Delray Beach Continues Its Winning Streak

John M Wieland
John M Wieland
Published on May 20, 2026

I’ve been in this business a long time, and I’ve never seen a city rack up awards like Delray Beach. It’s almost unfair to everyone else.

And since more folks signed up for my weekly eLetter this month than any other month in the last six years, today I’ll give newcomers a taste of the winning formula upon which Delray Beach continues to thrive.  And for you longtime reader, here’s a little reminder of why we love Delray.

Let’s start with the big one: three-time All-America City. That’s 1993, 2001, and 2017. Delray is the only city in Florida history to pull that off. Oh, and Delray Beach was nominated as a finalist in 2025. At this point Delray is just showing off.

The Delray Beach, beach? #1 Best Beach in Florida two years straight, according to USA TODAY readers. And now we’re going for a three-peat in 2026 – did you vote?

Delray Beach also flies the international Blue Flag — one of only three Blue Flag certified beaches in the entire continental U.S. — for the 4th consecutive year. It was the first to receive the award in America, and is the only city to win four times.

These awards alone are impressive, yet it get’s better…

Stroll down Atlantic Avenue and you’re walking one of America’s 10 Greatest Shopping Streets. The same street that earned Delray Beach the title “Best Run Town in Florida.” Not bad for a little Village by the Sea.

Coastal Living called us America’s Happiest Seaside Town. Rand McNally named us the Most Fun Small Town in America. Verizon Business ranked us 5th best city for small businesses in the country.

Here’s a clumping of more awards:

* Best Christmas Tree in Florida — Travel + Leisure (2016)

* America’s Best Small Towns for Christmas — Country Living (2015 & 2016)

* Travel Channel Top 10 Beaches in Florida (2015 & 2016)

* Playful City USA designation (2017)

* Expedia Top Honeymoon Destination (2017)

I could keep going — and trust me, the list doesn’t stop — but the point is this: cities don’t accidentally win this many awards. Delray Beach earns them, year after year, because our community cares about its people and our environment.

Next week I’ll return with more on our Delray Beach real estate as we’re in the early weeks of slow, hot, and rain season. The mood is changing, but sales activity remains strong.

(Main Photo: It’s Mango Season! Get a hefty bag, cruise the alleys and get yourself some Mangos – one of life’s more enjoyable adventures)

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*** Are you thinking about real estate investing but are on the sidelines paralyzed about it being the wrong time or too much uncertainty? I write about Three timeless Themes that work well for savvy folks

*** Enjoy and comment on my latest Delray Beach Real Estate Market Update video

*** Know anyone who may need to sell, or seeking help to buy? Your referral means the world to me… 

*** This downtown Delray condo oozes Delray lifestyle and amenities. It has a 94/100 Walkability Score to 110 restaurants and his/her DRY saunas 

                                          ———————————————

                           *** South Florida Inventory is BELOW 2019  ***

                                                Last week’s supply was 53,586

                                                       Today’s supply is 53,388

                            *** Supply is DOWN 41 of the last 55 weeks ***

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