St. Augustine
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Tucked among St. Augustine’s ancient coquina-crafted buildings, cobblestone streets and carved-wood balconies are modern finds in the form of eats, sleeps and beats. The 447-year old city offers everything from upscale hipster hangouts to breezy beach town B&Bs, Mediterranean revival architecture and historical monuments. It’s Old Florida at its best, mixed with nouveau amusement.
What to Do
- San Marco Avenue Uptown District: This area is home to one-of-a-kind gift stores, art galleries and adorable boutiques like Goldfinch, which offers trendy labels like LAmade and Dolce Vita.
- St. Augustine Eco Tours: During your kayaking tour, keep an eye out for bottlenose dolphins, eagle rays with wingspans as wide as a car and manatees wrestling in the shallows.
- San Sebastian Winery: This popular winery pumps out 960,000 bottles a year. Stop by the tasting room and sample until your heart’s content (or until you topple over).
Where to Stay
- The Casa Monica Hotel: This 1888 Moorish revival-style hotel boasts eclectic interiors, two restaurants and an eyeful of artwork.
- Casablanca Inn: This restored 1914 Mediterranean revival B&B comes with sweeping views of Matanzas Bay, plus the Tini Martini Bar where you can select from dozens of vintages by the glass and listen to live jazz.
- Beachfront Bed & Breakfast: Get away from it all at this charming cottage. The intimate setting lends itself to a heavy dose of R&R.
Where to Eat
- The Beachcomber: For breakfast, sit outside under the large umbrellas for a dreamy view of the Atlantic Ocean and chow down on oversized pancakes with all the right yummy toppings.
- Santa Maria Restaurant and Fisherman’s Wharf Lounge: Feeding the fish is encouraged here (there’s a trap door by each table so you can drop crumbs into the water), but eating the fish is even better.
- Columbia Restaurant: This eatery cooks up scrumptious favorites like Paella Campesina, a luscious combination of Valencia rice with tender bits of beef, pork, chicken and chorizo, and the 1905 Salad, which is mixed tableside with tender baked ham, olives and a blend of cheeses.
For more information, visit floridashistoriccoast.com
New Smyrna Beach
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Just an hour’s drive from downtown Orlando, New Smyrna Beach is everything a beach town should be: quaint and laid-back with a beautiful stretch of surf and sand. This barrier island offers both driving and car-free beach sections; most of the action, as well as food trucks and umbrella rentals, can be found at the drive-on areas. Off the beach, there are plenty of art galleries, shops and eateries to explore.
What to Do
- Jimmy Lane Surfing Academy: If you want to catch a wave your first time on a board, take a lesson here. Book a session (rates start at $55), then meet the “NSB Old Skool Surf Bus” at North Beach Park.
- Wild Side: Rent a moped—or a beach buggy or bike. Wild Side near the Flagler Avenue beach access has the wheels so you can explore the town and shore.
- Flagler Avenue: The beach side’s main drag terminates at the Atlantic and is lined with unique boutiques, including Friki Tiki, Beachsyde Jewelers and Island Images ResortWear.
- JB’s Fish Camp: Bring your own boat or hire a fishing guide here; the restaurant will cook whatever you catch and throw in a side of fries and coleslaw for $15 per person.
Where to Stay
- Night Swan Intracoastal Bed & Breakfast: This circa 1906 estate on the Indian River offers 15 rooms in three separate homes, each filled with antiques.
- The Riverview Hotel: This 19th-century Victorian hotel overlooks the Indian River and Flagler Avenue. There’s a spa, restaurant and gift shop on the property, too.
Where to Eat
- The Breakers Restaurant: A New Smyrna institution that sits right on the beach. Try the shrimp on a stick with Key lime seasoning or one of the restaurant’s popular “Breaker Burgers.”
- Gnarly Surf Bar & Grill: International cuisine inspired by surfing destinations. And when the North Causeway drawbridge goes up, beer prices go down: select drafts are just 25 cents apiece.
- International Deli: Authentic European cuisine with a pronounced German accent served in a casual setting.
- Mi Mexico: Good, cheap Mexican food in a place that doesn’t mind sandy swimwear. The à la carte tacos start at $1.25 each.
For more information, visit nsbfla.com
Mount Dora
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Don’t let the lack of mountain stop you. This slice of Old Florida is just 30 or so miles northwest of Orlando and lures visitors with charming boutiques and restaurants along downtown streets that overlook the shimmering waters of Lake Dora. Established in 1874, the town hosts several annual events, including the Mount Dora Arts Festival, which attracts more than 300 artists and 150,000 visitors each February.
What to Do
- Segway of Lake County: See the whole town in just over an hour on this no-sweat seven-mile tour.
- Premier Boat Tours: Glimpses of gators and tall tales from the captain make this narrated two-hour float through the Dora Canal more than just a scenic cruise.
- Orange Blossom Cannonball: The best views on this one or two-hour roundtrip jaunt from nearby Tavares are of the train itself; this vintage ride is a thrill for train enthusiasts.
