Clearwater Beach Itinerary For a Weekend – Fun Activities

Are you looking for a Clearwater Beach itinerary for a weekend that shows you how to use your limited time strategically? Then you’re in the right place.

This guide cuts right to the chase and points out which activities in Clearwater are actually worth spending your precious time on.

Clearwater Beach is an incredible beach destination in Florida for family vacations or a couple’s getaway.

There are a lot of amazing ways you can spend a weekend in Clearwater, so it can be hard to choose which ones to do.

My friends Sandra and Randy own A Boat Day Boat Charters in Clearwater and they are locals to the area. Safe to say, they are true experts on the subject, and they were kind enough to help me with this itinerary.

This weekend in Clearwater itinerary gives you a great mix of all of the best activities and things to do in Clearwater! 

Let’s get to it!

beautiful clearwater beach in florida top itinerary for a weekend

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A Weekend in Clearwater Beach Itinerary: at a Glance

If you just came here to quickly get the Clearwater itinerary and be on your way, look no further. For more details, insider tips, and instructions keep on reading.

Day 1: Downtown Clearwater & Clearwater Beach

  • Breakfast at Ryan’s Island Cafe
  • Clearwater Beach
  • Shopping at Pelikan Walk Plaza
  • Island Way Grill
  • Sunset at Pier 60

Day 2: Clearwater Marine Aquarium & Boating Adventure

  • Clearwater Marine Aquarium
  • Lunch
  • Go on a Boat Tour
  • Dinner at a Beach Bar

About Clearwater Beach

Clearwater Beach is in Florida, on the Gulf of Mexico coast. It’s known for its super white, powdery sand and clear, shallow waters. People love it for the sunny weather almost all year round.

The place is famous for Pier 60, which has nightly sunset celebrations. There’s music, vendors, and even fire jugglers sometimes. It’s a big hit for families, couples, and anyone who loves a good sunset.

Water sports like jet skiing and parasailing are huge here. You’ll also find great seafood restaurants and beach bars.

Day 1: Downtown Clearwater & Clearwater Beach

On your first day of your weekend in Clearwater Beach you’ll hang out on the beach and downtown.

Clearwater Beach is extremely walkable and has plenty of amazing restaurants, shops, and bars to explore. 

Ryan’s Island Cafe

To help you wake up for your first morning in Clearwater head over to Ryan’s Island Cafe.

There the iced coffee refills are flowing and the breakfast dishes are flavorful and filling.

The laid-back furnishings and bright pops of color represent that typical Florida beach style well

It’s unlikely that you’ll order something you won’t enjoy. My favorite dishes on the menu are the Eggs Benedict, Biscuits and Gravy, and the Fresh Toast! 

Clearwater Beach

It’s likely that you’re spending a weekend in Clearwater Beach to see the beach. So having some beach time on this weekend in Clearwater itinerary is obvious.

There are a few tips to make the best out of your day at Clearwater Beach. It can get extremely busy, especially during the weekends or peak season.

Here are my tips for visiting Clearwater Beach on the weekend:

🦀 Go early in the day (before 10 am), especially if you need to find parking

🦀 If you are staying close by you can use the Way2Go free ride service. This way you can avoid looking for parking. This is particularly ideal if you are going to the beach after 10 am

🦀 Consider booking a day pass for one of Clearwater’s beachfront resorts through Resort Pass. You’ll gain access to the resort’s facilities, the beach lounge chairs and cabanas 

picture of the beach in florida with a ferris wheel in the background

Go Shopping at Pelican Walk Plaza

Once you’ve decided you need some relief from the sun you can head over to the 2-story Pelican Walk Plaza.

You can go perusing the different boutiques, cool down with an ice cream cone, or enjoy a couple of rounds of drinks from one of the bars. This is one of the best activities in Clearwater to check out over the weekend.

Enjoy cigars? There is a Cigar Bar downstairs that you absolutely need to check out.

