Three Perfect Days in St. Pete-Clearwater

If you’ve got three days of PTO to use, this itinerary blends beach bliss, small-town charm and culinary adventures – all across St. Pete-Clearwater.

sunset

DAY 1

Morning: Java Jolt at Tukro Coffee

Start your day with a top-notch brew from this cozy Dunedin coffee shop that's considered a local gem. 

Mid-Morning: Island Time

Take the Caladesi Ferry to make a quick trip to a place that feels very far away – Caladesi Island. (Tip: You can also rent kayaks on the Dunedin Causeway and paddle over to this pristine state park.) Pack a picnic or stop in at the island cafe for lunch.

Afternoon: Explore Charming Dunedin

This friendly spot has a super-cute downtown you'll want to explore. Choose your own adventure:

 

Evening: Dinner & Sunset

When it comes to dining, you've got great options in Dunedin:

Be sure to time your dinner so that you can catch sunset - enjoy it from the Hi-Fi Rooftop Bar at The Fenway Hotel, or on the beach at Honeymoon Island State Park.

Day 2

Early Morning Walk on Clearwater Beach

Stroll Clearwater Beach in the morning calm to start your day in serenity. It's the perfect time to see sandpipers, terns and gulls at the water's edge.

When you're ready to head north to your next adventure, stop for coffee in Dunedin along the way at Veskolini Cafe (for European vibes) or Art Smart Coffee & Gallery (sip surrounded by art, Friday through Sunday only).

Afternoon: Explore Tarpon Springs

Discover this Greek town’s historic sponge docks, shops and rich heritage. Explore museums such as the Tarpon Springs Historical Society (housed in an historic train depot), the Safford House Museum or the Leepa-Rattner Museum of Art. You can even take a tour with St. Nicholas Boat Lines to learn about traditional Greek sponge diving in Tarpon Springs.

Have lunch at one of the wonderful Greek restaurants in town, such as Hellas, Mykonos or Mama's Greek Cuisine.

Evening: Seafood Dinner & A Spooky Tour

Enjoy dockside dining at Rusty Bellies Waterfront Grill, where the staff is friendly and the seafood is fresh-off-the-boat. After your meal, take a ghost tour to learn about this historic towns restless spirits.

Day 3

Morning: Have a Cuppa

Today will be spent exploring the vibrant city of St. Pete, so fuel up with coffee and a treat. Choose your morning vibe:

Late Morning: Time with Mother Nature

Meander the boardwalks at Weedon Island Preserve, or rent kayaks on-site and paddle through shady mangrove tunnels to spot crabs and wading birds. Or stroll through tropical beauty at Sunken Gardens, a 100-year-old attraction in St. Pete.

Midday: Lunch at a Local Favorite

St. Pete locals will tell you that the Cuban sandwich at Bodega on Central is a must-do. 

Craving diner fare? Trip's Diner (named for the owners triplets, Libby, Willy and John) offers a retro counter along with some great chicken & waffles. 

Or head to Three Birds Tavern, where you can sit on the deck under ancient oaks (your pup is welcome, too).

Afternoon: Artsy Explorations

Art lovers will want to explore one of St. Pete's amazing museums, such as The Chihuly Collection and The Dalí Museum. The city is also known for its 600+ murals, which you can view on a walking, bike or trolley tour.

Evening: A Dinner to Remember

St. Pete has earned renown as a culinary destination and, in fact, has three MICHELIN-recommended restaurants: Fortu, Il Ritorno and Sushi Sho Rexley (be sure to make a reservation). Some other top choices include Wild Child, Stillwater's Tavern and Allelo.

Evening: Fun & Games

St. Pete's nightlife scene is hopping, so there are plenty of places to dance and enjoy drinks. If you're looking for something a little more low-key, consider karaoke at LaLa, giant outdoor games at Park and Rec, or the "Friday Night Shuffle" at the world's oldest shuffleboard club.

Your Ready-Made Out-of-Office Reply

Because you really don't want anyone bothering you while you're enjoying your three-day getaway.

Subject: OOO: Currently Living the Beach Life

Hey there!

I’m out of office and off the grid, currently visiting America’s Favorite Beaches in St. Pete-Clearwater, Florida. My schedule is packed with world-class museums, seafood feasts, and serious sunscreen application.

If your message is urgent, please send a seagull. Otherwise, I’ll reply once I return on [return date] — hopefully a little tanner and a lot more relaxed.

Catch you after the tides,
[Your Name]

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