10 Reasons to Go To Pensacola

There was a time -- before tanning butlers and 20-story mega-resort complexes -- when Florida was the sort of place where you could roll up to the beach right in your pick-up, spend the day frolicking in transparent turquoise waves and sugar-white sand and then head off to the local roadside shack for a hearty fish sandwich and an ice-cold beer. Thankfully, this sort of destination still exists. Tucked into the western corner of the Florida panhandle, just shouting distance from the border with Alabama, is Pensacola, a small seaside community that is a little bit country and little bit rock 'n roll. This 450-year-old city, which has been administered at various points in history by the Spanish, the French, the British, the Confederacy and the U.S., offers up vintage forts for exploring, protected seashore for kayaking, and plenty of beachside accommodations -- all at a fraction of the price (and a fraction of the traffic) of southern Florida destinations like Miami.

The best part: it's all served up with a heaping dose of Southern charm. A round-up of our favorite spots:

Best time to go to Pensacola: May through August, but September is nicest if you like to avoid crowds.

1. The Paradise Inn

Situated right smack on the bay in Pensacola Beach, this vintage waterside motel not only offers newly-remodeled rooms with contemporary decor, firm mattresses, AC, internet and a swimming pool, it has one of the best bar scenes in town -- at the on-site Paradise Bar & Grill. Here you can sip on a cold one while catching live music and spectacular water views. Tired of looking at the bay? Cross the street and you'll be right on the beach -- an uncrowded array of undulating dunes made of dazzling crystal quartz sand.
850/932-2319; 21 Via de Luna Dr., Pensacola Beach; doubles from $90.
http://www.paradiseinn-pb.com

2. Peg Leg Pete's

There are oysters and there are oysters. And Peg Leg Pete's shucks only the finest bivalves in the state -- drawn from the clear waters of nearby Apalachicola. Even if you're a raw oyster purist, don't miss an opportunity to try their Spicy Lafittes: oysters doused with cheddar, bacon and jalapenos, quickly broiled and served with drawn butter. These sublime, artery-clogging treats are worth the price of airfare alone.
850/932-4139; 1010 Fort Pickens Rd., Pensacola Beach; raw oysters from $7.95/dozen.
http://www.peglegpetes.com

3. Key Sailing

Kayaking, sunset cruises, snorkeling excursions, waverunner and Hobie CAT rentals are what you'll find at this reliable, long-time outfitter run by blue-eyed charmer and Pensacola native Captain Kirk Newkirk. Looking for an adrenaline rush? Then sign up for a parasailing excursion, and glide more than 1,000 feet over the turquoise waters of the beach and bay.
850/932-5520; 500 Quietwater Blvd., Pensacola Blvd.
http://www.keysailing.com

4. The Sandshaker Lounge

This down-home drinking hole is equal parts honky-tonk and beachside party spot, known for its legendary nine-hour happy hours (which runs from 10 a.m. to 7 p.m.) and the spectacular array of local color that can be found bellied up to the small, interior bar. In the summer, the expansive outdoor decks get packed with vacationers sipping on the lounge's signature drink, the Bushwacker, a frozen, highly-intoxicating blend of Kahlua, rum, coconut and milk (among a variety of other secret ingredients). It's a grown-up milkshake of the dreamiest kind; just don't let the sweet taste fool you -- these seemingly-innocent cocktails pack a punch.
850/932-2211; 731 Pensacola Beach Blvd., Pensacola Beach, drinks from $4.
http://www.sandshakerlounge.com

5. Fort Pickens

Protected within the confines of the Gulf Islands National Seashore, this historic fort, which dates back to 1834, once guarded the entrance to Pensacola's harbor and was the site of some storied Civil War skirmishes. (Some of the first shots in the war were allegedly fired here.) In addition, the famous Apache military strategist Geronimo was imprisoned here from 1886 to 1887 (after outwitting the U.S. army for years). Visitors can explore the old cells and munitions chambers -- including the room that was rumored to have contained the infamous Geronimo. Pack a swimsuit and you can follow up your hike with a dip in the area's crystalline waters.
850/934-2600; Santa Rosa Island; admission $3.
http://www.pensacolasgreatest.com/FortPickens.html
http://www.nps.gov/guis/index.htm

6. Surf Burger

All that hiking and kayaking and swimming builds up and appetite. When you're feeling ravenous, head to this popular second-story burger joint run by two surfers named Mike and Dave. This is THE spot in Pensacola to pick up a juicy 1/3 lb. burger with all the fixings, as well as a basket of hand-cut fries. (No bags of frozen potatoes here.) What to wash it all down with? One of Surf Burger's legendary super-thick shakes.
850/932-1417; 500 Quietwater Beach Blvd., Pensacola Beach; burgers from $7.75.
http://thesurfburger.com

7. The Fish House

The best sunset and moonrise views in Pensacola can be found on the outdoor terrace of this bustling dockside establishment in the city of Pensacola proper. Night after night, locals and tourists alike pour in for the restaurant's excellent fresh seafood (don't miss the crab claws sauteed in garlic) and the voluminous house specialty: Chef Jim Shirley's Grits a Ya Ya, a cheesy mountain of hominy grits stacked with bacon and seared shrimp -- each order is so big it could easily serve four.
850/470-0003; 600 S. Barracks St., Pensacola, grits $19.95.
http://fishhouse.goodgrits.com

8. Paradise Beach Homes

http://www.paradisebeachhomes.com

If you can get a six-pack of friends together, avoid the expense of a hotel altogether by renting one of the sprawling beach homes located east of Pensacola Beach's main drag. Units -- many of which are right on the water -- come stocked with full kitchens, BBQs and ample terraces for lounging. If you reserve ahead, you can even have beach cruisers and groceries waiting upon your arrival.
850/916-0777; 27 Via de Luna Dr., Pensacola Beach.

9. Downtown Pensacola

Once you've had enough beach and are ready for a taste of culture, head into Pensacola's historic downtown, where narrow streets lined with vintage structures evoke the charm of French New Orleans. Here, the Pensacola Museum of Art stages art exhibitions in a building that once served as the town's jail (note the bars that still protect some of the galleries). On Palafox Place, the main drag, the Saenger Theatre, a Spanish baroque-style show palace that dates back to the 1920s, stands resplendent after a recent top-to-bottom makeover. And, across the street, at the Global Grill, in-the-know locals dip into a wide array of Cajun-meets-the-Mediterranean tapas prepared by the personable chef, Frank Taylor. (Don't miss his New Orleans-style BBQ shrimp in butter sauce.)
Pensacola Museum of Art: 850/432-6247; 407 S. Jefferson St.; admission $5.
http://www.pensacolamuseumofart.org
Saenger Theatre: 850/595-3850; 118 S. Palafox Place.
http://www.pensacolasaenger.com
Global Grill: 850/469-9966; 27 S. Palafox Place; tapas $3-14.
http://www.dineglobalgrill.com

10. The Mullet Toss

If there's one reason to make the journey to this corner of the state, it's to visit the Flora-Bama bar for the annual mullet toss competition, now in its 25th year. Every April, without fail, hundreds of devoted mullet tossers (as in the fish, not the haircut) arrive at this ramshackle bar that sits right on the Florida-Alabama state line on Perdido Key to throw freshly caught mullet as deeply into Alabama as they possibly can. (In '09, one participant managed to toss his mullet a whopping 198 feet.) The rest of the year, this is a great spot to kick back a cold one while taking in the views of the broad, white-sand beach.
850/492-4611; 17401 Perdido Key Dr., Pensacola.
http://www.florabama.com