A Travel Expert’s Guide to Island-Hopping in the Caribbean

Are you not sure where to begin when it comes to Caribbean island-hopping? Jackie, our Caribbean specialist is here to share her expert guide for the best island-hopping holiday, with knowledgeable top tips from her own travels.

After 25 years of experience and multiple visits to the islands (some more than once!), Jackie’s expertise can help you create your perfect island-hopping experience.

From finding the best ways to get between the islands to discovering which ones to combine and how long to go for, she answers all questions here.  

Jackie Sampson

Caribbean Travel Specialist

‘Nothing excites me more than planning an extra-special island-hopping itinerary, with every detail arranged to seamless perfection.‘ – Jackie, Travel Specialist


Why you should try island-hopping in the Caribbean

“So, why should you choose a Caribbean island-hopping trip?

There are so many islands and so much choice outside the key gateway islands of Barbados, Antigua and St Lucia. Although these more well-known islands are lovely and offer their own lively vibe and colourful Caribbean cultures, taking that extra (and often easy) step to visit the less developed islands shows you a world of undisturbed beauty that makes your adventure even more memorable.

In fact, I would say that island-hopping is the best way to see the Caribbean at its most authentic. It’s also ideal if you’ve already ‘done’ some of the bigger islands, and are looking for some new and inspiring ideas to try.

Instead of sticking to just one place, venturing to the outer islands means that you can experience the unparalleled charm of peaceful beaches, and get that sense of extra adventure.”

Fort Rodney, St Lucia, overlooking the colourful buildings along the coastline
St Lucia

Where to stay when island-hopping in the Caribbean

“The likes of St Vincent and the Grenadines, the British Virgin Islands and St Kitts and Nevis are a lot smaller than the more popular islands. They have an unspoiled feel to them, and offer a contrast to the livelier and well-known spots on the main islands.

You can expect the full experience of authentic and traditional Caribbean from your hotel alone, where you can immerse yourself in the rhythms of nature, from beachfront private island resorts with lush rainforest backdrops to hillside hotels overlooking the sweeping ocean and tropical gardens.”

Sugar Beach, A Viceroy resort

The Gateway islands are the perfect place to start your Caribbean adventure but then you can go back and back and back and experience something different every time you go. Every island is different with its own feel, style and vibe. It’s a wonderful place to keep going back to.’ – Jackie, Travel Specialist


How to island-hop in the Caribbean

“Your Caribbean island-hopping journey will begin on one of the gateway islands such as Barbados, St Lucia or Antigua. These islands offer direct flights from and to the UK, which take around 8-9 hours.

I recommend spending a least a few nights, maybe more, on your gateway island to give yourself time to wind down and relax before setting off to your next stop.

You can get to your next island by shared or private charters. This option is the easiest option, and you can soak in the stunning views of the Caribbean waters and sweeping mountains as you sail through the crystal blue ocean. Scheduled operators are also available, such as InterCaribbean.”

Small yacht sailing the blue waters of the Caribbean Sea with lush rainforest backdrop
Charter sailing the Caribbean Sea

“Alternatively, you can sit back and let the Caribbean come to with a luxury cruise between islands. With a Caribbean cruise, you’ll be able to see more islands than you would by any other cruise ship as you can access the more idyllic islands that are more difficult to access.

You might opt for a Barbados roundtrip, our a cruise to the exotic Caribbean Isles, enjoying life at sea and letting the captain take you to some of the most beautiful islands of the Caribbean in between.”

Cruise ship cruising the Caribbean sea.
Caribbean cruise ship

My top tips for Caribbean island-hopping

“Don’t think that Caribbean island-hopping is too difficult – taking the extra steps is worth it to see as much of this beautiful part of the world as possible. With some expert help, your trip will run seamlessly. I can help plan the trip carefully so that your time on each island is as relaxing as possible.”

The British Virgin Islands coastline

How long do I need to go island-hopping?

“Timing is very important when it comes to this type of holiday. Two weeks is the perfect amount to hop between up to three islands, so you get a well-rounded holiday that has a sense of adventure while still offering enough time to unwind.

Make sure to plan well ahead of your trip! The outer islands tend to book up fast because they are smaller. Over packing might conflict with your connecting flights. Be sure to pack as light as you can, as other flights may have smaller luggage allowances.”

When is best to visit the Caribbean islands?

“Also, keep in mind the low and high seasons. Although the Caribbean is sunny year- round, the weather is so important to your experience. Between December and March is the peak time where temperatures are warm and rainfall is at a minimum.

The low season is after Easter until mid-December, where you can expect higher rainfall. During this season, some islands are drier than others, such as low lying coral islands which tend to be drier than the volcanic islands like St Lucia.”

