Updated April 11, 2021
Reliable sources claim that Florida has about 50,000 restaurants. Add to that wineries, bars, diners, and you have countless opportunities to enjoy good spirits and good times.
We scratch the surface here with some of the oldest and most popular establishments.
You can enjoy a wide variety of food, drinks, and entertainment at these places.
Alabama Jack's, Card Sound Road, Key Largo
Bern's Steakhouse, Tampa
Cap's Place Island Restaurant, Lighthouse Point
Chattaway, St. Petersburg
Clark's Fish Camp, Mandarin
Columbia Restaurant, Ybor City, Tampa
Henscratch Farms Vineyard and Winery, Lake Placid
High Tides at Snack Jack, Flagler Beach
Joe's Stone Crab, Miami Beach
Lakeridge Winery and Vineyards, Clermont
San Sebastian Winery, St. Augustine
Schnebly Redlands Winery, Homestead
Sloppy Joe's, Key West
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DAY TRIP 1
58000 Card Sound Rd, Key Largo, FL 33030.
When you are traveling to the Florida Keys down U.S. Highway 1, there are only two ways to get there.
One way is to turn left on Card Sound Road after leaving Homestead.
This takes you through mangrove swamps to a bridge that crosses Card Sound onto north Key Largo. Alabama Jack's is on the right side of the road just before the bridge.
It is a typical old waterfront restaurant. There is a nice bar inside, and plenty of inside and outside seating.
They have good seafood, including grouper sandwiches, grilled dolphin platter, crab cake sandwiches and conch fritters.
You don't go here as much for the food as for the experience. The bar serves great margaritas and there are lots of beer, wine and hard liquor choices.
They often have live music in the Jimmy Buffett style.
DAY TRIP 2
1208 S Howard Ave, Tampa, FL 33606.
When I lived in Tampa, I always took my out of town visitors to Bern’s if I had a chance.
It is one of the earliest examples of “farm to table” restaurants in Florida.
In addition to perfectly aged steaks, it has one of the largest wine collections in the world. It also has an internationally famous dessert room.
All guests are invited to enjoy tours of the huge wine cellar and kitchen. These features have made Bern’s a local favorite since 1956.
Their prime steaks are cut to order, vegetables are grown locally on the Bern's farm and sourced from the finest purveyors, and the menu includes 21 choices of caviar.
Each visit to Bern's Steak House is a memorable experience.
DAY TRIP 3
Cap’s Place Island Restaurant
(Dock Location) 2765 Northeast 28th Court
Lighthouse Point, Florida 33064.
Historic Cap’s Place was established in 1928 and is an Old Florida icon that should be visited at least once by everyone interested in Florida History.
It is on the U.S. National Register of Historic Places.
The food and service get mixed reviews on all rating sites, but people go to Cap's for the ambiance more than the food.
Many famous visitors have dined and drank at Cap's including Al Capone, Jack Dempsey, Myrna Loy, and other celebrities.
Cap’s is on the tip of a residential peninsula. You get there by a 5-minute boat ride that operates out of Lighthouse Point Marina.
The walls of the restaurant are filled with photos and newspaper clippings of the old days.
Cap’s overlooks the water with views of yachts, mansions, and shoreline mangroves.
The menu specializes in fresh fish, scallops, crab cakes, shrimp dishes and lobster. They also have heart of palm salad (swamp cabbage), and Key Lime Pie.
DAY TRIP 4
358 22nd Avenue S, St. Petersburg, FL
This old Florida establishment has been serving casual diners in St. Petersburg since 1951. It features outside dining and is a favorite of the locals.
Tourists have a bit harder time finding it because it is a little south of the downtown district of marinas and museums.
The main decorating item in this restaurant’s décor is the claw foot bathtub. They are everywhere your eye takes you and are used as planters for a botanical treasure of exotic flowers and tropical plants.
