2 DAY T WO: 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 . TREASURE ISLAND & MADEIRA BEACH 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! MORNING AT THE BEACH 3 Browse the boardwalk shops for souvenirs, and when hunger strikes, have lunch at Walt’z Fish Shak or The Friendly Fisherman. VISIT JOHN’S PASS VILLAGE 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. ANCHORS AWEIGH SUNSET SERENADE Wind down with a casual seafood dinner at Gulf-front Caddy’s Madeira Beach or Mad Beach Cantina . DINNER BY THE WATER SHELL KEY & CHARMING GULFPORT DAY THR EE: 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. ISLAND ESCAPE 4 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. JAVA WITH A VIEW DAY FOUR: ST. PETE 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. MUSEUM MORNING After your island adventure, explore the tiny town of Gulfport . Wander the artsy downtown and visit local shops. EXPLORE GULFPORT 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 . DINNER OUT 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. ARTSY LUNCH 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. NIGHTCAP & LIVE MUSIC 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. EXPLORE ST. PETE’S COOLEST STREET Relax with a glass of wine and sample the bold flavors at Allelo , Ceviche Tapas Bar & Restaurant or cozy Lolita’s Wine Market . EARLY DINNER, TAPAS-STYLE 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. AN ENTERTAINING EVENING