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Let’s Go Sailing! The Best Destinations for Island Hopping

  • April 1, 2025
  • Jules

Close your eyes. Feel the sunshine on your face. Can you taste the salty sea air? The sun casts amber shadows over the skyline and you spot a white sandy beach on the horizon. You’ve manifested this vacation for so long and now finally, you’re here. 

Wouldn’t it be lovely if it wasn’t a dream? In that case, what’s stopping you? Is it the thought of spending long hot summer days cooling off in the ocean and falling asleep to the gentle lap of waves? 

Didn’t think so. 

These days travelers want to immerse themselves in their vacations by answering the call of adventure. What better way of doing so than on a sailing holiday?

The world is filled with wonder, from exploring deserted beaches to anchoring at secret coves. Fancy yourself a captain of your destiny? Check out our favorite island-hopping destinations below.

Ionian Islands, Greece

The land of Zeus and Poseidon is a sailing lover’s dream. Boats are constantly seen dotting the shores of the Ionian islands.

National Geographic suggests a week aboard a yacht or a catamaran to make the most of your sailing adventure. Enlist the help of a skipper whose knowledge of the area can guide you to unexpected places.

Lefkada is one of the most popular islands in the Ionian Sea. Connected to the mainland by a causeway, it has prolific connections to Homer’s poem ‘The Odyssey’. 

You’ll be rewarded with turquoise beaches, seafront, and mountainous villages if you can beat the crowds.

This is why anchoring off the coast of Lefkada is an ideal choice. No need to book into already-full hotels or join the tourist trappings. You can enjoy the sights and sounds from the comfort of your sailing vessel.

Another island in the Ionian Sea worth visiting is Meganisi. Home to sea caves and the mysterious Papanikolis Cave, you’ll get the chills when you first step onto its craggy outcrops.

Authentic Travel

The only way to experience Greece’s majestic islands is on the water.

When chartering a catamaran, ensure it has a catamaran trampoline made from architectural net materials. Throw in shade nets and a few sailor’s pillows and you’re good to go.

Sailor pillows designed for catamaran nets can be tied down with clips so they don’t blow away. Made from industrial UV-proven mesh, they are abrasion-resistant and durable.

Sunrise Yacht Products suggests choosing a cruising catamaran with comfortable and durable catamaran nets made from UV-resistant polyester with a decent mesh size. Multihulls also allow for more stretch and durability, enhancing customers’ experience.

Sardinia, Mediterranean Sea

Lonely Planet rates Sardinia as a justifiable beach destination. However, the inland has just as much to offer.

The limescale escarpments of Golfo di Orosei are a scene from a painting. Dramatic is the only way to describe it. A meeting of land and sea is so precipitous that the only way to access Cala Mariolu beach is via boat or an arduous hike.

Spend your days exploring caves and coves while shaking off the last of the sun’s rays with a cool evening dip in the warm Mediterranean.

Want to take a tour off the beaten track? Selvaggio Blu is the ultimate prize at the end of a multi-day hike. The route takes you up cliff faces into idyllic seaside landscapes that few visitors ever see.

British Virgin Islands 

The British Virgin Islands (BVI) are considered one of the world’s best destinations for less experienced sailors.

Calm seas, sheltered anchorages, and steady trade winds. What more could you ask for? An archipelago of 60 isles, the best way to tour the BVI is via private catamaran.

A Lagoon 620 catamaran, painstakingly restored by the Nomada Hotel Group, takes guests on five days of island hopping. The Nomada at Sea introduces visitors to a luxury version of glamping.

The immersive voyage within an upscale boutique hotel-like setting is only the beginning. Paying attention to every small detail, the crew leaves little to chance, writes Veranda’s Grace Haynes.

Every item complements its surroundings, from the fringed Matouk beach towels to the L-shaped banquette within the bleached wood interior.

The itinerary varies, depending on your mood. Norman Island offers snorkeling around Treasure Point, while Dog Islands are virtually uninhabited. 

Planning on doing nothing? Spend your days lounging on the lower deck with a cocktail and a book.

Island Life

Island-hopping is a splendid opportunity to immerse yourself in the culture and is best enjoyed with a few pals.

You get to live like a local, albeit in the lap of luxury. But, the experience will leave you with a deeper appreciation for travel and exploration. So, what are you waiting for? Let’s go sailing!

Image: Patrick Lalonde, Unsplash

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  • Catamaran
  • island hopping
  • sailing
  • sailing charter
  • sailing holidays
Jules

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