Dunedin: Delightful biking, breweries, beaches and historic downtown

Downtown Dunedin may surprise you.

A decade ago, I bicycled on the Pinellas Trail through Dunedin and I remember I thought it was cool that there was a great ice cream shop and a brewery right off the bike path. It was a charming little downtown, but I don’t recall there was a lot else there.

Today it’s a busy and vibrant place, home to eight craft breweries, popular coffee shops, great restaurants plus boutiques and galleries. Its historic downtown buildings have been restored. Two blocks from Main Street, the grand Jazz Age 1924 Fenway Hotel was renovated and reopened a few years ago. The nearby TD Ballpark, Spring Training site of the Toronto Blue Jays, was renovated in 2020. And two great state parks with award-winning beaches are moments away.

There’s no question, biking the Pinellas Trail is still one of the best things to do in Dunedin, but it’s far from the only thing.

Dunedin, a historic enclave amid the suburban sprawl of the Tampa Bay metro area, has become a great weekend getaway and makes an excellent base for exploring this section of beautiful Gulf Coast.

13 delightful things to do in Dunedin, Florida

1. Bicycle the Pinellas Trail, of course

The Pinellas Trail is a wide, paved, well-marked bicycle trail that extends for 54 miles through St. Petersburg, Clearwater, Dunedin and Tarpon Springs to the Pasco County line. You can ride the whole trail if you’re that sort of bicyclist.

You also can stay in Dunedin and ride the trail on outings to interesting places. It’s so refreshing to travel in Florida and just park your car and leave it behind!

If you’re looking for places to go in Dunedin by bike, here are a few suggestions of varying length:

• Take a quick two mile ride to Hammock Park, a 90-acre wooded preserve with boardwalks, trails, picnic pavilions and restrooms. As you reach the park, stop to admire the historic Andrews Memorial Chapel, a charming Victorian church moved to this location adjacent to the park. It’s now a popular wedding venue.

• Ride south and take a spur off the Pinellas Trail out to the Honeymoon Island causeway for an eight mile roundtrip. Here you can rent a kayak to paddle in St. Joseph Sound. If you’re looking for a more ambitious kayak outing, you can paddle from here to Caladesi Island State Park, described below. Or continue down the causeway a few miles and visit Honeymoon Island State Park for a 14 mile round trip.

• Head north on the Pinellas Trail for 7.5 miles and you reach Wall Spring Park, a historical, natural spring, once used as a spa and swimming area. Today, there’s a boardwalk around the old spring with interesting displays explaining the history.

There are several places to rent bikes in Dunedin.

2. Kayak to Caladesi Island State Park

This remote state park reachable only by boat is Paradise. If you don’t have a boat, you can take the ferry from Honeymoon Island State Park. (See details in story link below.) We think an even better experience is paddling a kayak to Caladesi Island. You can bring your own or rent one at Sail Honeymoon on the causeway. It’s about a half hour paddle across Hurricane Pass. Once at Caladesi, you can walk the beach, take a hiking trail on the island or paddle a beautiful kayak trail through the mangroves along the eastern coastline. It’s easy to spend several hours here.

Here’s a Florida Rambler story on kayaking to Caladesi Island.

3. Explore Honeymoon Island State Park and its outstanding beaches

One of the best beaches on the Gulf Coast is 20 minutes from downtown Dunedin on a barrier island, Honeymoon Island State Park. The 385-acre park has four miles of beach in three distinct sections plus 2.5 miles of hiking trails through pine flatwoods.

Lots of people set up shade canopies and coolers at the main beach, which also is served by a café and well-tended restrooms. Nearby is a separate beach for people with their canine friends.

My favorite, though, is the northern-most Honeymoon Island beach. This beach wouldn’t win awards for its sand, because it is studded with rocks and seashells, and the beach is much narrower. But the north beach goes on and on and the farther you walk, the more stunning the scenery. This Honeymoon Island beach is actually a sand spit extending more than two miles into the Gulf of Mexico.

I also recommend the Osprey Trail, a beautiful shaded hiking trail through pine flats, where we saw osprey nests on a March visit.

