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Planning a Family Trip to Clearwater Beach, Florida

May 29, 2019
18 min read
Clearwater Beach, Florida
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Recently voted the No. 1 beach in the United States by TripAdvisor, Clearwater Beach on Florida's west coast is as family-friendly as it gets. With sugar-white sand, many low-key restaurants, a ton of activities, huge playground and nightly shows, your family will absolutely love vacationing here.

Clearwater, Florida. (Photo by John Coletti/Getty Images)

How to Get to Clearwater Beach

Two airports, within 20 miles of the beach, make it easy to reach your destination. The closest and most convenient airport is St. Pete-Clearwater Airport (PIE), which is 12 miles from the beach, so you can land and be swimming in the ocean in no time. Only two domestic airlines fly into this airport.

The largest presence is with Allegiant Air, which flies nonstop to more than 50 destinations. This low-cost carrier often provides discounted fares, although service is typically only a few times a week and you'll most likely only find one flight a day per city pair. If you live near an airport serviced by Allegiant and you have flexibility, this can be an inexpensive way to fly into Clearwater. For example, we priced a round-trip ticket from Cedar Rapids, Iowa, at $130 all-in with taxes for July dates. Or, if you live near Gulfport–Biloxi, Mississippi, you can fly Sun Country Airlines.

Tampa International Airport (TPA) is the other airport serving visitors to Clearwater. Depending on traffic, it takes 35-50 minutes to get to the beach after landing. The airport serves most major airlines, with routes across the US, on Southwest, Delta, American, United, Alaska, JetBlue, Spirit and Frontier. This is the perfect opportunity to fly two-for-one with the Southwest Companion Pass or Frontier's Kids Fly Free and Friends Fly Free promotion.

Must-Dos for Families

The most popular area of Clearwater Beach is Pier 60. Although the pier is great for fishing, the main attraction for kids happens right off the pier. Starting at around 6pm every evening, there are a ton of activities for kids -- typically two or three street performers ranging from escape artists to stilt walkers. There are also craft booths with vendors selling jewelry, offering to braid hair and even spray painting art for sale. On Friday and Saturday evenings, there is a sunset cinema -- an outdoor movie theater under the stars. There is also an amazing beach playground right in the mist of it all for kids to play morning, noon and night. These activities are free and open to the public.

An awesome playground at Pier 60 in Clearwater Beach, Florida. (Photo courtesy of Jennifer Yellin/Deals We Like)

Most tours leave from the docks slightly north of Pier 60. Since you are on the water, there is everything from sunset boat tours, dolphin-watching tours, a thriller speedboat ride and even a pirate cruise. The Thriller Powerboat Tour costs $28 for adults; $19 for children, ages 4–12, and free for kids 3 and under.

(Photo courtesy of Jennifer Yellin/Deals We Like)

If you continue down the road and over the bridge, about a mile from Pier 60, you'll find the Clearwater Marine Aquarium. This is home to Winter the Dolphin who made an appearance in the movie "Dolphin Tale." In addition to touring the aquarium, there are many different animal encounter opportunities that allow you to get close to the dolphins, sharks, otters and pelicans (some have additional admission fees). General admission is $25 for adults; $23 for seniors, ages 60 and older; $20 for kids, ages 3–12, and free for children ages 2 and younger. The aquarium also has a sundown special admission that costs $13 if you enter after 4pm.

The Clearwater Marine Aquarium (Photo courtesy of Visit St. Pete/Clearwater)

If you walk the opposite direction (south) from the Pier, you can rent a Surrey bike to cruise the boardwalk. This was a fun pastime for my kids, especially since they got to ride up front and pretend to drive. Of course, the adults did all the peddling, but we all had a blast for an hour. Companies also rent coupes, gliders, scooters and regular bikes. There are a few different rental places at the beach, but the Fun Ride Rentals was conveniently located right at the Hyatt Regency. Surrey bike rentals start at $29 per hour.

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(Photo courtesy of Jennifer Yellin/Deals We Like)

Next to the Hyatt Regency was the Flow Rider. While my family did not participate in this surfing activity, the beach store next door has glass windows looking into the simulator where you can have a seat and watch others try to surf the waves. One 30-minute session is $30.

The Flow Rider surfing simulator. (Photo courtesy of Visit Clearwater Beach/Facebook)

Best Points Hotels in Clearwater for Families

Clearwater Beach has many chain hotels where you can redeem your points for a free-night stay.

Wyndham Grand Clearwater Beach

This new-ish property is one of Wyndham's nicest hotels and possibly one of the best chain properties in Clearwater Beach. The Wyndham Grand Clearwater Beach is located across the street from the beach and in an ideal location near restaurants, activities and Pier 60. There is a lively outdoor pool with a whirlpool on the ground level. There is also a full spa and multiple dining options.

