The Hermitage
A snug 1670 greathouse (reputedly the Caribbean's oldest surviving wooden building) forms the heart of this hillside hideaway, run by two (going on three) generations of charmingly "loopy" Lupinaccis, who keep things lively, down to earth, and family friendly—rare for such a refined, smart-set retreat. Painstakingly restored or meticulously re-created stone-and-gingerbread cottages have hardwood floors, four-poster canopy beds, and hammock-slung patios or balconies. Families and honeymooners adore the two-story Blue Cottage. The Loft, Pink House, and Goosepen Cottage are equally sybaritic, and the three-bedroom Manor House has a pool and wraparound porches. In genuine plantation fashion, the inn has its own stable and livestock, as well as English Romantic–style gardens (pluck your own fruit, or ask the kitchen to prepare a homeopathic bush tea). The Blue Iguana is arguably the island's most interesting boutique. A renovated motor yacht offers sailing, fishing, and St. Kitts transfers.