If you happen to be a Hulk Hogan fan, there is an entire restaurant and lounge themed after him. There is even a gift shop filled with merch and memorabilia. 

Note: For a point of reference, The Pelican Walk Plaza is only around a 10-minute walk from the main Clearwater Beach parking lot. There is a parking garage right behind it but it is one of the most expensive places to park so it is not recommended.

Dinner at Island Way Grill

An incredible dinner spot for fresh seafood with a gorgeous view from the outside deck is Island Way Grill. It is located right on the Intercoastal Waterway. 

This is the place to be if you’re looking for more of a fine dining atmosphere. They offer great service, signature cocktails, and elevated eats.

They serve freshly caught fish, hand-cut steaks, some of the world’s finest oysters, and an assortment of daily specials.

Even if you have young kids with a picky palate, Island Way Grill has simple choices to accommodate them.
Tip: Come before 5:30 pm to take advantage of the deals on their early dining menu.

beautiful restaurant in clearwater beach in florida island way grill on a patio with a stunning sunset view

Sunsets at Pier 60

Something to make a priority during your weekend in Clearwater is the nightly event that happens at Pier 60. It is the long pier that you can see from the beach.

As long as the weather is good, the Sunsets at Pier 60 event is a tradition that has gone on for the past 27 years.

On the Pier, you will find local vendors, artists, and musicians providing fantastic entertainment. This is the perfect backdrop for your sunset experience.

The festivities begin 2 hours before sunset and end 2 hours after sunset. There is plenty of time to enjoy dinner before doing this activity on Clearwater Beach.

Tip: The best pictures can be taken from the end of the pier. It only costs $1 to access this recreational area which is typically used for fishing. Plan in advance and find the nightly sunset time here.

stunning sunset at clearwater beach in florida

Day 2: Clearwater Marine Aquarium & Boating Adventure

The second day of your weekend in Clearwater itinerary will be much more explorative and action-packed!

In the morning you’ll learn about native sea life at a non-profit animal aquarium.

Then, spend the majority of the afternoon out on the water on a boat tour.

Lastly, you’ll cap off the evening at a beach bar and have the perfect end to a weekend in Clearwater Beach.

Clearwater Marine Aquarium

The Clearwater Marine Aquarium is not your typical aquarium.

This non-profit organization works to rescue, rehab, and release injured marine animals. This is something I take very seriously, as I do not recommend activities that condone poor treatment of animals.

If you’re coming with kids this is one of the best activities in Clearwater for families.

You’ll get to see dolphins, sea turtles, and white pelicans up close. There is also stingray feeding available daily and a range of different animal care experiences to choose from. 

The Marine Aquarium is open from 10 am to 6 pm daily. The last entry time is 30 minutes before close. 

This activity can be done either before or after your boating tour. That depends on which time of day you prefer to schedule your boat trip. 

cute dolphin making a small show in nicely blue waters in sea aquarium

Go On a Boat Tour

The emerald-colored waters of the Gulf of Mexico are one of many reasons why Clearwater Beach is so special.

While you should most definitely enjoy relaxing on the beach during your weekend in Clearwater, there is nothing that can top getting out on a boat and exploring!

Clearwater Beach is an excellent area to join a boat tour or book your own private boat charter.

There are several different types of boat cruises that you can do from Clearwater Beach.

Some of the most popular choices are dolphin cruises, shelling excursions, sailing, and sightseeing lunch and dinner cruises. 

A popular choice is the Calypso Queen Cruise. It’s a triple-deck ship where you can enjoy some sightseeing, a live DJ, and either a lunch or dinner buffet. This cruise experience is great for all ages, families, or couples. 

The ultimate boat day experience would be on a private boat charter. These experiences last between 4 to 6 hours and include your own captain. He will take you out to the beautiful unexplored barrier islands!

