Title: The Caribbean’s Most Charming Family-Run Resorts
Imagine arriving at your hotel and being greeted not by a front desk clerk, but by the owner themselves — handing you the key, showing you to your room, or even joining you for dinner. Maybe their daughter is serving breakfast, or their son is mixing your welcome cocktail. Across the Caribbean, a special group of family-run resorts offers this kind of personal, heartfelt hospitality — where service isn’t just a job, but a family tradition.
These resorts are more than just places to stay — they’re homes, legacies, and labors of love. You’ll find owners in the kitchen, walking the beach with guests, or tending to the gardens. It’s a rare, authentic style of hospitality that leaves a lasting impression.
Here are some of the Caribbean’s finest family-run resorts — each with its own story, soul, and sense of place.
Bay Gardens Resorts — St. Lucia
What started as a single property envisioned by legendary hotelier Joyce Destang has blossomed into one of St. Lucia’s most successful hospitality brands. Still operated by the Destang family, Bay Gardens now includes five distinct properties, from the original Bay Gardens Inn to the luxurious Waters Edge Villas. A new all-villa resort, Sapphire Sands, is also on the horizon. Each property reflects the family’s dedication to community, culture, and warm, welcoming service — and it’s not uncommon to meet a Destang family member during your stay.
Boardwalk Boutique Hotel — Aruba
Sisters Stephanie and Kimberly Rooijakkers have turned this vibrant hideaway near Palm Beach into one of Aruba’s most beloved boutique hotels. With cheerful casitas, thoughtful service, and a relaxed island vibe, Boardwalk feels like a true home away from home — lovingly maintained and full of heart.
Graycliff Hotel and Restaurant — Bahamas
Step into the historic Graycliff in Nassau and you’re stepping into the vision of the Garzaroli family. This grand estate, with its world-class wine cellar, cigar factory, and fine dining, is steeped in old-world charm. But it’s the personal touches and decades of family stewardship that make Graycliff unforgettable.
Spice Island Beach Resort — Grenada
Located on the stunning Grand Anse Beach, this all-inclusive resort is a beacon of elegance and warmth. Founded by the late Sir Royston Hopkin and now run by his daughter Janelle, Spice Island blends luxury with genuine Grenadian hospitality. From beachfront suites to gourmet island cuisine, every detail reflects the family’s pride and passion.
Montpelier Plantation & Beach — Nevis
This historic sugar estate has been transformed by the Hoffman family into a serene, sophisticated retreat. With its lush gardens, gourmet dining in a centuries-old mill, and even a resident golden lab named Cosmo, Montpelier offers timeless charm with a modern, personal touch.
Half Moon — Jamaica
Spanning 400 acres near Montego Bay, Half Moon is one of the Caribbean’s most iconic resorts. Since 1954, the Steuart family has helped shape its legacy. Today, Guy T. Steuart III continues to guide the resort’s vision, ensuring that despite its size and amenities — including a golf course, spa, and equestrian center — Half Moon retains a sense of intimacy and authenticity.
Secret Bay — Dominica
Perched on a cliffside with sweeping ocean views, Secret Bay is the dream of husband-and-wife team Gregor and Sandra Nassief. This ultra-private resort features a handful of villas, each with a private pool and personal attendant. Sustainable, soulful, and stunningly designed, Secret Bay feels more like a private home than a hotel — because in many ways, it is.
Rollezz Villas — Cat Island, Bahamas
Tucked between a creek and six miles of untouched beach, Rollezz Villas offers a peaceful, authentic Bahamian escape. Owners Yvonne and Carl Rolle are hands-on hosts, welcoming guests to their colorful, colonial-style villas and ensuring every stay is memorable.
Frangipani Beach Resort — Anguilla
Located on Meads Bay, this boutique resort is run by Scott and Shannon Kircher, who live on-site and treat guests like family. With just a handful of rooms, Frangipani offers a rare blend of luxury and warmth — where elegance meets ease and every stay feels personal.
Bolongo Bay — U.S. Virgin Islands
Since 1974, the Doumeng family has infused Bolongo Bay with energy, fun, and genuine hospitality. With eight family members working on property, it’s a resort where the staff feels like old friends. From beachside cocktails to live music and sailing adventures, Bolongo is Caribbean joy at its most authentic.
Cap Maison — St. Lucia
Overlooking the sea near Rodney Bay, Cap Maison is a Mediterranean-inspired retreat created by the Gobat family. With red-tiled roofs, cliffside Champagne ziplines, and one of the Caribbean’s top restaurants (The Cliff at Cap), Cap Maison is refined but never stuffy — a reflection of the family’s love for style, food, and good living.
True Blue Bay — Grenada
Owned by Russ and Magdalena Fielden since 1998, this colorful waterfront resort is a hub of creativity, sustainability, and community spirit. Their daughter Marie is now part of the management team, continuing the family’s legacy. Guests can enjoy yoga, chocolate-making, or simply a chat with the owners over drinks.
Fond Doux — St. Lucia
Nestled in the lush hills of Soufrière, Fond Doux is a 19th-century cocoa plantation turned eco-resort. Owned and operated by St. Lucian couple Lyton and Eroline Lamontagne, it’s a place where heritage meets sustainability. With artisan-built cottages and a deep respect for the land, Fond Doux is a true labor of love.
These family-run resorts are more than just places to stay — they’re places to connect, to feel at home, and to experience the Caribbean through the eyes of those who know and love it best.
Source: caribjournal.com