Best Things to Do with Friends in Clearwater Beach
Updated: October 25, 2023
By AAA Travel Editor Sherry Mims
Sugary white sand beaches and the spectacular Gulf of Mexico make Clearwater a great place for trips of all kinds. Whether you just need a beach day or, like me, met up with friends for a weekend girls’ trip to Clearwater Beach, expect plenty to see and do in this scenic Florida community near Tampa and St. Petersburg.
With group travel especially, you’ll want to enlist some help, such as a AAA Travel Agent, who can search around for the best deals and locate accommodations in an area surrounded with food and entertainment options. For this trip, a travel agent helped me book an amazing suite with Gulf views at AAA Four Diamond Hyatt Regency Clearwater Beach Resort & Spa, and I was even upgraded upon arrival. Other perks anyone can get from their Hyatt stay include a free welcome beverage (prosecco for me) and a guide to that week’s offerings, including in-room movies, board-game rentals and poolside activities.
One of the things to do pre-trip is determine when you want to go, which you can discuss with your travel agent. If spring break is on the agenda, be sure to book in advance. Luckily I had learned from Hyatt’s front desk agent that I had timed my reservation right. Starting in mid-February, most Clearwater hotels, including mine, require booking as early as October and November for spring; some 90,000 people (as opposed to the typical 60,000 in 2023) are expected to come through Tampa International Airport for a weekend visit around spring break, according to the Tampa Bay Times.
How to Get To Clearwater
How are you getting to Clearwater? Local airports range from St. Pete–Clearwater International Airport (PIE) to Tampa International (TPA) and farther out, Orlando International Airport (MCO). There are services that provide a private transfer from Tampa to Clearwater, while Hertz, one of AAA’s preferred travel partners, offers special savings and benefits to AAA members, such as one additional qualified AAA driver and complimentary use of one child, infant or booster seat.
Though a number of our group flew into these airports from places as wide ranging as Wyoming and Oregon, I drove from Orlando to Clearwater. I used I used AAA TripTik and drove from I-4 and I-275 South to FL-60 W/E State Rd 60 West – a route that can take anywhere from two-and-a-half hours to four-plus, depending on traffic. Go early to avoid traffic hot spots in Orlando and Tampa.
Day 1: Sunset and Social Time
Sunset views accompanied me as I drove over the causeways into Clearwater. Along the way, there are pullouts to strips of beach along both sides of the road, signs directing you to baseball and concert venues, and Clearwater Marine Aquarium, which was the setting of the “Dolphin Tale” movies.
Our group planned a meetup at the hotel and then ate dinner together. With such differing schedules earlier in the day, some went to the beach or made spa appointments with Hyatt’s Sandava Spa. This is a great idea if your group has some members traveling from elsewhere – a little downtime before the adventure begins! (Note: Book ahead for the spa treatments.)
The Hyatt is conveniently on Clearwater Beach and the Beach Walk and features trendy SHOR American Seafood Grill on the second floor, across from the Market on-the-go store. Though walk-ins are allowed, our group made reservations and took in some live music, available Friday and Saturday, while enjoying our cocktails (most notably the raspberry martini, which led to many an ooh and ah) and specialties like lobster mac ‘n’ cheese ($58) and Shor signature burger ($28). To make dining decisions easier, the menu noted items that were gluten-free and dairy-free. Some entrées also came à la carte, so thanks to my friends, I was able to try standout sides like pancetta mash and harissa-roasted carrots. For my main course, I ordered the pan-seared Florida Grouper ($44), which was a succulent, locally caught seafood option that came with roasted cauliflower, hazelnuts, charred lemon, golden raisins and capers. Full, I ordered dessert to-go — tiramisu, nicely presented in a recyclable cardboard container — to place in my room’s refrigerator for a late-night snack.
Now well-fed, the question became: What is there to do for nightlife? There are a number of well-known Clearwater options, such as AAA Three Diamond Shephard’s Beach Resort with its happening nightclub and entertainment as well as the poolside bar at Edge Hotel Clearwater Beach or 10th floor Jimmy's Crows Nest at Pier House 60.
