• Excellence in Real Estate

Compare Listings

Wine and Night Life in Clearwater Beach

Bistros & Wine Bars:

Bobby’s Bistro & Wine Bar: The original bistro & wine bar on Clearwater Beach is Bobby’s Bistro & Wine Bar created by the owners of Bob Heilman’s Beach Comber. They do have plenty of parking, a valet, and generally cater to the well to do. Juliana & I love this little place! It opens at 5pm and closes when people begin to leave, generally around 11pm. I highly recommend this place! Decent wine and scotch selection! 447 Mandalay Avenue Clearwater Beach, FL 33767

Forlini’s Italian & Seafood Cuisine: This restaurant initially opened on Clearwater Beach in 1981 bringing the taste of Umito Italy to Clearwater Beach! This may be the beaches largest wine selection, offering more than six hundred fifty different selections in a temperature controlled wine cellar! Come for cuisine and stay for the wine and conversation! 435 Mandalay Ave. Clearwater Beach, FL 33767

Cork & Brew: Next on our list is relatively new on the beach, Cork & Brew. They have live entertainment nightly, decent wine selection, many beers on tap, and a great atmosphere with lights on the patio and happy people all around! 524 Mandalay Avenue Clearwater Beach, FL 33767

Clearwater Wine Bar & Bistro: 2013 Award of Excellence Winner, Clearwater Wine Bar & Bistro, makes the number three spot on my list. This place has a great selection of wine, great live music, and a cheerful ambiance. This place really feels like a wine lover’s heaven, especially when the outdoor music is playing, palm trees are swaying, and the ocean smell is in the air! Come have a glass and enjoy the good life!

Tate Island Grill: Located in the Sand Pearl, this is a great place to watch sunset with wine in hand! They have an actual fire pit, sit directly on the sand, and overlook the Gulf of Mexico! We really enjoy the music, the people, and the fire pit! The food is great, the wine selection is good, and the view is breathtaking. Known for tropical drinks, appetizers, and a great place for sunset toast! 500 Mandalay Clearwater Beach, Florida 33767

Fusion Cigar Lounge :This has become a great place to unwind, grab a glass of your favorite wine and light up a Cuban cigar! Fusion is located at 483 Mandalay Avenue Clearwater Beach, FL 33767.

Clear Sky: When it comes time to relax, my favorite place is Clear Sky, brought to you by the owners of Frenchy’s, and the location of my first date with Juliana! Come for a glass of wine and stay for the relaxing live music and great food! They are more of a restaurant than a bar, however, there is always live entertainment, and it has that bistro feel to it. Clear Sky is located at 490 Mandalay Ave, Clearwater, FL 33767.

Bob Hielmans Beachcomber: I am including my favorite restaurant, Bob Hielmans Beachcomber, on this list because of the live piano music at night, the GREAT steak, relaxing ambiance, and superior service. Bob Hielmans has been around since the early 1950s and is the original, now considered, high end restaurant on Clearwater Beach. This place really reminds you of Clearwater Beach in the late 1950s, when everyone in America was successful, motor cars were a new fad, and the service people wore suits and acted like they cared about both you and the product they were serving. This is by far the best restaurant and nicest bar on the beach. The bar tenders remember your name, wear suits, and serve you a healthy glass of scotch the way your grandfather drank it! If you visit Clearwater Beach, visit the Beach Comber!

The Lobster Pot: Great upscale wine and jazz location featuring local and well known jazz musicians, fine wines, and caviar. The summer jazz series completely sold out! Let’s see what they bring in 2014. 478 Mandalay Avenue Clearwater Beach, FL 33767

The Columbia: Built in YBOR City back in 1906 by Casimiro Hernandez Sr., the Columbia originated right here in the Tampa Bay market! Much like the Beachcomber, The Columbia is more of an upscale restaurant, but I am listing it here because it has an awesome bar and great wine selection. The bar area overlooks Clearwater Harbor and features a real island style atmosphere. This restaurant is one of seven.

