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My Top 5 Caribbean islands you simply must experience

The Caribbean, it really does live up to the hype!

Stefanie Hayes on 21 Aug 2026

I have been fortunate enough to travel extensively in the Caribbean over the years with family, friends and colleagues. From fly-and-flop beach escapes and USA & Caribbean twin-centre stays to transatlantic island-hopping cruises, every trip has given me unforgettable memories and a real love for this incredible part of the world.

Here is my personal Top 5, and why I think they deserve a firm place on any Caribbean bucket list:

  1. Barbados
  2. St Lucia
  3. St Martin
  4. St Kitts & Nevis
  5. Tobago

I tend to travel to the Caribbean at the end of October and start of November. It is classed as off season and hurricane season has usually passed by then, so I have always enjoyed good weather. It is a little less hot than peak summer, noticeably quieter, and very good value compared with the busiest months.

As a huge foodie I love seeking out local specialities, and the Caribbean does not disappoint. Fresh seafood and traditional Bajan and Creole dishes have been a real highlight of every trip.

Barbados

Arriving into port

With daily direct flights from the UK, the 9‑hour journey to Barbados feels very manageable for such a rewarding long-haul escape.

I always recommend staying on the west coast, on the Caribbean Sea side of the island, where the water is typically calmer and wonderfully inviting. At just 21 miles long and 14 miles wide, Barbados is very easy to explore by hire car, taxi or even local bus, with many services stopping outside hotels along the west coast.

Often described as the culinary capital of the Caribbean, Barbados is a must for food lovers. A Friday night at Oistins fish fry is essential for an authentic taste of local nightlife and fabulously fresh seafood. Marlin, flying fish and red snapper are particular standouts.

US dollars are widely accepted, but change is usually given in the local Barbadian dollar. The island is also excellent for duty free and tax free shopping, especially for jewellery and of course Mount Gay Rum. A visit to Cave Shepherd in Bridgetown is ideal if you plan to take rum home, as they can package it and send it to the airport for you to collect on departure.

With more than 70 miles of beaches, there is plenty of space for couples to enjoy romantic walks and for families to make the most of the water sports. Add in visits to rum distilleries, plantation houses and botanical gardens and you have an island that really does offer something for everyone.


St Lucia

Paradise In The Pitons

St Lucia absolutely took my breath away with its dramatic beauty, framed by the iconic Pitons.

A real highlight for me was a catamaran trip along the rugged coastline, with unspoilt views and the peaceful feeling of being out on the sunlit ocean, rum punch in hand. St Lucia offers a great range of activities at different levels of adventure, from rainforest hikes and half-day island tours to a visit to the Rabot Hotel by Hotel Chocolat.

The island has a vibrant cultural calendar too. From the Jazz and Arts Festival in May and the Calypso carnival in July to the Creole Heritage Festival in October and the Festival of Lights in December, there is always something going on, whether you prefer to dip in or fully immerse yourself.

Gros Islet’s Friday night street party is a fantastic way to experience the island’s energy, with barbecues, seafood, rum bars and reggae bringing the streets to life.

With daily direct flights from the UK launching in October, it is an ideal time to consider a trip to St Lucia.


St Martin

St Martin is a laid-back island with both Dutch and French influences that give it a very distinctive feel. I have visited twice as part of cruise itineraries, and both times I was delighted that we were calling here.

Marigot, with its outdoor markets, offers a lovely glimpse into local life. Great Bay Beach is a short walk from the cruise terminal and rewards you with a beautiful stretch of white sand, calm water and a lively boardwalk lined with shops, bars and restaurants. It is a perfect place to while away an afternoon and simply watch the world go by.

If you are new to cruising, the Caribbean is a superb place to start. Waking up to a different island to explore each day is a real joy, and it is a very relaxing way to experience a mix of Caribbean cultures from the comfort of your “resort at sea”.

Coming into port


St Kitts & Nevis

St Kitts & Nevis enjoy a good climate year-round, which makes them a great option whenever you are able to travel.

St Kitts is the larger of the two islands and an excellent base. There is a regular ferry service across to Nevis, so it is very easy to enjoy a day on its pristine, uncrowded beaches.

St Kitts has a similar feel to St Lucia, with rugged volcanic mountains and a strong sense of heritage. You will see references to Christopher Columbus, but there is also a rich blend of British, African, Caribbean and French influences that shape island life today.

Carnival season begins towards the end of November and runs through to the end of January, culminating in a Grand Parade. Expect pageants, parades and plenty of calypso music, with a warm and welcoming atmosphere.

Expolre Island life!


Tobago

Tobago is ideal if you are looking for rest, relaxation and an easy all-inclusive beach escape.

I stayed at Coco Reef Resort & Spa and my week there was pure bliss from start to finish. It is only about a mile from the airport, so the transfer is just a few minutes, which feels very welcome after a long flight.

The service was wonderfully attentive, and nothing was too much trouble. The beach is quite literally on your doorstep, with a good selection of activities available if you want them, or you can simply relax and enjoy the peaceful setting.

Tobago feels intimate, friendly and laid back: a perfect slice of Caribbean paradise where you can genuinely unwind and leave day-to-day stresses behind.


With so many jewels in its crown, the Caribbean really does live up to the hype. I genuinely believe everyone should treat themselves to experiencing these magical islands at least once.

If you would like to chat about a Caribbean holiday, I would be delighted to help you find the island (or islands) that fit you perfectly and that you will never want to leave.

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