Southern Charm: 5 Perfect Days in the Florida Keys

Day 1: Upper & Middle Keys

If you aren’t within driving distance of the Florida Keys, you’ll likely fly in and out of Miami and rent a car to head south. While you can do Key West alone without a car, wheels are pretty necessary to see all of the hidden gems throughout the Keys that we’re going to list here.

Unlike other parts of Florida, the Keys maintain a cooler temperature in the summer thanks to the breezes. In fact, it's usually in the 70-80 degree range most of the summer months. Spring Break travel can bring peak prices, but the weather is often milder (can dip into the 60-70 degree range). Be cautious of planning a trip in September & October because of hurricane season. 

Tip: Consider flying into Miami but flying out of Key West. You will pay a little more to drop your car off at the Key West airport (budget an extra $100) but you may find it’s worth it so you can see it all. 

Key Largo

Once you’ve navigated out of Miami metro area Key Largo makes the perfect stop for a bite to eat. A sleepier Keys town, with most of the obvious amenities along Hwy 1. Hit Mrs. Mac’s Kitchen (99336 Overseas Hwy., Key Largo, FL) for a super kid-friendly environment, great food and your perfect first Florida Keys vaycay photo opp.

If you have a few hours to spare, it’s well worth a stop to go swimming or even snorkeling excursion at John Pennekamp Coral Reef State Park. Snorkeling tours are about 2.5 hours long, as are glass bottom boat tours. You can book everything at the park or in advance online if you want to guarantee your window. If you have a little less time, you can stop and let the kids enjoy the sand and surf at Canon Beach, where the remnants of a Spanish shipwreck is just 100 feet offshore.

Tip: Get a good map. We found a few dead zones, especially in the Middle Keys.

Overnight: Hawks Cay Resort at Duck Key

Make Hawks Cay Resort (61 Hawks Cay Blvd., Duck Key, FL) home-base for at least two nights if you can. We met tons of families that stay their entire week-long break right there, venturing to nearby Marathon and even driving down to Key West as day trips.

There are 5 pools + hot tubs and a salt-water swimming lagoon. The resort has a ton of daily, exciting activities for kids (like diving for jewels with the Pirate Queen Priscilla or swimming with the resident Mermaid, Coral). There’s an entire, well-stocked, craftacular Camp Hawk area that’s just a 30-second dash to a Pirate Ship splashpad (and another pool). There’s also a soccer field, playground and an 18-hole Putt-Putt course.

The resort offers everything from breezy hotel rooms to multi-bedroom villas (some with their own pools!). Following Hurricane Irma, which devastated this area, the 60-acre property underwent a 50 million dollar renovation and not a detail was left out.

Included in your resort fee you’ll get valet parking, paddle boarding and kayaking (perfect for the lagoon), bikes and access to all of the above amenities. There is also a spa and fitness room right next to the Camp Hawk, where kids ages 5 and up can hang while you treat yo’self. 

Book your room now at hawkscay.com.

Tip: Camp Hawk features environmental education camps and adventure camps for kids 5 and up, but those under 5 can use the rec area with parental supervision.

Day 2 Middle Keys

Animal Encounters, Marathon

If Hawks Cay is your base, pry yourself off the glorious grounds and head a few minutes south to Marathon where you will find the Turtle Hospital (2396 Overseas Hwy, Marathon, FL). This is the perfect family stop to teach kids about the unique habitat of the Florida Keys, and raise awareness about the threats to the local (and global) sea turtle population. We highly recommend making a reservation in advance to visit. Tours are timed and—because it’s Florida and rain can come (and go) quickly—a rainy day crowd will quickly sell the tours out.

If you’re craving more animal interaction, you can stop off at Florida Keys Aquarium Encounters (11710 Overseas Hwy, Marathon, FL) which features a ton of touch tanks—and even the opportunity to get in the tanks with the animals. If you’re staying at Hawks Cay Resort you can arrange to meet their resident dolphins through the Dolphin Connection program. (Brunch + dolphin encounter = best day ever.) Allow about an hour and 15 minutes for this experience from start to finish. 

