Miami
Orlando
United States · Multi-city itinerary
Florida itinerary — May 2027
By Tripsapien Research · Updated May 20, 2026
May 2027 is a shoulder-season time for the Florida trip (Miami & Orlando). Daytime highs run from about 30°C / 86°F to 31°C / 88°F across the stops. Plan around 7–9 days for the full Miami & Orlando loop. Tripsapien checks every place on your list against your exact dates — hours, closures and booking pressure at each stop.
The route
About 7–9 days · 2 cities
Sunshine-state classics: Art-Deco South Beach, Cuban culture and the Everglades around Miami, and the theme-park capital of Orlando inland. The Brightline train now links the two in around three and a half hours.
Miami
Miami in May
Temperature
82°F / 75°F
27.9°C / 23.8°C
Precipitation
20d
3.6in · 92.5mm
Daylight
13.2h
Sea
84.6°F
29.2°C
May starts the humid wet season, so plan Wynwood and museum time around afternoon storms.
May starts the humid wet season, so plan Wynwood and museum time around afternoon storms.
City overview
Miami is the Biscayne Bay gateway where the Miami River, Brickell towers, Little Havana cafecitos, Wynwood murals, and Miami Beach barrier-island surf sit within one short but traffic-sensitive map. The city feels most distinct when a trip mixes Downtown Metromover stops, Coconut Grove banyan shade, Coral Gables Mediterranean Revival streets, and late light along Biscayne Bay.
Food & drink
Miami eating means Cuban sandwiches, ropa vieja, stone crab claws, ceviche, fritas, croquetas, pastelitos, and cortaditos. Calle Ocho, Versailles, Joe's Stone Crab in season, Coconut Grove waterfront tables, and the Lincoln Road-South Beach strip are practical first food routes.
Top sights
Ranked for May suitability using weather, setting, ratings, and review volume.
- 1Vizcaya Museum and Gardens
- 2Perez Art Museum Miami
- 3Freedom Tower
- 4Phillip and Patricia Frost Museum of Science
- 5South Beach Art Deco Historic District
- 6Wynwood Walls
- 7Fairchild Tropical Botanic Garden
- 8Bill Baggs Cape Florida State Park
- 9Little Havana and Calle Ocho
- 10Venetian Pool
1Vizcaya Museum and Gardens
4.7★ · 15,999indoorClosed TueIndustrialist James Deering built Vizcaya between 1914 and 1922 with architect F. Burrall Hoffman, designer Paul Chalfin, and garden designer Diego Suarez. The Italianate villa, formal gardens, and Biscayne Bay stone barge sit south of Brickell near the Vizcaya Metrorail station.
WikipediaTimed admission is useful on weekends because the house and gardens are a common wedding-photo stop.
2Perez Art Museum Miami
4.5★ · 7,806indoorClosed Tue/WedThe Herzog & de Meuron-designed museum opened on Biscayne Bay in 2013 after moving from the former Miami Art Museum. Its Latin American, Caribbean, and contemporary collections share Museum Park with the Frost Science campus and sit a short Metromover ride from Brickell.
Wikipedia
3Freedom Tower
4.6★ · 584indoorClosed Mon/TueThe 1925 Mediterranean Revival tower on Biscayne Boulevard became known as Miami's Ellis Island after it processed Cuban refugees in the 1960s. Its cupola stands across from Kaseya Center and near Bayfront Park, making it an easy Downtown history stop.
Wikipedia
Show 7 more sights
- 4Phillip and Patricia Frost Museum of Science
- 5South Beach Art Deco Historic District
- 6Wynwood Walls
- 7Fairchild Tropical Botanic Garden
- 8Bill Baggs Cape Florida State Park
- 9Little Havana and Calle Ocho
- 10Venetian Pool
Neighborhoods
1Downtown Miami and Brickell
The core is vertical and transit-friendly, with the Miami River, Bayfront Park, Kaseya Center, Brickell City Centre, and Metromover loops packed into a compact skyline.
2Wynwood and Midtown
This warehouse belt feels graphic and late-night, with Wynwood Walls, NW 2nd Avenue murals, breweries, galleries, and Midtown restaurants between I-95 and the Design District.
3Little Havana
Little Havana is warm, Cuban, and street-level, with Calle Ocho, Domino Park, Tower Theater, cigar counters, salsa bars, and cafecito windows.
4Coconut Grove
The Grove is leafy and bay-facing, with Peacock Park, Dinner Key Marina, Vizcaya nearby, old Bahamian roots, and shaded restaurants under banyans.
5Coral Gables
Coral Gables is polished and Mediterranean Revival, with Miracle Mile, Venetian Pool, the Biltmore Hotel, Books & Books, and broad streets from George Merrick's 1920s plan.
6Miami Beach and South Beach
The barrier-island side is beachy and theatrical, with Ocean Drive neon, Lincoln Road, Art Deco hotels, Lummus Park, and late-night Collins Avenue energy.
Getting around
Metrorail, Metromover, Metrobus, Brightline, Tri-Rail, and the EASY Card cover the useful transit spine from MIA through Downtown and Brickell. Cars and rideshares are still fastest for Miami Beach, Wynwood, Coconut Grove, Coral Gables, and Key Biscayne, but bridge and I-95 traffic can reshape a day.
Orlando
Orlando in May
Temperature
88°F / 66°F
31.3°C / 19.1°C
Precipitation
8d
3.9in · 100mm
Daylight
13.4h
May brings summer heat, making midday pool breaks useful before evening park returns.
