Florida

A three-city loop through Miami, Orlando, and Tampa covering Art Deco beaches, Cuban food and culture, theme-park-adjacent gems, and Gulf Coast day trips.

Miami

Name	Info	Details
South Beach / Ocean Drive	Art Deco district · must-do	The pastel Art Deco hotels along Ocean Drive are worth a slow walk even if you never touch the sand. The beach itself is wide, clean, and easy to combine with lunch at one of the sidewalk cafes.
Little Havana (Calle Ocho)	walkable · free · culture	Cuban American culture concentrated into a few blocks, with the Celia Cruz mural, domino players in Maximo Gomez Park, and cigar shops. Best experienced on foot with no fixed itinerary.
Versailles Restaurant	Cuban · $ · casual	The classic Little Havana institution for a Cuban sandwich, café con leche, and people-watching. Loud, bright, and exactly what a first Cuban meal in Miami should be.
La Camaronera	seafood counter · $ · walk-in	A no-frills seafood counter loved by locals for fried fish sandwiches and ceviche. Order at the window, eat standing up, skip the tourist-trap seafood spots elsewhere in town.
Ball & Chain	live music · free entry most nights	A 1930s Little Havana club that still does live salsa and Afro-Cuban jazz nightly, with free salsa lessons on Thursdays. Small cover on weekends but worth it for the atmosphere alone.
Wynwood Walls	street art · $$ entry	An open-air museum of large-scale murals in the Wynwood arts district. Pair it with the surrounding galleries, coffee shops, and breweries for a half-day.
Cape Florida Lighthouse, Key Biscayne	state park · optional · half-day	Miami-Dade's oldest standing structure, inside Bill Baggs Cape Florida State Park with a calm swimmable beach. A quieter, less crowded alternative to South Beach.
Everglades airboat tour	day trip · $$-$$$ · book ahead	A guided airboat ride through the sawgrass wetlands just west of the city, with real odds of seeing alligators and wading birds. Highly rated operators run out of the Miami area with round-trip transport included.

Orlando

Name	Info	Details
Winter Park Scenic Boat Tour	1 hour · $ · running since 1938	A slow pontoon ride through Winter Park's chain of lakes and narrow canals, past old estates and the Isle of Sicily. Guides are known for dry humor and pointing out wildlife along the way.
Park Avenue, Winter Park	shopping/dining · half-day	A tree-lined strip of boutiques and European-style cafes just north of downtown, a good antidote to theme-park crowds. Briarpatch is the go-to for brunch.
Disney Springs	free entry · dining and shows	Disney's shopping and entertainment district doesn't require a park ticket, so it's an easy way to get a taste of Disney atmosphere without the admission cost. Cirque du Soleil's Drawn to Life performs here.
ICON Park / The Wheel	International Drive · $$	A 40-story observation wheel that gives one of the better skyline views in Orlando, especially near sunset. Surrounded by other I-Drive attractions like Madame Tussauds if you want to make a night of it.
Lake Eola Park	free · downtown · morning walk	A downtown park built around a lake with swan-shaped paddleboats and a walking path. Good for a quiet morning before or after park days.
Gatorland	quirky · half-day · optional splurge for zip line	An old-school Florida attraction with a zip line that runs directly over live alligators. A fun, campy break from the polish of the major theme parks.
Judson's Live	speakeasy · live music · reservations recommended	A moody, speakeasy-style venue with nightly live music and a themed live-music brunch on Sundays. A solid evening option that has nothing to do with theme parks.

Tampa

Name	Info	Details
Tampa Riverwalk	free · 2.6 miles · waterfront walk	A paved path along the Hillsborough River connecting downtown parks, museums, and restaurants. Consistently rated the top free thing to do in Tampa and an easy way to get oriented.
Armature Works	food hall · $-$$ · rooftop bar	A restored 1910 streetcar garage turned food hall with a wide range of vendors and a rooftop bar overlooking the river. Good for a group where everyone wants something different.
Ybor City	historic district · nightlife	A former Cuban cigar-manufacturing district now full of cigar lounges, cocktail bars, and live music, with brick streets that make it easy to wander. Livelier at night, especially on weekends.
Columbia Restaurant	Cuban/Spanish · $$ · historic	Florida's oldest restaurant, open since the early 1900s in Ybor City, known for paella and the original 1905 salad. A sit-down meal worth the slightly higher price for the history alone.
Bern's Steak House	steakhouse · $$$$ · reserve well ahead	An old-school Tampa splurge with an enormous wine cellar and kitchen tours included with dinner. Reservations book up fast and there's a business-casual dress code, so plan ahead rather than walking in.
Busch Gardens Tampa Bay	theme park · optional · full day	A theme park built around roller coasters and an actual zoo/safari component, a different flavor than the Orlando parks. Worth it if you want thrill rides plus animal encounters in one stop.
Clearwater Beach	day trip · 30-35 min from Tampa	The easiest beach day trip from Tampa, with soft white sand, a walkable strip of restaurants and bars, and a lively marina. Good option if a full drive to Siesta Key or Sarasota doesn't fit the schedule.