Clearwater Beach Itinerary – Resident’s Trip Plan

Last Updated October 28, 2025

We see it all the time! Visitors come to our beach island and spend half their time trying to find out where to go and what to see on one of Florida’s top beaches.

We live here! We decided that a Clearwater Beach Itinerary was the best way to introduce all the possibilities to explore the island. We have included the most popular things to do and places to visit to add to your itinerary planning.

Planning Your Clearwater Beach Itinerary
Planning your itinerary for Clearwater Beach is a way to save time and money while here.

Highlights of Clearwater Beach Itinerary

We will point out –

    • The best things to do on Clearwater Beach.
    • The best restaurants from breakfast to dinner.
    • The best rooftop bars and best tiki bars.
    • The best things to do with children.
    • The off-the-beaten-path places that locals go.
    • The best hotels to consider.

Get ready for a journey through our island.

Clearwater Beach and Pier 60
Our beautiful Clearwater Beach and Pier 60.

The Must Do Things in Clearwater Beach

    • The Beach – Most likely, you came here for the famous Clearwater Beach. You will find it is everything you have heard – pure white sand! 2.5 miles of it! The beach is free. Parking is not. You can reserve cabanas and umbrellas on the beach or bring your own. Many visitors plan their day around beach trips and fill in with other things to do on the island.
    • Pier 60 – As the sun lowly disappears into the Gulf, Pier 60 comes alive with vendors and performers. Sunset is a celebration at Pier 60 each evening.
    • Clearwater Marina – Our word-class marina is a hub of things to do on the water. The list below represents the most popular activities –
        • Captain Memo’s Pirate Cruise – fun cruise around the island with cannons blaring. Reservations & info.
        • Dolphin Cruise – take a cruise for a guaranteed sighting of dolphins at play in the harbor and Gulf. Many choices.
        • Sunset Dinner Cruise – don’t miss the sunset and night lights on the beach. Cruise info.
        • Parasailing – see the beach and island from 100 feet above the water. Choose your time.
        • Deep Sea Fishing – The Marina hosts numerous fishing vessels with all types of trips. Book a trip full day or half day.
    • Clearwater Marine Aquarium – this is the home of the movie Winter the Dolphin. Located just s short distance off the beach, the CMA is loved by adults and children. Buy Your Tckets Online.
    • Caladesi Island Day Trip – While Clearwater is one of the top beaches in the country, just a few miles away is a remote island beach that is one of the best in the world. Discover Caladesi Island.

Add these activities to your Clearwater Beach itinerary.

Clearwater Marina
The Clearwater Marina is loaded with tour boats, fishing boats and cruise ships. There are a lot of activities to choose from.

Top Clearwater Beach Restaurants – Breakfast to Dinner

Like most popular Florida destinations, the island has dozens of restaurants. As residents, we have tried most all of them. Here are our suggestions.

Breakfast – The best breakfast in the area is Maggie Mae’s Waterfront. Visit Maggie’s if you have a car since it is over a bridge from South Beach. With hundreds of five-star reviews, you won’t be disappointed.

Near the center of the beach is a place called Ryan’s Island Cafe. You will find a good breakfast there. Further north Another Broken Egg does a good job for breakfast.

Lunch in Clearwater Beach – For a unique waterfront lunch, try the tiki bar at Opal Sands. Called the Sandbar, the Opal serves the best grouper sandwich on the beach.

Another of our favorite lunch places is the Palm Pavilion on North Beach. For decades, this beachside restaurant has served tourists and locals alike.

If you like tacos (and a budget-friendly option), try the Taco Bus on Gulview in front of the Edge Hotel.

The Frenchy’s Restaurants are advertised heavily. One restaurant we would point out, owned by the Frenchy’s group, is Clear Sky Cafe. We consider Clear Sky our favorite lunch is you don’t care about the view.

Caretta Food
The food, view and ambience is superb at Caretta on the Gulf.

Dinner in Clearwater Beach – You have many options for dinner in Clearwater Beach. The best dinner restaurant in Clearwater is Caretta on the Gulf at the Sandpearl Hotel. Great for that special occasion or romantic dinner on the beach.

One of the oldest restaurants on the beach is Bob Heilman’s Beachcomber on Mandalay. They have been serving great food for two generations.

A relative newcomer is the Mandalay Prime (formerly Blinkers). Both steaks and seafood have been good on our visits.

