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2 Day Miami Itinerary | Chase the Pigeon

2 Day Miami Itinerary

Two full days, split so you’re not driving between neighbourhoods twice, with South Beach on day one and Wynwood and Little Havana on day two.

Two days in Miami is enough to properly do South Beach’s Art Deco charm and still get out to Wynwood’s murals and Little Havana’s Cuban heart. Here’s how I’d split it, day by day.

Day 01

South Beach & Art Deco

Start at South Pointe Park for sunrise or an early morning walk, then work north along Ocean Drive to see the Art Deco Historic District, over 800 preserved buildings, the Beacon, the Cardozo and the Park Central among the classics. A guided walking tour from the Art Deco Welcome Center is worth it if you want the history explained rather than just the photos.

Spend the afternoon at Lincoln Road for shopping and people-watching, then relax at the beach or pool through the hottest part of the day. End the day with sunset at South Pointe Park or a rooftop bar, then dinner in Sunset Harbour, noticeably better value than the Ocean Drive tourist strip a few streets over.

Morning South Pointe Park, Ocean Drive, Art Deco walking tour
Afternoon Lincoln Road, beach time
Evening Sunset, dinner in Sunset Harbour
“Skip the Ocean Drive restaurants with a guy outside trying to wave you in. Walk ten minutes to Sunset Harbour instead, the food’s better and the prices are considerably more honest.”
Day 02

Wynwood & Little Havana

Start at Wynwood Walls, murals and street art covering a former industrial neighbourhood, one of Miami’s most photographed spots and worth a couple of unhurried hours. Stay in Wynwood for lunch, the neighbourhood has become a genuine food destination in its own right, tacos, craft beer, and inventive small plates.

Spend the afternoon in Little Havana, Calle Ocho for Cuban coffee and pastries, Domino Park for a look at the retirees playing dominoes most afternoons, and Versailles, Miami’s most legendary Cuban restaurant, for dinner if you want the full experience. End the second night with live music and salsa dancing at Ball & Chain, a Little Havana institution.

Morning Wynwood Walls
Afternoon Little Havana, Calle Ocho, Domino Park
Evening Dinner at Versailles, drinks at Ball & Chain

Getting around across both days

South Beach itself is walkable, but Wynwood and Little Havana both require a car or rideshare, this isn’t a city you can cover entirely on foot. Traffic builds fast during rush hour, factor extra time into any drive between neighbourhoods during the late afternoon.

If you only have time for one thing each day

Day one, make it sunset at South Pointe Park, free, and the single best value moment on the whole itinerary. Day two, make it Wynwood Walls, genuinely unlike anything else in the city and worth the drive out on its own.

That’s everything I’ve got.

A note before you plan around this: prices, opening hours, booking requirements and admission details in this guide were correct at the time of writing, but venues change these often and sometimes without notice. Always check directly with the attraction or its official website before you travel or build a schedule around a specific time or price.

Before travelling to any destination featured on this site, please also check your government’s latest travel advice, as safety situations, entry requirements and travel warnings can change.

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