A mix of nature and adventure. A moderate mix of walking and active experiences, with plenty of guided experiences. Includes 8 must-see landmarks across Key West and Miami and Upper Keys.
Highlights: Old Town Key West, South Beach & Art Deco District, Dry Tortugas Day Trip, John Pennekamp Coral Reef State Park, Wynwood Walls & Design District
This variant starts in Key West instead of the default, with the route re-optimized from that entry point.
Your Route — ordered to minimize backtracking
25+ activities scored and ranked · route optimized across 3 cities
Day-by-Day Schedule — heavy and light days alternate so you don’t burn out
Key West
Key WestWander Old Town's pastel conch houses, Hemingway Home, and the Southernmost Point marker
Best Nov-Apr. Summer is hot and humid. Hurricane season Jun-Nov.Ferry to Dry Tortugas National Park for Fort Jefferson, pristine snorkeling, and remote island beauty
$250 Verified Mar 2026 Best Mar-May and Oct-Nov for calm seas. Ferry may cancel in rough weather. Peak bird migration Apr-May.Old Town / Duval Street / Bahama Village
Sail into a legendary Key West sunset with cocktails, music, and Gulf of Mexico views
$70 Verified Mar 2026 Year-round sunsets. Calmest seas and clearest skies Nov-May.Taste Key West's signature flavors on a guided food tour through Old Town's best kitchens
$69 Verified Mar 2026 Year-round. Key West Food & Wine Festival in late January.Old Town / Duval Street / Bahama Village
Swim and snorkel at Fort Zachary Taylor, Smathers Beach, or Higgs Beach with reef access
Year-round swimming. Water warmest Jun-Oct.Paddle through mangrove channels and snorkel a shallow reef on a guided Key West eco-tour
Year-round. Calmest paddling Nov-May.Old Town / Duval Street / Bahama Village
Tour President Truman's winter retreat — the only presidential site in the Florida Keys
$23 Verified Mar 2026 Open daily year-round. Book this tour →Combine reef snorkeling with a sunset sail for a two-in-one Key West evening on the water
Best visibility and warmest water Apr-Oct.Old Town / Duval Street / Bahama Village
See the island's coral reefs, shipwrecks, and turquoise waters from above on a scenic helicopter flight
Best visibility Nov-Apr. Flights may cancel in storms.Float on a floating tiki bar through Key West harbor while watching the sun dip into the Gulf
Year-round. Most enjoyable in dry season Nov-May.Old Town / Duval Street / Bahama Village
Explore Bahia Honda's beaches, the National Key Deer Refuge, and quiet backcountry of the Lower Keys
Year-round. Key deer are most visible at dawn/dusk.Explore Key West's food scene with a small group and learn directly from a local expert. On this tour, you'll get a uniq
$88.68 Verified Mar 2026 Book this tour →Old Town / Duval Street / Bahama Village
Explore Key West's food scene with a small group and learn directly from a local expert. This is recommended for those w
$88.68 Verified Mar 2026 Book this tour →Budget some free time in Key West to explore at your own pace, unwind from your travel or follow your own itinerary outs
Old Town / Duval Street / Bahama Village
Opt for a premium experience as a private guide leads you to Dry Tortugas National Park and handles all of the logistics
$361 Verified Mar 2026 Book this tour →Old Town / Duval Street / Bahama Village
Miami
MiamiStroll 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.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.South Beach / Mid-Beach / Brickell
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.Venture into the Everglades for an airboat ride through sawgrass marshes and alligator sightings
$29 Verified Mar 2026 Best Dec-Apr (dry season) when wildlife concentrates around water. Summer is hot, buggy, and prone to afternoon storms.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
Upper Keys
Upper KeysSnorkel 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.Dive or snorkel the spectacular coral reefs of Key Largo with expert local guides
Best visibility Apr-Oct. Winter swells can cancel trips.Key Largo / Upper Matecumbe Key / Venetian Shores
Discover Islamorada's sportfishing capital with Robbie's tarpon feeding and oceanside parks
Year-round. Tarpon feeding best Mar-Jul.Get up close with Atlantic bottlenose dolphins at this Key Largo marine research facility
Year-round. Book well in advance — programs are limited capacity.Key Largo / Upper Matecumbe Key / Venetian Shores
Check out of your hotel, grab a final breakfast, and head to the airport. Safe travels from Upper Keys!
Where You’ll Stay
Estimated total: $2,448–$3,676
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
$1,400 – $7,000 per person for 14 days
Similar Destinations
Similar vibes, fewer crowds — destinations our algorithm rates as close matches to Florida Keys.
🧳 Practical Info for Florida Keys
- Visa
- ESTA required for Visa Waiver Program countries. CA citizens visa-exempt. See US entry requirements.
- Tipping
- 18–20% tip expected at restaurants. Standard US tipping culture applies.
- Currency
- US Dollar ($ 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.
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