The Ultimate Friends Getaway in St. Pete-ClearwaterThree days built around shared breakfasts and dinners, with open days between to split off and choose your own path: spa time, golf, kayaking, galleries, or chasing down the region's best food. A St. Pete-Clearwater trip made for friend groups wanting structure and freedom in equal measure.AuthorsSteller
DestinationsSt. PetersburgItinerary

Day 1: Start the Day Together

The Library - inspired by the George Peabody Library
Tucked inside Johns Hopkins All Children's Hospital in downtown St. Pete, The Library takes its theme from Baltimore's George Peabody Library, with books stacked floor to ceiling and a coffee bar running all day. The brunch and dinner menu covers New American plates like smoked gouda grits and burrata salad, served in one of the more unexpected settings you'll find for a meal out.
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Day 1: Choose Your Coastal Adventures

Gulfport Waterfront
Beach Boulevard forms the spine of Gulfport's Waterfront District, a stretch of independent boutiques, art galleries, and working studios that runs right along Boca Ciega Bay. The scene shifts with the calendar too, from the weekly Tuesday market to the First Friday Art Walk, when artists set up along the sidewalks and live music spills out of doorways up and down the street.
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Pia's Trattoria
Pia's Trattoria has been serving scratch-made Italian food on Beach Boulevard since 2005, with pasta, sauces, and desserts all made in house. Lunch only runs Friday through Sunday, so plan around dinner hours the rest of the week.
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Reel Deal Sportfishing
Family-owned by Captain Steve Hunsucker for over a decade, running two 34-foot charter boats out of Clearwater Beach Municipal Marina, each capped at six passengers for a more personal trip. Half-day, full-day, and extended offshore charters chase grouper, snapper, amberjack, and king mackerel in the Gulf, with all gear, bait, and licensing included.
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Gulfport Brewery + Eatery
Gulfport Brewery + Eatery brews its own beer on site out of an old beach bungalow, with playful names like Hippie Oasis and Martian Mallow on tap. The kitchen serves up loaded hot dogs, Mahi Mahi tacos, and flatbreads, and there's regular live music too.
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Suncoast Watersports
Suncoast Watersports runs off the sand behind Sirata Beach Resort on St. Pete Beach, best known for parasailing but covering jet skis, waverunners, banana boat rides, paddleboards, and kayaks too. They also run dolphin watching and sunset cruises for a slower option on the water.
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Get Up and Go Kayaking - Shell Key Preserve
At Shell Key Preserve, Get Up and Go Kayaking offers clear-bottom kayaks for a straight view down to the fish and sea life below. The route winds through mangrove tunnels when the tide allows, then out to Shell Key's beach, reachable only by water, with sightings that shift by season: roseate spoonbills and manatees in summer, white pelicans in winter, and dolphins year-round.
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Saint Pete Beach
St. Pete Beach stretches roughly 5.5 miles along a slim barrier island called Long Key, with the Gulf on one side and Boca Ciega Bay on the other. Corey Avenue anchors the shopping and dining scene, while the southern tip gives way to Pass-a-Grille, a charming, quieter historic pocket lined with beach houses.
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Day 1: End the Day Together

Cassis Restaurant St. Pete
Cassis sits on Beach Drive in downtown St. Pete, blending an American brasserie with French and Mediterranean touches on the menu. It runs the full spread from brunch through dinner, with sidewalk seating to take in the waterfront scene.
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Day 2: Start the Day Together

Cafe Clementine
Café Clementine sits inside the Museum of Fine Arts on Beach Drive, with terrace seating overlooking the North Yacht Basin. They offer croissants and choux buns, alongside a rotating brunch menu with savory options like breakfast sandwiches, and no museum admission is needed to eat there.
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Day 2: Choose Your Art & Wellness Adventures

The Dalí Museum
The Dalí Museum holds one of the largest collections of Salvador Dalí's work outside of Spain. On the third Sunday of each month, Lucky Cat Yoga leads a vinyasa class in the Raymond James Community Room or the outdoor Avant-Garden, both looking out over the waterfront. Bring your own mat, and stick around after to explore the galleries.
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Glass of Life
Glass of Life runs a hands-on stained glass studio in St. Pete's Historic Uptown District. You can work through a two-part intro class covering scoring, foiling, and soldering, or knock out a quick make-and-take workshop and leave with a finished suncatcher the same day. There's even a small wine shop inside, so a glass in hand while you work is part of the deal.
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Chihuly Collection
The Chihuly Collection fills a building on Central Avenue built specifically for Dale Chihuly's stunning glass work. Eighteen installations glow through darkened rooms, ending in Mille Fiori, a sprawling glass garden whose name means "thousand flowers," and admission includes a live glassblowing demo next door at the Morean Glass Studio.
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The Vinoy Resort & Golf Club, Autograph Collection
The Vinoy Spa is an intimate wellness retreat with just four treatment rooms, one designed for couples, and an elegant, newly renovated interior of marble, warm wood, and a calming coastal palette. Treatments cover massages, facials, and full body work, with sauna, steam room, and whirlpool access included.
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Vinoy Golf Club
Vinoy Golf Club sits on Snell Isle, a quiet residential peninsula a couple miles from the resort, with fairways threaded through palms, pines, and live oaks. The course holds certified Audubon sanctuary status, and it's not unusual to spot herons or roseate spoonbills along the way. If you'd like to build this into the trip, definitely book a night at the resort, as play is reserved for Vinoy Hotel guests and club members.
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Nordic Spa Klub
Nordic Spa Klub brings Danish cold plunging and sauna culture to St. Pete's Warehouse Arts District, with multiple cold plunge tubs, infrared saunas, and red light therapy on offer. There's a private café and lounge for settling in afterward, all built around the Danish idea of hygge, cozy communal ritual over trendy wellness spot.
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The Body Electric Yoga Company
The Body Electric Yoga Company runs out of a converted ice factory in St. Petersburg, offering everything from Ashtanga and Power Flow to Hot Hatha and Restorative Yin. New visitors can grab a short unlimited pass to sample a few styles to find their comfort zone.
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Day 2: End the Day Together

