Discover Dunedin: The Perfect Place to Stay, Stroll, and Explore
Dunedin isn’t a beach town. It’s something better — a Gulf Coast community that built its identity around Main Street, not shoreline. Just north of Clearwater, Dunedin is where walkability, history, and baseball come together in a way that feels entirely its own.
This episode of The Gallivanter Podcast explores what makes this small Florida town stand apart — and how to experience it like someone who’s been coming here for years.
🏨 Where to Stay
Grant Street Inn — A newly constructed inn just off Main Street, offering a quiet, comfortable stay within easy walking distance of shops, restaurants, and the Pinellas Trail. Elegant rooms, friendly hosts, and that perfect “in-the-middle-of-everything” location without the noise.
🏙️ What to See and Do
Main Street — The heart of Dunedin. A pedestrian-friendly corridor filled with locally owned boutiques, cafés, art galleries, and craft breweries.
Dunedin History Museum — Set inside a restored 1924 railroad depot, the museum traces the town’s transformation from a small Scottish settlement into one of Florida’s most livable communities.
Artisan District — A colorful stretch of breweries, eateries, and murals where Dunedin’s creative energy comes into focus. Great for a relaxed afternoon walk.
TD Ballpark — Spring training home of the Toronto Blue Jays. Even if you’re not a baseball fan, there’s something charming about how the whole town shows up for a game.
Pinellas Trail — A 45-mile rail-to-trail path running through downtown Dunedin. Ideal for walking or cycling, and perfect for exploring neighboring towns like Palm Harbor or Clearwater by bike.
☕ Food & Drink Highlights
7venth Sun Brewing — Small-batch craft beer and a local hangout known for creativity and collaboration.
Lane’s Lemonade — A Main Street favorite for a refreshing stop between shops.
Café Alfresco — A downtown classic serving breakfast, lunch, and dinner with sidewalk seating right on the trail.
🌅 Insider Moments
Plan your visit around a Blue Jays spring training game for a sense of how deeply baseball is woven into local life.
Wander the side streets off Main — they’re filled with public art, hidden courtyards, and the kind of architectural details that make Dunedin memorable.
End your day with a walk toward the marina at Edgewater Drive, where locals gather for sunsets that rival any beach view.
🎧 Listen & Subscribe
Hear the full story on The Gallivanter Podcast, available on:
Apple Podcasts, Spotify, and iHeartRadio
The Smart Traveler’s Guide to One Day in St. Augustine
Most travelers only have one day in St. Augustine, but that doesn’t mean you have to rush. This episode breaks down a smart, time-based strategy for experiencing the nation’s oldest city in just 24 hours. From morning light on the Castillo to a peaceful walk beneath the evening glow of the Bridge of Lions, you’ll learn how to see more, stress less, and end the day with a genuine sense of connection to this remarkable city.
Morning: Foundations and First Impressions
The city wakes slowly, so those first hours are your secret advantage. Arrive before 9 a.m. and park at the Historic Downtown Parking Facility next to the Visitor Information Center. It’s $20 for the day and positions you perfectly for exploring the historic core.
Walk toward the Castillo de San Marcos National Monument, the coquina fort that anchors the city’s story. Arrive at opening time to avoid lines and enjoy quiet views of Matanzas Bay. This is the ideal spot to orient yourself with St. Augustine’s history before the crowds roll in.
From the fort, wander down to the Plaza de la Constitución. It’s the ceremonial center of the city, surrounded by key landmarks like the Cathedral Basilica of St. Augustine, Government House Cultural Center, and the Public Market site that dates back to the 16th century. If you visit during the Nights of Lights season, this is where the city’s tree and light displays begin.
For breakfast or coffee, stop by Maple Street Biscuit Company for Southern-style comfort food. Morning in the plaza is slow and authentic, with locals walking dogs and church bells echoing through the historic streets.
Afternoon: Digging Deeper, Eating Smarter
By midday, crowds fill St. George and Hypolita Streets, so this is when you pivot to quieter spots and smarter dining choices. Head north into Uptown San Marco or west along King Street to find excellent food without long waits. Try The Blue Hen Café for a local brunch favorite.
Choose your afternoon adventure based on interest.
If you love history, explore the Colonial Quarter for hands-on exhibits about life in the 1700s.