For more budget-friendly options, try The Boxer, Salty’s or Crabby Bill’s across from the main Beach. Many of our lunch choices also serve dinner.

Most Popular Roof Top Bars and Tiki Bars on Clearwater Beach

Sandbar Tiki bar
The Sandbar tiki at the Opal Sands is our favorite.

For a complete guide to the tiki bars on Clearwater Beach, we have a complete article. 

To summarize all the options, our choice for a tiki bar is the Sandbar we mentioned for best lunch.

The views are amazing from the Sandbar of the Gulf, the beach and Clearwater Pass. Even in the middle of summer, cool breezes keep you comfortable out on the jetty of North Beach.

Rooftop bars on Clearwater Beach have become very popular to build in the new hotels. The latest one is becoming our favorite. It is the rooftop at Hiatus Hilton Hotel.

Our previous choice for a rooftop bar in Clearwater Beach was the Crow’s Nest at the Pier 60 Hotel.

Kids Love Fireworks on Clearwater Beach

On July 4th and many other special occasions on Clearwater beach, the city sponsors fireworks that are spectacular. We captured one of these events in this video.

Best Things To Do With Children in Clearwater Beach

It seems we have something for everyone on the island. Children have plenty to do on the beach or around the island.

The most popular things children like to do are:

    1. Spend the day at the beach. There are volleyball courts, slides, swings and attractions bunched around Pier 60.
      Captain Memo's Pirate Cruise
      Captain Memo’s Pirate Cruise is one of the most popular things to do in Clearwater Beach.
    2. Kids from 8 to 80 really enjoy Captain Memo’s Pirate Cruise. Kids come back made up to look like a pirate. The crew on the boat engages them in games and fun throughout the voyage.
    3. Clearwater Marine Aquarium is a must for kids. Even if children haven’t seen the Dolphin Tale movie, they will be engaged in all the fun things dolphins do. The whole process is a huge learning experience despite feeling like just another aquarium.
    4. Children love boat rides. Whether it be the fast Sea Screamer or the dolphin cruise Little Toot, the experience, water and sights will keep them entertained.
    5. While the beach is number one, children love hotel pools. Make certain you choose one of the hotels with large pools. See our list of hotels below that have a “kid Friendly” tag noted.

Off the Beaten Path – Where Locals Go on Clearwater Beach

Every major travel destination has places where the local residents hide or at least get out of the tourists’ way! Our beach is no exception. Some of our recommendations include:

  • Lunch – head over to The Bait House near the Clearwater Marina. This place is built out over the water by locals who pride themselves on offering fresh off the boat fish. It’s a great place for a fresh fish of the day sandwich and a couple of beers under an umbrella!
    Captain Gary and Grouper
    Captain Gary and the Strike Zone is our favorite near shore fishing charter.
  • Best Fishing – If you are not into long offshore fishing trips, head over to the Marina and look for the smaller boat called Strike Zone. Captain Gary specializes in catching big fish in near-shore waters. He is also patient with newcomers to fishing and children.
  • Sports Bar – A relative newcomer to the sports scene has become the hangout for locals who want to watch sports. Hogg Daddy’s on South Beach is the place to go to watch that big game. They have plenty of TV’s and decent bar food.
  • Bistro – Looking for that little out-of-the-way bistro for a great dinner experience. Try Bobby’s Bistro, located behind Bob Heilman’s Beachcomber.
  • Sailing – Looking for a safe, fun sailing experience the whole family can enjoy. Look for the Kai Lani in the Clearwater Marina. Captain Mike has been on the local waters for 3 decades. He can give you some history and a few sailing lessons. Have a big wedding party, business group or family outing? The Kai Lani is a fun way to spend the afternoon.
Beach Walk Clearwater Beach
To give you a perspective, this is Beach Walk on Clearwater Beach. The hotels on the left include Opal Sands, the round building in the distance and the Hyatt Regency is the pinkish building on the left. This half mile walkway includes hotels, restaurants and shops with the main beach on the right.

The Best Places To Stay on Clearwater Beach

There is no such thing as a one-size-fits-all for hotels on the beach. We have very nice resorts, budget friendly hotels, great places for kids and some more romantic places for adults. As residents, we know them all. 