Eating in Marathon

Don’t miss out on the authentic cuban cuisine you’ll find throughout the Keys. Cuban sandwiches come on the kind of soft roll kids adore. In Marathon you’ll find La Niña (1571 Overseas Hwy., Marathon, FL) or the Juice Paradise Cuban Cafe and Restaurant (2603 Overseas Hwy, Marathon, FL) where you can get smoothies for the kiddos and a Cuban coffee (called a colada). Pick up some Cuban sandwiches and head down to Sombrero Beach for the day. Gentle surf, turquoise waters and fine, white sand plus showers, restrooms and parking make this the perfect place to do a low-key beach day.

For dinner, try the Lighthouse Grill at Faro Blanco  (1996 Overseas Hwy, Marathon, FL) where you can eat outside in a casual-but-upscale atmosphere. There’s even a pool for the kids to splash in while you wait for dinner! Back at Hawks Cay Resort, the Angler & Ale is boathouse chic with a menu that is varied enough for adventurous palettes but tame enough for the littles. This is also another great excuse to eat Key Lime pie before heading back to your room.

Day 3 Middle & Lower Keys

Grab a leisurely breakfast buffet on the property at Hawks Cay Marketplace, or hit up the Starbucks in the gift shop for lattes and pastries. If you haven’t had a chance yet, arrange an onsite dolphin encounter at Hawks Cay, let the kids swim one last time in the pool, and then hit the road south. 

The drive to Key West takes a little over an hour with no stops but we think you’re going to want to make at least a couple stops on the way. Just past Marathon proper, you’ll cross the infamous 7-mile bridge and not long after the end of the bridge you’ll find Bahia Honda State Park (36850 Overseas Hwy, Big Pine Key, FL) arguably one of the best places to snorkel in the keys. The park itself has amenities so you can arrange your excursion there.

Detour into Big Pine Key for healthy roadside sandwiches at Good Food Conspiracy. (30150 Overseas Hwy., Big Pine Key, FL) before continuing south. 

Continue on to Key West.

Key West has a rep for being a party town, but we promise you any time of year it’s kid-friendly and a real delight for families. Parking in Key West can be tricky, so if you decide to drive to the heart of the area, be prepared for a lot of pedestrian traffic and narrow streets. There are a number of paid parking lots, some of them down little side streets, so do yourself a favor and map out a few before you get there. 

We recommend you check into Oceans Edge Resort & Marina (5950 Peninsular Ave, Key West, FL 33040) on Stock Island (Key West). It’s across the island from the downtown area of Key West, but it offers a complimentary daily shuttle to downtown every hour between 9 a.m. and 11 p.m. (picks up downtown at 30 minutes past). When traveling with kids, this takes a lot of the stress out of it. You can relax, explore and then hop on that last shuttle home! 

The Oceans Edge Resort is safe, secure and chic: the property boasts six oceanfront pools, a 165-slip marina, private balconies, a scenic harbor walk, the Yellowfin Bar & Grill for onsite dining, and access to fishing charters and snorkel boats. The resort fee ($37/day) includes access to 1 hour of complimentary paddleboard and kayak rental, free bike rentals, the shuttle, wi-fi and more. (Parking is $20/day.) The concierge can hook you up with outings and coupons for all kinds of discounts around town. Book online at oceansedgekeywest.com 

DAYS 4 & 5: Key West

Museums Not to Miss

In spite of Key West's active night life, most attractions and museums open up by 8:30 or 9 a.m. which means you can get a full day in before the cocktail crowd comes out. There are no shortage of museums (we visited almost a dozen within a short walk of one another). Here are a few highlights you and the kiddos will love: 

The Ernest Hemingway Home & Museum (907 Whitehead St, Key West, FL ) is not only a sweet oasis from the busy streets, it also features the descendants of Hemingway’s own famous six-toed cats. These cats have the run of the place and are as mellow as they come. You can pet them (but no picking them up.) If the kids are little, skip the guided tour and explore the property and historic home on your own.

