Best Caribbean Family-Run Boutique Hotels

At these (small) boutique hotels, guests are treated like family, and the owners are the family


It’s great to be treated like family. And though many resorts will make that claim, the places that are best suited to deliver that special brand of warm, familiar service and welcome are those small hotels that are, in fact, family owned and operated. These are the places where the owners not only know your name, but also may stop by your table at dinner to share conversation and a drink. Here are three of our favorite family-owned Caribbean resorts.

Hotel Le Village, St. Barth

The red-roofed cottages of Le Village perch on a terraced hillside overlooking Petite Baie de St. Jean. A short walk from this scenic enclave brings you to St. Jean Beach. This lively strand is lined with trendy restaurants, casually elegant beach bars, and the fashionably chic shops that St. Barth is all about. It’s a great place to people watch as you soak up the sun. When its time to reconvene to your hideaway, Le Village offers peace and solitude, something the hotel has been known for since it first opened in 1969.

St Bart LeVillage Cottage

Rooms at Hotel Le Village open to hillside terraces that welcome sea breezes and provide a private retreat for guests who value both privacy and the intimacy. Photo: Le Village

The property is a 25-unit enclave of one- and two-story rooms and suites, each individually decorated in island colors. Each offers a kitchen and a large covered terrace that doubles as living and dining spaces, all opening to outdoor sundecks. Guests relax in the gardens that surround their cottage, lounge by the pool or head for renewal at the Well Being Cottage. This glass-enclosed space offers massages and yoga classes set against panoramic views of the bay. The Charneau family has been receiving guests—some famous, others not so much—in a relaxing yet elegant manner for decades, and happy guests keep coming back year after year.

St Bart Le Village Pool

Hotel Le Village provides elevated views of St. Barth’s St. Jean Beach and its namesake bay. Just a short walk down the hill, a collection of chic cafes and shops awaits. Photo: Le Village

The Hermitage Plantation Inn, Nevis

Guests of the Hermitage Plantation Inn are treated to cooling afternoon breezes, and monkeys. The inn sits near the base of rainforest-clad Nevis Peak. These forests are home to vervet monkeys, who come down from the slopes in search of sweet mangos, and their whimsical presence is a guest favorite. The scene is bucolic, with horses in the pasture and an English-style garden filled with fruit, flowers and herbs. This is what Maureen and Richard Lupinacci visioned when they arrived in Nevis in 1967 and discovered the property. This husband and wife team fell in love with the location and nurtured it into the splendid village it is today.

Hermitage Nevis Great House Living Room

Nevis’ Hermitage Plantation features furnishings and artwork from around the island. This meticulously restored structure is the oldest wooden building on the island. Photo: Hermitage

While the keys have since been handed to son Richie Lupinacci, the inn maintains a loving family essence with a bit of Italian heritage. Wednesday night’s West Indian pig roast spread is still hands-down the best on the island, and Friday nights now ring in the weekend with pizza and cichetti, as guests mingle around the bar and wander the great house filed with antiques and curios. Staying at the Hermitage is recasting the past, as each chattel house features a different motif. Furnishings and artwork collected from around the island are brought together in 15 individually decorated retreats, each of which feels like a private home. And being at home is exactly how you will feel when spending time on this family planation.

Nevis Hermitage Campus

Cottages at the Hermitage began as dwellings known as chattel houses, which were used to house farm workers. Today, they sit in the inn’s lushly landscaped grounds. Photo: Hermitage

Frangipani Beach Resort, Anguilla

On an island known for spectacular beaches, you’ll want to stay in a waterfront property. Frangipani is located in the center of Meads Bay. This mile long stretch of shore has powder-white sand so soft you’d think it could be used to bake a cake. The resort includes just 19 rooms and suites, sets just steps from the sand. The active young couple running the resort, Scott and Shannon Kircher, were married at the resort and now live and love it. When time permits they share their love of watersports with their guests.

Frangipani Breakfast On Balcony Anguilla

Frangipani Beach Resort’s private balconies open to expansive views of Meads Bay. This west-facing beach provides spectacular sunset views. Photo: Thierry Dehove/Frangipani

Water sports are a focal point at the resort, and all equipment is complementary for guests. Spend your days sailing a Hobie, waterskiing, paddle boarding or just float on a raft. Head directly from room to the sand, find your personal palapa and let the day unfold. In addition to the beach, there is an infinity pool backed by the salmon-tinted Spanish Mediterranean enclave from which the sea is always in view. The island’s famed Straw Hat restaurant is now located in the resort. Owned and operated by another husband and wife team, it serves breakfast, lunch and dinner 7 days a week. Another marriage made in heaven.

Anguilla Frangipani Night View

Frangipani Beach Resort is a boutique property of just 19 intimate rooms and suites. On site is one of the island’s favorite restaurants, the Straw Hat. Photo: Thierry Dehove/Frangipani