Our recommendations for a hotel that meets your needs –

Best Places to Stay for The Family on Clearwater Beach 

      • Hyatt Clearwater Beach
        Hyatt Regency Clearwater Beach
        The Hyatt Regency – located in the middle of the beach, the Hyatt is just steps away from the main beach. No car is necessary due to the central location. Great pool and kid-friendly.
      • Budget Friendly Option – The Sheraton Sand Key is located directly on the Gulf of Mexico. You can walk from your room to an all day beach party for your family. The Sheraton is on Sand Key just across the bridge from the main beach. There is a free trolley that runs every 30 minutes. You will love the location away from the crowded main beach.
      • Mid Range Option – The Hilton Clearwater Beach is located on the north end of the main beach. You can literally walk out of the hotel and onto the pure white sand beach. They have a good kid-friendly pool and the location is just steps away from Pier 60.

Best Places to Stay for Adults on Clearwater Beach

      • Opal Sands Clearwater Beach
        Opal Sands Resort
        The Opal Sands Resort or their new Opal Sol – Connected by a walking bridge over the main street, these two hotels offer great views of the main beach (just beside the Opal Sands). Both are relatively new and offer refined rooms and amenities, next to the beach. Both have excellent restaurants and the Sandbar tiki was discussed above.
      • Budget Friendly Adults – Shephards Beach Resort is on the water along Clearwater Pass, They offer lots of activities and afternoon entertainment while their beachside chairs view the boat traffic coming in and out of the island.
      • Complete Resort Experience – If you want a more intimate beach experience, The Sandpearl Resort offers luxury and a private beach right on the Gulf. They also house the best restaurant on the island, Caretta on the Gulf, we recommended above for dinner.

More hotels in Clearwater Beach and a Resort Comparison.

Frequently Asked Questions About Clearwater Beach (FAQS)

Directions to Clearwater Beach?

From Tampa and Places East –

Take FL-60 W (Courtney Campbell Causeway) toward Clearwater.
Continue on FL-60 W for about 20-25 miles.
Cross over the Clearwater Memorial Causeway.
Follow the road straight to Clearwater Beach.

What about Clearwater Beach parking?

Parking at Clearwater Beach can be a bit of a challenge during peak hours, but there are definitely solid options! Here’s a quick guide to locations you may find a spot without stress:

311 S Gulfview Blvd
1 Causeway Blvd
490 Mandalay Ave
Metered street parking throughout beach, varies (usually $3.50/hr)

You can put these addresses in your cell phone or GPS to locate.

How far is Clearwater Beach from Orlando?

Clearwater Beach is about 105 to 115 miles from Orlando, depending on your exact starting point. That’s around a 2 to 2.5-hour drive. More complete information at Florida Travel Blog.

What are unique things to do near Clearwater Beach?

The Gulf Coast is a virtual melting pot of Florida attractions. Here are some ideas:

A must-visit is Caladesi Island just a short distance from Clearwater Beach. It is accessible by ferry only. You can catch the ferry at Honeymoon Island State Park (30 minutes away).
Tarpon Springs is a Greek community with an active waterfront boardwalk full of attractions and restaurants the whole family will enjoy. About 45 minutes away due north on US Route 19.
John’s Pass is a beach community with over 100 restaurants, shops and waterfront attractions. You can find this fun place about 30 minutes south on Gulf Blvd.
If you want a fun place to take the kids, try Celebration Station about 25 minutes away on US Route 19 North.

Is the water clear at Clearwater Beach?

Yes – the water at Clearwater Beach is clear and calmer than many Atlantic Coast Beaches.

What is a rainy day thing to do on Clearwater Beach?

The Clearwater Marine Aquarium is a must-visit on bad weather days.

Are there hotels on the beach?

Yes – you have hotels like the Opal Sands on the beach and the Hyatt that is just steps away.

Do I need a car to get around Clearwater Beach?

No – cars are unnecessary. The beach and attractions, shopping, and restaurants are all within a half-mile of each other.

Is Clearwater Beach expensive?

No – not compared to many other places in Florida like Miami, Naples, Marco Island and Boca Raton.

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larry edger _ author About the Author: I’m Larry Edger, a Florida resident who’s spent decades exploring the state—beaches, islands, springs, small towns, and road trips. I publish practical Florida travel guides with real-world planning tips and seasonal updates. Read more about Florida Travel Blog →

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