Puerto Rico Trip: $229 Flight, $284 Boutique Hotel

Score a $229 flight to Puerto Rico and stay at a chic $284-a-night boutique hotel for an affordable Caribbean escape. Wander the vibrant, candy-colored streets of Old San Juan, where massive forts like Castillo San Felipe del Morro offer ocean views and rich history, and stroll Paseo de la Princesa amid vendors and performers. Relax on Condado Beach's soft sands or hike El Yunque National Forest to La Mina Falls for a refreshing swim amid unique wildlife and lush trails.