Petit St. Vincent
This tiny island in the Grenadines, south of the larger St. Vincent, is owned by one couple, who manage the 22 stone cottages on the island. There are no televisions and no phones―if you need something, raise a flag on your personal “message box” and a staff member will come running. (Doubles from $635, psvresort.com.)
There are no beaches on this island, which is the top of a volcanic cone; the biggest activity is diving, not lounging. “It’s enchanting and so different from what you normally think of with the Caribbean,” says Darwin Porter, coauthor of Frommer’s Caribbean 2008. Some of the residents originally came from Scotland, so you might be surrounded by red-haired, freckle-faced locals. For a luxury hotel, stay at Willard’s of Saba (doubles from $350, willardsofsaba.com) or the Cottage Club, which offers less expensive, gingerbread-style houses on a lush hillside (doubles from $105, cottage-club.com).
Tobago is known in connection with Trinidad, its sister island in the West Indies, but it is much more serene. The beaches are the main attraction; they are quiet and deserted (although Trinidadians often vacation here on weekends). You can also snorkel around the coral reefs. The Blue Haven Hotel has been popular with movie stars since the 1940s, and it now has historic charm with updated, stylish rooms. (Doubles from $185, bluehavenhotel.com.)