Isu
Isu sits below street level on Beach Drive, a small, dimly lit sushi bar blending Japanese technique with Peruvian flavors, a style called Nikkei. Much of the fish comes in whole from Japan and gets broken down in house, and the izakaya-style menu is built for sharing rather than ordering solo. Behind its quiet doorway, the mood stays unhurried all night.
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Day 3: Start the Day Together

The Hangar Restaurant & Flight Lounge
The Hangar Restaurant & Flight Lounge sits on the second floor of Albert Whitted Airport, looking out over the runway with Tampa Bay in view beyond it. The dining room is decked out in aviation-themed decor, with the kitchen running café by day and bistro by night, serving American comfort food like burgers, fried chicken, and biscuits with gravy. Live jazz takes over on Monday nights.
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Day 3: Choose Your Active Adventures

Empower Adventures Tampa Bay
Empower Adventures Tampa Bay runs a zipline and ropes course through the Mobbly Bayou Wilderness Preserve in Oldsmar, with five zip lines and a 200-foot suspension bridge strung through the treetops. An aerial obstacle course adds log bridges, catwalks, and shaky rope crossings.
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Cliff Stephens Park
Cliff Stephens Park wraps around Moccasin Lake with paved trails and boardwalks running through 44 acres of wetlands and wildlife. A 24-hole disc golf course, adopted by the Disc Golf Club of Tampa Bay, winds through the property and is free to play, drawing a steady stream of local leagues and tournaments. Watch for alligators and snakes along the way, this is Florida after all.
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Weedon Island Preserve
Weedon Island Preserve is best known for its mangrove tunnel kayak trail, a marked 4-mile loop where dolphins and manatees turn up regularly. Beyond paddling, there's birdwatching, boardwalk trails, and a 45-foot observation tower with skyline views, plus real archaeological history as the namesake site for the ancient Weeden Island culture.
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Dink House Pickleball
Dink House operates out of a converted warehouse space, home to four indoor pickleball courts. Play here comes with a bonus: an outdoor barrel sauna and cold plunge for cooling down afterward, and walk-ins are welcome alongside members.
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St. Pete Pier
The St. Pete Pier stretches out over the bay, lined with shops and restaurants along the pedestrian walkway. Along the way you'll pass the Bending Arc, a large-scale sculpture by Tampa Bay native Janet Echelman. At the very top sits Pier Teaki, a tiki-style rooftop bar with panoramic views that swing from the downtown skyline on one side to open Tampa Bay on the other.
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St Petersburg Shuffleboard Club
Billed as the world's oldest and largest shuffleboard club, this St. Pete institution runs about 74 courts and draws a surprisingly young crowd. Friday nights are the ones to catch, free and open to the public, with music and lights that turn a retiree pastime into a proper night out.
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Day 3: End the Day Together

Elliott Aster
Elliott Aster brings Italian cooking and a steakhouse sensibility together inside The Vinoy, with a Michelin Recommended kitchen known for its wood-fired steaks. Signature entrees include a 45-day dry-aged bone-in ribeye and a 48-ounce Bistecca Fiorentina built for the table, alongside handmade pastas like squid ink lumache.
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Other Experiences

Suncoast Sailing's Sunset Sailing Experience!
Suncoast Horizon is the only gaff-rigged schooner sailing the Tampa Bay region, launching out of Treasure Island roughly an hour before sunset. The route shifts with conditions, open Gulf water when it cooperates, the calmer Boca Ciega Bay when it doesn't, with dolphins a regular sight either way. It's BYOB, with a cooler and ice provided on board.
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Egmont Key Ferry from Ft. DeSoto Park
Egmont Key sits at the mouth of Tampa Bay, reachable only by boat, with a working 1850s lighthouse and the crumbling ruins of Fort Dade, a Spanish-American War-era fort now threaded with brick roads and gopher tortoises. The ferry from Fort De Soto takes under an hour each way, often trailed by dolphins, and leaves roughly 3 hours to explore the beaches, shell, and wander the old fort grounds before heading back.
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Stays

The Birchwood
Just 18 rooms fill this Spanish Mission-style building on Beach Drive, each done up in 1920s decor with clawfoot tubs and rainfall showers. Downstairs, Birch & Vine serves seasonal, globally inspired dishes, and the Canopy Rooftop Lounge tops it off with panoramic Tampa Bay views and craft cocktails.
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The Beachcomber
Almost six acres of tropical gardens give The Beachcomber a beautiful layout right on the beach, with direct beach access and two pools tucked in between. Jimmy B's Beach Bar keeps live music going daily, right on the sand along Gulf Blvd, and complimentary beach chairs, umbrellas, and cabana service are included for the day.
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Hollander Hotel St. Petersburg / Downtown
The Hollander's courtyard pool and poolside bar anchor a laid-back St. Pete stay, with Tap Room Bar & Grill serving New American fare and 21 craft beers on tap. A full-service spa, Common Grounds coffee shop, and rooms with a retro, eclectic style set it apart from the typical downtown chain hotel, and it's all walkable to the Dali Museum and the waterfront.
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