Art enthusiasts should visit the Lightner Museum, set inside Henry Flagler’s 1888 Alcazar Hotel. Its Victorian-era collections and architecture are stunning.
Families can head to the St. Augustine Pirate & Treasure Museum, which combines interactive displays with authentic maritime artifacts.
If you need a break from the bustle, drive or walk north to Mission Nombre de Dios and the Shrine of Our Lady of La Leche. The Great Cross rises 208 feet above the bay, surrounded by live oaks and quiet paths. It’s one of the city’s oldest and most contemplative spaces.
Evening: The City at Its Most Atmospheric
As the sun lowers, St. Augustine transforms. Walk the Bayfront Esplanade and watch the light shift over the Bridge of Lions.
Avoid the packed core around St. George Street and head for Aviles Street, the oldest street in the city, filled with galleries and restaurants. Consider Casa de Vino 57 for wine and live music or The Ice Plant for classic cocktails and dinner inside a converted factory.
For evening activities, take a Scenic Cruise of St. Augustine or join Florida Water Tours for sunset views across the bay. During winter, experience the Nights of Lights from the water for the best vantage point. Ghost tours like Ghosts & Gravestones offer storytelling and history blended together.
Reflection and Takeaway
You can’t see all of St. Augustine in one day, but you can experience its essence. Start early, walk often, eat smart, and give yourself permission to pause. The fort, the plaza, the neighborhoods beyond the crowds, the bayfront at night—it all adds up to something complete.
As the episode says: St. Augustine isn’t a checklist. It’s a story. One you write as you go.
Listen On
Apple Podcasts | Spotify | iHeartRadio
Winter Garden & Oakland: Central Florida’s Most Bikeable Escape
🎧 Winter Garden & Oakland: Central Florida’s Most Bikeable Escape
What happens when two small towns decide not to become suburbs?
That’s the story at the heart of this episode, an exploration of Winter Garden and Oakland, Florida. Just west of Orlando, these two connected communities have done what so many others have failed to do: preserve their history and authenticity while quietly becoming two of the most desirable places to visit (or live) in Central Florida.
In this podcast, we slow things down and take a deep look at the people, places, and planning that make Winter Garden and Oakland stand out. This isn’t a theme park story. It’s a story about intention, design, and a shared vision for livability.
🏙️ A Downtown That Got It Right
Winter Garden’s historic downtown has become a model for small-town revitalization across Florida.
Historic District: Once a fading citrus town, Winter Garden reinvented itself through smart preservation and streetscape planning. The brick streets, bike-friendly layout, and adaptive reuse of old buildings now define its charm.
Edgewater Hotel (99 W Plant St) — A restored 1920s hotel that now serves as both a boutique inn and a living museum of Florida hospitality.
historicedgewater.com
Adjectives Market (131 W Plant St) — A sprawling vintage and artisan marketplace perfect for home décor hunters and curious browsers.
shopadjectives.com
Ruby & Rust (49 S Main St) — Locally loved for its eclectic gifts, antiques, and modern Southern aesthetic.
rubyandrust.com
🎧 Listen for a reflection on how Winter Garden preserved authenticity without becoming artificial, a delicate balance few towns achieve.
☕ Cafés, Trails, and Everyday Life
What makes Winter Garden so livable isn’t just its shops, it’s the rhythm of daily life.
Axum Coffee (146 W Plant St) and Rosallie Le French Café (141 W Plant St) — Morning staples with strong local followings.
Crooked Can Brewing Company & Plant Street Market (426 W Plant St) — A communal hub blending craft beer, food stalls, and live music.
crookedcan.com
West Orange Trail — The 22-mile paved trail linking Winter Garden to Oakland and Apopka. Bike it, walk it, or just people-watch. It’s the social spine of the community.
Newton Park (31 W Garden Ave) — Overlooking Lake Apopka, this serene green space connects the town’s present to its natural roots.
💡 Pro tip: Rent a bike downtown and explore the trail’s shaded route toward Oakland—Florida’s most scenic suburban ride.
🌳 Oakland: The Town That Chose Stillness
If Winter Garden is the heartbeat, Oakland is the pause that gives it meaning.
Prairie House Coffee Co. (4 N Tubb St) — The town’s unofficial living room, serving espresso and small-town conversation.
prairiehousecoffee.com
Oakley’s Trailside Treats — A family-friendly ice cream stop along the West Orange Trail.
