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On the eastern shore of northernmost Florida amid live oaks dripping with Spanish moss sit two communities, one known for history and the other for luxury.  As one of the oldest cities in the United States, St. Augustine wears its Spanish heritage proudly as evidenced by the many preserved structures enclosing Old World gardens at the edge of cobbled streets.  On Amelia Island, it’s a new day and time to play, whether it’s golf, tennis, swimming or any number of activities graciously arranged by your full-service concierge.  This leisurely pace is a stark counterpoint to the full-tilt energy of Florida cities like Miami, Orlando and Tampa and sometimes, that’s a very good thing.

St. Augustine

A tip o’the cap goes to preservationists who have worked hard to restore St. Augustine’s Old City to a representation of its colonial days.  As a result, the history lesson for you and your kids is a worthwhile one and can be punctuated by the beaches and landmarks dotting the landscape.

Where to stay     The Casa Monica Hotel has as its roots the late 19th-century transformation of St. Augustine into a winter playground spearheaded by railroad tycoon Henry Flagler.  Purchased by the Kessler Collection in 1997, the century-old hotel underwent a complete renovation and today shines as a luxurious city-center hostelry.  A lobby rich in tapestries and chandeliers leads you to a room with creamy yellow walls, wrought iron bedding napped in high-thread-count sheets and seating area graced by a charming pullout sofa.  A shimmering cube of a pool rests on a second-story deck and is surrounded by plump, spacious chaises; back in the lobby, the buttery croissants served at Cafe Cordova will transport you to Paris.  Guest privileges at the Serenata Beach Club on nearby Ponte Vedra Beach must be indulged, since the Club is a seductive blend of pools, palm trees and Spanish-style breezeways guaranteeing a perfect day.  The Casa Monica’s many charms will not be lost on children – rather, they’ll be delighted to roam the halls and courtyards of their castle in the city.  95 Cordova Street  (904) 827-1888; casamonica.com.  Doubles from $149; Internet rates and special packages available.

History and Mystery     A walk through St. Augustine’s compact Old City is the first order of business.  Begin at the City Gates, connectors for a walled defense built by the Spanish in the late 1700s.  The gates are made of coquina, soft limestone quarried locally and embedded with countless tiny seashells.  You’ll spot coquina often as you walk about the historic district, to the delight of kids.  Heading down St. George Street, the area’s main thoroughfare, stop in at the Oldest Wooden Schoolhouse, dating to 1750 and staffed by mannequins playing the role of teacher and students.  Your latter-day student will quickly get how tough children had it centuries ago and find relief in the lush courtyard replete with ring-me bell and wishing well.  Across St. George is the Colonial Spanish Quarter, a re-created mid-18th century village where re-enactors in costume and in character ply their trades.  Expect your kids to be full of questions for the blacksmith, the woodworker and the sailmaker.  Further down the street is the Cathedral-Basilica of St. Augustine, a Spanish-Mission style building that is the oldest Catholic parish in the U.S.  Enjoy the cooling nave as you point your kids toward the stained glass windows depicting St. Augustine’s life and work.  The Plaza de la Constitucion sits across the street and is a leafy retreat that once was, and still is, the heart of the Old City.  Crossing busy King Street and a block to your right is the Lightner Museum, housed in the former Alcazar Hotel.  The present collection was the pride of Otto C. Lightner, former editor of Hobbies magazine; the museum cafe is a must for lunch and sunk into what used to be the hotel’s swimming pool.  Back on St. George, make your way to Artillery Lane, a narrow cobbled street that signals your entrance to the oldest of Old City.  It dead-ends at Aviles Street, considered the oldest street in America.  To your left is the Spanish Military Hospital Museum, which recreates a military hospital of the 18th century.  Rest assured you’ll be grateful for modern medicine once you leave.  From here, head back across the Plaza and one block over to Charlotte Street, which is brimming with shops, bed and breakfasts and outdoor cafes.

Return to the Spanish Military Hospital later that evening for “A Ghostly Encounter,” a walking tour offered by Ancient City Tours.  One of the city’s many ghost tours, this one starts in the city’s only certified haunted building.  The two-hour trek is chockablock with ghost stories and tall tales and it’s up to you to figure out what’s true.  When the tour concludes at the Tolomato Cemetery, you may be surprised to find your children more cheerful than concerned and props for that go to the amiable guide.  ancientcitytours.net

Beachy Keen     The beaches of St. Augustine are something of a closely-held secret, which may be why so many of them are pristine.  Ponte Vedra Beach, due north of the city center, is a wide expanse composed of millions of seashells that will tickle your feet and your fancy.  Nearby Vilano Beach is another relatively uncrowded beach while St. Augustine Beach is a happening stretch of hard-packed sand that is both car- and people-friendly.  The four-mile, soft sand beach found at Anastasia Island State Park, south of St. Augustine, is considered by devotees to be the most perfect stretch of beach in the region.  You can also bike, hike, fish or kayak within the confines of the Park.

