In 2019, we planned a quick long weekend getaway to Clearwater Beach, Florida for David’s birthday. Even though he isn’t the biggest beach person, there were plenty of other reasons he was drawn to this location. Namely, fishing and seafood. But there are plenty of other things to do during a weekend in Clearwater Beach! Read on for ideas on how to plan a weekend trip to this popular coastal destination.
FLORIDA IN SEPTEMBER
We found cheap tickets to fly out to Tampa on Friday after work and return on Monday evening. While we avoided Labor Day and the higher prices of travel that weekend, there is one other potential problem of visiting Florida in September: hurricane season. Of course, in the week leading up to our trip, there was a large storm forming near Florida. Never in our lives have we tracked an unnamed storm so closely. We observed “Invest 95L” turn into “Potential Tropical Cyclone 9”. But luckily, right before our trip, the storm took a turn to avoid the Gulf side of Florida where we were headed. We admittedly forgot the risks of planning a trip to this area during this time of year. But we definitely learned from this experience and will be sure to keep this in mind when planning future travel.
A WEEKEND IN CLEARWATER BEACH
When we flew into TPA late Friday, we chose to stay at a Hampton Inn near the airport. We weren’t planning on renting a car for the weekend, so it was nice to take advantage of the free hotel airport shuttle. The next day on Saturday, we spent a quick day in Tampa before heading to Clearwater Beach for the rest of the weekend. It also helped us save us some money with hotels. By staying at the cheaper Hampton Inn the first two nights, we only had to book just Sunday night at a hotel in the pricier beach area. This also allowed us to book the beach stay for a Sunday night, which is usually much cheaper than a Friday or Saturday night stay.
After a day in Tampa (which we’ll share more about at the end of this post), we headed for Clearwater Beach on Sunday morning. We checked out of the Hampton Inn, which offered decent complimentary breakfasts with options like biscuits and gravy. From there, we got a Lyft for the 20-mile drive to the beach. We were dropped off at the Hilton Clearwater Beach Resort & Spa, our hotel for the rest of the weekend. This is a great location with many amenities and is right next to the water and walking distance to many attractions. In fact, it’s right by the famous Pier 60.
If you choose this hotel, note that there is a resort fee per night. This covers things such as bike rentals, beachside activities like yoga, and a free hour of non-motorized water sports each morning. Click here to learn why we choose to stick with Hilton brand hotels on our trips.
We had a great experience with the Hilton Clearwater Beach starting with our arrival. Even though we got there mid-morning, they had a room ready for us. Otherwise, we had planned to leave our bags with the bellhop and check in later. So once you arrive for a weekend at Clearwater Beach, what should you do?
PIER 60
Fishing was one of the main reasons David wanted to come here for a birthday weekend. So the first place we headed to was the iconic Pier 60. You have to pay a small fee to get to the end of the pier, but it’s included if you purchase a fishing rental. We found the rates to be very reasonable. For the two of us, it cost less than $40 to fish for the whole day, which includes admission to the full pier, poles, bait, a knife and a bucket.
We chose to go with the frozen squid for bait based on their recommendation. If you’re squeamish, this may not be the best option. Karen became a pro cutting up the squid. Unfortunately, she did not have good luck catching anything, but David was able to reel in several fish. They weren’t big by any means, but it was still the first time both of us got to fish in an ocean!
We did find out if you go back to fish later in the day, we still had to buy bait again (which we thought was included in the all-day rental). If you have a way to keep your leftover bait, we would suggest doing so if you want to avoid buying more. We also warn that in the evening, the pier will get much more crowded due to people wanting to watch the sunset there. So be careful when you’re casting… you don’t want to accidentally hook someone! Don’t forget to check out the nightly crafts and entertainment at Pier 60 as well.
BEACH & WATER ACTIVITIES
Of course, when you’re staying on the waterfront, you’ll want to spend some time at the beach. Clearwater Beach is known for… you guessed it: clear water. This top-rated Florida beach also features soft white sand and is overall a great family destination. The Hilton has chair, umbrella and cabana rentals if you’re interested. They can also coordinate activities like jet-skiing for those looking for something more thrilling. They do have a free hour in the morning for non-motorized watersports (it is a paid rental at other times). We took advantage of this with a two-person kayak on Monday morning and enjoyed a beautiful paddle along the beach. The Hilton also has a couple pools for when you want to relax in the water but without the sand or salt. There is also a spa available for those who want some peace and pampering.