Here’s a Florida Rambler story on Honeymoon Island State Park.

4. Create your own craft brewery walking tour

There are eight craft breweries in Dunedin and most of them are in a small radius around downtown, so you can easily walk from one to another.

Several of the breweries are located right on the Pinellas Trail; the others are just a block off “the Trail,” as Dunedin residents call it.

The first craft microbrewery in Florida was in Dunedin – the Dunedin Brewery, founded in 1995, now serving food and offering live entertainment on most nights. It’s on the same street as Woodwright Brewing, a location where a historic woodworking shop once made the original Optimist Pram sailboats. The Painter family bought the site, at first continuing to use it as a woodworking shop until sister Eunice Painter began brewing German and European style beers at home. Pretty soon, the shop became a brewery and Eunice was head brewer.

A block north of these two breweries is 7venth Sun Brewing; a block west is the House of Beer (HOB) and Cueni Brewing. A block east is Caledonia Brewing. Go another block and you reach Soggy Bottom Brewery. You have to travel two miles north to reach Beach Island Brewery.

With such a wealth of local breweries, Dunedin restaurants also showcase local beers. All our dinners in Dunedin were accompanied by various Dunedin beers, some quite good.

5. Get coffee at a different cool coffee shop every day

Maybe after hitting the many breweries in town, folks need a cup of coffee in the morning. Maybe the many cosmopolitan retirees in town are meeting their friends for coffee and conversation. Whatever the reason, Dunedin has a lot of great coffee shops downtown.

Check out Tukro Coffee. It’s popular for its “liquid tiramisu” coffee and its outdoor seating on a side street in a converted house. Go to Veskolini Café, popular for its desserts, or Sandpiper Cafe, a cottage turned into a quaint café with good breakfast choices. And there are even more places to try.

6. Toast the sunset from a rooftop bar at the Fenway Hotel

The Fenway, a gorgeous hotel overlooking the water, was built in 1924 and it plays up its Jazz Age heritage everywhere it can. The lobby makes an historical exhibit out of the entrance to the original speakeasy in the basement. (It opened during Prohibition.) There’s live music in the lobby at night, and the night we visited, it was a jazzy saxophonist.

Unlike many grand Florida hotels, it remained open during World War II. Post-war, the property became the home of Trinity College for 25 years, then changed hands a few times and ended up in foreclosure in 2010.

The renovated Fenway opened in 2018 as part of Marriott’s Autograph Collection.

Today, its room prices start at $246 a night in the slow September to November period and go up to the $350 to $450 range at peak season.

Even if you don’t stay at the Fenway, however, one of the best things to do in Dunedin is go to its rooftop bar and watch the sunset. The view over the water is perfect and the bartender leads a countdown as the sun sinks. While there, soak up the atmosphere around the lobby, decorated with interesting historic photos, and hear a little live music.

7. Take a ferry to Clearwater Beach

While Dunedin is a great town for walking and biking, when you get on the nearby roads, there is traffic aplenty – especially if you’re heading for Clearwater. You can avoid the traffic on this outing by taking a delightful ferry from Dunedin to Clearwater Beach. It’s $16 roundtrip (just $12 for seniors and $10 for Dunedin residents).

The ferry operates Fridays, Saturdays and Sundays. It’s less than an hour ride, passing spectacular scenery and waterfront celebrity estates with frequent dolphin sightings. You can take the ferry to Clearwater’s famous white-sand beach (and avoid the hunt for parking) or to the Clearwater Aquarium. Be sure to book your tickets in advance.

8. Visit the Sponge Docks in Tarpon Springs and take a boat tour into the Gulf

A half hour north of Dunedin is Tarpon Springs, known for its Greek culture. Unlike Dunedin, where few residents actually have links to Scotland, in Tarpon Springs 10 percent of the residents have Greek ancestry, the largest percentage of any community in the United States.

Greeks came to Tarpon Springs to develop the sponging business, beginning in the 1890s and continuing until a blight on the sponge beds ended the industry in 1938.

Today, there are a few blocks of Greek-themed restaurants and shops along the harbor, so it can be a fun stop for Greek food or pastries.

