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In search of family fun in the sun? Look no further than the Florida Keys, a great place to vacation year-round, with plenty to see and do for all ages. Plan a week-long getaway starting in Miami and driving the Overseas Highway (Highway 1), making several stops in each direction to truly do this gorgeous stretch of the Sunshine State just right.
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Day 1
Hawk’s Cay Resort
Not much to see and do straight out of the gate, but about an hour-and-a-half south of Miami you’ll reach famed Key Largo, where weary travelers can put an end to repeated “Are we there yets?” and stave off hunger with a stop for lunch at the colorful Key Largo Conch House. It’s a great introduction to a more laidback lifestyle, where you may convince kids to forgo macaroni and cheese for mahi-mahi fish sticks, while you sample more sophisticated fare, like red snapper fish tacos.
Drive on to Hawk’s Cay Resort on Duck Key, newly reopened in August 2018 after a $50 million post-Hurricane Irma renovation. Most guests spend time on property at either the main pool and its adjacent, sheltered lagoon (great for kayaking and paddle boarding) or the adults-only pool, but little ones are better served at the Coral Cay activities center and its Pirate Ship Pool.
Venture off-property for dinner at Lighthouse Grill at Faro Blanco Resort in Marathon, where the sun sets over a historic lighthouse. Dine on everything from pasta (for little landlubbers) to dishes such as grilled yellowfin tuna with wasabi mashed potatoes. Listen to live music on the outdoor deck while capping off your day with what is sure to be the first of many Key Lime pies.
Day 2
Recovering sea turtle
Grab an early morning breakfast at the Hawks Cay Resort Marketplace before driving over to the Turtle Hospital in Marathon, a great place to learn about the treatment of injured and sick sea turtles with an ultimate goal of returning them to the wild. Educational tours showcase Loggerhead, Green, Hawksbill, Leatherback and Kemp’s Ridley turtles, while highlighting curative programs and surgeries. Since turtles here are strictly hands-off for visitors, plan your next stop at Florida Keys Aquarium Encounters for an up-close-and-personal experience with sea life you won’t soon forget, including touch tanks and opportunities to snorkel and dive with tropical fish and stingrays.
Grab a late lunch at Castaway Waterfront Restaurant & Sushi Bar. Though it may not look like much from the outside, this popular Marathon restaurant offers indoor and outdoor waterfront service, with an extensive sushi menu, shellfish dishes, kids’ options—such as popcorn shrimp, corn dogs and fish sandwiches, among more traditional fare. Adults can whet their whistles with one of 52 beers on tap.
Spend the rest of the afternoon back at Hawk’s Cay Resort, taking advantage of onsite activities like snorkeling, fishing kiteboarding, paddle boarding, SNUBA and sunset cruises via the marina. In the evening, take the resort trolley over to Angler & Ale for a casual dinner on the waterfront. Save room for their signature dessert—Caribbean Banana Split, or the white chocolate chip macadamia nut bread pudding. Take the trolley back to the resort and digest in front of the poolside fire pit.
Day 3
Havana Cabana at Key West
Check out of Hawks Cay Resort and head to Key West, stopping at Boondocks Grille in Ramrod Key for lunch along the way. The “Largest Tiki Bar in the Keys” boasts extensive main and kids’ menus, 18 holes of miniature golf, a gift shop and nightly live entertainment. Kids’ meals are served on take-home Boondock’s frisbees.
Continue south to Havana Cabana at Key West, a new resort boasting the largest pool in the city. Though the resort is about 15 minutes from downtown Key West, a free shuttle runs to and from the property, dropping off in the heart of the action. Spend the rest of the afternoon enjoying the pool, with its weekly live entertainment and events, poolside games, Mojito Pool Bar and Floridita Food Truck for libations and snacks.
Grab the shuttle into town in the early evening and join Sebago Watersports for a 6:30pm sunset sail. Opt for the more premium excursion, including an open bar and a variety of hors d’oeuvres to tide you over until dinner. The captain occasionally lets children steer the boat, which is equipped with a bathroom, and plenty of covered- and open-air seating.