The Bar & Sandwich Scene:

Frenchys Rockaway Grill: Everyone enjoys a good beach bar with live music, great bar food, sun set, and hot people. You will find all of this at Frenchy’s Rockaway Grill, located directly on the sand and facing the Gulf of Mexico. This rather large beach bar has been around since 1981 and has since become one of the best spots. The owner has a fleet of boats and catches his own fish, so you know it’s served fresh! We enjoy the classic rock music, the grouper sandwich, and the amazing sunsets! Frenchy’s Rockaway is located at 7 Rockaway Street
Clearwater Beach, FL 33767.

Frenchy’s South Beach: also has many of the same menu items and is located closer to my particular slice of the island directly on Beach Walk Gulfview Blvd. Clearwater Beach, FL 33767

Frenchys Dockside: located 27.58.75 longitude, 82.49.53 latitude offers dockside service right to your boat! Come tie up and enjoy some real Clearwater Beach original creations!

Frenchy’s Original Café, seems to have the best prices, the beer is ice cold a pleasant staff, the most local atmosphere, and where I tend to eat lunch in between deals. Walk, bike, or drive in for the best fish tacos in town! The original is located at 41 Baymont St Clearwater, FL 3376. This is becoming my favorite of the Clearwater Beach Island Chain! Come here when you stop being a tourist and become a real local.

Jimmy’s Fish House is awesome because for me its next door! You can sit steps, and I literally mean steps, away from the Gulf of Mexico! The food is reasonably priced, the bar tenders are decent, and the ambiance is everything you would expect to find great beach bar & sandwich shop. Most afternoons and evenings live music plays from a great classic rock band. You can listen to the sound of live beach music as the waves crash against the rocks, watch as the dolphins play in the foreground and sun sets across the gulf. This is where we tend to frequent the most because it is next door to 440 West, where we live overlooking the Gulf of Mexico and they serve free sun sets shots! Jimmy’s address is 521 South Gulfview Blvd Clearwater Beach, FL 33767.

Sheppard’s! (Night Club & Tiki Bar) Need I say more? Have you ever seen MTV’s The Grind? This place is a great spot for night life, dancing, and girls wearing sexy thong bottoms. Oh, and of course, men who spend every day in the gym. Sheppard’s located is two buildings from my condo and directly on the Gulf of Mexico. The tiki bar features amazing sunsets, the best bands on the beach, and the sexiest bodies. They bring in top ten pop, rock, and R&B artist from around the nation in order to enhance the already awesome experience! This has become a spring break heaven! It’s located at 619 South Gulfview Boulevard Clearwater Beach, FL 33767.

Tropix: is a local hang out, yet it is located behind the Quality Inn on South Beach.
655 South Gulfview Blvd Clearwater Beach, FL 33767. The food prices are decent and the drink prices are far bellow average for the area. This is a great place to come and unwind by the shore after a long day of beach boy surfing, kayaking, and writing your next novel.

Crabby’s Beachwalk Bar & Grill: has a great view of the Gulf of Mexico from the second floor and always has a live band playing in the evening. 333 S Gulfview Blvd
Clearwater Beach, FL 33767

Jimmy’s Crows Nest: has an amazing view of the city, the Gulf of Mexico, Pier 60, and Clearwater Harbor! They even have a large projector on the wall! This may be the best place to come and snap a few great area photos. The bar is located on the top of Pier House 60 and owned by the same person who created the original Jimmy’s Fish House. Pier House 60 Clearwater Beach, FL 33767

Hooters: Originally founded in Clearwater, it is fitting that the owners have opened one directly overlooking the beach, the gulf, and Pier 60. Come have a sunset shot on third floor balcony overlooking the Gulf of Mexico! Oh, the sunset shot is on the house! 381 Mandalay Ave Clearwater, FL

Toucans Sports Bar, owned by Atif, a local pizza shop man who built his dream bar with the help and guidance of my friends at European Equities Corporation. This bar has all of the latest televisions, great interior wood work, and a nice bar ambiance, not to mention the chef is fantastic (not your typical bar food)! Come have a drink with the locals and enjoy the nightly entertainment! 431 Mandalay Avenue Clearwater Beach, FL 33767.

