Caribbean Island Hopping Travel Article

Hopping mad in the Caribbean – a kaleidoscope of landscapes await

Caribbean island hopping article written by Travel Writer Linda Jackson

Just imagine… pristine powder-soft white sand beaches, azure-blue crystalline seas, lush tropical rainforests, vivid flora, abundant birdlife, towering palm trees… and year-round sunshine. You’ll find this paradise in one enormous treasure trove by Caribbean island hopping. But beware, if you want to holiday on an idyllic island in this region, you may encounter a problem. Namely, deciding which one to choose when they are all equally enticing. But, then again, why should you decide on just one island for your holiday. Why not visit more than one? The sky’s your limit… so be adventurous, go island-hopping by air.

Exploring the Leeward Islands by Caribbean island hopping

Why not explore the Leeward Islands – the northern half of the Lesser Antilles chain of Caribbean islands; they are closer together than the southern half (the Windward Islands) – and go for a glamorous two week Caribbean island hopping spree. Let’s stick a pin in the map and make our starting point the island of St Kitts, a well positioned springboard for Caribbean island hopping.

The quiet unspoilt and un-crowded island of St Kitts offers an experience you won’t find on another Caribbean island… a train. The double-decker ‘sugar’ train runs on tracks built in the early 1900s for transporting sugarcane to the factory. The air-conditioned railcars are specifically designed for visitors to enjoy a two-hour tour of the scenic island in comfort. Although only covering an area of 68 square miles, this volcanic island boasts a World Heritage historical site with breathtaking views (Brimstone Hill fortress); some great diving sites (Major’s Bay and White House Bay), including a sunken 18th century British troop ship complete with cannons; beautifully restored plantation houses, and quaint shopping areas. There are green Vervet monkeys chattering in treetops, golden sand beaches on the peninsula in the southeast and dark volcanic beaches in the north; a lush tropical rainforest to explore, and undulating mountains to hike including the extinct volcano Mount Liamuiga, reaching a height of 3,792 feet. For a rum ‘sun-downer’ head for South Friar’s beach in the southeast peninsula, it’s lined with beach bars; enjoy lobster at Mr X’s Shiggidy Shack, and reggae and soca music at Rainbow’s. June is music festival time, and in December the annual carnival brings St Kitts’ streets to life.

Caribbean Island hopping – St Kitts to St Maarten (30 minutes flight)

A hop to the dual French-Dutch island of St Martin/St Maarten, discovered by Christopher Columbus on St Martin’s Day in 1493, is next on the itinerary. Squabbled over for centuries by colonial powers, it was finally the Dutch and French in 1648 who signed a treaty dividing the island between them: 16½ square miles in the south to Dutch Sint Maarten and 20½ square miles in the north to French Saint Martin. But there are no borders to cross on this developed cosmopolitan island and each province retains its national culture and individuality. St Maarten is rich in Dutch colonial buildings and has a very busy cruise port, so as the airport is in the Dutch half first head for their capital, Philipsburg, for excellent duty-free shopping, lively evening entertainment and around thirteen casinos.

The French half has focussed more on luxury resorts; it has safe sandy beaches and a vibrant capital, Marigot, boasting over 50 restaurants. The capital also has a picturesque waterfront with a lively market-place full of stalls selling colourful clothes, tee-shirts, souvenirs and every spice imaginable. It’s crowded when a cruise ship is in, so choose your time to visit. Find time to wander Marigot’s narrow streets and to tackle the steep climb to Fort Louis for awesome views of the town, marina and lagoon; then take a taxi or hire car to hang out on popular Orient Beach for an abundance of water sports, sun-beds, pop music and beach bars; for lunch stroll into casual Waikiki Beach Restaurant on the beach, their rum punches have a kick and the crayfish are scrumptious.

Island hopping in the Caribbean – St Martin to Anguilla (20 minutes by ferry)

The ferry to unspoilt Anguilla, near enough for a day visit, leaves from the French capital Marigot. A hotspot hideaway for the rich and famous, this peaceful up-market island, just 16 miles long and three miles wide, has earned itself a big “foodie” reputation and is scenically contrasting to St Martin/St Maarten. It might be flat and mostly covered with small trees and shrubs, but Anguilla has some of the best beaches in the Caribbean, together with around 100 eating places ranging from roadside barbecue shacks and beachside cafés, to sophisticated international cuisine in luxurious settings. Don’t expect lively nightlife, it’s all about relaxing and eating… in style. Lunch is a must at Tasty’s, a mix of Caribbean and international flavours in a casual colourful ‘local’ setting; and dinner is ‘as good as it gets’ on the terrace of CuisinArt Resort & Spa; they use produce from on-site hydroponics and organic farms, herb gardens and fruit plantations.

Ferry from Anguilla to St Martin (20 minutes) + taxi from ferry port to St Maarten’s International Airport
Caribbean Island hoppingSt Maarten to Antigua (40 minutes flight)

With such English names as Falmouth Harbour, St John’s Harbour, Clarence House, Shirley Heights and Nelson’s Dockyard you can’t help but feel at home in historical Antigua, the next island hop. With a beach for every day of the year, stunning panoramic views, and what must be the most beautiful natural harbour in the world, this tropical paradise is a must for every island-hopping schedule. Lovingly restored to its 18th century glory, Nelson’s Dockyard is a superb example of a working Georgian naval dockyard, and is spectacular. So are panoramic views from Shirley Heights (Dow’s Hill) looking down on Nelson’s Dockyard, English Harbour and Falmouth Harbour; particularly when 130 boats or more take part in the annual Antigua Sailing Week (April/May). Before the allure of the beaches becomes irresistible, take a scenic drive along Fig Tree Drive, a roller-coaster road that winds through the south-western part of the island; it’s lined with lush vegetation, guava, mango and coconut trees. Visit St John’s, the capital; the cathedral which dominates the town; the Museum, Court House, and Clarence House where the future King William IV stayed when he was a midshipman in the 1780s. Now head for the beaches… to large crescent-shaped Half Moon Bay or Dickenson Bay, a striking half-mile beach with windsurfing, waterskiing, parasailing; snorkelling and diving activities. You won’t go hungry either, there’s a good selection of restaurants and bars.

Ferry from Antigua to Barbuda (90 minutes)

Antigua’s sister island, Barbuda, is renowned for its pink coral beaches, rare frigate birds and peaceful way of life, the island is well worth hopping to. Do it alone, or opt for a full day guided tour aboard the Barbuda Express, taking in the frigate bird sanctuary, beach time, ‘al fresco’ lunch and a short taxi tour of the island.

Caribbean Island hopping – Antigua to Nevis (30 minutes flight)
Ferry from Nevis to St Kitts (20 minutes)

From Antigua we fly to lush Nevis, the smaller of the two islands which make up the Federation of St Kitts and Nevis, separated by a two-mile stretch of sea, and our last port-of-call. The island, dominated by 3,200ft Mount Nevis, is filled with historical sites; take the twenty-one mile historic trail to discover them. Enjoy the charming capital, Charleston, its streets lined with classic West Indian architecture; hike in the rainforest, discover the island’s centuries-old plantation houses and savour the gentle pace of life before the last leg of our Caribbean island hopping expedition – a short ferry crossing to St Kitts where we finally embark our return flight with a suitcase of souvenirs and a treasure trove of memories that will last a lifetime.

Caribbean island hopping article
Images on this Caribbean Island Hopping Article page are copyright of