The most famous dish here is the 7-ounce hamburger loaded with everything you want and named the Chattaburger.
There are other menu items, of course, like salads and chili and they also serve beer and wine.
DAY TRIP 5
Clark’s Fish Camp
12903 Hood Landing Road
Jacksonville, Florida 32258.
You will not see another restaurant in Florida quite like Clark’s Fish Camp. It is truly unique and has been entertaining people with good food and atmosphere for decades.
The food is good, but the interior is what amazes visitors. It is stuffed with what may be one of the world’s largest private taxidermy collections.
You will be dining next to lifelike stuffed panthers, lions, deer, fish, birds and more.
Seafood is the big thing on the menu and you can find just about anything from the sea you might want. Enjoy oysters, catfish, mahi-mahi, trout, crawfish, frog legs and more.
If you are a landlubber, you can choose from a wide selection of beef offerings.
Clark’s also has a full liquor bar.
In addition to the taxidermy collection, you can watch a daily alligator feeding.
The gator, Lilly, lives in a glass cage. People waiting for their dinner table enjoy watching her lying there minding her own business.
DAY TRIP 6
2117 East 7th Avenue, Tampa, Florida 33605.
My first job after graduating from college was in Tampa. My boss took me and my wife to the Columbia, and it was one of the most fantastic experiences I have ever had.
It is the oldest restaurant in Florida, and one of the largest Spanish restaurants in the world. It has 1,700 seats in 15 different dining rooms and takes up an entire Ybor City block.
The interior architecture is breathtaking.
Columbia was founded in 1905 by a Cuban immigrant, Casimiro Hernandez, Sr., and is still operated by his descendants.
The food is delicious Spanish and Cuban cuisine, and the Sangria and other drinks are great. They have a 50,000 bottle wine inventory.
The entertainment is also fabulous, featuring a world-class Flamenco show.
The Columbia’s success has led to several other operations around Florida featuring the name, but this one is the original, and in my opinion, the best.
DAY TRIP 7
Henscratch Farms Vineyard and Winery
980 Henscratch Rd, Lake Placid, FL 33852.
Henscratch Farms Vineyards and Winery is a unique Florida winery. It's an actual small working farm.
There are 200 hens that free range under the canopy of the vineyard. Several breeds of laying hens wander the property, but one makes me think of the children’s author, Dr. Seuss.
The Aracaunas lay large green eggs. Remember the silly poem about green eggs and ham?
The winery’s small country store is built in the old-fashioned Florida Cracker style and sits above the ground with a crawl space beneath.
Inside you will find many types of wine, jams, jellies, sauces, and syrups. Products vary with the harvest season.
Strawberry preserves, blueberry dressing, and jams and jellies are displayed on the tasting counter, so you can try a sample and sip some wine.
They also sell eggs and raw honey from their own hives.
DAY TRIP 8
High Tides at Snack Jack
2805 South Oceanshore Boulevard
Flagler Beach, FL 32136.
Snack Jack has been at this beachfront location since 1947. It is directly on the ocean and every booth or table has a view of the rolling surf.
There is also outside dining.
The menu of course is loaded with seafood dishes, conch fritters, beer, wine, salads and a large assortment of options ranging from sandwiches to "surf side dinners".
The kitchen knows how to steam, grill, blacken and prepare all kinds of food the way you like including the good old frying method. They also have good salads.
The minute you walk inside the rambling rustic building, you will feel like you've been transported to a surfing museum. The walls and ceilings are festooned with all kinds of interesting objects including surf boards.
The main dining room also has a small bar that is inviting to the diner who likes to eat at the bar or just have a drink.
Don't dress up to go to Snack Jacks. Tee shirt, shorts and flip flops are always in style here.
DAY TRIP 9
Joe’s Stone Crab
11 Washington Ave, Miami Beach, FL 33139.
When I lived on my boat in Miami Beach, a favorite evening tradition was a stroll to nearby Joe’s Stone Crab for drinks and dinner.