On the Lookout     The Castillo de San Marcos is a quasi-star-shaped Spanish fortress made of coquina surrounded by a moat once stocked with...alligators!   The Spanish, apparently, were not messing around.  Dating to the late 1600s, it was alternately in Spanish, British and U.S. hands and is still topped by nearly a hundred cannons.  The fort was attacked over a dozen times and repelled each and every one and if you time your visit for Friday-Sunday, you can witness the cannons being fired.  nps.gov/casa  Pacifist by nature is the St. Augustine Lighthouse, one of nine Florida lighthouses open to the public.  Striped much like a barber pole, it’s topped by a first order Fresnel lens that operates automatically and has cannibalized the light keeper’s role.  By all means climb the 219-step, wrought iron spiral staircase all the way to the top for a panoramic view of land and sea.  staugustinelighthouse.com

Where to eat     At O’Steen’s Restaurant, fried seafood may be the reason for coming (and come they do – arrive early) but there are many other pleasures.  The Minorcan clam chowder is a tomato-based stew flecked with datil peppers, grown hot and spicy in these parts for centuries.  The fried shrimp and, in particular, scallops are as good as advertised and sides such as fresh squash and pickled beets are sure to please.  205 Anastasia Blvd.  (904) 829-6974.  Cap’s on the Water in Vilano Beach is blessed with a picture-perfect setting on the intracoastal waterway.  Come here early, too, the better to snag an outdoor table nestled between tall trees draped with Spanish moss.  Dig into the amazing seared sesame tuna and grilled grouper and choose the sparkling tomato salad and fried plantains as accompaniments.  4325 Myrtle Street  (904) 824-8794; capsonthewater.com.  Dropped into what was a former hotel swimming pool, the Cafe Alcazar at the Lightner Museum speaks to a more genteel era.  A guitarist plays in the background while the accommodating server offers to whip up a dish for hungry kids.  Parents will revel in the cool cucumber soup and enjoy heartier fare like the curried chicken sandwich or shrimp and scallops nestled in a creamy white wine sauce and resting atop garlic mashed potatoes.  25 Granada Street  (904) 824-7813; cafe-alcazar.com.  The Cafe de Hidalgo serves salads and sandwiches but is favored by many nationalities for its singular gelato.  Open morning till evening, it’s always a good time to stop by for creamy refreshment and a refresher on your high school French or Spanish.  35 Hypolita Street  (904) 823-1196.  Spanish in name only, the Cafe Cordova at the Casa Monica Hotel is the place for singular French pastries and a warming cafe au lait.  Lobby level, Casa Monica Hotel.

What else?     This most walkable of cities needn’t always be navigated by foot.  Consider jumping on the ubiquitous red trains or green trolleys for narration as well as transportation.  The 90-minute round trip provides a good overview of the area and hopping on and off for further exploration is encouraged  redtrains.com or historictours.com/staugustine/ for the green trolleys...The St. Augustine Scenic Cruise leaves several times a day from the Municipal Marina.  The captain provides the commentary as you view now-familiar sights while at sea.  scenic-cruise.com

Amelia Island

It helps to love golf when you come to Amelia Island, seeing as how there’s a grouping of links around most every corner.  That said, there’s much more to do on this snug  island lapped by soft waves and populated with resorts that personify Southern charm.

Where to stay     The Ritz-Carlton Amelia Island is nestled amid protected sand dunes and marries nature and nurture.  The resorts’ 444 guest rooms come with ocean view and your every request will be met with “It’s my pleasure.”  Having fun yet?  Back to your room, where lemony walls are the sunny foil for the tropical duvet that drapes the king bed.  The flat-screen HDTV and iPod docking station cater to techies (wi-fi, too) while the marble bath is a nod to luxe-leaning moms.  At the heart of the resort is a meandering pool ringed by a multi-level terrace dotted with chaise longues.  Interested?  In a jiff, a smiling attendant will greet you and promptly set up your chairs.  Sunshine is in ample supply and when the gang is done, it’s time to split up:  children ages 5-12 will have a blast at Ritz Kids, a half- or full-day program of fun (animal-shaped balloons), games (limbo contest), work (digging for shark’s teeth and periwinkles) and play (sand castles and water slides); teens will be grateful for Our Space, a haven of X-box and air hockey where conversations are age-appropriate and parents and siblings won’t listen in; and mom and dad will report to the Spa, a 27,500-square-foot sanctuary whose raison d’etre is to feed body and soul.  Opened in 2006, the spa is easily one of the resort’s best features and one that cannot be missed.  The wet lounges’ sauna and steam are a pampering dream, as is the indoor lap pool with waterfall-soothed hot tub.  Treatments range from Heaven in a Hammock, a zero-gravity massage, to Hadashi, wherein the therapist is balanced from bars while using the feet to provide smooth, healing strokes.    Hard to beat, however, is the Couples Massage, where you and your beloved receive  tailor-made treatments side-by-side in a womb of a room.  More energetic are the resorts’ tennis courts, clay beauties pleasingly available on this golf-centric island.

