Key West Trip Itineraries

Plan your Key West trip with curated day-by-day itineraries.

• 1 Day in Key West — The absolute must-sees for day trippers from cruise ships or Miami.
• The Long Weekend — The classic Key West experience - history, water adventures, and island vibes.
• The Ultimate 5-Day Key West Itinerary — A balanced insider guide featuring the best of Key West — from sunset sails and offshore fishing to luxury yachts, fresh seafood, and Duval Street nightlife.
• Key West for Art Lovers — A walkable day through Key West art history, local cooperatives, contemporary exhibitions, working studios, and Duval's famous gallery row.