Shipwreck is the last remaining real bar on Clearwater Beach. They do not serve any food, allow smoking inside, have a juke box, and serve up stiff drinks for very little cost. This is the local dive bar. Have a drink, shoot some pool, and stumble back to your dock, if you can. 647 Mandalay Ave Clearwater Beach, FL 33767

Billy D’s is almost a dive bar, but with food served late into the evening. When people get tired of dancing and paying for expensive drinks, they stumble over to the more localized scene to shoot some pool, sing karaoke, and have a late night chicken sandwich. Don’t be fooled, I have seen girls dancing on the bar in bikinis during the day! 656 S Gulfview Blvd Clearwater Beach, Florida 33767

Cooters Raw Bar and Restaurant: Great food on Clearwater Harbor! They have really perfected the beach décor and have created a Jimmy Buffet style atmosphere complete with wood trim, beach style music, and gift shop! This place is unique and a must visit if you vacation on the island! 423 Poinsettia Ave. Clearwater Beach, FL 33

The Original Boardwalk, located on the side of Publix Shopping Center Island Estates, is a nice little bar featuring karaoke, daily beer specials, and almost all the games. Yet again, this is defiantly a local spot! Fun Fact: The benches outside are original Coney Island benches! 126 Island Way Clearwater, FL 33767

Les Partners Lounge on Island Estates is smoker friendly, has live piano on the weekends, and plays everything from oldies to R&B. They are located at 144 Island Way Clearwater Beach, Florida 33767

Swim Bar & Grill is located in the Hyatt and features amazing sunset views from both the inside windows and the outdoor deck! This bar directly overlooks the public beach Pier 60, and the Gulf of Mexico! 301 S Gulfview Blvd, Clearwater Beach, FL 33767

Tavern Bar & Grill is located inside the Sheraton, has a friendly staff, and features live entertainment Tuesday through Saturday 1160 Gulf Boulevard Clearwater Beach, FL 33767

Kokomos Poolside Grille & Bar is located in the Marriot Hotel and serves tropical drinks right at the waters edge! 1201 Gulf Blvd, Clearwater Beach, FL 33767

Tommy’s Tiki is located inside the Hilton and features both food and beverage service on the sand! Listen to live music, enjoy a tropical drink, and realx in this real island tiki! 400 Mandalay Avenue, Clearwater Beach, Florida 33767

Palm Pavilion: This is the island’s original beach bar! It’s laid back and casual and has been that way since they started in 1926. The Palm Pavilion directly overlooks the Gulf of Mexico and the beach is at “their front door”. The sunsets are terrific and there is live entertainment most days, “so long as they can find the extension cord”. Great seafood, sizzling steaks, chicken and seafood wraps, shrimp and crab chowder, smoked ribs and famous beach burgers. Click here for entertainment updates. Happy hour: Monday – Friday 4-7 p.m. 18 Bay Esplanade Clearwater Beach, FL 33767

Caesars Italian Restaurant: Winners of Dinners Choice Award 2013, this neat little spot is located at the end of the main island and offers authentic Italian cuisine, a great wine selection and a cozy environment to relax. 794 South Gulfview Blvd. Clearwater Beach, FL. 33767

Gondolier Pizza: Italian Restaurant offering beer, wine, great pizza, Italian cuisine, and Greek food. They are open late, deliver to the surrounding condos, and the food always taste great! We have found this to be the best everyday combination of quality, quantity, and price. This is where we dine the most often! Always very clean! 674 S Gulfview Blvd Clearwater Beach, FL 33767