The Mel Fischer Maritime Museum (200 Greene St, Key West, FL ) tells the story of this world-famous treasure hunter and includes many of the spoils he salvaged from the wreck of the Atocha. Upstairs you’ll find pirate history and a few interactive exhibits for the kids.

The Shipwreck Museum (1 Whitehead St, Key West, FL) has plenty of interactive fun for the kids but the real highlight is the view from the top of the tower. 

See what all that salvaging can buy you by paying a visit to the Audubon House & Tropical Garden, (205 Whitehead St., Key West, FL)

The Key West Lighthouse & Keepers Quarters  (938 Whitehead St., Key West FL) is right across the street from the Hemingway Home. Kids 6 and under are free and you can climb the 88 steps to the top of the lighthouse. 

Hidden gem: The Florida Keys Eco Discovery Center (35 E Quay Rd, Key West) offers free admission, educates kids about the delicate and unique eco-system of the Keys through hands-on exhibits, and is located just a short walk away from a big public playground and splashpad. 

Tip: Fort East Martello Museum (3501 S Roosevelt Blvd, Key West, FL) is located (literally) right next to the Florida Keys airport, so make a pitstop there before departing to see Robert the Doll, a reputedly haunted doll who now makes this cool old brick fort his home. 

Adventures on Land & Sea

There are a great variety of sailing excursions you can embark on, but skip them all and book on one of the historic wooden Appledore schooners. The Appledore II sails in Key West during the winter months (she heads north to Camden, Maine for the summer) and the Appledore Star sails Key West year round. This is no party pontoon—the captain and his crew work the rigging and hoist the main right before your very eager eyes. Book at appledore2.com. 

Nearby, just off Mallory Square you'll find the Key West Historic Memorial Sculpture Garden, an impressive collection of the busts of famous people who lived in Key West, from shipwreck salvagers to confectioners to playwrights. 

Tip: Don't forget to stop at the Southernmost Point in the Continental US (Whitehead St & South Street) for your classic Key West photo. 

Swap the narrow cobblestone streets for some serious sand at Fort Zachary Taylor State Park. The beach area itself offers cabana rentals, concessions, and killer turquoise water and the park include a historic fortress. 

Hidden gem: Every day at Sunset off Mallory Square there's a Sunset Celebration where buskers and performers delight locals and tourists alike. 

If you have more time at all, we recommend dedicating an entire day to visiting the Dry Tortugas National Park to explore a 19th century fort, snorkeling shipwrecks and coral reefs and more. It requires most of a full day, and it can get costly, but it's definitely a unique and memorable experience. 

Where to Eat in Key West

The rich culture of Key West, from Cuban influences to the abundance of fresh seafood, means there's no shortage of amazing cuisine. It is impossible to try every place and the beauty of Key West is once you visit, you just want to go back again and again. These are just a few spots you cannot miss. 

Blue Heaven (729 Thomas St., Key West) is an oasis unto itself. They don't take reservations, so its first-come, first-served but trust us: it is worth the wait. We love it for breakfast where the crowd is mellow and hungry for Key Lime Hollandaise on their eggs. The vibe, which includes wandering chickens, is like an artsy backyard in the tropics. Oh, and it's located where Hemingway once refereed boxing matches. 

Cuban Coffee Queen has two locations and some of the best Cuban coffee you can find in Key West. It's uber-casual and quick, meaning you can feed your hungry kiddos on the fly while upping your affine intake in style. Look for the location off Key Lime Square for real hidden gem. 

Tip: Rule #1 when you're in the Keys: you will eat Key Lime Pie. And you might even eat it for breakfast. Nearly every place has it, and they all claim to be the best. It's your duty to try them all and compare.