San Juan, Puerto Rico
Think gorgeous beaches and colorful architecture. San Juan offers this and so much more in nightlife, culture, music, and latin cuisine. You can soak in the sun all day on at Playa Condado, then have a spectacular Caribbeandinner at Santaella, and dance the night away La Factoria.
Direct flights start at $100 from JFK to SJU.
[Photo via @liligo_official]