Florida Keys Travel Itineraries
378 itineraries · 5 trip lengths · 373 variants — routes scored by distance, days balanced by intensity
Florida Keys leans heavily into nature — expect parks, scenic views, and outdoor activities throughout. A moderate mix of walking and active experiences, with plenty of guided experiences. Focused more on hidden gems than tourist highlights, and options span budget to mid-range.
Top attractions include South Beach & Art Deco District, Old Town Key West, John Pennekamp Coral Reef State Park, Dry Tortugas Day Trip, Wynwood Walls & Design District, Little Havana, Turtle Hospital, Everglades Day Trip.
📅 Best Time to Visit Florida Keys
Best months: November–April
Dry season (Nov–Apr) is ideal: warm, low humidity, no hurricanes. Hurricane season runs June–November. Summer is hot and humid.
- Best Nov-Apr (dry season). Jun-Nov is hurricane season with afternoon thunderstorms.
- Open daily 10:30am-6:30pm year-round. Best Nov-Apr to avoid summer heat.
- Best visibility Apr-Oct. Water temp pleasant year-round. Winter can have choppy seas canceling boat tours.
- Best visibility Apr-Oct. Winter swells can cancel trips.
- Year-round destination. Best Nov-Apr for comfortable walking weather.
Choose Your Florida Keys Itinerary
5 route options optimized for different trip lengths and travel styles
3 Days — Quick Escape
Miami → Upper Keys
4+ activities
South Beach & Art Deco District, John Pennekamp Coral Reef State Park, Wynwood Walls & Design District
View itinerary ›5 Days — Classic Tour
Miami → Upper Keys → Marathon
8+ activities
South Beach & Art Deco District, John Pennekamp Coral Reef State Park, Wynwood Walls & Design District
View itinerary ›7 Days — Classic Tour
Miami → Upper Keys → Marathon
12+ activities
South Beach & Art Deco District, John Pennekamp Coral Reef State Park, Wynwood Walls & Design District
View itinerary ›10 Days — Extended Journey
Miami → Upper Keys → Marathon
18+ activities
South Beach & Art Deco District, John Pennekamp Coral Reef State Park, Wynwood Walls & Design District
View itinerary ›14 Days — Grand Tour
Miami → Upper Keys → Marathon
26+ activities
South Beach & Art Deco District, John Pennekamp Coral Reef State Park, Wynwood Walls & Design District
View itinerary ›Trip Lengths
Pick a length, we'll handle the routing. Every itinerary can be tweaked by style, pace, and budget.
Quick Getaways 2–4 days
Week Trips 5–7 days
Best 5 Days in Florida Keys
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys
Miami → Upper Keys → Marathon
Extended Trips 8–10 days
Grand Tours 11–28 days
By Travel Style
Same cities, different lens. We reshuffle activities so the trip matches what you actually care about.
Best 7 Days in Florida Keys — Food & Wine
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Walking Tours
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — History
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Art & Culture
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Family Friendly
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Romantic
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Photography
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Adventure
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Nightlife
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Nature
Miami → Upper Keys → Marathon
Best 3 Days in Florida Keys — LGBTQ+ Friendly
Miami → Upper Keys
Best 7 Days in Florida Keys — Solo Travel
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Workation
Best 7 Days in Florida Keys — Vegan & Plant-Based
Combined Interests
Two themes, one trip. Activities scored for both interests so nothing feels forced.
Best 7 Days in Florida Keys — Food & Wine & Walking Tours
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Food & Wine & History
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Art & Culture & Food & Wine
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Adventure & Food & Wine
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Food & Wine & Nightlife
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Food & Wine & Nature
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Food & Wine & Vegan & Plant-Based
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — History & Walking Tours
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Art & Culture & Walking Tours
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Photography & Walking Tours
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — LGBTQ+ Friendly & Walking Tours
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Art & Culture & History
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Family Friendly & History
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — History & Photography
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Adventure & History
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — History & Nature
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Art & Culture & Family Friendly
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Art & Culture & Photography
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Art & Culture & Nature
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Art & Culture & LGBTQ+ Friendly
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Family Friendly & Romantic
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Family Friendly & Photography
Miami → Upper Keys → Marathon
Best 3 Days in Florida Keys — Adventure & Family Friendly
Miami → Upper Keys
Best 3 Days in Florida Keys — Family Friendly & Nature
Miami → Upper Keys
Best 7 Days in Florida Keys — Adventure & Romantic
Miami → Upper Keys → Marathon
Best 3 Days in Florida Keys — Nature & Romantic
Miami → Upper Keys
Best 7 Days in Florida Keys — Adventure & Photography
Miami → Upper Keys → Marathon
Best 3 Days in Florida Keys — Nature & Photography
Miami → Upper Keys
Best 7 Days in Florida Keys — Adventure & Nightlife
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Adventure & Nature
Miami → Upper Keys → Marathon
Best 3 Days in Florida Keys — Nature & Nightlife
Miami → Upper Keys
Best 3 Days in Florida Keys — LGBTQ+ Friendly & Nature
Miami → Upper Keys
Best 7 Days in Florida Keys — Adventure & Walking Tours
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Adventure & Art & Culture
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Nature & Walking Tours
Miami → Upper Keys → Marathon
Best 14 Days in Florida Keys — Photography & Romantic
Miami → Upper Keys → Marathon
By Pace
Relaxed means fewer cities and more breathing room. Fast packs in more stops. We re-optimize the route either way.
Skip a Theme
Not your thing? We rebuild the itinerary without activities tagged with that theme.
Best 7 Days in Florida Keys — Without Walking Tours
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Without Art & Culture
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Without Adventure
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Without Nature
Miami → Upper Keys → Marathon
Best 3 Days in Florida Keys — Without LGBTQ+ Friendly
Miami → Upper Keys
Best 5 Days in Florida Keys — Without Food & Wine
Miami → Upper Keys → Marathon
Best 7 Days in Florida Keys — Without Family Friendly
Miami → Upper Keys → Marathon
Travel Rhythm
Slow down or work remotely — the itinerary adapts to your pace of life.
By Season
Activities reshuffled for the best experiences each season — cherry blossoms in spring, beaches in summer, foliage in autumn, snow in winter.
City Focus
Spend more time in one city — the route rebalances around your base.
More Options
Different airport, different budget — the route adjusts automatically.
Best 3 Days in Florida Keys — from Key West
Key West
Best 3 Days in Florida Keys — Budget
Miami → Upper Keys
Best 3 Days in Florida Keys — Luxury
Miami → Upper Keys
Best 5 Days in Florida Keys — from Key West
Key West → Miami → Upper Keys
Best 5 Days in Florida Keys — Budget
Miami → Upper Keys → Marathon
Best 5 Days in Florida Keys — Luxury
Miami → Upper Keys → Marathon