- Renninger’s Antique Center: Two miles from downtown, the 40,000 square-foot antique mecca is a must for treasure-seekers, especially during Renninger’s three-day antiques extravaganzas held in January, February and November.
Where to Stay
- Adora Inn: In-house custom dinners and gourmet lunch baskets set this chic and contemporary B&B apart.
- Heron Cay Lakeview Bed & Breakfast: Perks include spacious bedrooms, fresh juice from onsite orange trees, and hot air balloon rides that take flight from the front yard.
- Lakeside Inn: Check into one of 86 rooms or just sip a mint julep on the veranda overlooking Lake Dora. This historic landmark is celebrating its 130th birthday this year.
Where to Eat
- The Goblin Market: Shoot for a seat on the tree-shaded courtyard where views of the bricked side street and slurps of the Irish Whiskey Onion Soup alone are worth the drive from Orlando.
- Windsor Rose Restaurant & Tea Room: Traditional cucumber sandwiches and homemade pastries in a charming true-to-form British tea room.
- Cody’s on 4th: This modern neighborhood sandwich shop makes for a good lunchtime stop, especially if the tomato bisque soup is on the chalkboard menu.
For more information, visit ci.mount-dora.fl.us
St. Petersburg
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Once mocked as “God’s waiting room’’ because of its reputation as a bastion of retirees, St. Pete today boasts a vibrant downtown, grand hotels, top-flight museums and one of the best baseball teams in the major leagues. Florida’s fourth largest city, located across the bay from Tampa, is an easy 100-minute drive from O-Town on I-4.
What to Do
- Tampa Bay Rays: The Rays more than hold their own with pro baseball heavyweights like the Yankees and Red Sox. Tickets for games at air-conditioned Tropicana Field are among the most affordable in the majors.
- Beaches: Best bets are Fort De Soto Park and Pass-A-Grille. Rent a kayak at Fort De Soto and paddle out to Shell Key, where you’ll find an unspoiled beach and thousands of pristine shells.
- Salvador Dali Museum: The waterfront museum, which moved into stunning new quarters two years ago, holds the largest collection of works by the surrealist master outside of Europe.
Where to Stay
- Courtyard by Marriott/St. Petersburg Downtown: This restored 88-year-old hotel provides a reasonably priced base from which to explore the waterfront or take in a baseball game at the Trop.
- Loews Don CeSar Hotel: The pink Don, on St. Pete Beach, is breathtaking whether seen at a distance or up close. Rooms are generally small in this restored beauty, built in 1928, but the waterfront location can’t be beat.
- Vinoy Renaissance Resort & Golf Club: This grand dame could be the Don’s twin, built three years earlier. There’s nothing like sipping a drink while ensconced in a wicker chair on the Vinoy veranda.
Where to Eat
- Hurricane Seafood Restaurant: A mainstay at Pass-A-Grille Beach for more than 30 years. The Hurricane’s claims to fame—and rightly so—are its fried grouper sandwich and clam chowder.
- Ted Peters Famous Smoked Fish: This unpretentious open-air eatery is a throwback to the 1950s. The smoked mackerel—the smokehouse is on the premises—is heavenly, as is the warm German potato salad.
For more information, visit visitstpeteclearwater.com
Fort Myers
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The Fort Myers area offers soft, white sand beaches, beautiful blue skies and turquoise water. Tour the peninsula on foot or by boat, or make the trek to Sanibel Island for an afternoon of swimming and shelling. When you’re ready for a break from the sand and sun, Fort Myers Beach has a variety of shopping choices, from souvenir boutiques to surf shops. End the day with a tropical cocktail at one of the area’s many beachfront bars—and don’t miss the stunning sunset.
What to Do
- Salty Sam’s Marina: A Fort Myers Beach recreation destination for pontoon, kayak and small boat rentals, and more.
- Lovers Key State Park: This barrier island is a refuge for wildlife such as manatees, roseate spoonbills, bald eagles and bottlenose dolphins to name a few. The beach is accessible by tram or boardwalk.
- Boston Red Sox spring training: Catch a Grapefruit League game at Fort Myers’ new JetBlue Park at Fenway South, a ball field modeled after the original park. The season starts in late February.
- Edison & Ford Winter Estates: Both Thomas Edison and Henry Ford had winter retreats here. Their neighboring historic estates now form a 20-acre compound, which is open daily for tours.
Where to Stay
- Matanzas Inn: It’s easy to feel at home at this low-key boutique resort on Matanzas Pass Harbor. Shopping and restaurants are within walking distance, plus there is deepwater dockage in case you arrive by boat.
- Sanibel Harbour Marriott Resort & Spa: Located at the tip of Fort Myers, this luxury resort sits on 85 waterfront acres and features spectacular views of Sanibel and Captiva islands.
Where to Eat
- Reese’s Restaurant: Great for breakfast or lunch, Reese’s is located in a Fort Myers Beach strip mall. This family-friendly spot is ideal for casual fare on a budget, and the portions are large.
