"Boaters looking to trade the open seas for dry land have plenty of reasons to dock at Union Island’s Anchorage Yacht Club. The 1975 stalwart, which was renovated in 2018, offers a collection of understated rooms and cottages overlooking a small marina and white-sand beach, where you can catch some serious airtime during a three-day kitesurfing intensive at the on-site center. Don’t have a skiff of your own? The staff can arrange for catamaran tours of nearby Tobago Cays or deep-sea fishing trips for mahi, tuna, and amberjack, all of which make appearances at the hotel’s waterfront restaurant depending on the daily catch. Before you turn in for the night, order a rum punch under the stars at the thatched-roof bar next door."