When it’s time to unwind, head for the Lobby Lounge, where the drinks are well-mixed and an order of Yukon fries helps them go down easy.  Friday nights at the Ritz-Carlton are extra-special for both parents and kids thanks to Princess Amelia’s Treasure Hunt, a scavenger hunt conducted along the property’s many corridors and the ensuing Pirate Toast, where guests meet in the lobby and raise a glass to the weekend.  The grace note is an en-suite Pirate and Princess Tuck-in with the Princess bearing gifts and reading a bedtime story while the Pirate and his aide-de-camp, a colorful macaw, yuk it up.  Young princesses and budding buccaneers will swoon over the experience.

Mealtime is also prime time at the resort thanks to options such as Cafe 4750, which serves all day and is consistently seasonal and flavorful (do snag an outdoor table every chance you get) and the Ocean Grill, where the hearty burgers and sandwiches seem to taste better because they’re served next to the pool.  A special summertime treat is a marvelous picnic dinner served on the Great Lawn – yet another must.  During the winter months, heartier dinners can be served by request next to the Lawn’s warming chimineas.  Has this resort thought of everything?  Oh yeah, there’s also the Magic of Mixology class come cocktail hour Saturday night, where parents receive pointers and pours while kids sit wide-eyed through the barman’s sleight of hand.  Indeed, the Ritz-Carlton Amelia Island has thought of it all and all you need to do is go along for the ride.  4750 Amelia Island Parkway, Fernandina Beach  (904) 277-1100; ritzcarlton.com.  Doubles with balcony starting at $199; package rates available.

Sports of Sorts     The folks at Kelly Seahorse Ranch have set up camp at Amelia Island State Park and start their guided rides in a thickly-wooded grove.  It’s not long, however, before the trees part and you are greeted by a breathtaking ocean view.  The rest of your hour-long ride aboard your oh-so-mellow steed will be at the water’s edge, with a skittering sandpiper or two providing amusement.  kellyranchinc.com  The vibe is also mellow with Kayak Amelia, where you put out with twenty or so of your new best friends and paddle in and around the Fort George River for the next three hours.  Pass salt marshes and inlets and make your way to the Kingsley Plantation, part of the Timucuan Ecological and Historic Preserve and the designated spot for homemade chocolate-chip cookies provided by your guide.  On the way back, a sandbar beckons and everyone will be up for a swim in the warm, shallow waters.  The trip is sporting and sweet and even expert kayakers won’t feel cheated.  kayakamelia.com

More Outdoors     Fort Clinch State Park is a natural playground with numerous maritime hammocks busting forth with Spanish moss-draped live oaks.  The man-made attraction is the actual masonry fort begun prior to the Civil War and never completed, though it did serve as a military post.  No matter, the cannons are in place and kids will climb up, down and around while their parents stand top-side and take in the Atlantic view.  floridastateparks.org/fortclinch/  Equally enjoyable for hiking and beach-combing is Little Talbot Island State Park, an undeveloped barrier island with miles of white-sand beaches and plenty of wildlife viewing.  floridastateparks.org/littletalbotisland/

Where to eat     Barbara Jean’s is known for its Southern cuisine – think crab cakes, pot roast and dirty rice though it’s the homemade breads that keep guests coming back.    960030 Gateway Blvd.  (904) 277-3700; barbarajeans.com.  The Crab Trap prides itself on serving the day’s catch, which could be scallops, flounder or shrimp served alongside cole slaw and hush puppies.  Crab served, too – bib provided.  31 N. 2nd Street, Fernandina Beach  (904) 432-8578; crabtrapamelia.com.  Brett’s Waterway Cafe is a comfortable indoor/outdoor space favored by locals eager to dig into everything from fried green tomatoes to key lime pie.  Along the way, enjoy the salmon or scallops or any one of the many well-prepared entrees.  1 S. Front Street, Fernandina Beach  (904) 261-2660; brettswaterwaycafe.com.  Colorful yet low-key is Cafe Karibo, where a sprawling oak tree shades the outdoor patio.  The menu is global, eclectic and delectable and special theme nights (Wednesday is pad thai, Thursday’s curry) will win over adventurous palates.  27 N. 3rd Street, Fernandina Beach  (904) 277-5269; cafekaribo.com.

What else?     Fernandina Beach is a seaside Victorian village stocked with shops, galleries and cafes and I dare you to stay away from Fantastic Fudge, which has been making hand-dipped chocolates and thick-as-a-brick fudge for over twenty years  218 Centre Street, Fernandina Beach  (904) 277-4801; fantasticfudge.com...Just across the border in Brunswick, Georgia sits the Georgia Pig, as rough around the edges as Amelia Island is serene.  No matter, you’ll still beat a path to this pig shack for meaty ribs and sinfully-delicious pulled pork.  Choose a lacquered picnic table indoors, where the Elvis poster confirms the hunk a burnin’ love roasting out back.  2712 US Highway 17 S., Brunswich, GA  (912) 264-6664.

Elaine Sosa Labalme is a food and travel writer based in San Francisco, California. When she's not busy as a domestic goddess she's out traveling with husband Fen and seven-year-old son Steven. She hopes to be the next Charles Kuralt.