Why: Tiny Anguilla, just 16 miles long and three miles wide, is one of the most exclusive spots in the Caribbean, and it is peppered with upscale resorts, four-star restaurants, unspoiled scenery, and pristine white beaches (no cruise ships, high-rises, or casinos allowed). You won't get a direct flight from the States (you'll have to take a boat from St. Martin), but you and your guests will consider the destination well worth the extra travel time. As a bonus, native Anguillans are known for their hospitality, and the island is virtually crime-free.
When to go: While you should be aware of hurricane season, which runs from June through November, temperatures are perfectly pleasant (highs in the low 80s and lows in the low 70s) year-round.
Guest activities: Any Anguillan agenda should include swimming, snorkeling, and savoring the chance to wear shoes as infrequently as possible. Guests who are less beach-focused will enjoy exploring the island's archaeological and cultural sites, such as the Heritage Collection Museum in East End, and taking a guided bird-watching tour. The island is known for its delicious food (some of the best in the Caribbean) at both beach shacks and elegant restaurants such as Blanchard's, which may be its most famous. For first-rate nightlife, send guests to Elio's, a small but stylish Valley bar that offers a selection of high-end sipping rums and two hundred brands of cigars.
Best spots for weddings:
Cap Juluca: With 18 stark white, Moorish-style villas set against the bright blue sea, this resort looks like no other in the Caribbean. Its long list of celebrity guests guarantees it doesn't feel like anything else either. Choose from intimate villa ceremonies or beautiful vow exchanges right on the beach.
Carimar Beach Club: These seaside villas are each outfitted with outdoor grills and fully-equipped kitchens, making Carimar an excellent choice for couples inviting guests on a variety of budgets. The resort can accommodate weddings of all types, from casual lawn lunches to formal beach ceremonies.