The sun is going down over Key West as my family strolls around Mallory Square. There is perhaps no place that typifies the Florida Keys more than this historic square along the pier at the southern tip of the United States. Every evening before sunset, the pier comes alive with perhaps the most eclectic assembly of street performers imaginable. And that’s what the Florida Keys are all about—eclectic and quirky, charming and rustic, what the locals call “Keysey.” Throw in sea, sun, and a myriad of fun and intriguing attractions, and it’s easy to see why this destination is among the most endeared of vacation spots.

The Keys comprise a 125-mile long island chain south of Miami that begins with Key Largo, of Bogey and Bacall fame, continuing on down to the Middle Keys of Marathon and culminating in Key West, the southernmost point in the United States. U.S. Route 1 connects the island chain with highlights along the way easily navigated by mile markers (“MM”), Key West being at MM zero and the numbers climbing up from there.

Upper Keys—Snorkeling & Fishing Mecca

• The sunset celebration is a daily ritual where performers and crowds gather to enjoy the fading sunlight at Mallory Square in Key West.
• Bob Krist

The Upper Keys around Key Largo are perhaps best known for their good snorkeling and diving. John Pennekamp Coral Reef State Park, site of the nation’s first underwater park, is one of the area’s highlights at MM 102.5. The colorful coral reef, complete with a famed bronze statue of Christ of the Abyss, can be viewed via glass-bottom boat. John Pennekamp is also a popular spot for camping, canoeing and kayaking.

Islamorada in the Upper Keys is a center for fly-fishing. “This was the birthplace of fly-fishing,” Sandy Moret, owner of Florida Keys Outfitters in Islamorada, told me. “It’s a mecca. Any avid fly fisherman is likely to come to Islamorada at some point. The most world records are here.” (I know this all too well as an acquaintance of mine holds several of those records.) Moret cites the appeal of seemingly endless flats, where bonefish, snook, and tarpon are easily visible for the taking.

It is just such tarpon that make for a fun family activity at the Hungry Tarpon restaurant overlooking Robbie’s Marina at MM 77.5 in Islamorada. Robbie’s Marina is renowned for drawing enormous tarpon that can be hand fed, though sometimes even grown men jump as the tarpon hurl their bodies above water for handouts.

• The 13,000-square-foot Key West Butterfly & Nature Conservatory is one of three major butterfly facilities in Florida and houses between 750 and 1,200 butterflies.
• Roberto Rodriguez

The Marriott Key Largo Bay Beach Resort or Ocean Pointe Suites at Key Largo are good family friendly places to stay in the Upper Keys, as is The Islander Resort, Cheeca Lodge & Spa, and Pines and Palms Resort in Islamorada.

Middle Keys—Dolphin Central

In Marathon, the halfway point between Key Largo and Key West, don’t miss the Dolphin Research Center at MM 59. The center is home to 19 dolphins, who educate guests on the sea mammals’ likes and dislikes (hula hoops are a favorite of one dolphin), as well as a research hub, where scientists study dolphin behavior. It’s also where the original Flipper movie was filmed. The center’s setting is like old Florida, with sand underfoot and the wind rustling the tiki roofs surrounding the lagoons—very “Keysey,” as I’m told. Plan on visiting the center for an hour, and you may stay the day. Read more about dolphin-related adventures in the Florida Keys here.

In nearby Duck Key, you’ll find the Hawks Cay resort, which recently completed a $35 million renovation. It’s a luxury property, marina and spa that is quite family friendly. There’s a pirate ship pool for younger kids (one of five pools in all), a ‘tween and teen room, snorkeling, kayaking, parasailing and more. And here too, you’ll find dolphin activities. My 6-year-old daughter and I each participated in dolphin encounters, getting up close and personal with the mammals in a very natural setting. It was like the dolphins had invited us into their world, instead of us intruding on them. The resort’s villas are perfect for family travel and relatively reasonable in cost. Rates start at $395 a night.