This history itinerary reshuffles the schedule around history activities — historic sites, UNESCO heritage, and ancient landmarks. A moderate mix of walking and active experiences, with a mix of self-guided and guided activities. Includes 4 must-see landmarks across Miami and Upper Keys and Marathon.
Highlights: South Beach & Art Deco District, John Pennekamp Coral Reef State Park, Wynwood Walls & Design District, Little Havana
This 10-day Florida Keys itinerary follows the historical thread — 8 activities take you through ancient sites, monuments, and stories that shaped Miami, Upper Keys, and Marathon.
Your Route — ordered to minimize backtracking
18+ activities scored and ranked · route optimized across 3 cities
Day-by-Day Schedule — heavy and light days alternate so you don’t burn out
Miami
MiamiExplore Wynwood with a small group and learn directly from a local expert. As part of this Cycle Party, you'll pedal you
$44.8 Verified Mar 2026 Book this tour →Enjoy a personalized adventure led by your very own private guide. Get comfortable as you join your driver in a luxury c
$248.61 Verified Mar 2026 Book this tour →South Beach / Mid-Beach / Brickell
Avoid the hassle of transport, traveling to with a small group and the support of a local guide. This is recommended fo
$219 Verified Mar 2026 Book this tour →Stroll the iconic Art Deco Historic District and soak up South Beach's vibrant oceanfront scene
Best Nov-Apr (dry season). Jun-Nov is hurricane season with afternoon thunderstorms.South Beach / Mid-Beach / Brickell
Discover world-class street art murals and cutting-edge galleries in Miami's creative heart
$13 Verified Mar 2026 Open daily 10:30am-6:30pm year-round. Best Nov-Apr to avoid summer heat.Experience Miami's Cuban soul with cafecito, cigars, live salsa, and Domino Park on Calle Ocho
Year-round destination. Best Nov-Apr for comfortable walking weather.South Beach / Mid-Beach / Brickell
Escape to Key Biscayne for pristine beaches, the historic Cape Florida Lighthouse, and kayaking
$8 Verified Mar 2026 Open 8am-sundown daily. Arrives early on weekends — park closes at capacity.Drive the Overseas Highway to Key Largo and Islamorada for snorkeling, wildlife, and island vibes
Best Nov-Apr. Hurricane season Jun-Nov.South Beach / Mid-Beach / Brickell
Sail Biscayne Bay on a private charter with skyline views, snorkeling, and sunset options
Year-round. Calmest waters Nov-May.Explore Miami Zoo, the Children's Museum, and Jungle Island with the whole family
Year-round. Indoor/outdoor mix works in any weather.South Beach / Mid-Beach / Brickell
Spend a half-day exploring the top sights. With the help of your personalized App Guide, you can pick and choose what yo
Explore Wynwood with a small group and learn directly from a local expert. On this graffiti tour, explore this artistic
$39 Verified Mar 2026 Book this tour →South Beach / Mid-Beach / Brickell
Upper Keys
Upper KeysDiscover Islamorada's sportfishing capital with Robbie's tarpon feeding and oceanside parks
Year-round. Tarpon feeding best Mar-Jul.Drive the full Overseas Highway to Key West for Old Town, Duval Street, and a sunset celebration
Year-round. Best Nov-Apr for comfortable weather.Key Largo / Upper Matecumbe Key / Venetian Shores
Explore John Pennekamp Coral Reef State Park with a group and learn from a local expert. This is recommended for those w
$24 Verified Mar 2026 Book this tour →Snorkel or dive America's first underwater park with vibrant coral reefs and tropical fish
$39 Verified Mar 2026 Best visibility Apr-Oct. Water temp pleasant year-round. Winter can have choppy seas canceling boat tours.Key Largo / Upper Matecumbe Key / Venetian Shores
Marathon
MarathonDrive the scenic Overseas Highway from Marathon to Key West for a full day of island exploration
Year-round. Best Nov-Apr for comfortable weather.On this tour, you'll get a unique experience as you explore the Seven Mile Bridge, Sombrero Lighthouse and Duck Key by a
$325 Verified Mar 2026 Book this tour →Vaca Key / Sombrero Beach / Boot Key Harbor
Check out of your hotel, grab a final breakfast, and head to the airport. Safe travels from Marathon!
Where You’ll Stay
Estimated total: $1,436–$2,154
Trip Budget Estimate
Estimates based on listed activity prices and hotel rates. Actual costs vary by season, availability, and personal spending.
Typical range for Florida Keys
$1,000 – $5,000 per person for 10 days
Similar Destinations
Similar vibes, fewer crowds — destinations our algorithm rates as close matches to Florida Keys.
🧳 Practical Info for Florida Keys
- Visa
- ESTA required for Visa Waiver Program countries. CA citizens visa-exempt. See US entry requirements.
- Tipping
- 18–20% tip expected at restaurants. Standard US tipping culture applies.
- Currency
- US Dollar ($ USD). Cards accepted everywhere.
- Power
- 120V, Type A/B plugs. EU/UK/AU travelers need an adapter.
- Connectivity
- Good coverage along the Overseas Highway. Some remote keys may have weaker signal.
- Emergency
- 911 (general emergency)
🚗 Getting Around Florida Keys
Drive the Overseas Highway (US-1) from Miami through all the Keys — one of America's most scenic drives.
Keys Shuttle runs between Miami Airport and Key West with stops along the way.
Frequently Asked Questions
What is the best time to visit?
Spring and fall offer the best weather and fewer crowds. Summer is peak season. Check regional weather patterns for specific conditions.
Do I need to rent a car?
A car is essential for road trips and national parks in the US. Public transit is limited outside major metro areas.
How much does a week cost?
Budget: $100-150/day. Mid-range: $200-350/day. Luxury: $500+/day. Costs vary significantly by region and season.