- Ford’s Garage: This neighborhood burger and beer joint in historic downtown Fort Myers is reminiscent of a 1920s service station and promises the “Ultimate Burger Experience.”
- Mucky Duck Neighborhood Pub: This beachfront restaurant on Captiva Island has been dishing up a varied menu of favorites for 37 years. Plus, they have a celebration for each sunset. That’s right, every time the sun goes down.
For more information, visit fortmyers-sanibel.com
Treasure Coast
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Florida’s Treasure Coast is an idyllic stretch on the Atlantic seaboard that holds exciting promise for travelers in need of a short weekend to unwind. Among the many cities are Vero Beach, home to a tropical paradise; Jupiter, a well-heeled beach community full of history; and Stuart, known as the “sailfish capital of the world.”
What to Do
- McKee Botanical Garden: This 18-acre jungle-like oasis is a Vero Beach landmark. Within the garden is The Hall of Giants, built in 1941 by Vero Beach entrepreneur Waldo Sexton. The unique structure houses the largest mahogany table—at 38 feet—ever created.
- Jupiter Inlet Lighthouse and Museum: Climb to the top of this historic vantage point, built in 1860, for gorgeous views of the Jupiter Inlet.
- Blowing Rocks Preserve: Jupiter’s limestone beach terrace is a dramatic sight at high tide, when the incoming waves can shoot six feet into the air over the limestone barrier.
- Treasure Coast Sailing Adventures: The historic wooden vessel Schooner Lily departs from the Stuart Riverwalk Pier for a two-hour tour.
- Lady Stuart I Deep Sea Fishing: A trip aboard this 65-foot boat, docked near the St. Lucie Inlet in Stuart, includes fishing gear, tackle, bait and license.
Where to Stay
- The Driftwood: Established in the early 1900s by Waldo Sexton, the Vero Beach
- resort has a comfortable beach house vibe. It’s appeal lies in its aesthetic—the villas appear to be built of driftwood.
- Jupiter Beach Resort: Exceptional restaurants, a spa and Caribbean-themed accommodations with ocean views await. Hammocks and fire pits are available on the path to the beach.
- Old Colorado Inn: This casual boutique hotel in downtown Stuart is located minutes from the waterfront.
Where to Eat
- Ocean Grill: This Vero Beach favorite offers top-notch ocean fare, and the beachfront location provides breathtaking views of the Atlantic.
- Coolinary Café: An innovative Jupiter eatery that mixes retro comfort food—like deviled eggs—with cutting-edge specials, such as rabbit tacos.
- Sailor’s Return: Located on Stuart’s waterfront, this popular seafood mainstay serves large, homestyle portions and offers endless drink specials.
For more information, visit treasurecoast.com
Close to Home
Here are five great escapes within a half-hour drive of downtown Orlando.
Rosen Shingle Creek
Hotelier Harris Rosen’s crown jewel is all about luxurious choices. There are four pools (from adult quiet to kiddie wading) so you can choose your noise level. The restaurants range from Cala Bella’s delectable Italian cuisine to A Land Remembered’s memorable steaks to Banshoo Sushi’s signature rolls. Each room has a view of the challenging golf course or the real Shingle Creek and its picturesque cypress trees. And the spa and fitness center can fulfill your need to relax your tired muscles or build them up. The resort also offers great golf and seasonal packages. rosenshinglecreek.com
Grande Lakes Orlando
The toughest decision you’ll have to make at Grande Lakes is whether to stay at the JW Marriott or the Ritz-Carlton. Either way, you’ll enjoy a AAA four-diamond resort with access to a stellar spa, Greg Norman-designed golf course and luxury amenities. Dine at Norman’s for Chef Norman Van Aken’s New World Cuisine at the Ritz, or take culinary lessons from a master chef at the Marriott’s JW Griffin Cooking School. grandelakes.com
Grand Bohemian Orlando
It’s the ultimate getaway without getting away at all: You’re captive at a downtown hotel laden with fine art, in a luxe room with a huge Jacuzzi and a pillowtop-mattress bed. Want more? How about jazz and signature martinis at the BÖsendorfer Lounge? Or fine dining at The Boheme Restaurant? The city views aren’t bad either. grandbohemianhotel.com
Hyatt Regency Grand Cypress
A longtime favorite of locals who want to get away without going far, Grand Cypress boasts a lagoon-style pool with water slides, and there’s also a spa, tennis, rock climbing, biking and boating. Cure your slice at the Grand Cypress Academy of Golf, tee off at one (or more) of the three award-winning nine-hole courses, or play the Scottish links-style 18 holes on the New Course. grandcypress.hyatt.com
Disney’s Animal Kingdom Lodge
Where else can you see wild animals roaming just off your balcony? These are exquisite surroundings, with the savanna-view rooms offering a parade of giraffes, gazelles, ostriches and more. Another wow factor: The African art in the lobby, rooms and hallways. All three of the restaurants are first-rate, but an absolute must is the breakfast at Boma: The goat-cheese scrambled eggs are to die for. disneyworld.disney.go.com