think about is which islands you want to hop between. Below, we look at three very different cruising regions – New England, Greece and Thailand – to find out what to expect.

The world’s best yacht island hopping adventures


Greece has so many island groups that it’s hard to know where to start

Greece has so many island groups that it’s hard to know where to start. The beautiful Cyclades are perhaps the country’s most famous, all white and blue architecture and dramatic mountainous peaks. Crescent-shaped Santorini is the chosen destination for honeymooners here and it’s easy to see why, with crystal-clear waters and secluded beaches. In fact, Santorini is actually a tiny island group in itself; all the more reason why to explore it by yacht! Meanwhile other islands such as Anasti and Folegandros offer pristine beaches, Sifnos is loved for its gastronomy and Delos for its UNESCO world heritage history.

If you want to head slightly off the beaten track, the Dodecanese are a great bet, boasting some of the less visited but most beautiful islands. Kalymnos’ interlinked caves offer a fantastic opportunity to test out the yacht’s superior diving gear, with an onboard commercial grade nitro compressor that will help you dive longer and deeper, opening your eyes to even more exotic sealife. Out of all the yacht island hopping holidays in Greece, the Dodecanese is the best spot for scuba exploration. Medieval architecture dominates this island group, providing a fascinating alternative to the sugar-cube houses elsewhere.

On the Ionian islands lush vegetation rules, with its rugged terrain and azure blue ocean making the perfect backdrop for Instagram shots. Zante promises wild nights where you’ll dance until dawn, while Lefkada is the spot for kitesurfing. The idyllic Sporades island group contains the film location for Mamma Mia, alongside forests full of wildlife just waiting to be explored. Lastly the Northern Aegean archipelago, the most remote of the all the island groups, contains hidden gems such as Limnos, where you can have the beach all to yourself – on HAPPY DAYS, this means you and up to 13 friends soaking up the sun uninterrupted.


Phuket is Thailand’s largest and most well-known island

Now on to Thailand, where we start in Phuket – Thailand’s largest and most well-known island. However, prepare to discover some much less frequented spots, with hundreds of beautiful islands scattered across the Andaman Sea. It’s only a short cruise to Koh Khai Nok, where you’ll have your first diving opportunity amongst incredible coral reefs. Next, we head to the Phi Phi Islands, best known for featuring in The Beach with Leonardo diCaprio. This is the perfect place to take HAPPY DAYS’ 4.2m tender for a spin, making a splash in the crystal-clear waters before relaxing on the vast expanse of beach with a cocktail. As night descends, catch a fire show and experience the wild nightlife.

At Koh Hong Krabi, prepare to be amazed by the natural lagoon that dominates the island, and spend the day exploring the caves before watching the sunset on the palm-fringed sands. In Ao Thalin, explore the thick forests by kayak and make some new furry friends – some extremely cheeky monkeys live in these trees. Koh Chong Lat promises stunning scenery and the chance to have this beautiful island almost to yourself. If you’re craving something exhilarating, have the crew organise a trip to Khao Phing Kan, best known for its use in James Bond movie The Man with the Golden Gun, and feel like 007 as you explore its limestone scenery.

Thailand island hopping holidays also shouldn’t miss the Similan Islands, home to some of the best diving in the country, where exotic marine life – from barracuda to whale sharks – awaits. Koh Similan in particular is usually counted amongst the top ten dive spots worldwide, offering particularly vibrant coral reefs. However, bear in mind that these islands are only officially open to the public from 15 October until 15 May, so check with your yacht crew to make sure that you will be able to get there. After a long day of diving, head back to HAPPY DAYS and relax on the sunbeds while your yacht chef prepares a feast. Enjoy it alfresco and watch the sunset over this beautiful Thai island chain.

New England

Head to Martha’s Vineyard, beloved holiday destination of presidents, celebrities and yachtsmen

We’ll admit it – not all of these New England destinations are actually islands. However, this region was too charming to miss off the list, with a mixture of beachfront mainland towns and exclusive islands perfect for a romantic windswept escape. Newport is the perfect place to start your yacht island hopping adventure, with the town’s famous Gilded Age mansions welcoming you ashore from the cliff-top. A global centre for yachting, Newport has all the excitement and glamour you could wish for while still retaining its own quaint personality.

Just a short cruise away is laid-back Block Island, the perfect place to take advantage of scuba diving gear. This spot promises white-sand beaches to rival the Caribbean, cycling routes where beautiful views surprise you at every turn and historic lighthouses to explore. Then for ultimate relaxation, Cuttyhunk awaits with a small beach, beautiful hiking trails and not a whole lot more.

Craving a bit of celebrity? Head to Martha’s Vineyard, beloved holiday destination of presidents, celebrities and yachtsmen. Amble round chic boutiques, soaking up the 19th century architecture, before dining in style at one of Edgartown’s many exquisite restaurants. In flamboyant Provincetown back on the mainland, discover radical art galleries, vibrant nightlife and bustling beaches.

Which is the best region for yacht island hopping?

They all have their own unique charm, making it kind of impossible to pick! If you are looking for quaint, beachtown community charm and historic lighthouses, New England is the place to go. For beautiful architecture and even more stunning natural beauty, head to Greece. For world-class diving and off-the-beaten-track exploration, Thailand is the place for you. Wherever you go, island hopping holidays are best by yacht, and ideally one like HAPPY DAYS which is kitted out for adventure. If this has made you desperate to get your hands on a yacht, then you can find out more about luxury yachts for sale here.

Image at the very top of the article credit: Malcolm Birkett-Header