- Tradewind Aviation makes visiting the top Caribbean islands seamless: Connect through San Juan with scheduled and private charter flights to key islands in the Eastern Caribbean.
- Different islands, distinct escapes: Tortola provides lush hills to explore and vibrant sailing culture; Virgin Gorda delivers The Baths and North Sound’s yacht-country energy; Anguilla is all about pristine white-sand beaches; and St Barths exudes French-Caribbean glamour.
- Prime-season / Low season: From mid-November to May, expect warm, sunny days and a busy social calendar, from BVI regattas to Anguilla music weekends and St Barths’ gourmet events. Spring and summer low season means fewer crowds plus a roster of carnivals and festivals.
With more than 7,000 islands across a turquoise-hued sea, the Caribbean isn’t about a single destination; it’s a region comprising 28 nations. Every island is framed by turquoise water and sun-warmed sand, yet each is uniquely shaped by a cultural mosaic of Indigenous, African, European, and Asian influences. Experience this variety by visiting the top Caribbean islands in the region, made effortless with Tradewind Aviation. Here’s how to do it.
Make San Juan, Puerto Rico Your Hub
Begin in San Juan, Puerto Rico, Tradewind’s gateway to the Caribbean. From here, seasonal scheduled service makes it easy to reach the British Virgin Islands (Tortola and Virgin Gorda), Anguilla, and St Barths. Prefer to move on your own timeline? Tradewind can arrange private charter flights throughout the Caribbean, tailored entirely to your schedule.
When you fly personal with Tradewind, you don’t have to trade comfort or an entire beach day during a travel day. Seamless travel begins in Tradewind’s private lounge, which offers a quiet space away from the main terminal, equipped with complimentary snacks, refreshments, and WiFi. Guests are escorted through expedited security and welcomed aboard a modern Pilatus PC-12, featuring a pressurized and air-conditioned cabin. Settle into comfortable seating and enjoy complimentary snacks and refreshments. Want to add an extra layer of ease? Opt for Tradewind’s VIP Experience in San Juan, a meet-and-greet service designed to streamline connections, airport navigation, and luggage handling.
Below are some islands to consider for the best Caribbean vacation destinations. The British Virgin Islands are a mecca for sailing and snorkeling; Anguilla has some of the region’s most celebrated beaches; and St Barths delivers a touch of French glamour.
Tortola, BVI
Nicknamed the sailing capital of the Caribbean, the British Virgin Islands are all about barefoot luxury and boating. The calm, protected waters of Sir Francis Drake Channel run between Tortola and Virgin Gorda, creating ideal conditions for relaxed cruising with plenty of infrastructure.
When it comes to the best Caribbean vacation destinations, Tortola is a main point of entry and the largest of the 60 islands and cays. Secluded private island resorts like Scrub Island lie just minutes off Tortola’s coast. Road Town, the capital, is a major hub for yacht charter companies like The Moorings and Sunsail. If you’ve ever imagined bareboating or sailing on a skippered yacht, this is the place to live the dream.
From a charter boat, you’ll be able to snorkel reefs like The Indians, part of the National Parks Trust, and Norman Island Caves to see multitudes of colorful fish, corals and sponges. Scuba divers will want to explore the 19th-century wreck of a Royal Mail Steamer, the RMS Rhone, which lies 82 feet below on the seabed.
Back on land, spend a morning at Smugglers Cove, one of Tortola’s most serene and secluded beaches. Located on the west end, the clear, shallow water is perfect for a morning swim or snorkeling the reef amidst fish and leatherback turtles. Brewers Bay in the northwest is another good choice for snorkeling in a protected bay. For a livelier crowd scene, head to the island’s north side where the pretty beach of Cane Garden Bay is lined with beach bars, restaurants, and the Callwood Rum Distillery.
Tortola’s green mountains are part of this volcanic island’s natural beauty. The highest point is Sage Mountain at 1,716 feet, and you can climb right to the top. Located in Sage National Park, it has a unique rainforest ecosystem with trees and plants seldom seen on other islands. As you hike the trail, look for Elephant ear vines, tree ferns, hermit crabs in the underbrush and kili kili hawks perched in trees. An unbelievable panoramic view awaits at the summit.
For local eats, stop in at D’CoalPot on Carrot Bay for an ice-cold passionfruit juice, conch chowder or jerk pork. On Long Bay Beach, the 1748 Restaurant serves an island-to-table menu inside an 18th-century rum distillery.
Seasonal events include the 29th Annual Dark & Stormy Regatta; the BVI Spring Regatta & Sailing Festival; the BVI Music Beach Festival; and Trellis Bay’s famed Full Moon Party on nights of the full moon.
Getting there: Tradewind offers seasonal scheduled flights daily from San Juan (SJU) to Tortola (EIS). Flight time is just under 45 minutes. Tradewind also provides year-round private charter flights throughout the Caribbean.
Virgin Gorda, BVI
You can’t travel to BVI and not experience Virgin Gorda. Just across the Sir Francis Drake Channel, Virgin Gorda is one of the most beautiful islands in the BVI archipelago. Surrounded by cool blue grottos tucked along white sand beaches, this island is rich with reefs and wrecks to explore, and six national parks for hiking.
Stay at a legendary resort, on a private island, or in a private villa with a dedicated concierge. On the south side of the island, Rosewood Little Dix Bay is set on a half-mile of sandy crescent beach. Tradewind guests who fly to Virgin Gorda and stay three or more nights at the property receive complimentary VIP Experience at the San Juan airport and a resort credit.