(Photo courtesy of the Wyndham Grand Clearwater)

Unfortunately, this was one of the 200 properties that was hit with Wyndham's recent category changes. This property now costs 30,000 Wyndham Rewards points for an award night. When using your points, you can book a room with one king bed or two queen beds. Or, you can redeem just 6,000 Wyndham Rewards points to reduce the paid rate for its Deluxe King Bunk room, which books you into a room with one king bed, plus twin bunk beds.

Hyatt Regency Clearwater Beach Resort and Spa

The Hyatt Regency Clearwater Beach Resort and Spa is the best option for large families looking for a spacious hotel room. Most of its rooms start at a whopping 600 square feet (with a full kitchen) or you can go all-in and book one of the two-bedroom suites ranging from 1,200 to 1,600 square feet. The massive rooms, ideal location, on-site kids club for ages 3–12, and the status recognition make this is an ideal hotel when traveling with a family.

Similar to the Wyndham Grand Resort, this hotel is also across from the beach, but I did not find this to be an issue. My main gripe with this property is that everything seemed to be on different levels so we found ourselves taking the elevator up and down quite often. The beach was on the ground floor; the restaurants on the second floor; the pool deck (with a baby pool) was on the eighth floor and the hot tub was on the 16th floor. We eventually got used to it, but it was definitely confusing at first.

(Photo courtesy of the Hyatt Regency Clearwater)

The best thing about this property is that it treats Globalist guests like royalty. While you can use one of your Globalist Suite Upgrades to upgrade to a one-bedroom suite, don't be surprised if you're offered a complimentary upgrade to a two-bedroom suite upon check-in. Even with a lower-level status, or no status at all, this property offers more one- and two-bedroom suites than standard rooms, so you have a shot of an upgrade, especially if you are traveling during an off-peak time.

Those with Globalist status will also receive complimentary breakfast at the SHOR restaurant for up to two adults and two kids, which will give you access to the full buffet or the regular menu. Unfortunately, this property does not have a club lounge for those with Explorist status looking to redeem a Club Lounge Certificate.

This property is now a Category 6 hotel within the World of Hyatt program and thus requires 25,000 World of Hyatt points a night. There are many times where you'll find reasonably priced paid rates or promotional offers, so you might find that redeeming your points will give you a lower value than TPG's valuation. If you travel during peak dates, the World of Hyatt Credit Card can get you two award nights with the current up to 60,000-point welcome bonus offer (30,000 Bonus Points after spending $3,000 on purchases within the first 3 months from account opening. Plus, up to 30,000 more Bonus Points by earning 2 Bonus Points total per $1 spend on purchases that normally earn 1 Bonus Point, on up to $15,000 in the first six months of account opening). You can also transfer Chase Ultimate Rewards points to Hyatt at a 1:1 ratio.

Sheraton Sand Key

The Sheraton Sand Key is in a slightly different location than all of the other properties listed above. It is in a quieter part of Clearwater Beach, away from the shops and activities. It is located on its own private beach, next to Sand Key Park. In this more resort setting, you'll find beach volleyball, beach tennis and other beach games. There is a large pool deck with a heated pool, a kiddie pool and a hot tub. There is also a children's playground on-site, as well (or you can head to Sand Key Park for an even larger playground). Despite its more remote location, there is a free trolley to the "main" Clearwater Beach area.

Sand Key Park (Photo courtesy of Drdisque/Wikipedia)

This property costs 35,000 Marriott points a night for a free-night stay. The room can actually fit up to five guests with two queen beds and a roll away. With the Marriott Bonvoy program, your fifth night is free when you use points. For a five-night stay, you are really looking at just 28,000 points a night. This is also the perfect opportunity to use a free-night certificate from any of the Marriott credit cards that are capped at 35,000 points per night.

The Sheraton Sand Key (Photo courtesy of Marriott International)

Hilton Clearwater Beach Resort & Spa

The Hilton Clearwater Beach Resort & Spa might have one of the best locations in Clearwater Beach because it is right on the beach with Pier 60 just a stone's throw away.

This property charges a daily $25 resort fee (waived if you use points), but you'll get a lot of value for your family including complimentary access to nonmotorized water sports from 9–10am, bike rentals, beach photo shoots, morning yoga and beach-side activities.

Points range from 44,000 to 60,000 Hilton Honors points a night for a room with two double beds. When using your Hilton points, those with status receive a fifth-night free. Fortunately, earning any sort of Hilton status is quite easy since all of the Hilton credit cards come with elite status.

Related: Best Hilton Credit Cards for Family Travelers

Holiday Inn & Suites Clearwater Beach

The Holiday Inn & Suites Clearwater Beach is a waterfront hotel -- although you'll have to walk up the street to actually play on the sand and jump in the water. As with most other properties at the beach, the Holiday Inn has a heated outdoor pool and a heated kids' pool. There is also an outdoor restaurant on the waterfront with nightly live entertainment.

