Setting sail on 2026 Caribbean adventures with luxury cruises, island escapes, and tropical highlights from St. Maarten to Barbados, St. Lucia, St Barths and more.
2026 is creeping closer, and if the calendar is anything to go by, it’s going to be one wild, sun-drenched ride. We’re starting smack in the middle of winter—well, everyone else’s winter—by ditching the jackets for swimsuits and hopping aboard Silversea’s Silver Shadow in St. Maarten. I swear there’s something magic about that first moment on the ship, fresh out of the freezing temps and airport chaos, greeted by soft Caribbean air and the gentle thrum of engines ready to whisk you away. Bags dropped, welcome cocktail in hand, we’re off for seven days of bliss. Think St. Barts with boutique shops and croissants that taste suspiciously like Paris (cashmere shops and pastries? Yes please), Grenada bursting with color and heat (and, let’s be honest, probably a rum punch or two), dreamy Trois Ilets in Martinique for that laid-back “let’s never leave” vibe, and finally—Barbados to wrap things up, with those milky beaches that practically beg you to stay just a little longer.
After the cruise, the year just keeps giving. St. Lucia is calling again—can you sense a theme? It’s one of those islands that hits a little different every time you visit. This round, we’re shaking things up by checking into Coconut Bay Resort for the first time. Rumor has it the pools are epic, and the sunsets? Let’s just say my phone storage is about to take a beating. Whether it’s wading right into the sea with a cold Piton beer, joining a random game of volleyball, or just falling asleep in a hammock (intentional or not), it’s tough to imagine a better way to recharge. Plus, returning to St. Lucia always feels like meeting up with an old friend—you already know the spots you love, but there’s always a new little discovery hiding down some side road.
And then, just as you’re thinking you’ve maxed out the year’s highlights, autumn drops a bomb—Virgin Voyages is officially on the list, with Bimini in the Bahamas as a must-do. It’s got that exclusive “cool kids’ clubhouse” energy, all white sand and turquoise water, hammocks swinging in the breeze, and enough beach bars to make the afternoon a party if you want it. There’s something wild about rolling into a brand-new port for the first time, knowing you’re about to collect new memories to swap over dinner with fellow adventurers. Can’t wait to experience this Virgin adventure first hand.
So yeah, 2026 is officially our “Caribbean Deep Dive” year—chasing new islands, old favorites, and all the big and little things that make travel worth it. There’s a stack of swimsuits prepped, maps marked, and sunscreen at the ready. Bring on the adventures, the unexpected detours, and the post-trip stories we’ll probably only half-remember (that’s why we take way too many photos, right?). Who’s dreaming of joining next? Trust me, there’s room on this ride.