Grenada coastline with boulders and hilly backdrop
Grenada coastline and landscape

‘”The British Virgin Islands are the ideal location, filled with the most beautiful and unspoilt landscapes you can imagine. However, now that they are becoming more developed, I recommend visiting before it changes too much.’” Jackie, Travel Specialist


Which are the best Caribbean Islands for island-hopping?

“I have so many options for you to choose from when it comes to finding the best twinning Caribbean islands together! With multiple stays and day trips to other islands, you can see the more developed islands with the more idyllic experiences.”

Antigua & British Virgin Islands

Birds eye view of the coast of Antigua with yachts and
Antigua coastline

Get a taste for easy-going island living on two different Caribbean Islands by opting for a 10-night Antigua and British Virgin Islands twin-centre itinerary. Soak up the landscapes of white sand beaches, lush green foliage and sweeping blue waters that frame both resorts on each islands, whilst immersing in the very inviting activities to become closer to Caribbean nature.

Whilst staying on the coast of Antigua, get up close to the tropical wildlife by snorkelling in the crystal waters on the pristine beaches. After hopping to the British Virgin Islands by boat, you see the difference in scenery by walking through one of the island’s natural wonders, a labyrinth of giant granite boulders.

Antigua & St Barths

St Barths Harbour with yachts, boats and mountainous backdrop
St Barths harbour

Explore two sides of the Caribbean in one holiday with a twin centre getaway to Antigua and St Barths. This is the perfect twin-centre opportunity to enjoy the contrast of Antigua’s British heritage, and discovering the chic French charm of St Barths.

The diversity of the Caribbean Islands is profound on this twin-centre, and you can see the steep differences between the two islands. In Antigua, you’ll be entranced by its renowned snorkelling spots and serene coves, a popular spot for beach lovers and the perfect place to begin your Caribbean escape.

Next is St Barths, drenched in French boutique influence and packed with designer shops and cultural sites of historical monuments.

Bequia & Barbados

Pastel-coloured buildings on Barbados with palm trees
Buildings of Barbados

Get the best of both Caribbean worlds with this twin-centre itinerary that takes you to Bequia and Barbados. Not only will you be soothed into a tranquil trance in the calming elements of Bequia, you’ll also be in the welcoming bustle of Barbados. From enjoying cocktails and fresh seafood on the beachfront to the indulging in the spa paradise, you’ll enjoy no limit to luxury.

Exploring the contrasting sides of one Caribbean Island

Looking for contrasts between each Caribbean island is a great place to start, as you can pair the livelier islands with more laid-back ones. Don’t just limit yourself to one Caribbean atmosphere, experience it all!

Barbados has got everything you could want. With vibrant culture and friendly locals, as well as a myriad of things to see and do including snorkelling to see colourful coral reefs and, you could visit Barbados multiple times and have a different experience each time.

It’s often called ‘little England’, with a welcoming atmosphere along the West and South . The East Coast, meanwhile, reminds me of Cornwall, with crashing waves and gusty breezes. There’s a huge variety on such a small island, with something for everyone.

If you have your own Caribbean Island-hopping ideas, simply let us know. This is your holiday, and we can tailor-make it for you.

There are the quaint, secluded bays of Virgin Gorda in the British Virgin Islands, breathtaking dormant volcano landscapes in Nevis, and an underwater sculpture park on the coast of Grenada – why wouldn’t you want to see it all in one?’ – Jackie, Travel Specialist


Common FAQ’s about the Caribbean

What is the best Caribbean Island for food?

It’s very hard to be disappointed by the food in the Caribbean because of how many options there are across the islands. If you’re in the more developed islands such as Barbados, you can find high-end, fine dining restaurants to diners selling burgers and chips with everything in between.

If you’re dining in a beach shack on the pristine coast of Antigua, you can expect more traditional creole cuisine, with delicious spices and tasty chicken, rice and peas.

It also depends on what you’re looking for, and speaking to us can help us get in touch with your hotel. This is generally for the outer islands, where there are less food choices. We want you to have the best experience in the Caribbean, and your dietary and food preferences are important to us.

Praen dish from the Caribbean, seasoned with herbs and lime
Popular Caribbean prawn dish

‘I’ve had some of the best food in the world in the Caribbean! There are hotels that stand out to me that have outstanding dining and I’ll happily recommend the cuisine to everyone.’ – Jackie, Travel Specialist

Start planning your island-hopping holiday with Jackie

If you want to listen to more expert insights on the Caribbean, be sure to listen to Jackie’s podcast also has a podcast on Spotify (or wherever you prefer to listen to them.)

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