The Holiday Inn & Suites Clearwater Beach (Photo courtesy of IHG)

This property costs 35,000 IHG Rewards Club points per night. If you have the IHG Rewards Premier Credit Card, you'll receive your fourth night free when redeeming points. This will bring your nightly rate down to just 26,250 IHG points per night. With many opportunities to purchase IHG points with a bonus, this means you can purchase the required number of points for just $131 a night when there is a 100% bonus opportunity. And, since you can use the free-night certificate that comes with the credit card each account anniversary year at this particular property (capped at 40,000 points a night), you can also tack on an extra night for free.

Quality Hotel Clearwater Beach Resort

The Quality Hotel Clearwater Beach Resort is on the most southern part of the island, so you are slightly removed from the main beach strip and Pier 60 -- but you are never truly far away from anything in Clearwater Beach. Fortunately, this property has access to a private beach and a heated outdoor pool.

(Photo courtesy of the Quality Hotel Clearwater Beach Resort)

Although the Quality Hotel is not as luxurious as some of the other properties mentioned, if you are just looking for a decent place for your family to sleep, this hotel might be the perfect place. Prices are significantly less expensive and the points rate starts at 12,000 Choice Privileges points a night. Since Choice allows you to book any rooms available at the same number of points, you can book a room with two king beds, plus a sofa bed. The main issue with redeeming Choice Privileges points for a free-night stay is that you can only book 100 days out. For families who like to plan in advance, this can definitely be problematic.

Planning Tips

Best Time of Year to Visit

The absolute best times to visit Clearwater Beach, and really many other Florida beach destinations are in late October - early December or during the spring. Weather is more guaranteed with sunshine and sunbathing weather, but you will not be faced with the hot and muggy temperatures. The time between late October and early December will allow you to snag the best off-peak hotel prices if paying with cash (aside from long weekend holidays and Thanksgiving week). Be prepared for larger spring break crowds in March and April, as this is a popular time for many families to head south to sunny beach destinations.

(Photo by Rachelle Vance Photography/Getty Images)

Everything at Your Fingertips

Clearwater Beach has everything you need for a family vacation. There are grocery stores, multiple drug stores and even beach supply stores. This means you don't have to over-pack and, if you run out of something, you can go to the store and easily buy it. I hate packing a ton of diapers that will take up a suitcase space, so on my recent trip to Clearwater, I packed just a day's worth and then purchased a package at CVS. This also comes in handy if you do not want to check luggage because you are carrying sunscreen or other liquid items. Just leave them at home and buy what you need when you arrive.

Car Not (Necessarily) Required

Clearwater Beach is a walking community. This means a car is not a necessity, unless you want to leave the beach area for other activities, such as visiting Busch Gardens. Car rentals in Florida are relatively inexpensive (use the site AutoSlash to find good deals). Although the cost of a rental car might not be expensive, daily parking at your hotel can definitely add up. For example, standard daily parking at the Hyatt Regency Clearwater Beach & Resort costs an extra $25 per day (unless you are a Globalist or on an award stay).

If you decide to forgo a car rental, you can always take a taxi/Uber to and from the airport. The estimated Uber ride is $40. Once at the beach, there are many transportation options, such as Florida Free Rides, which runs on tips; the Clearwater Jolley Trolley costs $2.25 per ride (children 5 and under are free), or Uber.

Plenty of Low Key Restaurants

Going to a restaurant with my two kids can be a hit-or-miss experience. We avoid white tablecloth restaurants with our 2-year-old for obvious reasons. Fortunately, Clearwater Beach was the perfect place for us to dine out. There are a many low-key restaurants where you can sit outside and your kids can run around on the grass and play a game of corn hole.

Frenchy's Restaurant across the street from the beach. (Photo courtesy of Jennifer Yellin/Deals We Like)

There are also plenty of order-at-the-counter places, where you can order a pizza and picnic on the beach. This not only helped relieve the stress of dining out with my kids but also helped our wallets with inexpensive meals. Just something to know when planning out your days ahead of time. Tip: Order the grouper at Frenchy's.

Related: The Best Credit Cards for Dinning Out

Bottom Line

Clearwater Beach was the absolute perfect vacation for my family. We loved our four-night stay and easily could have tacked on another extra day or two. We are definitely a beach family, but we loved that there were more than enough daytime activities and nightly entertainment to ensure we never got bored.

Keep planning your Florida trip:

Jennifer Yellin is a Boston-based travel blogger who covers family travel deals for TPG and blogs at Deals We Like. Follow her family’s adventures on Twitter and Instagram.

Featured image by Getty Images/Image Source
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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