A Relaxing Afternoon in Historic Downtown Dunedin, Florida

Dunedin is most famous for being home to famous Honeymoon Island State Park, one of the most popular white sand beaches on the Gulf Coast. However, a trip to the area would not be complete without taking a stroll through the city’s beautiful, historic Main Street district. It’s one of my favorite small towns in the Bay area. Visiting this quaint Main Street which is lined with local restaurants, shops, and businesses, is a refreshing alternative to shopping & dining at the chains overpopulating the metro.

During our time living in the Bay, Mike and I enjoyed convenient access as we lived for a year in Palm Harbor, another low-key gem. We love the absence of national chains, the colorful buildings, direct access to the Pinellas Trail, and beautiful views of the marina. If you are looking for a daytrip away from the noisy beach crowds, I recommend planning a visit.

The downtown is clean, well-maintained and quiet. The trees lining the streets, quiet atmosphere, and predominance of local business over chains reminds me of the quaint villages I frequented while living in New England (we located from Massachusetts).

The ambiance here is very different from the big suburbs populating much of the metro. It’s got that old-fashioned charm that it is vanishing by the year. I recommend visiting these cute small towns and enjoying all the local businesses before the big chains take over. I find so many towns and suburbs all look the same today, so it is exciting to find anything different.

Note: This post includes a combination of activities, restaurants, and events I have enjoyed throughout my 3 years living here. I wrote this post in 2014 and continued to add more as I relocated here once again in 2019 and 2023 for a total of about ~3 years.

Dining & Shopping

It’s not a huge space, but you will find a nice variety of restaurants, bars, and novelty stores. Restaurants options vary, from cafes to Italian restaurants to Irish pubs. I recommend starting your day at Cork and Bean, a local coffeehouse which serves delicious coffee and pastries. I really love the bar seating and dim ambiance. It’s usually pretty dark in here which makes for a nice escape from the sun. On the other hand, there is also a nice patio if you want to soak in that Florida sunshine.

Another great low-key breakfast/coffee cafe is The Sandpiper. I love the beachy theme and laid-back vibe here. You will find lots of mermaid signs and other beachy novelty items, many of which you can purchase. The coffee is great and the breakfast is decent, although a tad overpriced. They offer a nice patio you can enjoy anytime outside of the hot and humid summer months.

There are plenty of bars in the area, many with outdoor seating to enjoy the “cooler” nights. Shopping includes a selection of: jewelry and apparel shops, antiques, and specialty gift and decor shops. I love browsing through the Celtic Shop, Knot on Main (lots of great antiques), and the Great Giftsby. You will also find a handful of health and wellness studios and several galleries.

For lunch, I recommend a stop at The Living Room on Main. This is an eclectic international restaurant which offers a diverse menu. There is always something new you can try and I love that they offer a number of healthy and vegetarian choices. What I love most is their gorgeous patio which is great for people watching.

Museums and other attractions

A massage is the perfect treat, in my opinion, especially to escape the heat for a while. One day, Mike & I both got a relaxation massage at A Perfect Pair Nail Salon & Spa. Hot Stone, deep tissue, and a legs/feet combo massage are also offered. The massage was a perfect way to wind down after being on our feet all day. I love the location in a cute little house.

If you feel like taking in some culture, the city offers a small selection of art galleries and museums. The Fine Arts Center is worth checking out. The Dunedin Historical Society & Museum is another option. Baseball fans visiting during the spring months can check out a Toronto Blue Jays game, as this is their spring training location.

Music fans will want to plan for a quick tour of The Beatles Museum. This museum is really small but colorful and jam packed with cool memorabilia. I definitely recommend a visit if you are a fan. it will only take a half hour or so to browse, but it’s free so why not? I loved the classic British red telephone booth.

The Pinellas Trail

Another highlight in the area is the beautiful Pinellas Trail bike path, which runs from St. Petersburg to Tarpon Springs, passing this historic city along its’ course. The trail currently covers about 54 miles and is the best place in the metro for a long bike ride or run. I trained for a number of races here including the Gulf Coast half marathon in Pensacola beach a few years ago. I placed in my age group, so I guess this trail served its’ purpose.

It ranks as one of the country’s top rail trails (which basically are old railroads converted into multi-use paths). I like parking in Dunedin (it’s free), stopping for breakfast and then riding over to Tarpon Springs. The ride to Tarpon is very nice – mostly flat, scenic, considerably shady, and the perfect distance (~10 miles) for a long, yet leisurely weekend ride. Once arriving in Tarpon, I like to stop for some greek fare at a local gem like Hellas or Mr. Souvlaki. They both serve great Greek salads and Hellas overs the most enticing bakery you will find in the Bay.

Also check out this handy Pinellas Trail guide to plan your route.

Also be sure to take a walk down to the marina, located just a short walk away from downtown. Take in a few great views from the pier, and even do a little fishing if you are interested. The Best Western Yacht Club Inn, located directly on the marina, offers a waterfront restaurant which looks out upon the water. Bon Appetit and the Marina Cafe offer a brunch, breakfast, and lunch/dinner menu, with the option of indoor dining or outdoor dining, both featuring amazing views.

On a side note, I see tons of weird looking birds here. Almost everywhere in the Bay is an awesome place for birdwatching. While you are in Dunedin, I recommend checking out one of the local parks. Hammock Park is a pretty place to birdwatching and take a nature walk. Here are a few of my other favorite parks in the metro if you are looking for more to do. I see gopher tortoises and armadillos at almost all of them, so any way you go, you should leave satisifed.

Annual events

The city hosts exciting events throughout the year. Farmers markets are held on Friday and Saturday mornings, July through October. Art walks take place on the second Friday of each month. Every month you can look forward to exciting cultural and holiday activities, such as: holiday boat parades, Mardi Gras and St. Patrick’s Day celebrations, and the Dunedin Orange Festival.

One of the most fun events I’ve attended is the holiday boat parade, which is held during the first week of December. Being originally from the Midwest, it’s not something I’ve ever seen before. I loved the high energy and the over-the-top decor on some of the boats. Check out the city website for this year’s calendar of events.

Plenty of side street parking and free lots are available. This is a great, no-hassle place to start the Pinellas Trail as parking is free and located adjacent to the trail.