Miami is the best-positioned city in America for international weekend trips. The Caribbean and Latin America are closer than most US domestic destinations.
Under 2 Hours#
Nassau, Bahamas (50 min)
Crystal water, conch fritters, fish fry on the beach. $100-200 RT flights. Day trip possible.
Havana, Cuba (1 hour)
If regulations allow: classic cars, Malecón sunsets, rum, and the most fascinating city in the Caribbean. Check current US-Cuba travel rules.
2-3 Hours#
Santo Domingo, DR (2.5 hours)
Oldest city in the Americas. $150-250 RT. A weekend here changes your perspective on the Caribbean. Zona Colonial Friday night is unforgettable.
San Juan, Puerto Rico (2.5 hours)
No passport needed. Old San Juan, El Yunque, La Placita. $100-200 RT.
Cartagena, Colombia (3 hours)
Colonial Walled City, Caribbean coast, incredible food. $200-350 RT. Friday evening flight → Sunday night return = perfect weekend.
3-4 Hours#
Medellín, Colombia (3.5 hours)
Spring weather, amazing food, nightlife that doesn't quit. $200-350 RT. Thursday night → Sunday = ideal.
Bogotá, Colombia (4 hours)
Museums, food scene, nightlife in Chapinero. $250-400 RT.
Mexico City (3.5 hours)
Tacos, museums, mezcal. Direct flights. $200-350 RT.
The Weekend Formula#
- Friday: Evening flight after work. Arrive by midnight
- Saturday: Full day exploring with a Local Friend
- Sunday: Morning activity, afternoon flight home
A Local Friend maximizes your 48 hours — no wasted time figuring out where to go or what to eat.
Find a Local Friend on Roavi Turn any weekend into an international adventure.