Walkable Towns

Related Cities & Topics:

View Full Size

Downtown Winter Park.

Photo Credit: Contributed Photo

View Full Size

St. Augustine is the nation's oldest continuously-occupied city.

Photo Credit: Contributed Photo

View Full Size

Sunset at Mallory Square in Key West is an event in itself.

Photo Credit: Donna McLaughlin

If gas prices are hitting hard, or you're just looking to ditch the car on your next trip, check out these excellent walkable towns in Florida.

When you really think about it, every trip we take begins and ends with walking.

Putting away the car keys and setting out on foot helps us save money on fuel and rental cars, allows for more social interaction and keeps us feeling fit.

Florida has no shortage of walkable towns that make for excellent vacation spots: Ybor City, Coral Gables, Key West, Seaside and Pensacola are just a few. Below, you’ll find details on some of my favorites, chosen for their charm and natural beauty.

All you have to do is figure out how to get there … then let your feet take care of the rest.

Winter Park

This quaint community near downtown Orlando, approximately 25 miles from Disney, has long been praised by residents and visitors for its pedestrian friendly roadways.

Nestled among the Chain of Lakes, Winter Park is brimming with history, culture, shopping and recreation. The area boasts more park – not parking – space per capita than any other Florida city.

There are numerous places to park your car, and free valet service is available on Park Avenue at the south end of Central Park. Otherwise, stay at one of several area hotels and forget about driving at all.

Two spots I recommend in Winter Park for lodging are the Best Western Mt. Vernon Inn (110 S. Orlando Ave., 407-647-1166) and the Park Plaza Hotel (307 S. Park Ave., 407-647-1072).

Visitors can stroll down tree-lined streets and browse boutiques in the Winter Park Village, Park Avenue and Hannibal Square shopping districts; or visit one of the area’s four museums. Sites on the National Register of Historic Places include the Annie Russell Theatre and the Knowles Memorial Chapel.

The Saturday Farmers Market (200 W. New England Ave.) is a great place to shop for local crafts or grab a picnic lunch. At 761 Old England Ave., the historic Winter Park Country Club golf course is open to the public.

Winter Park’s Welcome Center is the perfect place to begin your journey. There you’ll find maps, brochures and knowledgeable volunteers who can help plan your adventure. Be sure to ask about the Scenic Boat Tour.

Open from 9 a.m. to 5 p.m. Monday through Friday and 9 a.m. to 2 p.m. Saturday, the Welcome Center is located at 151 W. Lyman Ave., one-half block from Park Avenue South. Visit www.winterpark.org or call 1–877-972-4262 for information.

Key West

This tropical paradise at the southern tip of Florida is an ideal walkable destination. Narrow streets flanked by historic buildings draw you into a maze of intoxicating sights and sounds. All you need to get by in Key West are comfortable shoes, sunscreen, a bottle of water and an urge to explore.

Old Town, on the west side of the island, is the most popular destination among visitors. This area encompasses the Key West Historic District, with natural sites like Fort Zachary Taylor State Park and Mallory Square, which overlooks Key West Harbor, where sunset celebrations take place every night.

Duval Street caters to visitors, and is usually packed with pedestrians taking in the local restaurants, bars and shops. It makes for a rowdy and adventurous stroll.

Off the beaten path, you’ll find quieter streets lined with wood-frame homes dating from the 1880s to early 1900s. The Historic Seaport District will take you toward fishing piers and several rustic seafood restaurants.

Parallel to Duval, Whitehead Street leads to the Southernmost Point monument and other historic sites such as the Ernest Hemingway Home and Museum and Key West Lighthouse.

Stroll through the Key West Cemetery (in the center of Old Town) for an unusual lesson in island history, then grab a Cuban sandwich at a local restaurant and picnic at nearby Bayview Park or the White Street Pier.

A common way of getting to Key West is by flying into Miami, then renting a car and following the Florida Turnpike to U.S. 1 at the start of the Florida Keys. Beginning at Key Largo, this road runs some 100 miles to the end of the line (Mile Marker 0) in Key West. Overseas Highway is Florida’s only All-American Road and contains 42 bridges across blue water. After parking at your destination hotel, you won’t need to car again until it’s time to leave.

For your drive there and back, though, do keep informed about traffic problems and local events during your journey by tuning in to 104.1 FM – US1 Radio, broadcast along the Overseas Highway. They also broadcast on the internet at www.us1radio.com.

Nonstop flights are available from Atlanta and Orlando, and a number of airlines serve Key West out of Miami or other Florida destinations for easy connections from anywhere. From the Key West airport, a $10 taxi ride takes you straight into Old Town in minutes.

Learn more by visiting www.fla-keys.com/keywest. 

St. Augustine

Founded in 1565, St. Augustine pre-dates automobiles by a long shot, making it an obvious choice for your walkable vacation. The city’s narrow brick street is much more suited to walking than driving.

From antique shops along San Marco Avenue to historically significant architecture on St. George Street, the nation’s oldest city offers up scores of historic sites and museums, restaurants and pubs. All are within easy walking distance of local hotels such as the budget-friendly Days Inn (1300 N. Ponce De Leon Blvd., 904-824-3383) or quaint Casa de Solana (21 Aviles St., 904-824-3555).

Begin the day’s journey with a stop at the Visitor Information Center (10 W. Castillo Drive) to pick up maps and helpful tips. The adjacent parking facility offers a place to stow your vehicle if needed.

In the northernmost section of Old City, the historic Spanish fort Castillo de San Marcos is open to visitors year-round (except Dec. 25). West of the fort stand the original city gates at the beginning of Saint George Street, where restaurants, galleries, boutiques and antiques proliferate.

St. George Street only allows foot traffic, and numerous themed walking tours are available, highlighting everything from historic sites to ghostly tales.

Gain perspective on life during St. Augustine’s earliest years at museums such as the Colonial Spanish Quarter (29 St. George St.), where re-enactors perform daily. Housed in a former hotel, the Lightner Museum on King Street includes a breathtaking collection of Tiffany art glass.

When your feet get tired, get a lift from the narrated trolley train or a horse-drawn carriage, or jump on the Victory III, a popular sightseeing boat at the city marina (111 E. Avenida Menendez, 904-825-1026) for a view from the water’s edge.

The closest major airport is Jacksonville International Airport, about 40 miles away. From there, visitors can rent a car and follow I-95 South toward US 1, which leads to Castillo Drive and the center of St. Augustine. For a slow, scenic route, stick close to the Atlantic Ocean along A1A.

Airport shuttles are also available from the Jacksonville Airport into St. Augustine. Get details on schedules and rates by visiting www.airportexpresspickup.com.