What is island hopping? Where can you do it?


If you’re hungry for adventure but want maximum relaxation, an island hopping tour is the perfect pick. Rather than restricting yourself to one location, you can relish time in some of the most beautiful parts of the world, flitting from one magical island to the next at your own pace.

Part of the charm lies in the scenic journeying between destinations. Float or fly across glittering turquoise oceans and stretches of spotless sand, experiencing places in ways you never normally could.

Of course, this kind of vacation abroad isn’t run of the mill. You’ll likely travel for longer, frequently upping sticks and tackling outdoor activities such as scuba-diving or sailing.

Subsequently, you’ll face increased exposure to risks such as theft or accidental injury as you’re travelling to multiple destinations. 

Here at Insurance Choice, we know how rewarding a trip of a lifetime can be. You’ll make treasured memories and see magnificent sights, but the investment’s significant.

You want peace of mind that you’re covered, should any problems arise. That’s where we come in. We’ll find you quality non-standard travel insurance, tailored to your specific needs and budget, so you can holiday headache-free and enjoy every second of your trip.

We’re adventurers, too, so we’ve come up with some of the best island hopping tips and adventures for you to enjoy. Take a look…

Where can I go island hopping?

The world is your oyster when it comes to island hopping – literally!

Places such as French Polynesia, Greece and the Caribbean tend to be the top picks, and for good reason.

Famed for their exquisite natural beauty and diverse cultures, these three locations guarantee plenty of sun, sea, delicious food and fun. 

They’re tourist-friendly, with a variety of transportation available to take you from island to island. Whether you’re on a limited budget or fancy a luxury retreat, there are options for all.
An older couple sitting on the edge of a sailing boat looking out to sea

How to plan your island hopping adventure

Part of the charm of island hopping is its loose, laid-back structure.

You may take a particular liking to one specific place, and decide to spend a few extra days there, sunning yourself on a soft, sandy beach while sipping cocktails.

You may decide to move on faster than you’d planned, should the need arise.

While you don’t have to set a rigid plan for your trip abroad, it’s useful to prepare a little and avoid practical headaches down the line, remembering to secure straightforward non-standard travel insurance as well.

Getting from A to B

Before you jet off to faraway lands, you’ll need to consider how you’ll get from place to place, once you reach your destination.

Some archipelagos are more accessible than others, so assess how realistic your desired route is – don’t assume you can simply hop on a ferry.

If you plan on chartering a yacht, research reputable rental companies and find out what criteria you’ll need to fulfil.

You may not have the experience required, if you’re planning to sail the boat yourself, in which case you’d need to hire a skipper, which will increase expenditure.

It’s worth drawing up a general list of the islands you’d like to visit, then researching the available transportation and routes.

Flying from island to island could be feasible, so you could take a look at regional airlines or seaplanes and see what routes they serve.

Likewise, checking ferry timetables will help give you an idea of what is and isn’t practical, which is particularly important if you’re on a tight budget – you don’t want to book time at a hotel to find that it’s only reachable via expensive modes of transport.


Pre-booking your accommodation is particularly important if you’re adventuring during the peak times of year.

Demand will be higher, so you’ll have fewer options to consider. If your budget is high, this will pose less of a problem, as top-end hotels and retreats tend to maintain consistent standards.

Issues may arise if you have more limited funds, as you may end up settling for less than desirable accommodation, due to other, quality budget locations being snapped up by other lucky tourists.

If you’re travelling as a group, with kids, pets or with mobility issues, again, pre-planning your accommodation is a good idea.

An island hopping vacation is a hefty investment, so you want to enjoy every minute of it – make sure you secure dependable non-standard travel insurance as well.


Before you book anything abroad, consider the affordability of your dream location. The price of necessities such as food and hotels can vary dramatically according to location.

You don’t want to spend your holiday stressing over funds, so make sure you pick somewhere with budget-friendly activities, restaurants and rooms. Calculate approximate costs for travel, accommodation, food and extras, so you have a realistic picture of your holiday finances.


You can control some external factors, but weather definitely isn’t one of them. From storms to floods, islands are particularly vulnerable to a battering from extreme weather, so it’s important to research your chosen location’s seasonal climate before venturing there.

Aside from covering yourself with quality non-standard travel insurance, you can assess your destination’s weather patterns and make an informed choice about your trip’s timing.

You may be dreaming of a Caribbean vacation filled with water sporting activities, but this won’t be safe during hurricane season, which occurs from June 1 to November 30.

Weather can also affect the availability of certain transport routes: for example, in the Greek islands many ferry routes stop operating during the low season.

Where can you island hop in French Polynesia?

Tropical island of Bora Bora with huts on stilts in the sea and a mountain in the distance on a sunny day

From Tahiti to Bora Bora, French Polynesia conjures images of stunning azure waters, majestic mountains, lagoons and sandy beaches.

Island hopping enables you to soak up a diverse array of exotic natural landscapes, hiking, scuba-diving and sunbathing to your heart’s content.

It’s best visited during the dry season months, from May to October, steering clear of the cyclone season and more extreme temperatures.

Your magical Polynesian experience should begin in Tahiti, where you can see bright turquoise waterfalls and mountains, touring the Fautaua and Papenoo valleys.

Bora Bora is a must-see island, famous for its spectacular lagoon, bustling with marine life.

Glass-floored retreats can be rented here, allowing guests to gaze deep into the waters below bursting with colourful fish.

Venture to the stunning reefs of sites such as Tapu, and go diving alongside manta rays and lemon sharks – make sure you have watertight non-standard holiday insurance, in case of injury.

