Fort De Soto Park is one of Florida's most beautiful beaches.

Fun Itineraries & Trip Ideas

Vacation planning can be tons of fun... especially when you have the perfect guides to offer insights and local advice. Check out these itineraries and trip ideas, then plan a getaway that's just right for you!

Trending Now: Find Our Wicked Itineraries

If the characters from Wicked have captured your heart, check out this fun quiz and find your most magical vacation itinerary yet!

01/07

smiling women having drinks at Pier Teaki with the St. Pete skyline in the background

reveal your perfect trip

Elphaba or Glinda: What’s Your Vacation Vibe?

Are you the introspective wanderer who seeks sunsets and solitude, or the glamorous adventurer who loves the spotlight? St. Pete-Clearwater has more than a little magic for everyone! Discover your perfectly Wicked itinerary.

What's your perfect vacation morning?

Matcha & meditation

a latte with a tulip design at Craft Kafe

Latte with friends

Beach walk & journaling

Spa treatment

What's your ideal afternoon adventure?

a trail sign that says "Wilderness Trail South" at Brooker Creek Preserve

Nature hike

women sitting on the edge of the pool at the Saint Hotel in St. Pete Beach

Pool time

two smiling women carrying shopping bags while walking out of a store

Boutique shopping

red hibiscus flowers at Sunken Gardens in St. Pete

Garden stroll

When it comes to dining out, what sounds most appealing?

a fruity drink in a tall glass with a pink and white orchid and a straw on a pink table at Mullet's Fish Camp

Cocktails & small plates

A lady wearing sunglasses holding a shrimp right in front of the camera.

Relaxed waterfront meal

a couple out for dinner at Bacchus Wine Bistro

Cozy wine bar

a plate of shrimp scampi with pasta and asparagus at Grace restaurant on St. Pete Beach

Special occasion dining

What kind of evening calls your name?

a man with a surfboard walks along the water's edge in Treasure Island at sunset

Sunset walk

women dressed up for a night out on Central Ave., enjoying cocktails

Night out on the town

two people in clear kayaks with lights paddle near mangroves at night

Moonlit paddle

Rooftop drink with a friend

How do you like your adventures to take flight?

a view of Egmont Key from a helicopter ride

Helicopter tour

Parasailing

A man descends a zip line at Empower Adventures

Ziplining

Kitesurfing

Where would you most like to stay the night?

Luxury hotel

A couple walks away from a tent toward the water at Shell Key during sunset

Camping under the stars

Charming inn

a woman wearing a large sun hat perched on the edge of a pool at Opal Sands Resort

Classic resort stay

What best describes your personality?

three friends laughing and talking at Park and Rec in St. Pete

Social butterfly

a close-up image of a smiling woman on a paddleboard at Anclote Key

Introverted explorer

Yasmin, an influencer, standing in front of the Hollander Hotel

Curious wanderer

a smiling woman at the back of the Little Toot sightseeing boat

Sparkling optimist

two men hold up a young woman as if she is flying at Zubrick Magic Theatre

Results

You're a Glinda Glam Adventurer!

You shine brightest where the sun hits the sea – and the vibe sparkles just as much as your personality. Your dream St. Pete-Clearwater getaway is all about luxury, laughter and a little bit of magic – poolside cocktails, spa days, boutique shopping and golden-hour selfies from a rooftop bar, all with new friends who adore you (of course!).

See Your Glinda-Inspired Itinerary

Woman with sunglasses laying in a hammock with the beach and palm trees in the background

Results

You're an Elphaba Explorer!

You seek meaning in the quiet moments – the hush of a canopied trail at sunrise, the shimmer of moonlight over the Gulf, the hum of life in a destination that still has untamed places to explore. Your ideal St. Pete-Clearwater escape is reflective, moody and full of hidden magic. You’d rather wander through lush parks and indie bookshops than join the crowds.

See Your Elphaba-inspired Itinerary