Island Hopping in the Caribbean

Traveling to the Caribbean can seem daunting. With so many islands, how do you choose? And then there’s the “a beach is a beach” mindset. These were the thoughts I had going into my island-hopping adventure, but I left Antigua, Anguilla, and St. Barths pleasantly surprised and delighted. Each is unique and wonderful in its own way. 

Stop 1: Antigua, Jumby Bay Island 

Jumby is part of the Oetker Collection, so I had high expectations, and it didn’t disappoint. It’s my favorite island for families because of the many accommodation options, from beachside suites and villas to nine-bedroom private residences. My colleagues and I stayed in the eight-bedroom private residence known as Ty Compton. With a personal chef, butler, swimming pool with a built-in jacuzzi and swim-up bar, tennis court, soccer field, and pizza oven, it was our private slice of resort heaven.

Because Jumby Bay is an all-inclusive, private island, you have everything you need and want right at your fingertips. There are weekly special dinner events, a long beach for shell collecting, and water sports included. Energetic teens who want to jump from water skiing to tubing to wakeboarding can do so from morning until night. The Estate House for dinner is a must, and I was so impressed with how local Antiguan ingredients are highlighted with every meal. 

Stop 2: A 6-night stretch in Anguilla

When most people imagine Anguilla, they see a long, curved, private beach with a crisp, white backdrop and the lights of St. Martin twinkling in the distance. This is actually Cap Juluca, my home for four dreamy nights. Every accommodation is beachfront with either a private balcony or terrace. Some, like my Premium Beachfront Room, have an additional rooftop terrace to enjoy. Cap Juluca stretches along the sea with the restaurants, bar, and yoga pavilion at one end and the Cap Shack beach bar and newly built spa (coming soon) at the other. They can arrange a golf cart getting around, or there’s my preferred mode of transportation: the drop-and-go classic teal bicycles.

Anguilla was my favorite island for honeymooners and those seeking local island experiences. While it was hard to leave the resort, I did spend some time off-property, finding the hidden beach shack BBQs and cruising this island in my rental car. 

The Four Seasons, another exceptional Anguilla property, is perched high on a cliff between Barnes Bay and Meads Bay beaches, making for the most gorgeous views. Inside, the open lobby has a peaceful vibe, and beyond, there’s a lovely boutique store, three workout rooms, the best sushi rolls at the Sunset Lounge, and three pools. 

Every room category above the entry-level, resort-view rooms has a private plunge pool, and the thirty different villas all come with private pools. Or, if the beach is more your style, there are two to choose from, with Meads Bay stretching to Malliouhana. Along the way, you’ll pass favorite local spots like Blanchard’s Beach ShackJacala, and the newly opened Savi Beach Club.

The local vibes, the food, and the incredible people combined to create a trip I’ll never forget, and the new, non-stop flight now offered from Miami to Anguilla makes getting there a breeze. 

Anguilla Dining Shoutouts:

Best Drink – Famous rum punch on Sandy Island

Best Lunch – BBQ chicken and rib combo plate at The Sunshine Shack

Best Appetizer – Lobster Cake at Sharky’s

Best Dinner – Shared plates of crispy prawns and cauliflower at Pimms

Best Dessert – Sea Salt Chocolate Molten Cake at SALT

Stop 3: St. Barths, Le Toiny 

My last stop was at the iconic St. Barths. I dropped in (LITERALLY) for a special three-night stay in a Signature Suite at Le Toiny. St. Barths quickly became my favorite island for shopping and the scene. What I enjoyed most about St. Barths was the chance to be as casual or as dressy as I wanted to be. Le Toiny is nestled on a private mountainside, providing the relaxation guests need after living it up in the main town of Gustavia. The Le Toiny Beach Club is just one of many incredible beach clubs scattered around the island. Nikki Beach, perhaps? St. Barths had so many hidden gems, all of which can be explored with a day on the water. Celebrating my birthday while dancing the night away at Le Ti, a Parisian-inspired club, was the icing on top of an unforgettable Caribbean cake.

Emily, Nov. 2022

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