If You Have 1 Day
If you are headed to one of the islands for an overnight excursion, your best bet is Vieques. Get here by plane, either from San Juan or Ceiba, to maximize your time. Spend the day exploring the beaches, especially the half moon–shape Sun Bay. In the evening, dine at one of the oceanfront restaurants in Esperanza, then head off for an excursion to Puerto Mosquito, a bay filled with glow-in-the-dark dinoflagellates. Spend the night in Esperanza or Isabel Segunda.
If You Have 3 Days
Three days will allow you to see most of Vieques. Start your first day in Isabel Segunda, where you can take a few snapshots of El Faro Punta Mulas, then explore the hilltop Fortín Conde de Mirasol. Head off for an afternoon by the ocean, perhaps at Punta Arenas (aka Green Beach) or one of the delightfully deserted beaches in the north. Enjoy happy hour at Duffy’s, by far the most popular bar in Esperanza. In the cool of the evening, have dinner in one of the chic eateries nearby. On your second day, after booking a tour of Puerto Mosquito for later in the evening, go for an early-morning mountain-bike ride in the western portion of Vieques National Wildlife Refuge, a swath of wilderness that was once a naval base. Pack a picnic and head off to Playa Media Luna or another of the beautiful southern coast beaches. After dinner, head out on your tour of Puerto Mosquito. Spend your third day kayaking, snorkeling, and/or fishing.
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If You Have 5 Days
With a few more days, you can see both Vieques and Culebra. Follow the itinerary above, and then head to Culebra on your fourth day. (A 10-minute flight between the islands is the only way to travel between them directly.) Your destination should be Playa Flamenco, a long, curving beach of talcum-white sand and turquoise water; the mountains beyond make a striking backdrop. Dine that evening at Susie’s in the island’s only town: diminutive Dewey. On your last day, try snorkeling in Refugio Nacional de Vida Silvestre de Culebra, a lovely nature preserve. One of the best places for a morning boat trip is Isla Culebrita, an islet dominated by a lighthouse built in 1882, abandoned in 2003, and slated for restoration.