BIKING & SAND KEY PARK
The Hilton provides bike rentals as part of your stay as well, even after you check out! We purposely chose a later flight on Monday to maximize our time in Florida. Even though we checked out of the hotel in the morning, they mentioned we’d still be allowed to use their amenities for the rest of the day. So we checked our bags with the bellhop, grabbed some lunch and then went for a ride. Clearwater Beach has a great biking and jogging path along the island that’s friendly for the whole family. If you go south from the hotel, you will get to Sand Key Bridge. Across the bridge is Sand Key Park, another fantastic beach.
If you’re looking for a less-crowded beach, you’ll want to add Sand Key Park to your list. The bridge to get there is no easy feat though! It’s a decent length with a challenging ascent. No shame if you need to walk your bike up the first half! We actually ran to Sand Key Park on Monday morning from the Hilton as part of David’s training for the Disney World Marathon. And yes, the bridge was quite a climb while running as well! To cover 6 miles, we ran from the hotel to Sand Key Park and back. If you’re a runner, this is a beautiful run to do early in the morning before the heat rolls in for the day. Whether you walk, run or bike, we recommend adding Sand Key Park to your weekend itinerary.
DINING & DRINKS
Clearwater Beach has a plethora of great restaurants, especially if you’re a seafood lover. During our two days here over the weekend, we checked out the following spots. And of course, these are all walking distance from the Hilton:
- Frenchy’s Rockaway Grill: this is an excellent beachfront restaurant with live music and plenty of drinks in a colorful and fun atmosphere. Be sure to try their famous grouper sandwich, one of the best fish sandwiches we’ve ever had! We also had the chicken adobo tostones, which were not disappointing.
- Crabby’s Bar & Grill: this is another great option for both seafood and non-seafood lovers alike, as it is in our case. The wild red shrimp and cajun chicken pasta did not disappoint. The open-air seating and live music kept us dry and entertained as we ate dinner during a sudden downpour.
- Jimmy Hula’s: known for their fish tacos and burgers, this is one of the closest restaurants to the Hilton. We chose to go with a tasty poke bowl and a unique combination of toppings in the Street and Jimichurri tacos. This is a fantastic option if you’re looking for good food, drinks and a place to watch the game.
- Ice & Cream Creamery: Karen loves ice cream, so you know we’re going to stop at a local ice cream shop. Ice & Cream has a ton of flavor options and two convenient locations on Clearwater Beach. Be sure to stop here when you need a cool break from the Florida heat and humidity.
- Clearwater Social Brewing Company: if you’re looking for some drinks, this provides an alternative to the beach-themed bars and restaurants that are prevalent in this area. They have both their own beers as well as other options. This was the last place we stopped at on Monday afternoon before heading to the airport.
OTHER TIPS & SUGGESTIONS
We’re all about budget-friendly travel. So if you’re wanting to save some money on drinks, there is a Walgreens only a 2-3 minute walk away from the Hilton. Rather than going to the tiki bar by the pool or out to another restaurant, we picked up some drinks from the store and enjoyed them on our hotel room’s balcony. Of course, there are plenty of shops to get all sorts of Clearwater Beach-branded apparel and souvenirs. Other things that you may want to check out that we did not have a chance to experience include the Clearwater Marine Aquarium and Caladesi Island State Park.
TAMPA ATTRACTIONS
If you follow a similar itinerary as we used, here are some places in Tampa we enjoyed visiting on Saturday before heading to Clearwater Beach:
- The Florida Aquarium: We love aquariums, so this was a no-brainer to add to our trip. They have many great exhibits, a splash pad for kids and even a dolphin cruise available! Be sure to buy your tickets in advance to skip the long admission line.
- Tampa Riverwalk: This is a nice 2.6 mile path along the waterfront with various restaurants and activities along the way. Unfortunately for us, it began to rain soon after we started to walk, which cut short our time here.
- Tampa Bay Brewing Company: TBBC was one of our favorite restaurants of the weekend. Good food and a delicious variety of brews await you in Ybor City, the only neighborhood on Florida’s west coast to be named a National Historic Landmark District. Highly recommended!
- Cigar City Brewing: This popular brewery is well-known for its Jai Alai IPA. While it’s a favorite among many craft beer enthusiasts, we honestly weren’t a huge fan of it or the other beers here. It was also a bit of a rowdy and crowded atmosphere, but still worth a stop for beer fans.
So that’s how we spent a weekend at Clearwater Beach, with a bonus day in Tampa. What are your favorite things to see and do at a beach town? Let us know in the comments below and check out other recaps on our Trips & Tips page!