Oakland Manor House (620 N Tubb St) — A historic home turned inn, offering a quiet retreat surrounded by oak canopies.
Oakland Nature Preserve (747 Machete Trail) — 128 acres of protected land along Lake Apopka with boardwalks, trails, and education centers focusing on restoration and wildlife.
🌾 Oakland’s approach is slower, quieter, and fiercely intentional, a town that prizes green space over growth.
🧺 Events & Experiences
Winter Garden Farmers Market (104 S Lakeview Ave) — Saturdays year-round, 8 a.m.–1 p.m. Named one of the best in Florida, it’s a feast for the senses—local produce, flowers, baked goods, and music.
Garden Theatre (160 W Plant St) — A restored 1930s movie palace turned performing arts venue. Check their schedule for plays, concerts, and classic film nights.
SoBo Art Gallery (127 S Boyd St) — Home to the Winter Garden Art Association, featuring rotating exhibits and community workshops.
Festivals: From Blues & BBQ to Light Up Winter Garden, the town celebrates year-round with family-friendly events that never feel overrun.
📍 Featured Locations
Edgewater Hotel — Restored 1920s hotel in the heart of downtown
99 W Plant St • historicedgewater.com
Ruby & Rust — Locally owned boutique with vintage and modern finds
49 S Main St • rubyandrust.com
Adjectives Market — Marketplace for vintage, art, and design
131 W Plant St • shopadj.com
Crooked Can Brewing Co. — Brewery inside Plant Street Market
426 W Plant St • crookedcan.com
Prairie House Coffee Co. — Beloved small-town coffee shop
4 N Tubb St • prairiehousecoffee.com
Biketoberfest: The Truth About Daytona Beach's Big Bike Rally
Every October, the rumble of engines and the smell of leather and chrome transform Daytona Beach into the epicenter of biker culture.
Biketoberfest isn’t just another motorcycle rally - it’s one of the largest gatherings of riders in the country, bringing hundreds of thousands of people to Florida’s Atlantic coast.
But beyond the roar of Harleys and the rows of custom bikes, there’s a deeper story worth telling.
In this episode of the Chad Gallivanter podcast, we go beyond the surface to uncover the truth about Biketoberfest - how it began, how it compares to Bike Week, what it means for local businesses, and why the culture behind it is so much more than beer tents and burnouts.
You’ll hear about Main Street’s iconic hangouts, the traditions that keep riders coming back year after year, and the side of the rally most visitors don’t see. We also dive into the challenges: the safety concerns, the push-and-pull between city officials and the biker community, and the evolving image of what this event represents today.
Whether you’re a longtime rider, a curious traveler, or just someone who’s heard the thunder from a distance, this episode gives you the full picture of Daytona’s Biketoberfest.
It’s history, culture, and spectacle all rolled into one, and by the end, you’ll know why this rally continues to define the identity of America’s most famous beach town.
Chad’s Top Picks
Main Street Daytona Beach
The heart of Biketoberfest. Live music, packed bars, vendor tents, custom bikes on display, and nonstop action day and night. This is the strip where the energy never fades.
📍 Main Street, Daytona Beach, FL
Daytona International Speedway
The Speedway transforms into a biker’s playground during Biketoberfest. Expect demo rides, custom bike shows, gear vendors, and the chance to take it all in at one of the most legendary racing venues in America.
📍 1801 W International Speedway Blvd, Daytona Beach, FL
🌐 daytonainternationalspeedway.com
Destination Daytona (Ormond Beach)
A sprawling biker hub anchored by Teddy Morse’s Daytona Harley-Davidson (formerly Bruce Rossmeyer’s), with Biketoberfest® demo rides, bike shows, a huge vendor village, and daily live music at Saints & Sinners Pub; on-site lodging is available at the Clarion Inn. (Powersports Business)
📍 1637 N US Hwy 1, Ormond Beach, FL 32174
🌐 Main site: daytonaharleydavidson.com • Events: Biketoberfest® at Destination Daytona • Complex updates: Destination Daytona (Facebook)
Boot Hill Saloon
An iconic biker bar right across from the Main Street cemetery—known for its motto, “Come on in and have a cold one, or rest in peace.” Loud, rowdy, and unforgettable.
