A choice of main street or islands unto yourself.

If you’re enchanted by the small-town shopping districts of Mount Dora and Winter Garden, you’ll love their Gulf Coast counterpart: Dunedin.

Roughly five miles up the coast from Clearwater, Dunedin’s small-town charm belies its big-city population (35,444), and that may be because most visitors never even see the surrounding city. Instead they are drawn to Dunedin’s delightfully walkable downtown shopping village.


Serene Honeymoon Island

Grayton Beach
Wakulla Springs
Jacksonville East
High Springs
Coral Gables
Big Cypress Reservation

Anchored by a picture-perfect marina and pier where diners settle in at waterfront restaurants, Main Street is filled with visitors dropping into gift shops, antique stores, art galleries, coffeehouses, microbreweries, and outdoor cafés. Even more retail “shopportunities” can be found in surrounding neighborhoods where bungalows have been converted into arts and crafts boutiques and some historic homes have become bed and breakfast inns. 

Festivals and special events such as the annual Highland Games attract thousands throughout the year, but one popular attraction brings in visitors daily. In the center of the historic district, the Pinellas Trail is a popular “rails to trails” recreational path that stretches 38 miles from St. Petersburg (about 25 miles south) to the Greek/American community of Tarpon Springs (about 13 miles north). Like Winter Garden's West Orange Trail, the wide pathway attracts walkers, joggers, skaters, and bicyclists who have helped cultivate Dunedin into an oasis.


Bicyclists take to the Pinellas Trail

Outside the village, Dunedin’s appeal extends to neighboring Honeymoon Island State Park and must-see Caladesi Island State Park (floridastateparks.org/park/caladesi-island), an undisturbed collection of six barrier islands that include the main 2,400-acre island accessible only by a pontoon boat ferry (727-734-1501). 

One of the most picturesque and undisturbed corners of Florida, aside from a concession stand and walking trails, there are scant traces of civilization on Caladesi. Often ranked among the top five natural beaches in America, most visitors find their way to the waterfront while others enjoy time fishing, picnicking, shelling, hiking, or following kayak trails among the mangrove trees.

While rangers limit visits to the island to four hours (in order to make room for more guests), here’s a reminder: Your time in Dunedin is unlimited. And well worth it. dunedin-fl.com

Staying Over

The Yacht Harbor Inn is just steps from the shopping village, and right on St. Joseph Sound. The inn’s restaurant, Bon Appetit, offers fine dining (or just have a cocktail at the open-air Marina Lounge). Rooms have large-screen TVs, microwave ovens, and mini fridges. yachtharborinn.com

In the heart of town, the home-like Meranova Guest Inn offers themed suites, each with a private entrance. Some feature a private bath or kitchenette. Breakfast can be enjoyed by the pool, beneath the gazebo, in the garden, or on your porch or balcony. meranova.com

Dining Out

Located beside the Pinellas Trail, the Café Alfresco serves a little of everything (Cajun meatloaf, chicken curry, Maryland crab cakes, buttermilk ranch chicken) very well. Great prices—and a great place to relax and dine while people-watching. cafealfresco.com

A fixture since the 1980s, the seafood-centric Sea Sea Riders has a warm, home-like atmosphere (it’s in a vintage home). Our compliments on the setting, service, and dishes like Cedar Key clams, red brick chicken, and fresh Florida grouper. seasearidersdunedin.com

Side Trip

Honeymoon Island State Park
In 1939, the place locals called Hog Island received a new name when a New York developer constructed 50 palm-thatched bungalows and began catering his operation to honeymooners. Now known as Honeymoon Island State Park (floridastateparks.org/park/honeymoon-island), it’s still romantic in a natural way with quiet pine forests, nature trails, white sand beaches, and shorebirds. Located north of Caladesi at the end of the Dunedin Causeway.

Categories: Local Getaways