Miami South Beach Art Deco hotels and palm trees

Best 5 Days in Florida Keys — Winter

Miami → Upper Keys → Marathon

5 days · 3 cities · 8 activities · route optimized by distance

Expect lots of nature — parks, scenic views, and outdoor activities. A moderate mix of walking and active experiences, with a mix of self-guided and guided activities. Includes 5 must-see landmarks across Miami and Upper Keys and Marathon.

Highlights: South Beach & Art Deco District, Wynwood Walls & Design District, Little Havana, Turtle Hospital, Everglades Day Trip

Arriving Wed, Jul 1 Change

Your Route — ordered to minimize backtracking

8+ activities scored and ranked · route optimized across 3 cities

Where you'll stay
Hotel in Miami · From $180/night +2 more
See lodging →
Trip cost
~$922 total · $184/day
See budget →
Top picks
South Beach & Art Deco District, Wynwood Walls & Design District, Little Havana
See itinerary →

Day-by-Day Schedule — heavy and light days alternate so you don’t burn out

Miami

Miami Miami · Open in Google Maps ↗
Day 1 Wed, Jul 1 Full Miami
Morning
South Beach & Art Deco District$~3 hrs

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.
Afternoon
Wynwood Walls & Design District$~3 hrs

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.
🏨 Hotel in Miami

South Beach / Mid-Beach / Brickell

wifiparkingair-conditioning
Travelers book: The Setai Miami Beach $500-900/nightFontainebleau Miami Beach $250-450/nightGenerator Miami $100-200/night
Book Hotel in Miami from $180/night Affiliate link — we may earn a commission at no extra cost to you
Day 2 Thu, Jul 2 Moderate Miami
Morning
Little Havana$~3 hrs

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.
Afternoon
Everglades Day Trip$~3 hrs

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.
🏨 Hotel in Miami

South Beach / Mid-Beach / Brickell

wifiparkingair-conditioning
Travelers book: The Setai Miami Beach $500-900/nightFontainebleau Miami Beach $250-450/nightGenerator Miami $100-200/night
Book Hotel in Miami from $180/night Affiliate link — we may earn a commission at no extra cost to you
Miami → Upper Keys
1h 42m Drive straight to the Upper Keys without sightseeing along the route. This is recommended for those who want to maximize

Upper Keys

Upper Keys Upper Keys · Open in Google Maps ↗
Day 3 Fri, Jul 3 Full Upper Keys
Morning
Islamorada's Matecumbe Keys$~3 hrs

Discover Islamorada's sportfishing capital with Robbie's tarpon feeding and oceanside parks

Year-round. Tarpon feeding best Mar-Jul.
Afternoon
Dolphins Plus Marine Mammal Responder$$$~3 hrs

Get up close with Atlantic bottlenose dolphins at this Key Largo marine research facility

Year-round. Book well in advance — programs are limited capacity.
🏨 Hotel in Upper Keys

Key Largo / Upper Matecumbe Key / Venetian Shores

wifiparkingair-conditioning
Travelers book: Casa Morada $350-550/nightCheeca Lodge & Spa $300-500/nightKona Kai Resort and Gallery $200-350/night
Book Hotel in Upper Keys from $265/night Affiliate link — we may earn a commission at no extra cost to you
Upper Keys → Marathon
1h Drive straight to Marathon without sightseeing along your route. There aren't any major point of interest along the way

Marathon

Marathon Marathon · Open in Google Maps ↗
Day 4 Sat, Jul 4 Full Marathon
Morning
Turtle Hospital$$~1 hr

Tour the only state-licensed sea turtle veterinary hospital and meet rescued turtles up close

$35 Verified Mar 2026 Open year-round, tours on the hour 9am-4pm. Book in advance — spots fill quickly. Book this tour →
Afternoon
Dolphin Research Center$$~3 hrs

Meet Atlantic bottlenose dolphins at this nonprofit marine research and education facility

$35 Verified Mar 2026 Open daily 9am-4:30pm year-round. Interactive programs book separately.
🏨 Hotel in Marathon

Vaca Key / Sombrero Beach / Boot Key Harbor

wifiparkingair-conditioning
Travelers book: Isla Bella Beach Resort & Spa $350-600/nightTranquility Bay Beachfront Resort $250-450/nightHampton Inn Marathon $150-250/night
Book Hotel in Marathon from $185/night Affiliate link — we may earn a commission at no extra cost to you
Day 5 Sun, Jul 5 Marathon
Checkout & Depart

Check out of your hotel, grab a final breakfast, and head to the airport. Safe travels from Marathon!

Where You’ll Stay

Estimated total: $648–$972

Trip Budget Estimate

$922 estimated total per person
$184 per day
Lodging $810
Activities $112

Estimates based on listed activity prices and hotel rates. Actual costs vary by season, availability, and personal spending.

Typical range for Florida Keys

$500 – $2,500 per person for 5 days

Budget: $100/day — Budget motels, fast-casual dining, public transport Mid-range: $250/day — Hotels, restaurants, car rental Luxury: $500/day — Resorts, fine dining, guided tours

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

🚗 Car

Drive the Overseas Highway (US-1) from Miami through all the Keys — one of America's most scenic drives.

🚌 Bus

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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