Back on dry land, walk along the harbor to A & B Lobster House, a Key West fixture since 1947. Try the sesame-seared tuna tataki followed by a rich Caribbean lobster Oscar (served with crab meat and hollandaise sauce), any number of other fish and shellfish options, or an array of steaks, washed down with cocktails, such as the Hurricane or the Hemingway Mule. Grab the last hotel shuttle at 10:30pm for a much-needed night’s sleep.
Day 4
Don’t leave the island without first having a slice of Key lime pie.
Have breakfast in the thatched-roof-covered courtyard by the pool. The Floridita Food Truck serves up hearty fare, such as omelets and decadent French toast. Don swimsuits, hats and sunscreen, and grab the trolley to town for a Fury Water Adventures three-and-a-half-hour excursion. A catamaran travels offshore to a docking point and serves as home base for activities such as parasailing (up to three flyers at a time), jet skiing on a guided tour, banana boat rides and playing on a mini water park of inflatables. Activities are great, even for novice adventurers, and the staff is very amenable to modifying activities for less experienced participants. Snacks and drinks are included; restroom facilities and shade are available.
Back in Key West, stop to shop for all things Key Lime at Kermit’s Key West Lime Shoppe on Elizabeth Street, have a bite at the Kermit’s Kitchen Café, or sample a chocolate-covered Key Lime Pie on a stick and cool off on the patio by the Koi pond and garden.
Spend the afternoon at any number of local attractions, including the Ernest Hemingway Home and Museum, where kids can keep an eye out for descendants of the author’s six-toed cats; the Key West Butterfly and Nature Conservatory, featuring butterflies from around the world and exotic birds; or the Mel Fisher Maritime Museum, for brushing up on the maritime history of Florida and the Caribbean.
Do dinner at Turtle Kraals Bar & Restaurant, located along the historic seaport boardwalk. Head upstairs to the Tower Bar deck and dine outside for a perfect sunset view (try a Key Lime Martini). Twice weekly turtle races begin at 7pm in season, weather dependent, and are emceed by Turtle Master Clark Whitt.
Day 5
Lively Duval Street, home to Margaritaville and other Key West haunts
Take the shuttle into town for breakfast at Blue Heaven amid the roosters strutting freely on the lively outdoor patio. It’s a 20-minute walk from the shuttle drop off, or you can grab a ride share. Kids love the available assortment of pancakes, while Blue Heaven Benedicts, omelets and other fare more than satisfy adults. Save room for their famous Key Lime Pie, then walk off your indulgences as you head back to downtown.
Hop on the Conch Tour Train at one of its embarkation points for a fun ride past some noteworthy homes and attractions. Sit back and enjoy the ride while the driver provides colorful commentary; hop on/off at select points or take the whole trip at once. At the Front Street Depot, visit the Shipwreck Museum and the Key West Aquarium. These aren’t extremely comprehensive attractions, yet they are easily manageable for the whole family and perfect for an hour or so prior to grabbing lunch at Margaritaville on Duval Street, bringing to life singer Jimmy Buffet’s songs and a relaxed state of mind in a colorful, casual eatery.
In the evening, drive over to Stock Island for dinner at Matt’s Stock Island Kitchen + Bar. Dine on the patio overlooking a colorful, but much quieter marina than in Key West. Start with The Commodore for two or The Admiral for four, featuring a selection of seafood served in a fisherman’s tackle box. Black Grouper and Fish & Chips are among the house specialties. Kids love the s’mores milkshakes.
Day 6
Get an early start and splurge for one night at Casa Marina, a historic resort established in the 1920s and not far from all of the action. Polish off a quick breakfast at on-site Flagler’s Café before heading out to the oceanfront pool. Reserve a cabana for the day and head over to the beach for a private sand sculpting class with award-winning sculptor, Marianne van den Broek. She will tailor each session to the age and number of sculptors, helping them create anything from a castle to a family pet or portrait. Creations stay up for the entire day, so you’ll be able to come back and admire your handiwork later. Cool off in the pool post-session and then order lunch from Sun Sun to eat either on the restaurant patio or in your cabana, amid opportunistic iguanas. Sip a Casa Key Lime Colada while kids enjoy virgin frozen daiquiris or coladas. A menu featuring fish tacos, chicken tenders, burgers and more will satisfy your hungry crew.
