Florida during spring break hits that sweet spot for parents and teens: warm water, short travel times, and endless outdoor fun. This 5-day Miami and Key West itinerary balances thrill and chill—airboats and street art one day, dolphins and sunset sails the next.

Miami’s story is one of reinvention—from art deco boomtown to Latin cultural capital. Expect neon facades along South Beach, murals splashed over Wynwood, and the irresistible pull of Cuban coffee in Little Havana. It’s a city where a great day can be a gallery crawl in the morning and waves at dusk.

Key West, the southernmost point in the continental U.S., mixes Bahamian breezes with literary lore and coral reefs. The Overseas Highway is half the adventure: 42 bridges, turquoise water, and roadside seafood shacks. Spring break is popular, so book early, hydrate, and aim for mornings on popular beaches to sidestep crowds.

Miami

Miami is bold color and bigger flavors. Teens love the energy: street art you can touch, boats skimming Biscayne Bay, and wildlife just a short ride away in the Everglades. Expect late sun, easy beach time, and plenty of casual, tasty eats.

• Top sights: South Pointe Park and Pier, Wynwood Walls area, Little Havana’s Calle Ocho, Lummus Park Beach, Vizcaya Gardens (for a calm break).
• Food you’ll remember: Cuban sandwiches and pastelitos, stone crab claws (in season), Miami-style burgers, fresh ceviche, and key lime pie.
• Fun fact: Miami Beach’s art deco district houses the largest concentration of art deco buildings in the world, most from the 1920s–40s.

Where to stay: Browse family-friendly condos and hotels near South Beach, Brickell, or Coconut Grove: VRBO Miami | Hotels.com Miami

How to get here: From anywhere in Florida, driving into Miami is simple via I‑95 or the Turnpike. Prefer to fly? Check fares into MIA or FLL: Search flights on Trip.com or Search flights on Kiwi.com.

Day 1: Arrive, South Beach sampler, and sunset stroll

Morning: Travel to Miami. If you’re driving from within Florida, aim to arrive by early afternoon. If you fly, plan on an easy rideshare to your stay and a quick bite nearby.

Afternoon: Check in and walk South Pointe Park and Pier for big ocean views, ships sailing out of Government Cut, and space to move around even on busy days. Grab an energizing snack: try La Sandwicherie (legendary French-style subs on fresh baguette) or Joe’s Take Away (stone crab claws and key lime pie without the white-tablecloth fuss, seasonal).

Evening: Cruise Lincoln Road for people-watching and an open-air dinner. Teen-approved picks: Shake Shack for classic burgers and frozen custard; Huahua’s Taqueria for playful tacos; or Pizza Rustica for giant Roman-style slices. Wrap with gelato at Gelato-Go and an early night.

Day 2: Everglades wildlife, Little Havana flavors, and a Biscayne Bay thrill ride

Morning: Fuel up with coffee and pastries at Zak the Baker (Wynwood—great chocolate babka) or Panther Coffee. Then head to an airboat adventure in the River of Grass with hotel pickup, a teen favorite for up-close gator sightings and birds.

Book: Everglades Tour from Miami with Transportation

Afternoon: Dive into culture and eats on Calle Ocho. This walking tour weaves Cuban history with tastings—think croquetas, guarapo sugarcane juice, and a look at cigar-rolling and domino culture in Maximo Gomez Park. Great for teens who like learning through food.

Book: Little Havana Food and Walking Tour in Miami

Evening: Cap the day with a 45-minute offshore speedboat ride that zips along the skyline—big smiles guaranteed. Dine at Lokal in Coconut Grove (Florida-sourced burgers, key lime shakes) or Monty’s Raw Bar (waterfront, live music, kid-friendly baskets).

Book: Speedboat Sightseeing Adventure of Miami

Key West

Key West is an island of porches and conch houses, six-toed cats, and water so clear you’ll stare at it longer than you planned. Teens dig the hands-on adventures: dolphin spotting, snorkeling sandbars, and biking quiet streets.

• Top sights: Mallory Square sunset celebration, Ernest Hemingway Home & Museum (and its famed cats), Southernmost Point buoy, Fort Zachary Taylor beach, Key West Lighthouse.
• Good eats: Fresh-caught fish tacos, conch fritters, Cuban roast pork, and every form of key lime pie—frozen-on-a-stick included.
• Fun fact: Key West sits just about 90 miles from Cuba; the Conch Republic tongue-in-cheek “seceded” in 1982 to protest a roadblock—and the nickname stuck.

