San Juan to San Juan

Arrive on the northern coast of a tropical island and enter San Juan, one of the earliest European settlements in the Caribbean and the oldest city under U.S. jurisdiction. Walk along fortified stone walls and watchtowers built to defend against past attacks, including pirate raids and invasions such as those led by Sir Francis Drake. Explore Old San Juan, where colorful buildings, cobblestone streets, wooden balconies, and historic doors line the city. Move through plazas and fortresses that reflect centuries of colonial history. Visit beaches along the coastline and relax on soft sand near clear turquoise water. Take part in local culture through music, dancing, and street gatherings influenced by Spanish traditions. Spend time along the shore or enter nearby mangrove forests for a closer look at coastal ecosystems. Paddle through nearby waters after dark and observe glowing bioluminescence that lights up the sea with movement. Hike across limestone cliffs and karst formations, then enter sea-carved caves or follow cliffside paths for wide ocean views. Taste local dishes such as mofongo made from green plantains and chicken. Pair it with a chilled mojito made from mint and local rum while exploring the island’s food scene and coastal atmosphere.

Step into St John, an unspoiled island known for clear water, white sand beaches, and dense green rainforest. Walk along quiet shores where soft sand meets calm, transparent seas. Swim or snorkel in coral reefs filled with fish and sea turtles moving through seagrass beds. Visit Trunk Bay and move along its curved shoreline, bordered by vegetation and shallow blue water. Head inland to reach Bordeaux Mountain, where hiking trails lead to wide views over nearby islands. Follow jungle paths through rainforest slopes to reach hidden beaches and shaded coves lined with coconut trees. Travel by jeep on winding roads or continue on foot through forest routes. Discover ruins from old sugar mills that reflect the island’s plantation history, along with archaeological sites linked to early Indigenous groups. Explore protected areas within Virgin Islands National Park, created to preserve large parts of the island’s landscape. Stop at beach bars along the coast and try local drinks like the Painkiller, made with rum, pineapple, and spices, while staying close to the shoreline and ocean breeze.

Cherry red roofs, yacht-sprinkled bays, and a sophisticated French flavor all add to the gorgeous Caribbean allure of Gustavia. The island's capital rolls around a horseshoe-shaped harbor, where gleaming yachts hover and fancy shops, bars, and restaurants buzz with life and clinking cutlery. Head up to red and white Gustavia Lighthouse to look down over the revered waters, which attract many a celebrity guest and diving enthusiast to these shores. Christopher Columbus was the first European to discover this volcanic island in 1493, giving it the name St. Barthelemy in honor of his younger brother. The island has a unique history as a Swedish colony, following a deal with the French King Louis XVI to exchange the island with Sweden for better trading rights. It was returned to French control in 1878 and is now a French Overseas Collectivity. Learn more about the Swedish legacy at Fort Karl - which sits on a 29-meter-high hill above Shell Beach. The fort now lies in ruins, but you'll meet wandering iguanas, and the sweeping sea views and emerald coastline are some of the island's finest. Down below, a delightful spread of tiny pebbles and shell fragments scatter like confetti and is lapped by crystal-clear water. A little exploration uncovers countless other glorious beaches and natural wonders. Colombier Beach is a little out of the way but cradles silky-smooth sands and typically turquoise waters. If you have the chance, find somewhere to settle and sip fruity rum cocktails as the sunset flares across the waves.

Lush and lively, Antigua is a bedazzling Caribbean destination, gorged with sunshine and crisp white sand beaches. Historic forts, sparkling coastline, and dense rainforest all contribute to Antigua's land of thrilling natural beauty. With its bright blue to turquoise sea gradients - the beaches are vibrant and plentiful, and the island has no shortage to choose from, with a rumored 365 options. Experience the beauty on horseback, as your ride pounds across the sands, and the wind whips through your hair. Choose to loll in a catamaran offshore, or lay back on a bed of the softest sand to soak it all in. Beach shacks cook up fresh seafood and spicy goat meat curries if you're feeling hungry. St. John's glows in the sunshine, with flamingo pink and baby blue paint boldly coating vivid Georgian buildings. Lively markets offer an authentic slice of Antiguan life, while museums celebrate the island's revered cricketers like Viv Richards, and the story of independence. The whacks and whoops of makeshift cricket games hint at the island's British history, and you can see more of this heritage at Falmouth Harbor - which was center of the British presence in the Caribbean. The area is still filled with sailors and docked yachts, as well as the only working Georgian dockyard in the world. Constructed in 1725, the UNESCO World Heritage Site, Nelson's Dockyard, was led by the admiral Horatio Nelson himself and is a fascinating time warp. Hike up to viewpoints here, which offer glorious views of the forest-clad inlets, craggy cliffs, and pointed hills. The stone towers of sugar mills dot the island, and hint at the tragic history of slavery, amid the island's sugar trade past.

The largest of the Windward Islands, Martinique is 4,261 miles from Paris, but its spirit and language are decidedly French, with more than a soupçon of West Indian spice. Tangible, edible evidence of this fact is the island's cuisine, a superb blend of French and Creole. Martinique is lushly landscaped with tropical flowers. Trees bend under the weight of fruits such as mangoes, papayas, lemons, limes, and bright-red West Indian cherries. Acres of banana plantations, pineapple fields, and waving sugarcane stretch to the horizon. The towering mountains and verdant rainforest in the north lure hikers, while underwater sights and sunken treasures attract snorkelers and scuba divers. Martinique is also wonderful if your idea of exercise is turning over every 10 minutes to get an even tan and your taste in adventure runs to duty-free shopping. A popular cruise-ship excursion goes to St-Pierre, which was buried by ash when Mont Pelée erupted in 1902.

