Ultimate 5-Day Clearwater, Florida Itinerary for June 2025

Day 1: Beach Day

Clearwater Beach, Florida on June 1, 2025

8:00AM

Breakfast at Clear Sky Café

Start your day with classic American breakfast options at Clear Sky Café, known for its friendly atmosphere and diverse menu.
USD15, 1 hour

9:30AM

Clearwater Beach

Enjoy the sandy shores and vibrant atmosphere of Clearwater Beach, perfect for sunbathing, swimming, or building sandcastles.
Free, 3 hours

1:00PM

Lunch at Frenchy's Rockaway Grill

Enjoy a beachfront lunch with delicious seafood and tropical drinks, famous for its laid-back vibe and stunning ocean views.
USD20, 1 hour

2:30PM

Rent Jet Skis

Experience the thrill of jet skiing on the beautiful waters off Clearwater Beach. Rentals are available nearby.
USD60, 2 hours

5:00PM

Dinner at the Palm Pavilion Beachside Grill & Bar

Wind down with a relaxing dinner at this waterfront eatery, featuring a menu filled with local seafood and tropical drinks.
USD30, 1.5 hours

7:00PM

Sunset at Pier 60

Don’t miss the stunning sunset views from Pier 60, along with entertainment and local arts and crafts available every evening.
Free, 1 hour
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Day 2: Island Adventure

Caladesi Island, Florida on June 2, 2025

8:00AM

Breakfast at Cafe de Paris Bakery

Enjoy fresh pastries and artisan coffee to fuel your day of adventure on Caladesi Island.
USD10, 1 hour

9:30AM

Ferry to Caladesi Island

Catch the ferry to Caladesi Island, a natural paradise with pristine beaches, hiking trails, and wildlife.
USD18, 2 hours for ferry and exploration

12:30PM

Lunch Picnic on the Beach

Pack a picnic or get takeaway to enjoy on the beach amidst beautiful nature.
USD15, 1.5 hours

2:00PM

Kayaking in Mangroves

Rent kayaks to explore the mangroves and spot local wildlife, a unique experience that deepens your connection to nature.
USD25, 2 hours

4:30PM

Ferry Return to Clearwater Beach

Relax on the ferry ride back as you soak in the views of the water and coastline.
Included in ferry cost, 1 hour

6:00PM

Dinner at Crabby Bill’s

Savor local seafood specialties at this popular eatery known for its lively atmosphere and friendly service.
USD25, 1.5 hours
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Day 3: Nature Escape

Honeymoon Island State Park, Florida on June 3, 2025

8:00AM

Breakfast at The Breakfast Nook

Enjoy a hearty breakfast filled with omelets and pancakes before you explore Honeymoon Island.
USD15, 1 hour

9:30AM

Honeymoon Island State Park

Spend your day hiking the trails or relaxing on the beach at this stunning state park, famed for its natural beauty.
USD8, 3 hours

1:00PM

Lunch at Honeymoon Island Café

Stop for a relaxed lunch featuring sandwiches and salads in a casual beach atmosphere.
USD12, 1 hour

2:30PM

Shelling on Honeymoon Island

Stroll along the shore searching for beautiful seashells, a perfect souvenir from your trip.
Free, 1.5 hours

4:00PM

Return to Clearwater

Head back to Clearwater and relax at your accommodation or prepare for the evening.
Free, 1 hour

6:30PM

Dinner at the Seafood Company

Indulge in fresh seafood and signature dishes while enjoying the view of the bay from your table.
USD35, 2 hours
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Day 4: Cultural Experience

Tarpon Springs, Florida on June 4, 2025

8:00AM

Breakfast at Denny's Tarpon Springs

Start your day with classic breakfast options available all day at the local Denny's.
USD10, 1 hour

9:30AM

Sponge Docks Tour

Explore the famous Sponge Docks of Tarpon Springs, rich in Greek culture and history, through an educational guided tour.
USD20, 2 hours

12:00PM

Lunch at Hellas Restaurant

Experience authentic Greek cuisine at Hellas, complete with a delightful bakery filled with pastries.
USD25, 1.5 hours

2:00PM

Visit Tarpon Springs Aquarium

Learn about the marine life in the area through interactive exhibits and animal encounters at this family-friendly aquarium.
USD15, 2 hours

4:30PM

Explore Local Shops

Wander through quaint shops around the Sponge Docks, finding unique souvenirs and local art.
Free, 1.5 hours

6:00PM

Dinner at Kream 'n' Kone

Ending your day with comfort food from this popular fast-casual spot known for its fries and seafood.
USD15, 1 hour
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Day 5: Marine Wonders

Clearwater Marine Aquarium, Florida on June 5, 2025

8:00AM

Breakfast at The Good Dough

Enjoy unique doughnuts and coffee to kick off your last day of adventure.
USD10, 1 hour

9:30AM

Clearwater Marine Aquarium

Visit the renowned aquarium dedicated to marine life rescue and rehabilitation, featuring Winter the dolphin.
USD30, 3 hours

1:00PM

Lunch at Island Way Grill

Dine at Island Way Grill with a focus on fresh seafood and inventive dishes, all in a tropical setting.
USD25, 1.5 hours

2:30PM

Stroll Clearwater Beach

Take a leisurely walk along Clearwater Beach and enjoy the last rays of sun and the beachfront vibe.
Free, 1 hour

3:30PM

Souvenir Shopping at Pier 60 Shops

Pick up a few last souvenirs at the fun shops at Pier 60, perfect for remembering your trip.
Free, 1 hour

5:00PM

Dinner at The Salty Crab

Celebrate the end of your trip with a farewell dinner at The Salty Crab, featuring local seafood and a beachy atmosphere.
USD30, 1.5 hours
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