Flying into St. Maarten/St. Martin, with its large cruise port and world-famous runway over Maho Beach, you’ll quickly realize that this dual-personality island bustles with two distinct vibes (quainter and French on the St. Martin side and casino-centric and Dutch on the St. Maarten side). This makes it not only unique but also a great partner island for its smaller and more tranquil neighbor, Anguilla. Book a round-trip flight to St. Martin/St. Maarten, then simply hop a 25-minute ferry from Marigot to Blowing Point on Anguilla, where the laid-back vibe is perfect for winding down. Tickets are $20 per adult, and ferries depart daily.

Flat and sugarcane-covered and mountainous and rain forest-dotted – two islands could not be more different. Yet, with only about 100 miles between them, British-influenced Barbados and Creole-flavored St. Lucia make them a great vacation duo. Fly into Barbados and connect (via a 45-minute flight on LIAT) to St. Lucia. In Barbados, activities include rum tasting, scuba diving in Carlisle Bay, exploring the capital and UNESCO World Heritage Site of Bridgetown, and more. On St. Lucia, spread out on the famous Sugar Beach or climb to the top of Gros Piton. 

The colonial vibrancy of Old San Juan and the lively beach resorts and casinos of Condado and Isla Verde make Puerto Rico a perfect partner to blissful Virgin Gorda, located a 40-minute flight away in the British Virgin Islands, or low-key neighboring Vieques, located just off of Puerto Rico’s east coast. If you’ll be traveling without passports, take a quick flight to Vieques, where unspoiled beaches and a rare bioluminescent lagoon offer up natural splendor. To go international, fly to Beef Island/Tortola in the BVIs and hop the ferry to beach-fringed Virgin Gorda, where its boulder-strewn Baths landmark is extraordinary.

You have to fly to St. Kitts to get to Nevis, so why not check out what this big-sister/little-sister island combo offers in tandem? Start on St. Kitts, known for its monkey- and zipline-filled tropical landscape, then ferry over to historic, 36-square-mile, cloud-topped Nevis (home to monkeys, as well as romantic plantation estates).

The capital of the Bahamas has its colonial charms and quite a few splendid beaches, but they are regularly overrun by the hordes of cruise ship passengers who drop in daily. So after you enjoy a few days of duty-free shopping on Bay Street and gambling in the casino at Atlantis on Paradise Island, you can wing it over to sleepy Eleuthera or chic Harbour Island and chill “Out Island” style.