A Boat Day most recently won the Best in the Bay award in 2022 for Best Boat Charters. If you want to book this activity in Clearwater they’re a reputable company to book with. 

boat tours in clearwater beach

Have Lunch or Dinner at a Beach Bar

After a long day of boating, you’ll probably want to eat somewhere casual like a beach bar.

This way, you don’t have to put too much effort into your appearance. Beach bar restaurants are also great for another reason. If you go at the right time you’ll be able to witness another epic sunset to end your weekend on Clearwater Beach!

Palm Pavilion is an awesome choice for a quick bite. Their long outdoor patio gives you a great chance of getting a table with an ocean view.

They offer typical bar food like burgers, sandwiches, tacos, seafood, and more. 

Live music is pretty typical here during the weekends, which will only enhance your dining experience.

Another excellent local favorite with a similar outdoor patio is Frenchy’s Rockaway Grill. It is located right next door to Palm Pavilion.

They’re most famous for their mouthwatering Grouper Sandwiches and Frenchy’s Frozen Rum Runner.

stunning sunset at pier 60 in clearwater beach in florida that needs to be on your weekend itinerary

Best Hotels in Clearwater Beach Florida

Author’s Choice
clearwater beach hotels
Barefoot Bay Resort & Marina
  • Great Location
  • Family-Owned
  • Dockside Patio and Pool
  • Jetski Rentals
  • Free WiFi
  • BBQ Facilities

Clearwater Beach has a lot of great hotels for all different types of budgets.

Pretty much all of your options will leave you within walking distance of the beach (of course some places are a lot longer of a walk away than others).

If you fall into the budget category I’d recommend checking out Royal North Beach which is an updated condo boutique hotel. It’s right next to Hotel Cabana (the next hotel mentioned) so you’ll still be in a great location.

A boutique property with moderate rates is Hotel Cabana Clearwater Beach. It is clean, comfortable, and quiet. You’ll be provided with a bunch of extras, like umbrellas, chairs, and sunscreen.

They have many different sized rooms that can accommodate up to 6 people. The nearest beach access is a 10-minute walk away. It’s right across the street from both The Pavilion and Frenchy’s.

Right in the middle of everything is one of the nicest family-owned hotels, Barefoot Bay Resort & Marina. This is the place for you if you want to be close to the action.

The hosts who will go above and beyond to meet your needs. The hotel is right next to a dock on the intercoastal, so you can rent jet skis or scooters. There is also a dockside patio and a pool.

What is the Best Time to Spend a Weekend in Clearwater

The best time of year to plan your weekend in Clearwater will greatly depend on your personal preferences. 

Do you like the ocean to be like bath water? Then coming during the end of spring through the end of summer. However, during this time of year, there is the most humidity. Also, the crowds are at their peak as families are taking their summer vacation trips. 

Prefer less crowds, pleasant temperatures, and refreshing water? Visit between October through November or the end of February through May.

More Clearwater Beach Florida Activities


If you’re up for an adrenaline rush, this is it. You get strapped into a parachute and a boat pulls you up in the air.

You’ll be soaring above the water and get to see the beach from way up high. Super fun and not as scary as it sounds!

Renting a Kayak

You can rent a kayak and explore the waters at your own pace. It’s a chill way to get closer to nature. Paddle through mangroves or along the coastline, you might even spot some dolphins or manatees!

Caladesi Island

Caladesi island is a short ferry ride from Clearwater and it’s like a hidden gem.

Think less crowded, super clean beaches. You can hike, picnic, or just lay on the beach. It’s the perfect spot to disconnect and enjoy some quiet time.

stunning drone shot of caladesi island in clearwater beach florida

Are There Sharks in Clearwater Beach?

Yes, sharks do live in the waters around Clearwater Beach. But shark attacks are really rare.

Most sharks are not interested in humans, and the types you might find near the beach are usually smaller and less aggressive.

