Miami South Beach Art Deco hotels and palm trees

Best 14 Days in Florida Keys — Workcation

Miami → Upper Keys → Marathon

14 days · 3 cities · 13 activities · route optimized by distance

Expect lots of nature — parks, scenic views, and outdoor activities. A moderate mix of walking and active experiences, with plenty of guided experiences. Includes 6 must-see landmarks across Miami and Upper Keys and Marathon.

Highlights: South Beach & Art Deco Historic District, Miami, John Pennekamp Coral Reef State Park, Wynwood Walls & Arts District, Miami, Little Havana, Turtle Hospital

Arriving Wed, Jul 1 Change

Your Route — ordered to minimize backtracking

13+ 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
~$2,717 total · $194/day
See budget →
Top picks
South Beach & Art Deco Historic District, Miami
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

Remote work morning — find a café or coworking space

Afternoon
South Beach & Art Deco Historic District, Miami$~3 hrs

Walk Ocean Drive's pastel Art Deco buildings and hit the wide Atlantic beach in Miami's most iconic neighborhood

Best Nov-Apr (dry season). Jun-Nov is hurricane season with afternoon thunderstorms.
🏨 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 Light Miami
Morning

Remote work morning — find a café or coworking space

Afternoon
Wynwood Walls & Arts District, Miami$~3 hrs

Explore 40+ monumental street art murals and cutting-edge galleries in Miami's most colorful neighborhood

$12 Verified Apr 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 3 Fri, Jul 3 Light Miami
Morning

Remote work morning — find a café or coworking space

Afternoon
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.
🏨 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 4 Sat, Jul 4 Light Miami
Morning

Remote work morning — find a café or coworking space

Afternoon
Everglades Day Trip from Miami$~3 hrs

Venture into the Everglades for an airboat ride through sawgrass marshes, wildlife shows, and alligator sightings

$29 Verified Apr 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
Day 5 Sun, Jul 5 Light Miami
Morning

Remote work morning — find a café or coworking space

Afternoon
Key Biscayne & Bill Baggs Cape Florida State Park$~3 hrs

Escape to Key Biscayne for pristine Atlantic beaches, the Cape Florida Lighthouse, and quiet island atmosphere

$8 Verified Apr 2026 Open 8am-sundown daily. Arrives early on weekends — park closes at capacity.
🏨 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 6 Mon, Jul 6 Light Miami
Morning

Remote work morning — find a café or coworking space

Afternoon
Upper Keys Day Trip$$~3 hrs

Drive the Overseas Highway to Key Largo and Islamorada for snorkeling, wildlife, and island vibes

Best Nov-Apr. Hurricane season Jun-Nov.
🏨 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 7 Tue, Jul 7 Light Miami
Morning

Remote work morning — find a café or coworking space

Afternoon
Private Sailing Charter$$$~3 hrs

Sail Biscayne Bay on a private charter with skyline views, snorkeling, and sunset options

Year-round. Calmest waters Nov-May.
🏨 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 8 Wed, Jul 8 Light Miami
Morning

Remote work morning — find a café or coworking space

Afternoon
Miami's Kid-Friendly Must-Sees$$~3 hrs

Explore Miami Zoo, the Children's Museum, and Jungle Island with the whole family

Year-round. Indoor/outdoor mix works in any weather.
🏨 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 9 Thu, Jul 9 Light Miami
Morning

Remote work morning — find a café or coworking space

Afternoon
Wynwood and the Design District: Graffiti golf cart group tour$$~1 hr

Explore Wynwood with a small group and learn directly from a local expert. On this graffiti tour, explore this artistic

$39 Verified Apr 2026 Book this tour →
🏨 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 10 Fri, Jul 10 Full Upper Keys
Morning

Remote work morning — find a café or coworking space

Afternoon
John Pennekamp Coral Reef State Park$$~3 hrs

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.
🏨 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
Day 11 Sat, Jul 11 Full Upper Keys
Morning

Remote work morning — find a café or coworking space

Afternoon
Key Largo Reef Diving & Snorkeling$$~3 hrs

Dive or snorkel the spectacular coral reefs of Key Largo with expert local guides

Best visibility Apr-Oct. Winter swells can cancel trips.
🏨 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 12 Sun, Jul 12 Full Marathon
Morning

Remote work morning — find a café or coworking space

Afternoon
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 →
🏨 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 13 Mon, Jul 13 Light Marathon
Morning

Remote work morning — find a café or coworking space

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 14 Tue, Jul 14 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: $2,016–$3,024

Trip Budget Estimate

$2,717 estimated total per person
$194 per day
Lodging $2,520
Activities $197

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

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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