📍 310 Main St, Daytona Beach, FL
🌐 boothillsaloon.com
Iron Horse Saloon (Ormond Beach)
A legendary biker hangout famous for its massive outdoor stage, steel horses hanging from the rafters, and a gritty, one-of-a-kind atmosphere.
📍 1068 N US Hwy 1, Ormond Beach, FL
🌐 ironhorsesaloon.com
Ride the Ormond Scenic Loop
A 30+ mile ride of pure Florida beauty—live oaks, ocean views, marshland, and a stretch of Old Florida that feels untouched by time. It’s the classic ride every biker should take while in town.
📍 Access points in Ormond Beach; starts near North Beach St and Granada Blvd
Daytona Beach Bandshell
Catch live music overlooking the Atlantic. During Biketoberfest, the Bandshell keeps the soundtrack going with free shows that bring the community and bikers together.
📍 70 Boardwalk, Daytona Beach, FL
🌐 daytonabeach.com/bandshell
Cruising A1A
Roll along Florida’s scenic coastal highway. Nothing beats riding oceanfront with the salty breeze in your face and the endless Atlantic to your left.
One Day in Washington, DC: See the Most in 24 Hours
If you had only one day in Washington, DC, just 24 hours to take in the monuments, museums, and stories that define America’s capital, where would you go?
This episode lays out the definitive plan to see the very best of DC without wasting a minute. From sunrise at the Lincoln Memorial to standing under the dome of the Capitol, we’ll show you how to fit a week’s worth of history and culture into one unforgettable day.
Along the way, we’ll explore the highlights every visitor expects, the White House, the Washington Monument, the Smithsonian museums, but also the details most people miss. Where can you actually eat near the Mall without losing precious time? Which museums are worth stepping into when you’ve only got an hour? And how do you line up your day so you’re walking forward through history, not doubling back and losing daylight?
This is more than just a sightseeing checklist. It’s the story of Washington, DC told through its landmarks, its neighborhoods, and the way these places connect to the country’s past and present.
Whether you’re planning your first trip to the capital or just want to understand how the city works as a living stage of American history, this one-day journey will give you a new way to see DC, efficient, thoughtful, and unforgettable.
Chad’s Top DC Picks
Dupont Circle
A historic, stylish neighborhood and gathering point in NW DC, centered on a fountain-roundabout. Think elegant embassies, quiet residential side streets, lively shops and cafés, and a sense of constant energy—perfect for strolling and people-watching.
📍 Intersection of Massachusetts, Connecticut & New Hampshire Avenues NW, plus P St & 19th St NW, Washington, DC
🌐 washington.org – Dupont Circle
Kramerbooks & Afterwords (“Kramers”)
More than just a bookstore: a landmark indie bookshop with a café and bar. Browse new titles, linger over meals, catch an author event, or simply soak up the Dupont Circle vibe.
📍 1517 Connecticut Ave NW, Washington, DC 20036
🌐 kramers.com
Second Story Books
One of the best used and rare bookstores in the DC area. Great for uncovering out-of-print treasures, bargains, or rare finds. The Dupont Circle location is especially charming.
📍 2000 P Street NW, Washington, DC 20036
🌐 secondstorybooks.com
O Museum in The Mansion (Mansion on O Street)
A delightfully eccentric DC landmark with over 100 rooms, dozens of secret doors, and a rotating collection of art and memorabilia. Every visit is an adventure.
📍 2020 O Street NW, Washington, DC 20036
🌐 omuseum.org
Union Market
A bustling food and culture hub in NE DC. Part gourmet hall, part community space, with local vendors, global flavors, and plenty of energy.
📍 1309 5th St NE, Washington, DC 20002
🌐 unionmarketdc.com
Matchbox
A reliable neighborhood favorite for creative pizzas, sliders, and comfort food. Friendly atmosphere with multiple convenient DC locations.
📍 Capitol Hill: 521 8th St SE, Washington, DC 20003
📍 Penn Quarter: 750 E St NW, Washington, DC 20004
🌐 matchboxrestaurants.com
Franciscan Monastery Garden
A hidden oasis in Brookland featuring gardens, replicas of Holy Land shrines, serene walking paths, and beautiful architecture. A quiet escape within the city.
📍 1400 Quincy Street NE, Washington, DC 20017
🌐 myfranciscan.org
United States National Arboretum
A sprawling 446-acre research facility and public garden. Home to bonsai and penjing collections, wide meadows, trails, and the famous Capitol Columns. Free admission.
