“Let’s Eat!”: A Special Exhibit at Clearwater Historical Society

In 2021 the Clearwater Historical Society Museum and Cultural Center hosted a special exhibit called “Let’s Eat!” Open until the first week in December, the exhibit showcased the oldest restaurants in Clearwater. They chose those which have or were open at least 40 years. Though most are closed permanently, six of the restaurants still welcome patrons through their doors.

Kapok Tree Inn (1950 to 1991)

Old photos, newspaper clippings, memorabilia, and firsthand accounts bring these iconic restaurants back to life. For instance, the Kapok Tree Inn wowed diners for decades before closing permanently in 1991. Located on several acres on the east side of Clearwater, the restaurant was named for an enormous Kapok Tree. Exotic plants grew in the restaurant’s gardens (now part of Kapok Park).

“There were 12 elegantly themed dining rooms, lounges, and bars. Great care taken in selecting the decorations including grand chandeliers, polished marble, designer fabrics and statuary found all over the world. For example, the Zebra Lounge featured an authentic Panamanian canoe, found on one of their many buying trips.

The menu wasn’t as extravagant as the surroundings, serving fried chicken, ham, fried shrimp, and T-Bone steak. When you arrived, you bought a ticket and were assigned a dining room: the Balcony Room, Chandelier Room, Florida Room, Garden Room, Grand Ballroom and Patio Room. You could wander through the Grape Bar, the Kapok Lounge, the Red Lounge, or the Zebra Lounge to sample an exotic drink either before or after dinner. If you ordered Planter’s Punch, you could take home a souvenir glass with the Kapok Tree logo.

The meal started with a relish tray served on a silver lazy Susan filled with cottage cheese, sweet pickled vegetables, coleslaw and apple butter. The entrée was accompanied by roasted potatoes, creamed peas, and the most wonderful corn fritters, all served on silver platters.”

“After dinner, guests would stroll through the elegant Mediterranean gardens complete with Greek and Roman style statuary and columns, waterfalls, fountains, and exotic plants. No trip was complete without a visit to the gift shops to buy a souvenir to take home from Clearwater as it had become an exciting, exotic, international tourist destination. The Kapok Tree Inn received accolades for its concept and ambiance and was frequently named as one of the best restaurants for business dining.”

The Pelican (1946-?)

Brown Brothers Ice Cream Shop (1926-2002)

Pirate’s Table (1967-?)

Oldest Restaurants in Clearwater Still Open

The following restaurants stake their claim to being the oldest restaurants in Clearwater AND still operating. If you’re not from the area, some of these might surprise you. If you have visited, some of these might sound familiar. The history of each is fascinating. And their food and service continue to draw customers through their doors.

O’Keefe’s Tavern (1961 to present)

O’Keefe’s opened in 1961 at the site of the former Little Bohemia Restaurant. It has become a favorite spot for Clearwater High School alumni groups, St. Patrick’s Day celebrations, and a local photography group hangout. In 1969, the “Cedar Room” was added. The current owners continue the legacy created by previous owners.

“O’Keefe’s signature celebration, St. Patrick’s Day, has grown over the years to include over two tons of corned beer and semi-trucks of green beer.”

Palm Pavilion (1926-present)

If you’ve been to Clearwater Beach on vacation, you’re probably familiar with the Palm Pavilion. What is now a restaurant and bar started out much different. One of the oldest restaurants in Clearwater, this establishment began when five men “recognized a need and built a wooden beach pavilion on the water’s edge around 1920. Life was more formal then and wearing a bathing suit anywhere other than the beach was not an option. Beach pavilions where you could change your clothes, rent woolen bathing suits and shower became common in resort areas. The Palm Pavilion, which offered food, restrooms, a place to shop for swimwear and beach towels in addition to being a place store your belongings became a popular place.”

The integrity of the original building has been maintained with each renovation and expansion. Originally built with planks over pilings, it was so close to the water that customers could see waves beneath the floor planks when it was high tide or stormy. It is the oldest operating beach pavilion in Florida.

Bob Heilman’s Beachcomber (1944-present)

Another Clearwater Beach fixture, the Beachcomber offers classic dishes and one of the best burgers on the beach. The restaurant was originally built in the art deco style in 1944. Bob Heilman purchased it in 1948 and changed the name to Bob Heilman’s Beachcomber. White tablecloths, prime rib, seafood specialties, frog legs, and their famous fried chicken made the Beachcomber to place to go to celebrate special occasions. The original restaurant burned down in 1959 and was rebuilt in the same location. The legacy of Bob Heilman’s Beachcomber continues with his son, Bob Heilman, Jr. who put his own touch on the restaurant, a legendary wine list.

Frenchy’s Cafe (1981-present)

Frenchy’s Cafe opened in 1981 after owner, Mike Preston, worked and learned the restaurant business for 8 years at local restaurants. In 1983, he added the first fishing boat to a fleet which would grow over the years, insuring his restaurants always served fresh seafood. Since 1981, the Frenchy’s empire has grown to include four other restaurants on Clearwater Beach- Frenchy’s Rockway Grill, Frenchy’s Saltwater Cafe, Frenchy’s South Beach Cafe; Frenchy’s To-Go, a drive-through restaurants in Clearwater; Frenchy’s Outpost, one of the best restaurants in Dunedin; Frenchy’s Seafood Market also in Dunedin; a boutique hotel, fishing fleet, gift shop, and watersports store. Now famous for its fresh grouper sandwich and Stone Crab Festival, the original menu included shrimp, clams, oysters, and beer.

Hooters (1983-present)

Did you know the famous wing place started in Clearwater? It did! The original restaurant still stands on Gulf to Bay Boulevard. Incorporated as an April Fool’s joke in 1983, the concept began as a place where 6 local men could get together without being thrown out. They decided to serve their favorite finger foods and beer. They felt so assured of their failure, particularly in that location where many other restaurants had failed, that they created a graveyard at the entrance in homage to the failures before them. Little did they know how great a success they would achieve.

Capogna’s Dugout (1973-present)

Art Capogna dreamed of opening a family-friendly Italian restaurant in Clearwater. In 1973, he openend Capogna’s Dugout on Gulf to Bay Boulevard. Serving large portions and hand-tossed pizzas, the restaurant became an instant success. The Capogna family supported local sports and decorated the walls with photos from all of the local teams who celebrated wins at Capogna. It became the go-to spot after Friday night games. The city of Clearwater honored Art Capogna’s service and commitment to the community by naming one of the ballfields at Joe Dimaggio Park after him.

Lenny’s (1958-present)

Lenny’s on US 19 remains a staple for breakfast. Drive by any Saturday or Sunday morning to see a packed parking lot and a line out the door waiting for seating. Though all the food comes to the table piping hot and delicious, Lenny’s most famous item is their Danish basket. Not just popular on weekends, this restaurant has come to be known for serving great breakfast all day. Even during the week, it’s busy with tourists, young families, or businesspeople meeting for coffee.