A little bit Greenwich Village, a little bit Magaritaville, Delray Beach was voted in 2012 as “Most Fun Small Town in America” by Rand McNally.

By Michael Persson | Photo © Peter Cross

The free “green transportation” shuttles visitors to downtown shopping, dining, and the busy Pineapple Grove Art District along Atlantic Avenue, as well as to the bonanza of festivals year-round. “Florida’s Village by the Sea” has an elegance and Bohemianism that makes for dichotomy deluxe.

Friday

Pineapple Grove District

Art abounds in Delray, and one not-to-miss stop includes the contemporary art at Addison Gallery. Among its crisp white walls is a new open exhibit the third Friday of each month. Its artists are drawn to the surrounding beach scenes, like Anne Packard, the granddaughter of the impressionist painter Max Bohm and a preeminent painter from the Provincetown school of abstract expressionism.

Saturday

Wake-Up Call

If you’re a coffee connoisseur, then head to Caffe Martier for a strong, freshly ground cup. It’s the perfect pairing with towering Belgian waffles, wild mushroom omelets, and the much-lauded avocado mousse croissant. Perched just on the edge of Atlantic Avenue, it’s perfect for morning people-watching just feet from area art galleries.

Stroll

After, stroll along Delray Beach’s Historical Beach Walk, which will put you in the way of ocean breezes and sun. The path follows in the 1,885 footsteps of the famous “Barefoot Mailman,” who walked – on the sand – from Palm Beach to Miami. Start south of George Bush Boulevard at the intersection of North Ocean Boulevard and Beach Drive. From there, it’s north or south for approximately a mile.

Bird Watching

The Wakodahatchee Wetlands gets its name from the Seminole Indian word for “created waters” and has 50 acres of wetlands that house more than 140 different bird species. Visitors can see this ecosystem up close and perhaps catch one of the abundant Purple Gallinules that walk along the handrails of the three-quarter-mile boardwalk that winds through three of the wetland’s ponds.

Tribute to the Stars

The Delray Center for the Arts serves up a number of arts, theater, and music productions throughout the year. But for the more zany culture enthusiast – or, more specifically, the tribute band aficionado – the Outdoor Pavilion at Old School Square in downtown Delray Beach reads like a Rolling Stone magazine with a list of legendary acts. Cover bands, like Scott Ringerson and his Elvis Experience, The Petty Hearts, Galo Rivera and his tribute to Santana, and The Beatles-esque, Across The Universe, will make you look, listen, wonder, and bop.

Sunday

Up-Close History

The “Ride & Remember” Trolley Tour takes riders through the city’s five historic districts, the Spady Cultural Heritage Museum, and Old School Square. Guides let riders off at certain historic sites for an up-close-and-personal look at Delray Beach’s colorful backstory, like how draining the nearby Everglades west of the city put a halt to pineapple farming and started competition with Cuba for Northern markets.

Culture

The exhibitions at the Morikami Museum and Japanese Gardens change throughout the year. Created as a way to preserve the history and culture of the area’s first immigrant farmers. Tea ceremonies along with traditional Japanese festivals put on display an authentic learning experience from this 3,000-year-old culture.

Where to Stay Delray Sands Resort