For our first night, we wanted somewhere that was fun and walkable but also came recommended by one of our local friends, RockHouse Live Clearwater Beach. This rockin’ establishment, next to AAA Three Diamond SpringHill Suites by Marriott Clearwater Beach, is open daily from 11 to 3 a.m. Described as the only beachside bar with parking, RockHouse Live is convenient and offers a variety of food, beverages and entertainment. Large screen TVs adorn the walls, and live music is featured Thursday to Sunday (with karaoke from Monday to Wednesday). The atmosphere is both fun and lively; our group getting a shout-out by the band — a truly memorable end to the first night in Clearwater.
Day 2: Morning Fun in the Sun and Sightseeing
Early risers have a lot of options in this sunny destination. From my balcony, I saw beachgoers trying to beat the heat and crowds by arriving early and claiming their spots on the sandy beach. (Hyatt guests on-site get some amenities as part of the resort fee, such as two bike rentals, two beach chairs and umbrella per stay, as well as exercise classes like poolside yoga, offered weekly.) Some, including some of our group, ran on the beach. There’s also the Clearwater Memorial Causeway Trail and water sports available.
For my part, I woke up early and took in sunrise views, ranging from the Gulf of Mexico to Clearwater Bay. After taking photos of the Beach Walk, pier and marina, I settled down with my leftover tiramisu (#vacation) and a cup of coffee from the in-room coffeemaker to enjoy the panorama.
Mid-morning I met up with our crew. Breakfast spots recommended to us included Clear Sky Beachside Café, Salt Cracker Fish Camp and Another Broken Egg Cafe. We opted for Another Broken Egg and brought our order to the hotel — standout items were biscuits and gravy and the bacon lover’s “BLT&A” with bacon and fresh avocado —to plan our day over breakfast.
While some in the group decided to hit the beach and shop, I joined the others on a Segway tour, which runs three times a day — 10:30, 2 and 6. Intended for ages 10 and up, it introduces Clearwater points of interest like the Beach Walk and historic areas. Though advanced reservations are a must, I lucked out and booked the last spot on the 10:30 tour that morning.
Clearwater Segway Tours – The Segway Adventure – departs from a nondescript office at Captain Bligh’s Mini Golf, but you’ll be able to spot it thanks to the row of Segways lined up against a wall. We were ready to roll within minutes. Though I initially worried over my clumsiness, I shouldn’t have. Each person was trained and had space to whirl around the back parking lot to gain some comfort with the device.
I learned that a Segway, a two-wheeled personal transportation device, is a really easy way to see the sights without wearing yourself out. Note: Although some Segways come with a bag to hold things like keys and a bottle of water, it’s best to leave your valuables and personal items back at your hotel.
Our 2-hour tour covered a total of 7.5 miles with occasional stops for breaks and tips. The first stop was a short rest at the top of the Clearwater Memorial Causeway to take in the breathtaking views, including Clearwater Bay and downtown; also visible was the eight-pointed bronze Scientology cross atop Clearwater’s largest building, the Flag Building, in Downtown Clearwater. Then, we descended the two-story circular walkway to see local attractions, such as Harbor Oaks, an area with homes that are at least a century old, and a noteworthy local church with 49 bells known as The Betty Jane Dimmitt Memorial Bell Tower and Carillon (at Church of the Ascension). On the way back, we took a break by Clearwater Harbor Marina Yacht and Boat for some local history. We then zoomed back across the causeway to the Beach Walk, where we waved to our friends who were coming back from shopping.
Day 2: Afternoon Outdoor Dining and R&R
After building up an appetite, some of us decided to try an open-air beachfront restaurant. Frenchy’s South Beach Café, which we reached by foot, is a local favorite for food — and people-watching. There’s an expansive menu, so before we made up our minds, we ordered some starters like shrimp ($11.95) with Cajun seasoning. The restaurant’s best-known specialty is the grouper sandwich ($14.95), but as I had grouper the previous night, I ordered the hot-pressed Cuban sandwich ($10.95), which the menu described as “hands down the best Cuban on the beach!” And while I didn’t try every sandwich beachside, the hot-pressed sandwich with ham, cheese and mustard deeply satisfied.
Then the schedule was clear for some rest and relaxation. Convenient towel stations by SHOR restaurant made it easy to grab a towel and go. The blue-and-white beach cabanas beckoned.
Day 2: Evening Dinner Cruise and Pier 60 Sunset Celebration
How do you roll up extravagant sightseeing, dining and clubbing all in one? Our answer: A sunset cruise for starters; there were a variety of options for any price point.