Where to stay: Old Town puts you near sunsets and sights; New Town is quieter with easy parking. Browse: VRBO Key West | Hotels.com Key West

Getting from Miami to Key West (morning departure on Day 3): Drive the Overseas Highway (US‑1), ~165 miles, 3.5–4.5 hours depending on traffic—leave by 8:00 a.m. for the smoothest ride. Expect $25–$40 in gas roundtrip for most sedans. Prefer to fly? MIA–EYW is ~1 hour, often $100–$250 one-way: Trip.com flights or Kiwi.com flights.

Day 3: The Overseas Highway and Old Town Key West

Morning: Grab breakfast to-go in Miami at The Salty Donut (creative pastries teens love) or El Bagel (MiMo). Hit the road by 8:00–8:30 a.m. Scenic stops en route include Key Largo for a water view or Marathon for a quick bite of conch fritters.

Afternoon: Check in, then wander Old Town. Visit the Ernest Hemingway Home (the polydactyl cats are a hit), climb the Key West Lighthouse for a pano, and snag a photo at the Southernmost Point buoy. Recharge with tacos at Garbo’s Grill (Korean BBQ tacos, often cited as the island’s best).

Evening: Join the nightly festival at Mallory Square: jugglers, guitarists, and a fiery sky. Dinner picks: El Siboney (Cuban comfort food—ropa vieja, black beans, generous portions) or Half Shell Raw Bar (picnic tables, peel‑and‑eat shrimp, sunset views). Dessert at Kermit’s Key West Key Lime Shoppe—try the pie-on-a-stick dipped in chocolate.

Day 4: Dolphins, sandbars, and classic Key West sunset

Morning: Coffee and Cuban toast at Cuban Coffee Queen (waterfront location, fast and friendly). Pick up reef‑safe sunscreen; the sun bites here. Stroll Truman Waterfront Park before your boat tour.

Afternoon: Head out to a secluded sandbar with a stop at the “dolphin playground” to see wild dolphins in their natural habitat. It’s active but mellow—ideal for a 15-year-old who wants time in the water without heavy currents.

Book: All-Inclusive Sandbar Safari with Dolphin Playground Encounter

Evening: Dinner at DJ’s Clam Shack (lobster rolls and conch fritters featured on food TV) or Onlywood Pizzeria Trattoria (wood‑fired pies, breezy courtyard). For a second sunset, walk the jetty at Fort Zachary Taylor—usually less crowded than Mallory.

Day 5: Beach morning, brunch, and departure

Morning: Swim and snorkel at Fort Zachary Taylor State Park, the island’s best mix of sandy beach and rocky coral for fish spotting; bring water shoes. If you prefer a quick spin, rent bikes to cruise pastel streets and quiet lanes.

Afternoon: Brunch at Blue Heaven (Caribbean‑leaning plates, chickens wandering the yard—go early to avoid lines). Shop for last‑minute souvenirs on Duval, then depart by early afternoon for Miami or your home city.

Evening: Travel home. If you’re driving back to the mainland, plan a snack stop around Marathon to break up the ride.

Extra ideas if you have the energy in Miami

• Wynwood murals + treats: After photos, grab tacos at COYO Taco or a scoop at Wynwood Parlor.
• Frost Science Museum: Planetarium shows, an aquarium, and hands-on exhibits that land well with teens.
• Beach alternatives: Crandon Park (Key Biscayne) is calmer than South Beach and great for families.

Another teen-approved Miami boat option (swap if you prefer sightseeing to speed):

Miami Skyline 75 Minute Luxury Cruise of Millionaire's Homes

For accommodations, remember spring break fills quickly—book early near beaches or with parking included. For flights in and out of South Florida or the Keys, compare options here: Trip.com | Kiwi.com. For stays: VRBO Miami, Hotels.com Miami, VRBO Key West, Hotels.com Key West.

In five days, you’ll move from Miami’s mural-splashed streets and Everglades wildlife to Key West’s coral waters and postcard sunsets. It’s a spring break that blends thrills, culture, and easy beach time—perfect for making memories with a 15‑year‑old who wants “something cool” every day.