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30th July 2025
Why island hop?
There’s something magical about charting your own course from one turquoise-lagoon to the next, and Caribbean island hopping gives you the best of everything: vibrant culture, dramatic landscapes, unique culinary flavours, and that “you’re somewhere special” feeling each time you arrive.
With more inter-island flights, ferries, and private charters than ever before, island hopping in the Caribbean is no longer reserved for the adventurer only – it’s entirely accessible for anyone craving a multi-center beach escape.
From Barbados and Grenada in the south to Antigua & Anguilla in the east, each island offers something unique. Tasting the nutmeg-scented air of Grenada, relaxing on dunes in Anguilla, sailing between the Grenadines – it’s a sensory journey as well as a tropical escape.
Why book with swift travel?
The idea of a multi-centre island paradise holiday can often seem like too much hassle, but our experts at Swift Travel can make this a seamless experience. With first-hand experience of the different destinations, local partners, and the ability to organise every element of your proposed trip, we will ensure that your trip will be stress-free.
Where to Go on a Caribbean Multi-Island Holiday
Barbados & Grenada – Beaches and Spice
Begin in Barbados, an island where colonial heritage, friendly towns, and dazzling beaches combine. Spend days exploring coral stone plantations, sipping rum at historic distilleries, and swimming in calm bays like Carlisle Bay. For contrast, head to the wild east coast, where Bathsheba’s surf and rugged cliffs make a dramatic backdrop.
Fly south to Grenada, known as the Spice Isle. Here the air carries hints of nutmeg, cocoa, and cinnamon. Wander the colourful capital, St. George’s, snorkel at the Underwater Sculpture Park, and hike through Grand Etang National Park to cascading waterfalls. A tour of a cocoa plantation reveals how world-class chocolate is made, before you retreat to quiet coves along Carriacou or Petite Martinique.
This pairing offers a perfect week-long Caribbean island hopping itinerary – vibrant culture and nightlife in Barbados balanced with nature and serenity in Grenada.
Barbados & Bequia – Boutique Island Escape
Pair bustling Barbados with the charm of Bequia, one of the Grenadines’ most captivating islands. After enjoying the lively beaches and dining scene of Barbados, take a short regional flight or private charter to discover Bequia’s slow pace and authentic character.
Stroll through harbourfront villages, enjoy grilled lobster on the beach, and kayak around secluded bays. Bequia’s unspoilt beauty and laid-back atmosphere make it a favourite for honeymooners and couples wanting a boutique Caribbean multi-centre holiday.
Antigua & Anguilla – Heritage and Hidden Coves
Antigua is famous for its 365 beaches – a different stretch of sand for every day of the year. Beyond the coastline, history comes alive at Nelson’s Dockyard, a UNESCO World Heritage site, while the view from Shirley Heights is one of the Caribbean’s most iconic sunsets.
A short hop brings you to Anguilla, with its powder-white beaches and crystal-clear waters. This is Caribbean island hopping at its most luxurious: chic boutique hotels, world-class dining, and hidden coves that feel a world away from everyday life. Snorkelling, sailing, and barefoot beach bars complete the experience.
St Lucia – Pitons, Rainforests and Romance
St Lucia is the Caribbean at its most dramatic. The island is crowned by the twin volcanic Pitons, rising steeply from the sea and framed by emerald rainforest. This is a destination where relaxation and adventure sit side by side.
- Nature & Adventure: Hike through the lush rainforest, soak in mineral-rich mud baths at Sulphur Springs, or sail along the west coast for views of hidden coves and fishing villages.
- Beaches: Unwind on soft golden sands at Reduit Beach or discover smaller bays such as Anse Chastanet, perfect for snorkelling and diving.
- Culture & Flavour: Explore the capital Castries, visit local markets, and taste Creole-inspired cuisine rich in spices and fresh seafood.
- Romance & Luxury: St Lucia is world-renowned for its honeymoon resorts, cliffside infinity pools, and boutique retreats with breathtaking views.
St Lucia pairs beautifully with Barbados for a twin-centre holiday – cosmopolitan dining and lively beaches first, followed by rainforest adventures and mountain scenery. For a longer Caribbean island hopping itinerary, combine St Lucia with Grenada and Bequia, creating a journey that balances relaxation, culture, and natural wonder.
When to Go
- December to April – The dry season offers sunny skies and warm seas, perfect for a beach-focused itinerary.
- May to June & September to November – Shoulder seasons mean fewer crowds and good value, with occasional tropical showers.
- July to October – Hurricane season; some travellers still go, but flexibility is essential.
Travel Tips for Caribbean Island Hopping
- Flights & ferries – Regional airlines such as LIAT and Caribbean Airlines connect major islands. Ferries are available between certain islands, but schedules can be limited.
- Packing essentials – Reef-safe sunscreen, mosquito repellent, a light rain jacket, and a dry bag for boat trips.
- Currency – US dollars are widely accepted, though some islands have their own currencies. Always keep a small amount of local cash.
- Food & drink – Taste the Caribbean through its cuisine: jerk chicken in Antigua, roti in Barbados, fresh seafood and lobster in Anguilla, and Grenadian chocolate straight from the source.
To discover whats beyond the beaches, read our travel guide for experiences beyond the beach in the Caribbean here.
Plan Your Caribbean Island Hopping Holiday with Swift Travel
With nearly 40 years of expertise, Swift Travel designs tailor-made Caribbean island hopping itineraries that suit your style — whether that’s luxury resorts, boutique hideaways, or adventure off the beaten track. We’ll handle the flights, ferries, hotels, and details, so you can simply enjoy the journey.
Call 020 8502 8300 to start planning your bespoke Caribbean escape.
Hotel Inspiration
Explore some of our hotel inspirations below. If you’re dreaming of something truly unique, get in touch and let us help craft your perfect stay.
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