As for famous attacks, nothing really comes to mind for Clearwater Beach specifically. Most shark incidents in Florida happen on the Atlantic side of the state, not the Gulf side where Clearwater is.

So while it’s always good to be aware and follow safety guidelines, the chance of a shark encounter at Clearwater Beach is super low.

Just keep an eye out for any warnings or advisories from local authorities.

Is it Safe to Walk Around Clearwater?

Clearwater and especially Clearwater Beach are generally considered safe for walking around, especially during the day.

The beach area and main tourist spots are usually well-patrolled and busy. However, like any tourist destination, it’s good to be aware of your surroundings.

Nighttime is a bit different. While the beach and entertainment areas are still pretty active and generally safe, it’s always a good idea to stick to well-lit, populated areas. Avoid alleys or sketchy-looking spots.

As always, check out local advisories or news for any recent issues. Most visitors find Clearwater to be a safe and enjoyable place to explore on foot.

Do you need travel insurance in Clearwater Beach? Yes, travel insurance in Clearwater Beach is highly recommended.
Unsafe roads, water sports accidents, and food poisoning are only a few examples of when travel insurance could come in handy. EKTA offers worldwide travel insurance with 24/7 service and no hidden fees or restrictions.

Conclusion: Clearwater Beach Itinerary

This brings us to the end of this Clearwater Beach Itinerary for a fun weekend. I hope you liked my favorite activities and local tips for spending a weekend in the beautiful coastal area.

From fun boat trips to sunsets at Pier 60 – Clearwater Beach has a lot to offer. It is a perfect place for honeymooners, families, and younger people.

The weather is good year-round and the water is pristine – the perfect place for a tropical beach vacation in the US.

FAQ: Clearwater Beach Itinerary

Is Clearwater Beach on the Gulf of Mexico?

Yes, Clearwater Beach is on the Gulf of Mexico, located on the west coast of Florida. It’s famous for its white sand and clear waters. The Gulf side is usually calmer than the Atlantic, making it great for water sports and chill beach days.

Are there Sharks in Clearwater Beach?

Yes, there are sharks in the waters around Clearwater Beach, but shark attacks are really rare there. Most sharks near the beach are smaller and less aggressive. While it’s good to stay alert and follow safety guidelines, the risk of a shark encounter is pretty low.

What Part of Clearwater beach is nicest?

The nicest part of Clearwater Beach often depends on what you’re looking for. North Beach is generally quieter and less crowded, perfect for a chill day. South Beach, near Pier 60, is lively with lots of activities and restaurants. So, if you want peace, head north; for action and amenities, go south. Either way, you can’t go wrong!

What month is best for Clearwater Beach?

The best month for Clearwater Beach depends on your vibe. March and April offer warm weather and spring break crowds. For a calmer experience with great weather, try October or November. But honestly, the beach is pretty awesome year-round, thanks to Florida’s mild winters. Just pick your month based on the atmosphere you want!

Is Clearwater beach florida worth visiting?

Absolutely! Clearwater Beach is a must-visit for beach lovers. With its powdery white sand, clear blue waters, and awesome sunset views, it’s a slice of paradise. Whether you’re into water sports, seafood, or just chilling on the sand, there’s something for everyone. Plus, the Pier 60 sunset festival adds a unique, festive vibe.

Can you swim in the ocean at Clearwater?

Yes, you can definitely swim in the ocean at Clearwater Beach. The Gulf of Mexico waters are usually calm and warm, making it great for swimming. It’s super family-friendly too. Just keep an eye out for any safety flags or advisories, especially during jellyfish season or rough weather. Overall, it’s a swimmer’s paradise!

blonde girl pink dress in front of blue door santorini

About the Author

Sabrina is a passionate travel blogger and content creator, based in the Netherlands. She spends most parts of the year abroad at various destinations with her husband.

She provides slow-paced itineraries that focus on quality over quantity. Sabrina wants to help her readers to get more out of their travel experiences – while doing less. Read more.