Whether you’re looking to go deep-sea fishing or hoping to take in the sights, the variety of vessels and charter boats offer a range of experiences. The fleet of sport-fishing boats offer an opportunity for anglers of all levels to test their skills. Sightseeing cruises provide visitors a chance to appreciate the fascinating marine animals within a breathtaking landscape; often they’re accompanied by informative narrative, providing insight into the natural surroundings, as well as any historical buildings or landmarks that can be seen from the boat. And any cruise should give an up-close look at the coastline.
Luckily, the Clearwater marina is a hub of activity. If you plan ahead, you too can experience the beauty and serenity of Clearwater from a unique perspective with one of these tours, ranging from 2-hour guided tours, such as The Tropics Boat Tours' Dolphin Exploration Tour, to a tiki boat cruise or sunset sailing complete with a buffet (our choice). To make it easier, AAA lists several Clearwater sightseeing cruises, including Calypso Queen Cruises, Captain Memo's Pirate Cruise, Sea Screamer and StarLite Cruises. (Prices vary; phone ahead for reservations.)
Whether it is sailing up close to sandbars in search of dolphins or viewing the stunning sunset, there’s plenty to see and do. For us, we enjoyed the buffet (including a truly phenomenal clam chowder) before admiring sunset views and dancing on the dance floor to music from a live DJ. Our ship also featured an open bar while on the water. Should you partake, drink responsibly or choose a designated driver.
All too soon, it was last call, and we disembarked with the staff giving us cookies to go. Not yet read for the night to end, we headed back onto the Beach Walk and were easily captivated by the many stimulating sights and sounds of Pier 60. If you stroll along at dusk, soak in the stunning views of the sun setting over the Gulf Coast; if you come later like us, you can still experience Pier 60 and explore the rows of beach umbrellas, where artisans have gathered to show off their creations, ranging from crocheted turtles and manatees to caricatures.
Families with young children are sure to enjoy the playground at the waterfront park as well as diversions like tic-tac-toe and the premiere event, Sunsets at Pier 60. Weather permitting, this sunset celebration runs later in the day from 4:30-8:30, making Pier 60 the perfect place to spend some of your night.
Be sure to keep an eye out for talented street performers and aerial artists presenting stirring routines or even fire dances by the entrance of Pier 60. (Many of these entertainers undergo rigorous pre-performance screenings and travel from far and wide to entertain, so remember to bring some cash for tips if you watch.)
Though clubbing was certainly possible, we instead elected for a chill night by the hot tub, which had terrific night views from the 16th-floor deck. Despite a hot tub that was almost too hot to tolerate, we dipped in and out, catching up, chatting with other travelers and toasting to a successful girls’ trip.
Day 3: Morning Departure via Clearwater Memorial Causeway
A perk of being (relatively) local meant I didn’t have to rush out of Clearwater, so I requested a late checkout. Some rooms, due to incoming spring breakers, necessitated earlier leave times, but I managed a 1:30 checkout. I grabbed some leftover breakfast with my departing group members and wrapped up my time by some sunbathing on the beach and souvenir shopping. (Many shops are within walking distance.)
No doubt I’ll miss the stunning beaches, the magnificent sunsets and the exciting nightlife. Coming here has reminded me how fun and accessible Clearwater is. I’ve already found a concert in Clearwater that’s beckoning me back later in the year.
But, first, I had one last spot to revisit before I wrapped up this trip: The trail at the base of the Clearwater Memorial Causeway had been on my agenda to explore again on my way out of Clearwater. Though the Segway tour covered this ground already, I got longer to wander by foot. I spotted the distinctive marker for the Blue Star Memorial Highway, which honors those who have served and defended the United States, as well as a memorial to the Spanish-American War.
As joggers and cyclists blew past me on the trail, the sparkling waterway had one last surprise in store for me. A pirate ship leisurely glided by in Clearwater Bay, its black Jolly Roger flag waving as much as the passengers. This unexpected balm to the soul served as a fitting end to a weekend spent with friends offline and reminded me that fun Florida attractions are for tourists and residents alike.
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Sherry is an experienced #AAAEditor and former journalist who enjoys writing informative travel articles and reviews. Her commitment to making meaningful connections with people and places fuels her work for AAA. Sherry's favorite activities range from skiing to backpacking abroad and taking ghost tours.