We liked the boat tour from the Sponge Docks along the Anclote River out into the Gulf near Anclote Key and we also enjoyed bicycling around the Tarpon Springs historic district, with pretty waterfront Craig Park at its center. Here’s a Florida Rambler story about things to do in Tarpon Springs.

9. Take a scenic stroll along the Dunedin waterfront

One of the prettiest walks in Dunedin is the half mile on residential Victoria Drive along the waterfront between the downtown marina and Weaver Park. It’s a shell-rock road where driving is limited to residents. The historic homes overlooking the water have big lawns and gorgeous oak trees.

It’s a shady stroll and at the end you can walk out onto the 700-foot-long fishing pier at Weaver Park for spectacular views. The park has picnic pavilions, restrooms, a playground, fitness equipment and access to the Pinellas Trail, so you can make a loop of your route if you like.

10. Go to a baseball game

Located less than a mile from the downtown, many visitors walk or bike to the TD Ballpark for Toronto Blue Jay games during Spring Training. The Pinellas Trail runs alongside the ballpark, which is in the middle of a residential area and thus has no designated parking nearby. Fans who don’t walk or bike are encouraged to park downtown and take a free trolley to the ballpark.

Basevall fans, however, can still enjoy the game in summer, when the minor league Dunedin Blue Jays play at the stadium.

The renovated stadium gets good marks for its walk-around deck, its food offerings and kid’s play area. Do wear hats and sunscreen – shade is hard to come by.

11. Hear a bagpiper play as the sun sets at the marina pier

Every Friday and Saturday night from mid-November through the end of April, the Piper on the Pier plays Amazing Grace and other tunes as the sun sets over the water.

Dunedin has embraced its name, which is taken from Scottish Gaelic Dùn Èideann, the name for Edinburgh, and residents celebrate all things Scottish. A member of the City of Dunedin Pipe Band  draws a crowd for the unique bagpipe weekend sunset celebration.

In addition, one of the biggest festivals in town is the annual Dunedin Highland Games, which is April 1, 2023. It includes piping and drumming competitions, performances by line dancers, Highland athletic games and Scottish music and food. It has been part of Dunedin’s culture for six decades. It takes place at Highlander Park, 1920 Pinehurst Road, Dunedin, FL 34698.

12. Browse the Downtown Market on Fridays and Saturdays

From November to June, the downtown bustles on Fridays and Saturdays from 9 a.m. to 2 p.m. with tents, booths, arts, crafts, fruits and vegetables. The market is in Pioneer Park, 420 Main St. (Parking can be a challenge, and this is where the Pinellas Trail comes in handy.)

People like the variety of items available from dozens of vendors and the free samples. Here’s the market’s Facebook page.

13. Feast at local restaurants

In a downtown full of breweries and coffee shops, you would expect to find a great local food scene and Dunedin delivers. Most Dunedin restaurants are locally owned; you won’t find chain restaurants here.

You will find great variety and quality.

We loved the fresh seafood overlooking the water at a moderately priced Old Baye Cafe, offering a beautiful view at sunset plus a great selection of local craft beers. Our lobster pot pie was outstanding at Lucky Lobster, a casual cafe right on the Pinellas Trail.

And there were so many excellent alternative places to dine; we’ll have to return to try some of the others.

More things to do in Dunedin area

If you’re planning a trip to this region of Florida, there is a wealth of great destinations. Here are some Florida Rambler has written about:

Safety Harbor Spa: Healing waters are star of charming town

7 things to do in St. Petersburg for Old Florida delights

Pass-A-Grille: Top beach; charming old town in St. Pete Beach

Fort De Soto Park is Tampa Bay treasure

Best camping near Tampa Bay: 9 choice campgrounds

Paddleboarding Tampa Bay area: 5 awesome destinations

Frog Creek: Little-known Tampa Bay kayak trail

Egmont Key: 5 things I love about this wild island

3 new museums boost St. Petersburg as ‘City of Art’

Emerson Point Preserve: Four reasons to discover this jewel in Palmetto

Hillsborough River State Park adds ‘glam’ to its camping options

Arts & Brew walk: Explore St. Petersburg brewpubs and galleries