May brings summer heat, making midday pool breaks useful before evening park returns.
City overview
Orlando sits in Central Florida between Atlantic and Gulf coast day-trip range, but its visitor map is shaped by theme-park resorts southwest of Downtown and older neighborhoods around Lake Eola, Winter Park, and Mills 50. The city is most useful when Walt Disney World, Universal Orlando, International Drive, and quieter local districts are treated as separate travel zones rather than one compact downtown.
Food & drink
Orlando food stretches beyond theme-park snacks into Cuban sandwiches, Puerto Rican mofongo, Vietnamese pho, Brazilian steakhouse meals, smoked barbecue, gator bites, key lime pie, and citrus desserts. Mills 50, East End Market, Disney Springs, International Drive, Winter Park, and the Milk District are the most useful food zones.
Top sights
Ranked for May suitability using weather, setting, ratings, and review volume.
- 1Harry P. Leu Gardens
- 2EPCOT
- 3Disney's Animal Kingdom
- 4Universal Studios Florida
- 5Universal Islands of Adventure
- 6Lake Eola Park
- 7Magic Kingdom
- 8Disney's Hollywood Studios
- 9Universal Volcano Bay
- 10SeaWorld Orlando
1Harry P. Leu Gardens
4.7★ · 5,690mixedOpen dailyThe Leu family donated this 50-acre garden estate to the city in 1961, preserving camellias, roses, palms, oaks, and a historic house north of Downtown. It is a calm morning counterweight to International Drive crowds.
Wikipedia
2EPCOT
4.7★ · 161,965outdoorOpen dailyEPCOT opened in 1982 with Spaceship Earth, World Showcase pavilions, seasonal festivals, and science-and-culture attractions. It sits within Walt Disney World and pairs well with evening dining rather than a rushed park hop.
Wikipedia
3Disney's Animal Kingdom
4.7★ · 142,303outdoorOpen dailyAnimal Kingdom opened in 1998 with the Tree of Life, Kilimanjaro Safaris, Expedition Everest, Pandora, and animal trails. Morning starts matter because wildlife and heat both change the pace of the day.
Wikipedia
Show 7 more sights
- 4Universal Studios Florida
- 5Universal Islands of Adventure
- 6Lake Eola Park
- 7Magic Kingdom
- 8Disney's Hollywood Studios
- 9Universal Volcano Bay
- 10SeaWorld Orlando
Neighborhoods
1Downtown and Lake Eola
Downtown is civic and compact, with Lake Eola, the Dr. Phillips Center, Church Street, sports venues, courthouses, bars, and Sunday market traffic.
2Thornton Park and Milk District
These close-in districts are local and low-rise, with bungalow streets, coffee shops, Lake Eola access, murals, breweries, and casual restaurants.
3Winter Park and Park Avenue
Winter Park is polished and leafy, with Rollins College, Park Avenue, museums, lakes, boat tours, brick streets, and restaurant patios.
4International Drive and Convention Center
I-Drive is visitor-heavy and commercial, with hotels, outlet malls, ICON Park, restaurants, trolleys, and easy access to Universal and SeaWorld.
5Lake Buena Vista and Disney resort area
The Disney side is spread out and resort-built, with theme parks, Disney Springs, monorails, buses, hotels, and long parking or shuttle times.
6Mills 50 and Audubon Park
This north-central food belt is independent and casual, with Vietnamese restaurants, murals, craft beer, East End Market, vintage shops, and neighborhood bars.
Getting around
LYNX buses, SunRail commuter trains, the I-Ride Trolley, hotel shuttles, rideshares, and rental cars all matter because Orlando is spread out. Cars are usually fastest between Disney, Universal, Downtown, Winter Park, and the airport, while park shuttles are useful once inside a resort zone.
Best time to do the Florida trip
In May, the Florida trip runs daytime highs from 30°C / 86°F to 31°C / 88°F, with nights down to about 19°C / 66°F at the coolest stop. It is one of the wetter months, with up to 11 rainy days at the wettest stop. Weighed across both stops, May is a shoulder-season time to travel.
The most comfortable months across Miami & Orlando are February, March and January, based on average daytime temperatures and rainfall at every stop. May 2027 is a quieter shoulder season to go.
Check this route against your dates
Tripsapien starts with the sights on this page or places you paste, then checks hours, closures, booking pressure and neighborhoods for your exact May dates — across every city on the Florida trip.
Plan this Florida tripCommon questions about the Florida trip
- When is the best time to do the Florida trip?
- The most comfortable months across Miami, Orlando are February, March and January, based on average daytime temperatures and rainfall at each stop. May is a shoulder-season time — see the per-stop weather below for the exact picture in May 2027.
- How many days do you need for the Florida trip?
- A comfortable Florida trip runs about 7–9 days, allowing roughly Miami 4, Orlando 3 nights plus travel between stops. Add a day if you want a slower pace or extra day trips.
- What's the route for the Florida trip?
- The classic order is Miami & Orlando. Each city below has its own May weather, events and top-sights list.
- Will the sights be open during my May Florida trip?
- Opening days and hours vary by weekday, season and public holiday, and they differ from city to city on a multi-stop trip. Paste your Florida list into Tripsapien and it checks every place in Miami, Orlando against your exact dates, flagging closures and what needs booking ahead before you go.