If you’re looking to hike through dramatic mountain scenery, head for The Marquesas.

You’ll feel as if you’re on another planet wandering through Nuku Hiva, encountering wild jungles, imposing cliffs and rivers bordered by ancient, deserted villages.

The Tuamotu islands are a fantastic pick for scuba-diving fanatics, home to Rangiroa, an atoll celebrated for its phenomenal mix of coral, rays, sharks and fish.

Experience dolphins splashing about in Tiputa Pass, and take a boat excursion through Fakarava’s breath-taking lagoon.

How do you get around French Polynesia?

You’ll need to fly between most islands, using Air Tahiti – there’s only one domestic airline in French Polynesia.

Ferries are limited, but if your budget allows for it you could consider chartering a luxury yacht and live the ultimate Polynesian fantasy.

Where can you island hop in Greece?

White Greek buildings on the side of a sloping hill with the sea and another island in the distance at sunset

If you’re keen to soak up the beauty of the ocean, a Greek island hopping adventure more than allows for it.

The islands are well connected, although it’s best to focus on specific areas, as ferry lines commonly service select routes.

An ideal time to visit would be between April and May, or September and mid-October – services and hotspots will still be in full operation, the temperature is just right, and there’s less crowding.

You’ll likely arrive by plane, landing in Athens. Here, you can take in ancient wonders such as the Acropolis, a World Heritage site, where white marble sanctuaries and monuments tower majestically.

Don’t miss the Cyclades, a tourist trap in high season, but well worth a visit. Head for Santorini and drink in romantic sunsets, vineyards, towering cliffs and black-sand beaches.

Take a boat tour around the sandy beaches of Milos, marvelling at the white volcanic cliffs of Sarakiniko, and explore some of the scenic villages dotting the island.

If you’re looking for iconic Grecian scenery, be sure to journey to the Ionians, home to stretches of olive and cypress trees, mountains blanketed in dense forests and serene, sandy coves.

Go kayaking in Kefalonia amidst vivid blue bays and enjoy the quaint delights of Corfu, with its old-world arcades and eateries. For pure beach bliss, stop off at Lefkada.

How do you get around the Greek islands?

Focusing on a specific island chain? It’s a smart move to kick off by getting a domestic flight from Athens to your chosen spot, as it saves on money and time.

Depending on your budget, you can island hop via yacht, ferry, or catamaran taking advantage of a wide range of operators and routes.

Where can you island hop in the Caribbean?

A sandy beach on Aruba looking out to see with a dock behind some palm trees

An island hopping trip to the Caribbean doesn’t come cheap, but it’s well worth the investment – just make sure you have quality non-standard travel insurance.

Any Caribbean tour should include Aruba, a picture-perfect postcard come to life.

Here, you can visit some of the world’s most beautiful beaches, such as Eagle Beach, home to shimmering waters, spotless sand and the sculptural Fofoti tree.

Rent a cabana on one of Renaissance Island’s private beaches – as you wade through warm, clear waters, you’ll see pink flamingos nearby.

If you’re travelling by boat, sail to Anguilla, a magical island with an array of secluded, photogenic beaches often missed by tourists.

Visitors can dive into bright, coral-filled oceans and let their hair down a little, enjoying the island’s thriving rum and live reggae scene.

Head to Sandy Island, a small islet with powdery white sand, softly waving palms and aquamarine ocean, ideal for snorkelling.

You can even enjoy a fresh seafood barbecue at the beach bar – heaven.

Out of Anguilla’s 33 beaches, Shoal Bay East is the most sought-after, with pink-tinged sands, glistening turquoise waters, fun bars and unspoilt views.

For raw, dramatic natural beauty, make for exotic, mountainous Martinique. Boasting peaceful and protected beaches, lush scenery and an active volcano, it’s an unforgettable place.

A stone’s throw from quaint Sainte-Anne, Les Salines is an awe-inspiring expanse of white sand, coconut palms and sparkling ocean.

It’s somehow totally unspoilt, dotted with sweet snack bars and cooling shady patches – Caribbean beach heaven.

Don’t miss Diamond Rock, an ideal diving spot and photo backdrop.

For cosmopolitan culture, stop off at Fort-de-France, Martinique’s buzzing capital, and tour the vivid colonial architecture, dining on a diverse array of cuisines.

You definitely won’t forget your Caribbean adventure.

How do you get around the Caribbean?

The best way to island hop around the Caribbean is aboard a yacht charter, but this demands considerable expenditure – you can opt for a crewed or bareboat charter.

If you meet the criteria, you can skipper a bareboat charter yourself, while a crewed charter takes the hard work off your hands. Either way, you’ll be living the dream.

Ferries are few and far between, but they offer some of the most scenic routes between various island groups.

Regional airlines sell surprisingly cheap flights, and are well-connected. However, flight schedules are rather erratic, so you need plenty of time on your hands.

Your dream vacation abroad

A pool in front of a row of palm trees with the sun setting over the sea behind

An island-hopping holiday is a trip of a lifetime; one you’ve likely worked hard to afford.

You’ll see some of the most beautiful places in the world, discovering hidden gems and making wonderful memories along the way.

It’s a significant investment, which is why it deserves significant protection.

You’ll be in transit a great deal of the time, moving from place to place and you’ll want to take advantage of your surroundings, enjoying outdoor activities such as water sports and hiking.

While you can’t rule out risks such as injury, illness or theft, you can get quality cover.

Insurance Choice understand that every trip and traveller is different. We can find you reliable non-standard travel insurance, tailored to your needs and budget.

Give yourself peace of mind and enjoy travelling headache-free – get a quote today.