The Keys' Kickiest Resorts - Grandparents.com

Alma H. Bond discovered the magic of the Florida Keys and of being a grandparent about the same time. Bond, a psychoanalyst, was living in Key West when she wrote her book On Becoming a Grandparent: A Diary of Family Discovery (Bridge Works, 1994).

Her then-five grandchildren (now there are seven), "especially loved the Conch train. I had to ride with them every time they came, which was often," she remembers. "All five miss Key West dreadfully since I moved back to New York," she says. "They are always asking when we can (go back to the Keys)."

Photo courtesy of The Conch Tour Train

Mangrove shallows and sandy shores afford the same timeless, seaside discoveries that have always attracted families to the Keys. Yet, the hospitality scene has also gone upscale with fine dining and modern, luxury accommodations. The Keys’ old-line resorts, including Cheeca Lodge, Hawk’s Cay, and Casa Marina, have kept up to date and then some, while many glamorous new resorts pepper Florida’s Riviera.

Is this the year you’ll take your grandchildren to America’s drive-in Caribbean?

Keys to the Keys

As U.S. 1 hopscotches southwest to Key West, it touches only a fraction of the Keys’ 1700 islands. They’re referred to as the Upper (closest to Miami), Middle, and Lower Keys. Addresses are in Mile Markers (MM) indicating miles from Key West. The higher the MM, the closer you are to Miami. The Atlantic washes one side of the islands, the Gulf of Mexico the other.

By car it’s about 90 miles Miami to Marathon, 150 miles Miami to Key West. Flights go into Miami, Marathon and Key West; a high-speed ferry runs from Fort Myers Beach to Key West.

Until bridges were built in the 1930s, the Keys were so isolated that Key West had closer ties to the Bahamas than to Miami. Now this densely developed island is also the most unique. It’s rebellious to the point of what some call debauchery, yet it also offers some of the most sophisticated resorts, important historic sites, and a nightly sunset celebration.

Try these Keys resorts, where the generation gap is bridged as perfectly as U.S. 1 itself.

Mariner’s Club, Key Largo

Photo courtesy of Mariner�s Club

The closest resort to Molasses Reef, Mariner’s Club is a natural for divers, or you can charter a boat and teach the grandkids to fish. A day spa is nearby and golf courses are 35 and 45 minutes away. Book a townhouse with laundry and gourmet kitchen. Play tennis, swim in big pools, soak in the Coral Jacuzzi Grotto and rent canoes, kayaks, wave runners or boats. There’s live entertainment nightly in the historic (1947) Mandalay Restaurant.

Cheeca Lodge & Spa, Islamorada

Photo courtesy of Cheeca Lodge & Spa

You may remember Cheeca Lodge from fishing trips with your own grandparents. Now smartly refurnished, it offers family suites with one or two bedrooms. Children ages 3 to 12 play in Camp Cheeca while grownups bliss out in the spa, play tennis or golf, fish, sail or paddle. Dining ranges from dressy gourmet to tiki bar snacking. Small boats will take groups of six on an educational, entertaining, Indian Key environmental cruise.

Lime Tree Bay Resort, Long Key

Settle into a South Seas cottage with full kitchen at an intimate resort — just 33 units — with its own beach on the Gulf side of the Keys. Lime Tree Bay features 100 palm trees perfectly positioned for hanging up hammocks. Ask for the second-story Treehouse Suite with a tree growing through the covered porch. Beach comb and build sand castles with the grandchildren, then barbecue hot dogs in the cookout area. The resort has a swimming pool and tennis courts. Boat and bike rentals and an Italian restaurant are nearby.

Hawk’s Cay Resort, Duck Key

Hawk’s Cay Resort opened as a rustic Indies Inn in 1959. Still one of the Keys’ premier resorts, it’s undergoing a massive, $30 million makeover through 2008. Reserve one of nearly 300 two- or three-bedroom villas and sign up for fishing, dolphin encounters, eco-kayaking, sail school, tennis lessons, family noodle races and the hair plaiting that little girls love. There’s even a pirate ship beached in one of the pools. Children and teens have their own Indies Club.

Indigo Reef Marina Homes Resort, Marathon

Photo courtesy of Indigo Reef Marina Homes Resort

You can book a fully equipped, three-bedroom, 2.5-bath home overlooking the Gulf of Mexico at Indigo Reef Resort. It’s a low-key place where generations laze on the breezy porch, cook in the gourmet kitchen and get wet in pools or on a reef dive. Guests have privileges at neighboring Tranquility Bay, which has planned activities for all ages.

Tranquility Bay Beach House Resort, Marathon

Observe Gulf of Mexico sunsets from your two- or three-bedroom home while enjoying 24-hour room service and daily maid service at Tranquility Bay. Dine in the Butterfly Café with its delightful children’s menu and boffo Sunday brunch. Play castaway on one of the Key’s longest, whitest beaches or take your pick of planned activities. Fish, snorkel or go reef or wreck diving.

Westin Sunset Key, Key West

Photo courtesy of Westin Sunset Key

Have a Robinson Crusoe family vacation in a one- to three-bedroom cottage on a real island just off the Westin Key West Resort. Swim off sugar beaches or in the pool. Eat in the island’s own restaurant or have a chef come to your kitchen. If you want to go into Key West for dining and sightseeing, the free ferry runs around the clock.

Know Before You Go

When comparing rates, note whether the 11.5 percent tax is included. When resort fees of up to $40 per person per day are required, know what you get for the money. Weekend rates are often higher. Save by going Monday through Thursday.

If you’re staying in a cottage colony, maid service may be unavailable or at extra cost. Private home rentals may come with a private club membership (golf, private beach). Ask.

Find out whether children’s programs operate all year or just during school holidays.