A Beach Hopper’s Guide to the Caribbean

There are countless beaches to be found among the Caribbean’s iconic islands, each with a singular personality, splendor, and charm. Some of our favorite hidden shorelines harbor beautiful rock formations and coral reefs brimming with sea life, while ethereal white sands and crystal clear waters are an ever-present throughout the islands.

It’s the ideal setup for beach hopping, and with Tradewind’s regularly scheduled Caribbean flights, you can hop in private charter style for the price of a single seat. Having visited our fair share of the Caribbean (and our fair share of beaches), we’ve put together a guide for visiting thirteen of the islands’ best shorelines along with local recommendations. And better yet, most of them are just an hour’s flight away from one another.

Your first destination? Antigua.

Jolly Beach, Antigua

On an island that claims to have 365 beaches (one for each day of the year), it may be difficult to choose which coast you will visit first. Rent a car or taxi down the west coast to Jolly Beach, where you will find swathes of white sand and turquoise waters straight from your Caribbean dreams. The stunning, one-mile long shoreline is perhaps the widest on the island, offering calm seas shallow enough for children to enjoy.

Locals’ Pick: Treat yourself to freshly caught lobster, coconut shrimp, and other island delicacies at The Nest Beach Bar and Restaurant.

Half Moon Bay, Antigua

Across the island, Half Moon Bay provides an isolated escape from the bustling beaches on Antigua’s west coast. If seclusion is your style, head toward FreeTown and keep driving east until you find the bay. Its natural, half-moon shape and protective reefs keep the rougher Atlantic surf away and also afford spectacular snorkeling opportunities—just make sure to bring your own mask and snorkel because there are no watersports outfitters on the private shoreline.

Locals’ Pick: You won’t find any true restaurants nearby, but there’s a locally owned food stand on the beach where you can purchase snacks and cool drinks.

St. Jean Beach, St. Barths

A quick plane ride brings us to one of the Caribbean’s most glamorous destinations, St. Barths. A playground for celebrities and weekend vacationers alike, the island is known for its magnificent white sand beaches, chic boutiques, and luxury boutique hotels. You will likely spot St. Jean Beach upon your arrival to the island, as the airport’s famously short runway is located just next to it. (You will actually fly over it.) Stylish restaurants, bars, and watersports outfitters line the popular beach’s crystalline waters, contributing to the lively ambiance, and at the beach’s center, a rock promontory known as Eden Rock splits the coast in two.

Locals’ Pick: La Plage is the place to enjoy French and Latin fusion cuisine and live entertainment with your toes still in the sand.

Saline Beach, St. Barths

A more private destination can be found on the southern end of the island at Saline Beach. Renowned for its feathery white sands and undeveloped shoreline, Saline offers magnificent swimming and snorkeling on calm days. The incredibly beautiful, natural location can be accessed by way of a winding sand path—just head southeast from St. Jean Beach until you reach the end of the road.

Colombier Beach, St. Barths

Set among lush green hills on the northwest coast of St. Barths, Colombier Beach is considered by many to be the best beach on the island. The secluded bay is breathtaking both above the water’s surface and below with bountiful marine life such as starfish, colorful schools of fish, and sea turtles inhabiting the right side of the bay. It is accessible only by foot or boat due to its remote location, and consequently, you should bring your own snorkel and provisions for the day. Hike the 30-minute trails or hop on a boat for the 15-minute cruise from Gustavia Harbor to get to Colombier Beach.

Magen’s Bay Beach, St. Thomas

It’s back to the airport for an under-an-hour flight to St. Thomas, where pristine beaches lined with coconut palms abound. Perhaps the most popular coastline on the island is Magen’s Bay Beach, located in the curve of the bay with the same name. It’s also the only beach in St. Thomas that charges an entry fee, but the cost is well worth it when you see the turquoise sea framed by rolling hills, ideal for children in the shallows and more suited for watersports activities further out.

Locals’ Pick: You don’t even have to leave the water to enjoy a Rum Punch from Magen’s Bay Beach Bar & Café—the bartenders will deliver it to you while you float.

