The Caribbean has an impressive portfolio of historic properties — some that have always been hotels, others that have taken historic buildings and meticulously transformed them into havens of hospitality.
The lush estate’s signature pool is one of the most beautiful you’ll ever dip your toes into.
Graycliff, The Bahamas Centered around a mansion built in 1740 by legendary pirate John Howard Graysmith, Graycliff is the crown jewel of historic downtown Nassau, with one of the Caribbean’s most iconic restaurants and a boutique hotel with 20 rooms. It’s the sort of place where luxury abounds, from one of the largest wine cellars on earth to an on-site cigar factory and an exquisite chocolate factory. (Churchill even stayed in the property’s popular pool cottage). The rooms are spacious, with grand bathrooms and Bvlgari amenities, and the service is sublime. It’s a hotel that should be on the bucket list of every Caribbean aficionado — and one of the region’s truly special places.