Editor’s Note: Some of the information below may be out-of-date. British Virgin Islands, Puerto Rico and the U.S. Virgin Islands were heavily impacted by Hurricane Irma and Hurricane Maria. Please visit caribbeantravelupdate.com or the specific hotel’s website for updates.
Here are some of our favorite Caribbean boutique hotels that specialize in small destination weddings with big flavor.
Anse Chastanet – St. Lucia
STAY: The honeymoon starts on arrival at Anse Chastanet, one the Caribbean’s most romantic resorts. Not only do the open-air design and artistic decor pack wow factor, but there’s a lot to do and see too. The nearby marine reserve provides superb snorkeling right from one of the resort’s two beaches, and onsite plantation relics steep you in the evocative lore of the West Indies. Other activities include tennis, kayaking, sailing and spa-going.
CELEBRATE: Anse Chastanet is famed for its 49 hillside rooms, which feature open-air exposure to Saint Lucia’s iconic Pitons. These twin peaks become your backdrop when you wed on the Treehouse terrace (seats 20) or the resort’s double-decker catamaran Lucky T (for up to 60). Your reception soundtrack: a shak-shak band, whose lively, upbeat combo of shaker, fiddle, banjo and drum is St. Lucia’s contribution to Caribbean music. Do your day-after photo shoot in the ruins of adjacent Anse Mamin, an 18th-century French colonial plantation. –Dave Herndon
Bolongo Bay Beach Resort – St. Thomas, USVI
STAY: This family-owned and -operated Caribbean boutique hotel is homey in every way. Bolongo doesn’t aim for super-fancy; instead, it excels at capturing a laid-back island vibe and simple elegance done right. Sixty-two rooms offer ocean views (nine less-expensive “value” rooms offer garden views), and guests get full use of the resort’s windsurfers, kayaks and snorkel gear. Bolongo’s other great selling point is convenience: St. Thomas is a U.S. territory, so passports aren’t required and marriage legalities are straightforward.
CELEBRATE: Wedding host Lorie Leonard takes a maternal interest in her brides and handles all the details, so you can feel like a guest at your own wedding. Swap vows on the beach under the brand-new bamboo canopy, and have your reception for 49 aboard the resort’s own catamaran. Other event options range from pig roasts on the sand to fine dining at the Lobster Grille. The after-party is a shoo-in, with revelry going off seven nights a week at the onsite Iggie’s Beach Bar & Grill, a St. Thomas staple. – Dave Herndon
Guana Island – British Virgin Islands
STAY: Dotted with glossy sea-grape trees, this 850-acre former sugar plantation hides a lush orchard, a pond, a pool, caves and Monkey Point, the private island’s best snorkeling spot. Explore on foot via 26 wooded trails, or hop on a golf cart; rental is complimentary with a villa booking. Sleeping quarters include 15 rooms in whitewashed cottages or your choice of stand-alone villa: a two-bedroom or three-bedroom (each with an infinity pool and hot tub) or the sumptuous one-bedroom Beach Cottage, boasting a private pool and dock.
CELEBRATE: Guana Island is ideal for buyouts, where you and your guests have the entire isle at your disposal. After I do’s on White Bay Beach, hold cocktail hour in the Garden of Eden gazebo area. For the reception, The Club, the plantation’s 70-year-old great house (seats 32), specializes in just-caught seafood. Make your getaway on a golf cart decked out with tin cans, bougainvillea and frangipani. – Tara Bradley
Hotel El Convento – San Juan, Puerto Rico
STAY: This former 17th-century Carmelite nunnery oozes with so much old-world ambience — think high ceilings, thick stone walls, walkways that overlook a five-story atrium — that you might be tempted to cloister yourselves inside. But that would be a mistake, because the 58-room Caribbean boutique hotel is centrally located in the heart of Old San Juan, Puerto Rico, whose narrow streets, historic sites, shops and restaurants beg for exploration. Bonus: Since Puerto Rico is a U.S. territory, the travel is hurdle-free, and San Juan, the Caribbean’s busiest airport, has loads of direct flights from the mainland.
