- Discover six of the best Caribbean islands to visit: Anguilla, Virgin Gorda, Tortola, St Barths, St Lucia, and Dominican Republic, each offering a distinct mix of beaches, culture, dining, sailing, and outdoor adventure.
- Explore the highlights of these top Caribbean islands, from Anguilla’s coral reefs and Virgin Gorda’s Baths to Tortola’s sailing grounds, St Barths’ beach clubs, St Lucia’s rainforests, and Dominican Republic’s historic charm.
- Learn about Tradewind Aviation’s scheduled and private charter service with convenient on-demand flights from San Juan throughout the Eastern Caribbean.
The Caribbean is a sensualist’s delight. It begins with color: the ever-changing blues of the sea, the shifting hues of the sand, and the coral-pink glow of sunset. Warm trade winds brush the skin and carry the scent of flowering trees. Calypso music drifts through the air, while a chilled rum punch brings the sweetness of tropical fruit and the warmth of the islands to the palate.
The barefoot pleasures here are simple and timeless: swimming in a calm bay, sailing beneath a sunny sky, lingering over grilled fish and chilled rosé beside the sea. The Caribbean has a way of calling travelers back again and again, with the pull of a siren’s song.
Yet for all the sensuous beauty the Caribbean shares, each island has a character entirely its own. Centuries of African, French, Dutch, Spanish, and British influence are expressed through food, language, architecture, music, and traditions.
Tradewind Aviation makes the journey feel effortless en route to the islands. Scheduled flights depart from San Juan, where passengers enjoy private lounge access with complimentary snacks and refreshments, and continue direct to Anguilla, Virgin Gorda, Tortola, and St. Barths.
On-demand private charters are also available throughout the Caribbean, giving travelers the flexibility to fly on their own schedule to destinations such as St. Lucia and the Dominican Republic. While the most popular transfer point is San Juan, private charters are also available from St Thomas, St Croix, and beyond. Complimentary beverages and refreshments are offered onboard private charters, making the journey part of the escape.Â
Both private and scheduled flights are operated in Tradewind’s modern fleet of Pilatus PC-12 aircraft, featuring fully pressurized, air-conditioned cabins with comfortable seating for up to eight passengers and ample luggage space.Â
From the glamorous beach clubs of St. Barths to the powder-soft shores of Anguilla, the sailing waters of Virgin Gorda and Tortola, the championship golf courses of Casa de Campo in the Dominican Republic, and the dramatic rainforest landscapes of St. Lucia, these destinations reveal the Caribbean in all its variety. Read on to discover why they rank among the best Caribbean islands to visit and how Tradewind can take you there with comfort and convenience.
Anguilla
Anguilla, a British Overseas Territory, is celebrated for its 35 pristine beaches, with powder-soft white sand and warm, clear water perfect for swimming. On the northwest coast, Meads Bay is known for its wide, mile-long expanse of beach and beautiful Caribbean sunsets. To the southwest, Rendezvous Bay is the ideal place for barbecue, a rum punch, and live music at a beach bar. On the island’s northeastern side, Shoal Bay East offers a two-mile stretch of impeccable sand with offshore coral gardens overlooking the Atlantic.
With excellent underwater visibility and a marine park system that protects Anguilla’s coral reefs and seagrass beds, there is plenty to see below the surface. Snorkelers and scuba divers can explore coral reefs and shipwrecks that have become artificial reefs teeming with marine life.Â
To discover more of the island, rent a Moke for the day. These open-air vehicles come in a rainbow of tropical colors and are a fun way to beach hop; just remember that driving is on the left. Along the way, stop at a beach shack for hot johnny cakes and local grilled crayfish, which are sweeter than lobster and larger than their counterparts from the Bayou. It is one of the island’s quintessential dishes.
From late July, the two-week Anguilla Summer Festival fills the island with calypso and soca music, boat races, beach parties, street parades, and concerts.
