Miami Cruise, Wynwood and Little Havana Itinerary
Cruise and Miami neighborhoods
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Biscayne Bay sightseeing cruise — Downtown Miami/Biscayne Bay; enjoy views of the skyline and celebrity homes, ideally departing around 11:30 AM for a 1.5–2-hour cruise. Confirm the exact operator and route in advance, as schedules vary seasonally.
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Wynwood Walls — Wynwood; explore the landmark outdoor street-art museum and surrounding murals from approximately 1:30–2:15 PM.
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Versailles Restaurant — Little Havana; have lunch featuring Cuban classics and freshly made empanadas, approximately 2:45–3:30 PM, with about $15–30 per person.
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Cuban Cigar Factory — Little Havana; watch cigars being hand-rolled and purchase fresh cigars from an established local shop, approximately 3:30–4:00 PM.
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Calle Ocho Walk — Little Havana; photograph Domino Park, the Tower Theater exterior, and colorful Calle Ocho landmarks before returning to the hotel around 4:30 PM.
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Kitchen + Kocktails by Kevin Kelley — Downtown Miami; enjoy the confirmed 7:30 PM dinner reservation, budgeting approximately $50–90 per person before drinks, then consider a short Brickell bar stop afterward and return to the hotel by 11:30 PM–midnight.
Late Morning: Biscayne Bay Cruise
Start with the Biscayne Bay sightseeing cruise around 11:30 AM from downtown’s waterfront. Arrive 30–45 minutes early—boarding times and departure piers vary by operator, and December cruises can sell out. Allow 1½–2 hours for skyline views, Biscayne Bay islands, and the celebrity-home route; expect roughly $35–$60 per person, plus parking or rideshare. From the pier, a rideshare to Wynwood Walls takes about 10–15 minutes, though allow extra time for weekend traffic.
Afternoon: Wynwood and Little Havana
Explore Wynwood Walls from about 1:30 to 2:15 PM, then wander a few blocks for additional murals along NW 2nd Avenue and nearby side streets. Admission is generally around $12–$20, and the area is very photogenic in daylight. Continue by rideshare to Versailles Restaurant in Little Havana—usually 15–25 minutes depending on traffic—for Cuban sandwiches, ropa vieja, croquetas, and freshly made empanadas. Budget $15–$30 per person and expect a lively, casual lunch. Afterward, visit Cuban Cigar Factory to watch a torcedor hand-roll cigars and purchase from an established shop; bring identification if buying tobacco, and ask about storage and travel rules.
Late Afternoon and Evening
Finish with a relaxed Calle Ocho Walk, stopping at Maximo Gomez Domino Park, the Tower Theater exterior, and the colorful storefronts around SW 8th Street. Keep this portion flexible, since the best moments are often the small galleries, fruit stands, and walk-up coffee counters you notice along the way. Leave Little Havana around 4:00 PM for the hotel—15–25 minutes by rideshare—to rest before the 7:30 PM reservation at Kitchen + Kocktails by Kevin Kelley downtown. After dinner, a short rideshare to Brickell makes an easy final outing: have one drink at Rosa Sky Rooftop or stroll the illuminated Brickell City Centre before heading back by 11:30 PM–midnight. Reserve the cruise, Wynwood Walls, dinner, and any rooftop stop in advance; December evenings are busy, and rooftop dress codes are typically smart-casual.