CELEBRATE: El Convento is conveniently located across the street from the circa-1521 San Juan Cathedral, the oldest cathedral in the Western Hemisphere. Or hold your vows in the onsite chapel, with 50-foot ceilings and stained-glass windows. Receptions take place in the hotel’s courtyard (up to 300 guests), where onsite planners will help you select from a rich variety of international food and drink menus (paella station, anyone?), plus decor and entertainment options, from salsa lessons to a live Afro-Cuban band. – Dave Herndon
Laluna – Grenada
STAY: Tucked away on the southwestern tip of Grenada, Laluna’s eco-sexy vibe is designed to take full advantage of the natural setting. Sixteen Balinese-inspired cottages tumble down an emerald-green hillside toward a white-sand beach. After days spent diving, fishing and hiking, make the most of indoor and outdoor living rooms, open-air bathrooms (with ocean-view showers), king four-poster beds and private plunge pools.
CELEBRATE: Weddings here are mostly beach-based and casually chic, with receptions featuring tropical decor (bougainvillea, frangipani, seashells), live music from a local calypso or merengue band, and Italian-influenced cuisine at the resort’s thatch-roof restaurant (up to 80). Even easier: the all-inclusive buyout package, which covers meals, drinks, transfers and more for up to 32 people. – Joe Yogerst
Lodge Kura Hulanda & Beach Club – Curacao
STAY: This Dutch colonial-style property has attracted A-listers like Jennifer Lopez and Marc Anthony. Choose from ocean or garden views in the 74 one-bedroom villas, which all feature cool floor tiles, hand-painted walls and four-poster beds. (Connecting villas offer two-bedroom options for families.) Day play includes snorkeling the offshore reefs or basking poolside. The gratis shuttle whisks guests to nearby Willemstad, Curacao’s capital and home to the lodge’s sister property, Hotel Kura Hulanda — a great alternative for singles who want to be in the heart of the action.
CELEBRATE: Go incognito with a ceremony on the private beach or oceanfront Sun Terrace (seats 80). Have cocktail hour at the Christoffel Sunset Lounge (seats 50), the best place on the West End to savor the sunset. Private dinners happen at one of three onsite restaurants, or mix it up with a customized dinner set beside the clifftop pool (seats 50). Later, grab an Amstel (it’s brewed here) before hitting the dance floor set up under the thatch roof of the Watamula Restaurant (80 max). – Tara Bradley
Montpelier Plantation – Nevis
STAY: Step into another time at this 60-acre estate in the foothills of rainforest-cloaked Mount Nevis. A favorite retreat of the late Princess Di, this Relais & Châteaux gem offers 19 rooms and cottages, whose subdued hues, airy verandas and polished woods exude comfy British West Indian elegance. Relaxation here is instant, whether you fancy fine dining, horseback riding or hiking up the mountain to visit wild monkeys. Bonus: There’s a free shuttle to the plantation’s private beach club.
CELEBRATE: Montpelier has been perfecting weddings since hosting the Caribbean’s most famous nuptials: those of local girl Fanny Nisbet to British naval hero Horatio Nelson in 1787. For sand between your toes, choose Montpelier’s private beach; for tropical foliage and lofty vistas, opt for the hillside garden. Receptions take place in the open-air Terrace (seats 60) or intimate stone Mill, a 300-year-old sugar-mill ruin (seats 18). – Peter Zaremba
Sugar Ridge – Antigua
STAY: At this Antigua boutique resort, each of the 60 rooms features a king canopy bed and generous terrace; ground-floor rooms offer private plunge pools too. Sugar-themed decor — textures that recall sugar cubes, honeycombs and crystals in tones of caramel, vanilla and molasses — offers a nod to the island’s main export. Visit the Aveda Spa, hop the resort shuttle to white-sand beaches (10 minutes away) or book a group sunset cruise.
CELEBRATE: Stage an outdoor ceremony on the ridgetop terrace to take advantage of the unbroken views — on a clear day, you can see all the way to neighboring isles Nevis and St. Kitts. Host an elegant reception at Carmichael’s restaurant, which offers Caribbean-fusion cuisine like tiger shrimp and fried plantains. Then party the night away at the Sugar Club. – McLean Robbins