2026-08-24 13:28:28
This itinerary blends luxury, coastal charm and culture across St. Pete-Clearwater …
no vacation minute wasted.
WHY THIS FOUR-DAY GETAWAY ROCKS
DAY ONE: ST. PETE BEACH
SWEET START
Begin your day with flaky croissants and delicious coffee at La Croisette or Café Soleil.
TREAT YOURSELF
Mid-morning, book a luxe spa session at Spa Oceana at
The Don CeSar or try Lemon Tree Spa nearby. Prefer to shop? Explore Corey Avenue’s charming shops, or wander Eighth Avenue in Pass-a-Grille Beach.
BEACH LUNCH & CHILL TIME
Dig into a grouper sandwich and a piña colada at Paradise Grille, then spend the afternoon swimming and sunning at Pass-a-Grille Beach, a hidden gem. You’ll want a shower and a nap afterward to feel refreshed for your next adventure.
AN ELEGANT DINNER
Choose an elegant dinner at Grace, with a focus on local ingredients and fresh seafood. Or for refined cuisine with a Spanish flair, make a reservation at Maritana at The Don CeSar.
BEACHY NIGHTCAP
Cap off a wonderful night at Jimmy B’s Beach Bar or Undertow Beach Bar, where you can sip a fruity drink and enjoy soft Gulf breezes.
DAY TWO: TREASURE ISLAND & MADEIRA BEACH
MORNING AT THE BEACH
Fuel up with a hearty breakfast at Coconut Charlie’s Beach Bar & Grill in St. Pete Beach, then head to the soft, wide sands of Treasure Island Beach.
VISIT JOHN’S PASS VILLAGE
Browse the boardwalk shops for souvenirs, and when hunger strikes, have lunch at Walt’z Fish Shak or The Friendly Fisherman.
ANCHORS AWEIGH
Hop on an afternoon sightseeing cruise, a dolphin watching tour, a pirate ship or a floating Tiki boat from John’s Pass. You can also rent Jet Skis or paddleboards.
DINNER BY THE WATER
Wind down with a casual seafood dinner at Gulf-front Caddy’s Madeira Beach or Mad Beach Cantina.
SUNSET SERENADE
Sunset times change throughout the year, so you’ll want to adjust your dinner time before or after sunset. Just head to the beach: You don’t want to miss this show!
DAY THREE: SHELL KEY & CHARMING GULFPORT
ISLAND ESCAPE
Fuel up at Phila Deli in Tierra Verde (you gotta order the big crunch wrap), then head to Fort De Soto Park, where you’ll catch the 10 a.m. shuttle to Shell Key. Soak up the natural beauty and search for seashells.
EXPLORE GULFPORT
After your island adventure, explore the tiny town of Gulfport. Wander the artsy downtown and visit local shops.
DINNER OUT
Have a cozy dinner at Pia’s Trattoria, a local favorite for Italian cuisine. Or dine with a view of sparkling Boca Ciega Bay at O’Maddy’s Bar & Grille.
NIGHTCAP & LIVE MUSIC
Hit Gulfport Brewery + Eatery, a beloved local business, for craft beer and live music. Bonus idea: Check out the Gulfport Night Market if you’re in town the first Friday or third Saturday of the month.
DAY FOUR: ST. PETE
JAVA WITH A VIEW
Stop in at Patrona Coastal Café for coffee by the water, or grab a to-go latte and pastry from Black Crow Coffee Co. and enjoy it on a bayfront bench.
MUSEUM MORNING
Choose your own museum adventure: The Dalí Museum for surrealist art, the Museum of Fine Arts, St. Petersburg, for an expansive collection, or the St. Petersburg Museum of History for fascinating local stories. St. Pete has several wonderful glass art museums, too.
ARTSY LUNCH
St. Pete’s museums have wonderful cafes inside, such as Café Gala at The Dalí Museum and Café Clementine at the Museum of Fine Arts, St. Petersburg. Perry’s Porch is a lovely spot next to the history museum.
EXPLORE ST. PETE’S COOLEST STREET
On vibrant Central Avenue, browse local art at Florida CraftArt, shop for stunning glass art at the Morean Glass Studio and Hot Shop, and wander through indie boutiques.
EARLY DINNER, TAPAS-STYLE
Relax with a glass of wine and sample the bold flavors at Allelo, Ceviche Tapas Bar & Restaurant or cozy Lolita’s Wine Market.
AN ENTERTAINING EVENING
End the night with a mind-bending magic show at Zubrick Magic Theatre or catch a concert under the stars at Jannus Live. Night owls can check out St. Pete’s after-dark scene at local clubs and rooftop bars.
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