Lindquist Beach, St. Thomas

Take a drive across the island to explore the unique formations of Lindquist Beach near Smith Bay. Part of 21 acres of protected park land, Lindquist offers white sand beaches with a touch of pink, calm waters perfect for swimming or snorkeling, and a shallow shelf of tidal pools just waiting to be explored. You will have ample space to relax under the coconut palms and sea grape trees during the week, and then on the weekends, prepare for a livelier atmosphere as the locals make their way to Lindquist.

Pinney’s Beach, Nevis

To get to the island of Nevis, you’ll want to pass through St. Barths again—perhaps stopping for a gelato or a walk along the harbor. Once you arrive in Nevis, make for Pinney’s Beach on the outskirts of Charlestown. Three miles of stunning shoreline lined with rustic restaurants and bars will offer quite a different atmosphere depending on the time of year. During cruise ship season, the crowds come in during the day, but for the rest of the year the beach is quite secluded. One thing is for sure—Nevis’ most popular destination is home to incredible sunsets all year long.

Locals’ Pick: Sunshine’s Beach Lounge is the place for delicious island barbecue, the famous Killer Bee rum punch, and lively nightlife just steps from the sea.

Herbert’s Beach, Nevis

Escape to the windward side of the island for an underwater experience unlike any other. The reefs of Herbert’s Beach are positively teeming with marine life, making the beach a favored spot for snorkelers and fishing pelicans alike (although the shore itself is often empty). You can watch the seabirds resting on rocks while you lounge beneath palms on shore, and make sure to take a walk along the waterline too because Herbert’s Beach is known for having beautiful conches and other shells wash ashore.

Condado Beach, San Juan

When you’re ready to enter a completely different atmosphere, hop on a flight to San Juan, Puerto Rico. In many places, the vibrant city edges right up to the white sand beaches for an experience that is both relaxing and vivacious with casinos, shopping, and music just a few steps away. Trendy Condado Beach combines urban style with active pursuits like paddleboarding and kayaking, resulting in an exciting beach day that you won’t find anywhere else in the Caribbean.

Locals’ Pick: Locally sourced seafood and vibrant nightlife alike can be found at Oceano, a chic restaurant and lounge on the oceanfront.

Playita del Condado, San Juan

Close to Condado Beach, the family-friendly Playita del Condado (small beach of Condado) affords spectacular views of the city over the water. The calm ocean and quieter atmosphere is the perfect place for children or those searching for a break from city life, and the beach is easily accessible by way of Ashford Avenue. You’ll find many locals at Playita sitting in the shade of the trees lining the beach.

Locals’ Pick: The oceanfront Aqua Bar and Grill offers an array of fresh salads and delicious sandwiches large enough to share.

Shoal Bay East, Anguilla

It’s time to head to your final destination, the historic island of Anguilla. Two miles of stunning white sand beaches are beckoning at Shoal Bay East where the quiet island really comes alive. Regularly named as one of the world’s best beaches by the vacation experts, Shoal Bay is the place for snorkeling, beach bar hopping, and watersports. A point in the middle of the beach is bordered by reefs filled with marine life, and open-air restaurants and bars offer fresh seafood and good times just steps from the sand.

Locals’ Pick: Grouper curry, goat cheese salad, and fresh crayfish are a few of the delectable dishes awaiting you at Madeariman Bar & Restaurant.

Rendezvous Beach, Anguilla

At the end of your journey, make a return to the classic Caribbean with breathtaking turquoise seas and secluded white sand beaches to match. Rendezvous Beach is located along a bay by the same name and looks across to the island of St. Martin. When you step onto the beach, you’ll have to decide whether you want to walk east alongside the old, historic hotels of Anguilla or west to the funky-but-cool beach bars and live music. Either way, Rendezvous Beach is the ideal place to wrap up your Caribbean journey.

Locals’ Pick: Some of the most succulent and tender fish in the Caribbean can be found at Sunshine Shack. Just know that the little eatery runs on island time—and you should too.