St. Kitts's verdant volcanic slopes rise from crystal clear Caribbean waters, promising a land of escape, relaxation, and rejuvenation. A place for ‘limin’ - the local word for kicking back, Caribbean style, you’ll be welcomed to an island paradise blessed with swarming reefs, hidden white-sand beaches, and irresistible shallow seas. Bigger sibling to nearby Nevis, St. Kitts is a place of unrestrained natural beauty. Soak up the dreamy Caribbean bliss, or explore sprawling island rainforests, teeming with hummingbirds and the distant sounds of waterfalls, as you walk the island’s vine-tangled paths. A ride on Basseterre’s scenic sugar train is a rumbling, immersive journey through the heart of this Caribbean island of culture and vivid unspoiled scenery. Carriages that once transported crops of sugar cane to the city sweep around long curving bends, revealing a spectacular introduction to St. Kitts. The landscapes here are beautiful, and things are no less spectacular offshore, where glorious crystalline waters invite you to dive with turtles and explore doomed wrecks like the River Taw ship – which has now exploded with marine life. In Basseterre itself, stop off to see the pea-green Berkeley Memorial clock, which stands in the Circus, surrounded by busy St. Kitts life. Independence Square is also waiting among the city’s charming Georgian buildings. Renamed from Pall Mall on the 19th of September 1983 - to celebrate the island’s independence - the pretty square gravitates around a colorful burbling fountain, and has a dark history, as a former slave market. Wary canons watch out over the waves far below at Brimstone Hill Fortress, a site of significant history, which dates back to 1690. Known as the "Gibraltar of the West Indies" due to its importance at the heart of the British empire, St. Kitts was one of the first islands in the West Indies to be colonized. Nowadays, its World Heritage Site fortress offers panoramic views along the coastline it was built to defend.

Glowing turquoise waters, lazily bowing palm trees, and pristine white sand beaches – it's all waiting for you in Jost Van Dyke's picturesque Caribbean splendor. Slip off your shoes, you won't be needing them too much in these parts, as you wander soft, heavenly sands, and paddle out into impossibly clear waters. The island escape of choice for dallying yachts, which visit to soak up the off-the-beaten-path good life. Join them around the pristine beaches of this tiny celebrity magnet of an island. If this is your first experience of the Caribbean's splendor, you may be a little skeptical about the reality of those famed, shockingly bright colors that you see in photographs. If so, Jost Van Dyke will be love at first sight. Splash into water that glows with a bright teal hue and is blotched with occasional swells of deeper royal blue. Snorkelers will adore the explosions of colorful fish beneath the waves. White Bay is a slice of island perfection, with a neat hill of trees framing a sandy sweep of shaded beach bars. There's nothing for it but to indulge on a bed of soft pearly-white sand, and soak in the staggering beauty of it all. The wander up to Majohnny Hill is the most exertion needed to explore this four-square-mile island, and it's worth it to see the heavenly beaches emerging from tranquil waters below. Even the natural sea formations here encourage you to unwind, with waves gurgling and frothing over the rocks to create Bubbly Pool, a natural jacuzzi. Jost Van Dyke has a reputation as the off-the-radar island getaway of choice for celebrities like Keith Richards. A lot of that comes down to the calypso charm of its rustic beach bars - especially the legendary Foxy's Bar, which is run by island legend Foxy Callwood. Rum-drenched cocktails and icy buckets of beach beers await - sure to get you into the island’s party spirit in no time.

Sitting on the north coast of this lush, tropical island, San Juan is the second settlement founded by European settlers in the Caribbean, and the oldest city under US jurisdiction. The stocky walls and watchtowers here have stood the test of time, repelling notable invaders – such as Sir Francis Drake – and the pirates who historically looted these islands. With massive fortresses, airy plazas and sheer Caribbean beauty, San Juan is a beach-blessed star of these turquoise waters. With more than 500 years of European history, Old San Juan gleams In Puerto Rico’s sunshine, with sugar-almond painted facades and ankle-testing cobbled lanes. Decorative balconies and varnished wooden doors add everyday artistry to streets, dripping with history. Soak up the culture at rum-fuelled parties and salsa dances on this Spanish-culture infused island, or recline into afternoon relaxation sessions on sensational slivers of gleaming sand. Kick back on the beach, or satisfy a lust for adventure by exploring sprawling mangrove forests. The magic of sea kayaking after dark here is an experience you won't forget. Break the waves with your oar, and watch as the waters illuminate with neon color, as bioluminescence creates a mystical, peaceful spectacle. Pocked limestone cliffs and karst landscapes add rugged contrast to the serenity of the beaches, and you can walk into folds of the earth in sea-carved caves, or across cliffs to hidden views of the Caribbean’s expanse. Enjoy a taste of the island’s cuisine by sampling Mofongo – a local concoction of green plantains and chicken. Why not indulge and wash it down with an iced mojito, made from crushed mint and locally distilled rum?