How to get there: Tradewind offers seasonal scheduled flights to Anguilla from San Juan (SJU) to Anguilla’s Clayton J. Lloyd International Airport (AXA) with a flight time of approximately 45 minutes. For travelers considering flying to Anguilla privately, charters can also be arranged year-round from Caribbean hubs like San Juan, Antigua, St Thomas, and beyond.
Virgin Gorda
Virgin Gorda offers one of the quieter, more unspoiled escapes in the British Virgin Islands. With limited development and secluded beaches, it appeals to travelers seeking dramatic scenery and a slower pace.Â
The island’s signature attraction is The Baths National Park, where enormous granite boulders create a maze of tidal pools, tunnels, and cool blue grottoes leading toward Devil’s Bay. Offshore, reefs, and wrecks offer excellent snorkeling and diving, including the RMS Rhone, a 19th-century shipwreck featured in the 1977 film The Deep.
To the north, the sheltered waters of North Sound form a natural playground for sailboats and yachts. Waterfront favorites include the Bitter End Yacht Club with its marina, restaurants, and boutiques, and Saba Rock, a longtime gathering place for the ritual of sunset drinks.
On land, a forested trail through Gorda Peak National Park leads to an observation tower with panoramic views across the British Virgin Islands. For swimming, Savannah Bay offers calm, shallow water and a long, undeveloped curve of sand for beachcombing, and quiet afternoons by the water.
Dining highlights include farm-to-table cuisine at Reef House at Rosewood Little Dix Bay, Asian-Caribbean dishes at CocoMaya, and sunset dining at Sugarcane Restaurant.
How to get there: Tradewind offers seasonal scheduled service from San Juan (SJU) to Virgin Gorda (VIJ), arriving at the island’s compact airstrip. The flight takes just over half an hour.
Tortola
The largest of the British Virgin Islands, Tortola retains a British-influenced colonial character. It is the territory’s yachting capital and a major hub for charter fleets. Beyond Tortola, the archipelago is dotted with private islands, villa retreats, and exclusive resorts like Scrub Island, Guana Island, Peter Island, Necker Island, The Branson Beach Estate, and The Aerial.Â
Together these frame the Sir Francis Drake Channel, acting as natural breakwaters that shelter its waters from heavy ocean swells. The result is a celebrated cruising ground known for gentle tides, reliable trade winds, and line-of-sight navigation. Each spring, the BVI Spring Regatta draws competitive racing yachts and crews from around the world.
On the island’s western tip, secluded Smuggler’s Cove is known for calm water and sea turtles. Board a catamaran or private charter boat to explore the coastline and discover quiet beaches and coves for snorkeling and swimming
Sage Mountain National Park, with its focus on plant conservation and scientific research, offers fourteen loop trails through old-growth rainforest. Mist-shrouded paths shaded by mahogany trees and white cedar lead to the highest point in the Virgin Islands, where hikers are rewarded with stunning panoramic views.Â
A guided tour of Callwood Rum Distillery offers rum tastings and a glimpse into the island’s history. Set within the historic Arundel Estate, the centuries-old stone distillery has operated since the plantation era and continues to produce traditional pure cane rum.
Local dishes include fish with fungi, a cornmeal-based staple prepared with okra, onions, and peppers. Try it at island favorites such as Sappy’s or D’Coal Pot.Â
How to get there: Tradewind offers seasonal scheduled service from San Juan (SJU) to Tortola (EIS). Flights land at Terrance B. Lettsome International Airport and take just over a half hour.
St Barths
St Barths is the jewel of the French West Indies, a small, hilly island where Caribbean beauty meets French sophistication and a jet-set spirit. Villas spill down green hillsides toward peacock-blue water where sailboats and superyachts gather in Gustavia Harbour. Designer boutiques, elegant hotels, and acclaimed restaurants add to the island’s appeal.
The beaches are equally varied. Saline Beach feels quiet and secluded, while St Jean Beach is the center of the island’s glamorous beach-club scene, with lunches at Nikki Beach and Eden Rock–St Barths. A short walk from Gustavia, Shell Beach is covered in tiny, weathered shells and will soon welcome Loulou, the stylish French-Mediterranean restaurant and beach club, to the former Shellona space in October. For greater seclusion, Colombier Beach can be reached only by boat or by hiking a coastal trail.
