The Perfect Long Weekend in Dunedin: Biking Florida’s Coast-to-Coast Trail With Jeff Jenkins

This article was published in partnership with Visit Florida.

As a born-and-raised Floridian, I’ve explored much of the Sunshine State, from sailing the Gulf of Mexico, to wandering the charming city of Key West, to hunting for shark teeth in the Sarasota area. However, one of the best ways to explore Florida is by traversing its massive trail networks. I was pleasantly surprised to hear about the astonishing array of multi-use trails for biking, walking, hiking, and even kayaking. In fact, I recently learned that Florida is home to the country’s longest sea kayaking trail, comprising 1,515 miles of coastline. No matter your penchant, there's a trail for everyone.

One of the trails I was most intrigued by was the 250-mile, multi-use Coast-to-Coast Trail that spans from St. Pete, along the Gulf of Mexico on the West Coast, to Titusville, on the East Coast's mighty Atlantic.

The Coast-to-Coast Trail is 88 percent complete and connects dozens of communities, as well as designated “trail towns,” which are at the heart of Florida’s trails. These towns embrace the bike, hike, and paddling communities by providing Wi-Fi connectivity, shelters, information kiosks, restrooms, and bike-friendly establishments along the route.

No matter which portion of the trail you choose to bike, you'll mosey along these towns, nature preserves, rural landscapes, and wild beaches. You may not know, but Florida is one of the most biodiverse states in America. There are more than 3,000 plant species and a whopping 4,300 animal species—269 of which are exclusive to the state.

Coast-to-Coast Spotlight: Pinellas Trail

I chose to explore the Coast-to-Coast Trail from Florida’s bustling West Coast community of Dunedin, just 20 miles from the peninsular city of St. Pete. My weekend trip centered around the Gulf Coast cities of Dunedin and Tarpon Springs, with plenty of time to explore the Pinellas Trail.

I grew up in the Orlando area, but hadn’t explored this stretch of Florida before. In Dunedin, I loved exploring the vibrant downtown with bars and cafés. I was blown away by the food scene! There are also quaint boutiques, nearly four miles of scenic waterfront and annual Scottish celebrations.

In addition to a bike-centric culture, there’s a real outdoor-leaning vibe with joggers, inline skaters, and hikers. The Pinellas Trail—created along an abandoned railroad corridor—is a multi-use paved section of the Coast-to-Coast Trail that's a must for casual riders and easy to conquer during a three-day visit. From Dunedin, you can access Caladesi Island State Park and Honeymoon Island State Park, which are iconic for their natural landscapes.

In contrast to some of the elite sport communities in mountain towns, where everyone is dressed like they’re prepping for the Tour de France, there’s room for everyone in Dunedin. You needn’t be an expert to feel embraced or enjoy its spoils.

That’s what struck me immediately during my visit. I’m a National Geographic travel host and plus-sized adventure advocate. I've enjoyed bikes all my life. At some point, I had to figure out the right equipment to support my weight. I’m Black and plus-size, but felt super comfortable and safe riding the trail. I felt welcomed on the Pinellas Trail and found it approachable for anyone.

Pro tip: While you can bike the Coast-to-Coast Trail anytime of year, October through April is ideal for those who prefer moderate temperatures. I visited on a perfect December weekend and enjoyed crisp, cool mornings and evenings, paired with sunny days.

Where to Stay

Fenway Hotel

While there are plenty of places to stay, from high-end boutiques to traditional hotels to bed and breakfasts, I checked into the historic Fenway Hotel, part of Marriott’s Autograph Collection. For just shy of 100 years, this hotel has welcomed some of the world’s most celebrated musicians and artists.

There are instruments and memorabilia everywhere. The place literally hums with music history.

Fenway Hotel is a Jazz Age landmark, and home to the county’s first radio station. In addition to live music (don’t miss the jazzy weekend brunches), The Hew Parlor and Chophouse have out-of-this-world food. The menu is inspired by local ingredients, which means plenty of fresh seafood and thick steaks.