The restaurant was opened in 1913 by Joe Weiss. After all these years, Joe’s is still the top buyer of Florida stone crab claws. These claws are their most famous dish.
Joe’s is frequented by the rich and famous, but I used to go there so you can too.
The servers are professionals, many of whose fathers and grandfathers also worked at Joe's. The maitre d’ at Joe’s is king. They take no reservations, so you approach him and give him your name and size of your party.
You might give him a tip at this point, and I don’t mean a tip on the stock market like “buy low and sell high”. Then you will wait, but the wait is a lot of fun especially at the bar.
Although there are many other items on the menu, if you come for stone crabs, remember they are seasonal. Stone crabs must be cooked the day they are caught.
The best time to go to Joe’s for stone crabs is during season from October 15 to May 15.
Prices go up and down depending on when the harvest was and how much.
DAY TRIP 10
Lakeridge Winery and Vineyards
19239 US 27 North, Clermont, FL 34715.
This winery has become a very popular Orlando area attraction. The beautiful main building and vineyards are on a 127-acre estate in the hilly country about 25 miles west of Orlando.
The vineyard takes up 77 of the 127 acres and includes Florida hybrid bunch grapes and varieties of Muscadines. The winery has a large tasting room and an attractive gift shop.
Several types of wine are sold under the Lakeridge brands. In addition to their wines, the gift shop sells gourmet foods, cheeses, crackers, sauces and wine accessories.
There are probably more events held at this establishment than any of the other Florida wineries.
All year long there are art and craft shows, jazz concerts, harvest festivals, grape stomping events, vintage car shows and vintage music events.
Complimentary tours and wine tastings are offered seven days a week.
DAY TRIP 11
San Sebastian Winery
157 King Street, St. Augustine, FL 32084.
This winery has been in business since 1996 and has become a favorite St. Augustine attraction.
It is the second largest winery in Florida, and over 160,000 visitors a year come in to taste wine and tour the facility.
There is a gourmet gift shop, and the facility has 18,000 square feet with storage capacity of 40,000 gallons of wine. You can purchase appetizers and wines, as well as domestic and imported beers.
Native varieties of red Noble, bronze Carlos and Welder Muscadines are grown for the winery by Lakeridge Winery Estate and Prosperity Vineyards.
There is an open-air deck on the second floor where you can enjoy your wine and snacks while listening to music.
The view of St. Augustine is wonderful from the deck, and music is provided every weekend.
DAY TRIP 12
Schnebly Redland’s Winery
30205 SW 217th Ave, Homestead, FL 33030.
Schnebly Redlands Winery is noted not just for its exotic wine but because of its entertaining and comfortable venue.
The winery makes delicious wines out of all kinds of tropical fruits. The Redlands is a large agricultural area that gets its name from the clayey red soil that dominates the area.
Exotic plants and vegetables thrive in this soil that will not grow any place else in the United States.
The winery’s 96 acres of tropical fruits include carambola, mango, lychee, guava, passion fruit and gourmet vegetables.
The buildings and grounds are beautifully maintained, and there are a couple of fountains and waterfalls located among the lush tropical plantings that surround the building.
The retail store and wine tasting areas are up front.
DAY TRIP 13
201 Duval Street, Key West, Florida 33040.
Sloppy Joe’s Bar has long been a part of the quirky nature of Key West.
It was a favorite hangout of Ernest Hemingway, who made Key West his home for many years.
People visit mainly for its historic atmosphere, but it also serves good drinks and decent food including salads and pizza.
Millions of locals and visitors have come here since it first went into business under another name in the 1930s.
It was Hemingway who encouraged its name change to Sloppy Joe’s. The new name was adopted from Jose Garcia Rio Havana club selling liquor and iced seafood.
Because the floor was always wet with melted ice, his patrons taunted Joe with running a sloppy place. The name stuck.