📍 3501 New York Avenue NE, Washington, DC 20002
🌐 usna.usda.gov
Why Muscadine Grapes Are Unlike Any Other in America
Step into the vineyard and uncover the story of America’s forgotten grape, the muscadine. Native to the Southeast, this tough little fruit has been part of Southern life for centuries, long before European grapes ever took root here.
In this episode, we explore Florida’s muscadine heritage, its surprising history, and why this grape matters more than you think. Along the way, you’ll learn how muscadines shaped agriculture, culture, and even survival in the South.
From backyard vines to sprawling vineyards, muscadines have a legacy that connects deeply to the land, and to the people who’ve cultivated them for generations. If you’ve ever wondered what makes the muscadine different, why it’s been celebrated for centuries, and why you don’t hear about it nearly enough, this podcast-style journey is for you.
🎙 Spring Garden Vineyard
Key Facts & Details
Name & Location
Spring Garden Vineyard is located at 980 Reynolds Road, DeLeon Springs, Florida. springgardenvineyard.com
It’s run by the Lennon family.
What It Is / What They Do
It's a U-Pick vineyard specializing in muscadine grapes (a native Southeastern vine, well adapted to Florida’s climate).
They grow several muscadine varieties (Southern Home, Alachua, Black Ison, Supreme, Fry, Carlos, Noble) and sell grapes by volume.
Beyond fresh fruit, they produce homemade grape-jellies, grape butter, popsicles etc.
Season / Hours / Pricing (2025)
U-Pick season begins Friday, August 8, 2025, and runs on Fridays, Saturdays, Sundays from 8 AM to 5 PM until about Sunday, September 14 (unless they sell out earlier).
Prices:
• ½-gallon bucket (≈ 2.75 lb) - $9
• 1-gallon bucket (≈ 5.5 lb) - $15
• Discounts for multiple gallons (after first three) - each additional gallon ~$12
• Pre-picked gallons & quarts available.
Visiting Tips & What to Know
What to bring: Close-toed shoes, sun protection, water. Pets are allowed if restrained; kids must be supervised.
Rules: Only use the pails they provide, stay in assigned rows while picking, don’t pick grapes off the ground, etc.
Logistics: Parking is in the barn area; you might be transported to the vine rows.
Contact ahead for special arrangements: group tours, large pre-orders, picking outside regular hours.
🕰 Historical & Cultural Context
The area around the vineyard was historically known as Spring Garden Plantation. In 1804, a Spanish land grant of ~2,020 acres was made to William Williams.
The name “Spring Garden” predates “DeLeon Springs.” The shift to “DeLeon Springs” came later (in the late 19th-century) partly to attract tourism, with references to Ponce de Leon and marketing the spring as a “Fountain of Youth.”
Spring Garden Plantation’s history is complex: crops included cotton, sugarcane, corn. Enslaved labor was part of that early plantation economy.
Later, sugar mills and grist mills were built on the property; some destroyed during the Seminole Wars and the Civil War.
🌿 Flavor, Sensory & Miscellany
Muscadine grapes have thick skins, strong flavor. They range in color from bronze to dark purple.
They freeze well, making them good for preserving (jams, jellies, fruit stock).
Health-wise: skins are rich in certain antioxidants - ellagic acid, quercetin, etc.
Helen, Georgia: The Bavarian Town That Shouldn’t Exist
How a fading mountain town reinvented itself as an Alpine village in the Deep South.
Classic beer garden in downtown Helen, Georgia.
Nestled in the North Georgia mountains is a place that looks nothing like the South. Half-timbered chalets. Bavarian beer halls. Gingerbread rooftops. It’s called Helen, Georgia, a town that once teetered on the brink of collapse, until a handful of locals decided to gamble on a wild idea: transforming a former logging town into a Bavarian Alpine village.
In this episode, we dig into the improbable reinvention of Helen, from its boom days of timber, to its desperate pivot to tourism, to the Oktoberfest capital it has become today. Along the way, we’ll look at what worked, what didn’t, and why this “Alpine illusion” continues to draw millions of visitors a year.
Whether you love quirky roadside Americana or just wonder how a place like this even happened, Helen’s story is a reminder that sometimes, the strangest ideas are the ones that stick.