Freshen up for dinner and head back over to Stock Island for a meal at Hogfish Bar & Grill. The favorite local spot is a casual, thatched-roof-covered eatery right on the water. Sit at picnic tables inside the restaurant or on its adjacent pier alongside the marina. Hogfish is a specialty here, as is ceviche, fish spread, tuna nachos and the self-proclaimed “best Baja-style tacos in the Keys.”
Day 7
Playa Largo
Time to head back. Stop for brunch at the Hungry Tarpon at Robbie’s of Islamorada and enjoy pancakes, French toast, omelets, breakfast burritos, scrambles and more. There’s plenty to do here besides eating. Colorful outdoor shops and food vendors are scattered about and there’s tarpon feeding from the pier. You can also rent a boat, kayak or paddleboard, take a guided jet ski or kayak tour, book a fishing trip, parasail, snorkel or head out on a sunset cruise.
In the late afternoon, check into Playa Largo Resort and Spa in Key Largo. The newer, 14-acre, 177-room property opened in late 2016. A fitness center and full-service spa, beachfront water sports, large pool and hot tubs keep guests on property busy. Rent a cabana or grab a hammock or lounge chair and relax before freshening up for dinner at The Fish House, just a few minutes away.
A longtime local favorite, The Fish House specializes in seafood caught fresh daily, including crab, shrimp, lobster, scallops, oysters, clam and conch. The restaurant also features a fish market for those who want to bring local items home. A kids’ menu includes everything from baby back ribs and chicken fingers to a fried fish basket or fried shrimp. Save room for peanut butter or Key lime pie.
Day 8
Break the surface at Pennekamp State Park.
Grab breakfast on property at La Marea with an extensive hot and cold buffet (kids’ pricing available). Depart for a snorkel or glass bottom boat tour at Pennekamp State Park, the first undersea park in the United States, established in 1963 and extending three miles into the Atlantic Ocean. It’s also possible to scuba dive, kayak, paddleboard and rent a boat from here.
Grab lunch after your park visit at Snook’s Bayside Restaurant & Grand Tiki Bar, right on the beach in Key Largo. The casual eatery serves up everything from truffle lobster mac and cheese to a colossal crab meat cocktail, lobster Reuben, and a pistachio-encrusted mahi wrap. Sip a frozen Key Lime colada or piña colada from an extensive array of tropical drinks. Kids under age 10 can opt for a frozen fruit smoothie with their meal.
Head back to Playa Largo for a poolside afternoon. The resort boasts inflatables for the kids, while adults can relax on ledges in the water or on nearby lounge chairs. Later, watch the nightly sunset celebration, Eventide, where guests cast away bad energy by writing their intentions on paper that is thrown into a floating bonfire that’s sent out on the water. Live music plays in the background and drinks and food are available. After the sun sets, head down the beach to Sol by the Sea (advance reservations are essential) for an elegant meal with views of the marina and Florida Bay. Toast the end of your last night in the Keys with a Dragon Fruit Mojito or Largo Punch, saving room for make-your-own resort s’mores around the firepit.
Day 9
Before heading back to Miami, stop for breakfast at Mrs. Mac’s Kitchen, founded in 1976. The longest running restaurant in Key Largo offers a glass of champagne or a mimosa with any ordered board special or you can add your first glass to any breakfast for $2. House specialties include lobster and grits, crab cake benedict, and Juan’s caramel bacon waffle or French toast. This casual, laid back diner is the perfect place to end your days in the Keys.
Suzanne Carmel
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We head home tomorrow. We have followed almost your exact itinerary. This has been great. Thank you so much for putting it out there. We have 2 kids; 17 and 13, they have had a blast. Highly recommend.