Head to Savannah Bay, a gorgeous swath of secluded beach and a perfect place to enjoy a picnic. Rosewood Little Dix Bay offers guests “Beach Drops,” dropping you by boat on a beach for a few hours of swimming and snorkeling, umbrella included.
Take a hike up Gorda Peak, where you’ll find a different terrain from that of Sage Mountain. This 1,370-foot peak lies within a protected sanctuary unique for its dry forest. Two trails wind through dry scrub to a moister greener environment as you ascend the slope to a peak with magnificent views.
A must-visit is The Baths, and you want to do it first thing in the morning before the crowds arrive. (The park opens at 9am, and there is a small, cash-only fee). This national park is famous for massive, naturally-formed granite boulders that form a maze of grottoes, tunnels, caves, and tidal pools that spill into the ocean. Be sure to wear a bathing suit and reef shoes and bring your snorkeling gear to fully explore this natural wonder. Nearby, Devils’ Bay and Spring Bay offer more snorkeling in quiet coves off a sandy beach with giant boulders.
On the North Sound, a sheltered reef attracts superyachts and private island devotees. This is the place for sunset watching over cocktails at Saba Rock’s Sunset Bar, or Bitter End Yacht Club for rum punches on the waterfront. Dress up a bit for a barefoot, stylish evening at CocoMaya in Spanish Town overlooking the Sir Francis Drake Channel and dine on Asian-fusion fare like shrimp lettuce wraps, CocoMaya house ribs, and Thai Chicken Green Curry.
Seasonal events include the Taste of the BVI-Virgin Gorda; the North Sound Maxi Regatta, five days of invitational sailing competition amongst maxi-yachts; the Virgin Gorda Easter Festival with pageantry, elaborate Easter bonnets, and music in Spanish Town; and Xmas in July that welcomes seafarers to hitch their own boats to join the massive flotilla celebration at Pond Bay.
Getting there: Tradewind offers seasonal scheduled flights daily from San Juan (SJU) to Virgin Gorda (VIJ). Flight time is 35 minutes from San Juan. Tradewind also provides year-round private charter flights throughout the Caribbean.
Anguilla
Anguilla is the place to slow down. There’s no mountain to climb on this low-lying coral and limestone island—just 33 spectacular beaches. The vibe is quietly exclusive rather than flashy: barefoot elegance with low-key nights, and a reputation as a lo-fi, luxe escape.
There’s an Anguilla beach to suit every personality. Shoal Bay East is a favorite for its calm, clear water that’s ideal for easy swimming and excellent snorkeling, while Meads Bay offers a long, graceful sweep of sand perfect for a morning run or sunset stroll. Rendezvous Bay charms visitors with its powdery-soft sand and beach bars featuring live music, and Little Bay Beach feels like a hidden treasure – a tiny gem with a secluded cove tucked between steep cliffs and is accessible by boat or kayak.
The island’s exceptional collection of highly acclaimed restaurants makes it a true destination for discerning diners. Go toes-in-the-sand at Blanchards Beach Shack on Meads Bay, then dress up for Veya, beloved for its “Cuisine of the Sun” and atmospheric, tucked-away setting. For an easy, beautiful beachfront meal, Straw Hat is a classic.
Seasonal events include Moonsplash, a signature Anguilla music weekend; Festival Del Mar over Easter weekend for a spirited, sea-loving local celebration; and the Anguilla Culinary Experience.
Getting there: Tradewind offers seasonal scheduled flights daily from San Juan (SJU) to Anguilla (AXA). Flight time is about an hour from San Juan. Tradewind private charter flights to Anguilla are available year-round.
St Barths
St Barths is a sophisticated playground, a lush tropical landscape with French influences that attracts billionaires and their yachts. You can find fresh-baked croissants as easily as designer boutiques like Hermes, Louis Vuitton, and Patek Philippe tucked into the hills above the manicured marina. St Jean Beach is made for people watching with beach clubs like Nikki Beach and La Guerite. Reserve plush sunbeds with ocean views and toes-in-the sand dining over rosé-fueled celebrations. For a quieter space, visit Saline Beach, a remote and unspoiled beauty. Don’t miss Shell Beach, covered entirely in seashells, complete with a reservation at Shellona, a Greek restaurant directly on the sand, for dining with a million-dollar view. There’s no shortage of restaurants for romantic dinners or to see and be seen—Bonito is a favorite, offering French Pan-American cuisine set in a charming, upscale beach house overlooking yachts anchored in Gustavia Harbor.
Popular seasonal events include the St Barths Music Festival; the St Barths Bucket Regatta; the St Barths Gourmet Festival; and the Caribbean Rum Awards.
Getting there: Tradewind flies year-round, offering multiple scheduled flights daily from San Juan (SJU) to St Barths (SBH), or Antigua (ANU) to St Barths (SBH).
With an ever-evolving mix of cultures, landscapes, and experience, the Caribbean continues to call travelers back time and again. Tradewind’s scheduled and private charter flights provide an effortless connection to the region’s top islands, elevating the journey through this richly layered paradise.
To learn more about Tradewind’s private charter and scheduled flights to the top Caribbean islands, please visit our website. To receive a private charter quote, please submit an inquiry here or contact our specialists at sales@flytradewind.com or 1-203-267-3305 option 2. For questions regarding scheduled flights, contact our scheduled service team at scheduledservice@flytradewind.com or 1-203-267-3305 option 1.