In Gustavia, the island’s capital, historic Swedish landmarks sit alongside French bistros, harbor front restaurants, and designer shops. Dining is central to life here, from morning baguettes and pain au chocolat to long lunches of local spiny lobster, tuna tartare, chilled rosé, or Champagne. By evening, cocktail bars, restaurants, and late-night music carry the island from dinner into dancing.
How to get there: The most common route for flying to St Barths from the United States is through San Juan, Puerto Rico (SJU) connecting to Tradewind’s scheduled service to St Barths (SBH). Tradewind operates year-round, daily flights to St Barths from San Juan, with a flight time of roughly 50 minutes. For guests traveling from the UK and beyond in Europe, Tradewind also offers scheduled flights from Antigua (ANU), a more convenient connection point to St Barths. Private flights to St Barths can also be arranged on demand from San Juan and other regional gateways.
St LuciaÂ
In the eastern Caribbean, St Lucia stands apart for its dramatic natural beauty, defined by the twin volcanic peaks of Gros Piton and Petit Piton. Collectively known as the Pitons, the UNESCO-listed spires rise sharply above the sea. Gros Piton can be climbed with a guide on a challenging but manageable half-day hike.
Beyond the peaks, St Lucia is rich in rainforest, waterfalls, hiking trails, and birdlife. At Sulphur Springs, billed as the world’s only drive-in volcano, visitors can walk among steaming vents and soak in mineral-rich mud baths. Nearby, Diamond Falls Botanical Gardens combine tropical plants, hot mineral pools, and a waterfall colored by mineral deposits.
Offshore, snorkelers and shore divers can explore the protected reef at Anse Chastanet, a marine reserve with shallow coral gardens, a dramatic drop-off wall, and over 150 species of fish. The reef sits directly off Anse Chastenet Beach, known for its volcanic black-sand.
Each May, the Saint Lucia Jazz & Arts Festival brings musicians and artists from around the world to the island, accompanied by street food, art installations, and performances.
St Lucia’s cuisine reflects its African, French, British, and Caribbean influences. The Coal Pot pairs a romantic waterfront setting with dishes such as crab backs and mahi-mahi in coconut curry, while Martha’s Tables in Soufrière is known for saltfish, breadfruit fritters, and sticky guava chicken wings. High in the rainforest canopy, Treetop Restaurant serves Indian-Caribbean cuisine with mountain views.
How to get there: Book a Tradewind private charter to St Lucia. Their San Juan hub offers VIP transfers, an exclusive private lounge, and expedited security and boarding, allowing guests to transfer conveniently from a commercial airline or private jet. Popular charter routes to St. Lucia include San Juan (SJU), St Kitts (SKB), and St Thomas (STT).
Dominican Republic
On the Dominican Republic’s southeastern coast, La Romana offers easy access to Casa de Campo Resort & Villas, a 7,000-acre retreat known for its exceptional range of sports, recreation, and private accommodations. The resort is home to three championship golf courses designed by Pete Dye, including the celebrated Teeth of the Dog, as well as polo fields, an equestrian center, private beaches, a marina, and secluded villas. Altos de Chavón, a recreated 16th-century Mediterranean village overlooking the Chavón River, features galleries, boutiques, restaurants, and an amphitheater.
How to get there: Tradewind private charters fly directly to La Romana International Airport (LMR), located just minutes from Casa de Campo, making the resort convenient for a Caribbean escape.
From the beach clubs of St Barths to the rainforests of St Lucia, these destinations show why they are among the best islands to visit in the Caribbean. Whichever you choose, Tradewind makes the journey feel like part of your vacation.
To learn more about Tradewind’s private charter and scheduled flights to the best Caribbean islands to visit, please visit our website. For questions regarding scheduled flights, contact our scheduled service team at scheduledservice@flytradewind.com or 1-800-376-7922 option 1. To receive a private charter quote, please submit an inquiry here or contact our specialists at sales@flytradewind.com or 1-800-376-7922 option 3.