I Hop on the Beach: What more can I say? It’s an I Hop with good size portions, inexpensive prices, and it’s always open for breakfast. Many mid-twenties hangover mornings have been spent at this casual little beach I- Hop. Its walking distance to the nightlife and provides a relaxing setting for breakfast. 655 S Gulfview Blvd Clearwater Beach, FL 33767

McDonalds on the Beach: Located directly on Beach Walk, this McDolands offers an Inexpensive burger in a true American setting. 347 S Gulfview Blvd, Clearwater Beach FL 33767

Quizno’s Sub Sandwiches located in the Hess Gas Station on South Gulfview Blvd. Fresh sandwiches made daily. 601 Bayway Blvd, Clearwater Beach, FL 33767

Subway North & South Beach: Owned by my former employer and developer, David McComas, this nice little sandwich shop features fresh sub style sandwiches in a convenient beach location. South Beach: 696 S Gulfview Blvd, Clearwater Beach, FL 33767 North Beach: 409 Mandalay Ave, Clearwater Beach, FL 33767

Post Corner Pizza: Great local pizza and Greek food restaurant that has been on the island in the same location for almost forty years! They have excellent customer service, great views of the Gulf of Mexico and Clearwater Beach and some of the best tasting food on the island! 431 S Gulfview Blvd. Clearwater Beach, FL 33767

King’s Pizza: The owner drives here from Tampa every day, although I have tried many times to convince him to purchase a home here on the island. He makes a great tasting pizza and offers many good deals, such as 2 slices and a soda for only five bucks! 325 Coronado Dr, Clearwater Beach, FL 33767

The Beach Shanty: Now with two locations! This is definitely the local breakfast place offering a clean setting, good prices, and great tasting food! Try the eggs benedicts and you will be delighted! 397 Mandalay Ave Clearwater, FL 33767

Crabby Bill’s: This is a local beach chain offering nightly entertainment, drink specials from 11am until 7pm, and fresh sea food! Located right at the marina, you can dock your boat and come in for some boat drinks! 37 Causeway Blvd, Clearwater, FL 33767

Marina Grill: Great little breakfast and sandwich place. Located in the marina, people tend to eat here before an early morning boat ride. It’s a great little local spot with friendly service and great tasting food. 25 Causeway Blvd, Clearwater, FL 33767

Beach Fyre BBQ: This is a new restaurant and I have not yet tried it, but I hear that they have great tasting BBQ and as soon as we have tried the food, I will be certain to comment. 608 Mandalay Ave Clearwater, FL 33767

Kiku Authentic Japanese Sushi: This is a true authentic Japanese restaurant and one of my top favorites. Personally, I think they have the best sushi I have ever tasted anywhere, including off the island. This is one of my favorite restaurants on or off the island! Kiku is located in Pelican Walk upstairs. 483 Mandalay Ave. Clearwater Beach, FL 33767

Captain’s Pizza: Atif’s little pizza place located directly on Mandalay and offering home made pizza wither by the slice or by the pie. Good food at reasonable prices. 462 Mandalay Ave. Clearwater Beach, FL 33767

JB’S Island Café: This is a decent little lunch and breakfast place. It is locally owned and operated. Great tuna sandwich! 432 Poinsettia Ave #5, Clearwater, FL 33767

Caretta on the Gulf: Located inside the Sand Pearl, the view will take your breath away and the food is spectacular! This is a four diamond restaurant is located inside a world class five star beach resort. 500 Mandalay Ave, Clearwater Beach, FL

Backwaters: serves fresh sea food and is located directly overlooking Clearwater Harbor, just a short walk from the sailing center. They have an awesome seafood selection and great atmosphere. 1261 Gulf Blvd Clearwater Beach, FL 33767

Coffee Bar & Sandwich

Wyndham Garden on South Beach offers an incredible view overlooking the Gulf of Mexico and Shipping Chanel. They brew Star Bucks coffee and offer a full liquor bar with light sandwiches. 691 S Gulfview Blvd Clearwater Beach, FL 33767

Enjoy the Wine and nightlife in Clearwater Beach!

Authored by Andrew Cherry