Explore Tampa Bay

Plan a Getaway to Clearwater Beach

The perfect Florida retreat sits just outside Tampa along the Gulf of Mexico's white-sand beaches.

This time of year can get a bit hectic with traveling, planning, purchasing and preparing for the holidays. Give stress the weekend off and head to the Florida community of Clearwater Beach for the perfect weekend getaway. Just a little more than 100 miles away from my bustling city of Orlando (and only 20 miles away from Tampa), sits a seaside town filled with pristine white-sand beaches, spot-on Sunshine State weather and inviting gulf waters. Here you’ll find walkable streets filled with welcoming eateries, boutiques and kitschy shops, as well as authentic beachside bars.

Where to Stay

Clearwater Beach is home to the stunning Sandpearl Resort. Residing on the top of a hill set right off the beach on Mandalay Avenue, this Four Diamond rated resort offers ocean views, three on-site eateries, a zero-entry pool and décor so warm and Old Florida-inspired that you may, for a moment, feel like you’ve stepped into a scene from the Great Gatsby. In terms of relaxation, the rooms are warm and comfortable, but the real moments of “oohs” and “ahhs” happen inside the acclaimed Sandpearl Spa, which offers massages, facials and other state-of-the-art treatments. The resort also features private boat slips and daily excursions such as kayaking, a Sea Life Safari Eco Tour and sailing. Those traveling with children can take advantage of the nightly fire pits on the beach, complete with s’mores, family movies by the pool and childcare service at Camp Ridley (on-site) when a date night is necessary.

Sandpearl Resort in Clearwater Beach, Florida
The Four Diamond-rated Sandpearl Resort (Courtesy Sandpearl Resort)

Where to Eat

The area may be small but the dining options are aplenty. If authentic beach town grub is what you seek, look no further than Frenchy’s. Travel tip: There are actually four different Frenchy’s locations, each with a unique vibe, so choose the one that fits your personality best. Known for its grouper sandwich, fun bar and friendly staff, each outpost gets busier than the next.

Caretta on the Gulf is the beach’s only AAA Four Diamond restaurant, and one of the best places to enjoy a romantic dinner. Featuring menu items that change by the season and an impressive wine and cocktail list, it’s the perfect place for lighter fare like sushi and fine dining cuisine.

If Sunday brunch is on your mind, Island Way Grill, located right off the causeway, is your go-to spot for amazing food and even better views. The entire restaurant is set-up as one giant all-you-can-eat brunch buffet. You’ll find much more than eggs and bacon here (think sushi, raw oysters, pasta) and a complimentary mimosa or glass of Champagne is given with the brunch.

Where to Drink

The Brown Boxer features a classic sports bar and grille vibe. Catch a game on one of the flat screens or grab a seat at the outside bar to people watch and order from the bar’s great selection of craft beers.

Crabby Bill’s is everything a beach bar should be. The smell of salt water fills the air, the breeze from the ocean filters in and drinks are poured and enjoyed while a live musician entertains. There is no muss or fuss here. It’s beachside drinking done oh-so-right.

Where to Play

Clearwater Beach is home to the Clearwater Marine Aquarium, home to the dolphin named Winter, star of the movie “Dolphin Tale.” In addition to seeing this VIP castmember, guests can also feed stingrays and participate in fun activities like “Trainer for a Day.”

Enjoy nightly celebrations featuring live musicians, artisans and street performers at Sunsets at Pier 60, a free event that takes place in Pier 60 Park in the heart of Clearwater Beach.

Charter a boat. Whether you want to spend the day deep-sea fishing, parasailing, dinner cruises or dolphin watching, your ship (or boat) will definitely come in.

Pier 60
Sunsets at Pier 60 are free events offering plenty of fun in the sun or relaxation in the sand. (©Visit St. Pete/Clearwater)

Getting There

Coming from Orlando, Clearwater Beach is about one hour and forty minutes away by car (via I-4 to 275 to S.R.60). Coming from the Tampa Bay area, Clearwater is about a 30-minute car ride via S.R. 60. If you are visiting from a far, flying into Tampa International Airport is extremely convenient.