Day 1

Check in and explore on two wheels

Shake off any jet lag or travel malaise, grab one of the hotel’s complimentary bikes, and head to the historic riverfront town of Tarpon Springs, known for its Greek roots and gastronomy. Here you’ll find Dimitri’s on the Water, a local seafood joint established by the son of Greek immigrants, and learn why Tarpon Springs is known as the “Sponge Capital of the World.” (Hint: It has to do with Greek sponge divers discovering the natural sponge beds in the early 1900s.) Next, head to Tarpon Springs Distillery, with its convivial tasting room, for a pour of Anclote Conch Shell Rum, which took home Gold at the 2023 NY World Spirits Competition.

I left with a bottle of moonshine. Now that’s old Florida!

Make your way back to Fenway Hotel and head up to Hi-Fi Rooftop Bar in time for sunset. While Fenway Hotel was famous for its basement speakeasy during Prohibition, the bar has moved into the light, and this is the spot to watch the sun slip below the horizon with a local beer in hand. It’s a communal watering hole where locals and visitors coalesce.

After, enjoy local gastronomy at The Living Room. The family-owned-and-operated restaurant specializes in global cuisine and shared plates with the goal of making everyone feel at ease. Go for the daily happy hour with discounted fare and cocktails. I ate the best Thai mussels of my life here.

For an après-dinner cocktail, head to Sonder Social Club, Dunedin’s first hand-crafted cocktail bar.

The crowd is young—and the bar is relaxed and intimate. It’s a cool scene, where you can be as private or as social as you like.

Day 2

Bike the Pinellas Trail to Honeymoon Island State Park

Start the day off at Kafe Racer, owned and operated by Jan Heylen, a Belgium-born former car racer and passionate bike collector. Here you’ll pick out a bike based on your ability and preference (choose among mountain, road, electric, and even three-wheelers). For me, that was an e-bike.

After a chocolate croissant and an Americano, grab a map, and get expert advice on where to stop for rest breaks and photo ops along the Pinellas Trail.

The trail is beautiful. It’s urban, but travels through glades of ancient oaks, waterways, and tidal streams. Expect to see a menagerie of birds as the paved path winds over bridges, creeks, and through parks.

For me, the beauty of the Pinellas Trail is only rivaled by its bike-friendliness. It caters to cyclists, with plenty of stop signs and lights so you feel safe and better enjoy the surrounding landscape.

This slow-paced method of travel lets you soak in the beauty of Florida’s countryside—tropical one minute, wooded the next. As you pedal across the causeway toward Honeymoon Island, you’ll get to a drawbridge that rises and drops to accommodate both boat and car traffic.

It’s exciting to watch the bridge rise and let boats sail through. Then you add the potent combination of a light breeze and the smell of salt water—and it really is paradise.

From Honeymoon Island, you can lock up your bike (a lock is included when you pick up your bike from Kafe Racer) and take the ferry to Caladesi Island, an almost-untouched island that requires a ferry ride to reach. Peek out into the water for a glimpse of dolphins.

Caladesi Island is a protected island that’s ideal for a getaway. You can swim, lounge on the white sand, and explore the surrounding nature trails. If it’s leisure you seek, rent a beach chair and umbrella. This was how I chose to enjoy the island and I can tell you it was pure paradise.

Day 3

Explore the best of Dunedin

If you’re the adventurous type, get out on the water by paddleboard or kayak, or charter a boat to go fishing. If you’re visiting in the spring, you can nab tickets to watch the Toronto Blue Jays’ Spring Training.

As we alluded to Dunedin’s Scottish influence, the city is named for the Gaelic version of Edinburgh, and there’s plenty of Scottish heritage to soak up, including some great pubs and distilleries. You can explore the Beer-muda Triangle, which includes the oldest microbrewery in Florida. Just be sure to pace yourself for a tasting at Cotherman Distilling Company, a small-batch distillery that makes hand-crafted spirits (727 Vodka and Half-Mine Gin are both impressive).

Then, take your time walking through old town, with its mom-and-pop-style boutiques. For dinner, I recommend Bon Appetit, a landmark waterfront restaurant on a pier that extends out into St. Joseph Sound.

Go during sunset. The views of the Gulf are spectacular.

It’s a fitting finale to a three-day weekend in Dunedin.