Second Blog Post in a Series – Jonathan Kelly, The Tenpenny Collection
In 2021, we embarked on the snowbirds’ journey to find a perfect winter home in Florida. The plan was simple: winters in St. Pete, summers in Boston. But by 2023, it was clear we weren’t snowbirds anymore. We fell in love with the first-class amenities, walkability to restaurants and museums, and the friendly community that St. Petersburg has to offer.
However, St. Pete is typically overshadowed by bigger cities like Miami, Naples, and Sarasota, and like me, most people stumble upon it by accident.
One of my favorite New York Times features is “36 Hours in St. Petersburg, FL”, which features short itineraries for world-class cities. As someone who lives and works downtown, here’s my version: 72 Hours in Downtown St. Petersburg. The longer time frame allowed for a more comprehensive visit. Think of it as your invitation to explore the city, especially if retirement, downsizing, or a second home in Florida is on your horizon.
Direct flights to Tampa International Airport (TPA) are available from numerous cities, including Boston, New York, Chicago, Philadelphia, Washington, D.C., and beyond, on carriers such as JetBlue, Delta, United, and others. From the airport, an Uber or Lyft to downtown St. Petersburg takes about 25 minutes and costs around $50. Once you arrive, you won’t need a car, downtown is highly walkable with easy rideshare access. The new SunRunner Bus runs along Central Avenue, connecting the Downtown Pier to St. Pete Beach for just $2.25.
The Hollander Hotel – Boutique energy with a lively pool and bar.
AC Hotel by Marriott – Sleek, modern convenience with on-site dining at Olivia.
The Vinoy Resort & Golf Club – Mediterranean Revival luxury right on the waterfront, complete with marina access if you arrive by boat.
Start your day with coffee at Intermezzo. Then stroll the waterfront to the world-class Dalí Museum or, if design is your passion, explore the Museum of the American Arts & Crafts Movement. Don’t miss its well-curated gift shop.
Dine at Olivia (yes, it’s that good) or the eclectic Wild Child. After dinner, enjoy a performance at The Mahaffey Theater, home to the Florida Orchestra. End your first evening with cocktails at Pluma Lounge overlooking Tampa Bay.
Grab a latte at Paradeco Coffee Roasters, then enjoy a waterfront walk along the St. Pete Pier and Vinoy Park. It’s here you’ll see why so many snowbirds and retirees decide to stay year-round.
Explore downtown living firsthand with a tour of premier residences: ONE St. Petersburg, Saltaire, Signature Place, 400 Central, and Art House. Each offers modern amenities, panoramic views, and that lock-and-leave condo lifestyle perfect for second homes. In full disclosure, I now live in one of these exceptional buildings.
Keep things light and social at Ceviche Tapas Bar & Restaurant. Then, depending on your mood:
Cheer on the Tampa Bay Rowdies.
Swim in the 50-meter pool at the North Shore Aquatic Complex.
Or try your hand at the quirky St. Petersburg Shuffleboard Club, a local institution since 1924.
Savor a Japanese-inspired dinner at Fortu, then pick your night out: a sleight-of-hand performance at Zubrick Magic Theatre, live music at Jannus Live, or stand-up comedy at the St. Pete Stand-Up Comedy Club. Finish with a creative cocktail at Lost & Found Cocktail Lounge.
Begin with coffee and a croissant at Café Clementine, tucked inside the Museum of Fine Arts. Then grab a paddleboard from Urban Kai and spot dolphins in the bay.
Head to St. Pete Beach for sugar-sand and Gulf breezes. If you’d rather stay closer, enjoy a waterfront lunch at Perry’s Porch by the marina. Spend your final hours browsing Beach Drive’s boutiques or exploring the Museum of Fine Arts.
Say goodbye the St. Pete way: cocktail in hand, watching the sky turn gold from Pier Teaki.
If you’re like me, you probably open Zillow whenever you’re in a new city. Downtown St. Petersburg has condos from the $400s to over $10 million, offering a lifestyle that blends waterfront living, fine dining, cultural richness, and effortless convenience.
I’d be delighted to take you on a convertible tour of my neighborhood. Downtown St. Pete isn’t the Florida you thought you knew. It’s unique and something better.
Jonathan Kelly is a Realtor with The Tenpenny Collection, bringing more than 25 years of experience in the art and science of real estate. A resident of St. Petersburg since 2021, Jonathan previously lived and worked in Connecticut, Boston, Martha’s Vineyard, and Washington, D.C.
Before residential sales, Jonathan built a national career in community and economic development finance, structuring projects that brought health centers, grocery stores, and charter schools to underserved communities in Baltimore, Chicago, New Orleans, Los Angeles, New York City, and San Francisco. His financial expertise in commercial development gives him a unique edge in evaluating property value, investment potential, and market dynamics.
Today, Jonathan and his husband Michael enjoy life in a downtown St. Pete high-rise condo, often walking the waterfront with their rescue terrier, Milo. Whether guiding clients toward their first Florida purchase, a lock-and-leave condo, or a retirement dream home, Jonathan draws on decades of expertise to help buyers and sellers navigate the market with confidence.