Find The Perfect Blend of Upscale and Laid Back in Delray Beach, Florida

Often “upscale” means we need to scrutinize our wardrobes before packing for a trip, making sure we up our game from merely “Make sure your t-shirts don’t have stains” to “I’m bringing my Old Navy sandals, not my Old Navy flip flops.”  You know the feeling:  walking down a sparklingly well kept, tree-lined main street filled with boutiques and hip restaurants, secretly coveting the fashion-forwardness of passersby, you feel like everyone is working to hide the disdain on their faces at your comfy mom-jeans and those comfy grandpa sandals a family member insisted on wearing.

(I don’t own mom-jeans but certain Triple B teammates just may occasionally sport those strappy black Tevas, you know the ones…)

Thankfully, for us, Delray isn’t as notoriously glam as its northern neighbor Palm Beach, but the upscale look and feel is mixed with a delightfully laid back and welcoming vibe. Come one, come all, it says. And you look just fine in your surf shop sundress and Old Navy sandals.


I swear I didn’t plan it but when I discovered I matched, I made my sweet, patient husband take pics


Diving into the history of this small town, who aptly calls itself “Village by the Sea” – we find that it has always been culturally and racially diverse and filled with artists, makers and doers. For the full, fascinating history check out the Delray Beach Historical Society, but for us some important facts foreshadow how Delray would continue through the years to be a dynamic place where everyone is welcome.

  • The earliest settlers were Seminole Indians, and when a U.S. Congressman bought land in anticipation of Henry Flagler’s railroad, and a commissary was created, the first “shop” was opened and everyone traded happily and peacefully.
  • This congressman, William S. Linton, named the town after himself: a bold move that was later knocked down when he defaulted on his land payments – a hard freeze ruined the crops – and he left town.
  • Delray was named after a town in Michigan by a transplanted resident with fond memories of his home. “Del Rey” means “of the king” in Spanish.
  • Various races came to settle in Delray through the years, joining black families who already lived there and who started the first school, two churches, and a masonic lodge.
  • An African-American trained midwife and nurse practitioner from the Bahamas, Susan Williams, handled medical needs for all races. In 1898. Wow. Would that we could all be like her, and them….
  • Japanese settlers came in the early 1900s to help Henry Flagler build an agricultural community, and these men were later joined by their families who came for shopping, recreation, and participation in civic events.  Shopping and enjoying the town’s events back then! A promising start.



Atlantic Avenue – the town’s main street – is the longest main street in Florida and Delray has one of the few downtowns in Florida with a beach attached. A delightful place to stroll under shade trees, walking the mile from the beach you’ll pass approximately 50 restaurants! Unique, locally owned boutiques are interspersed with art galleries, and the Pineapple Grove Arts District is close by with its eclectic mix of cafés, salons, galleries and antiques stores.


Related:  Other Florida towns that have downtowns with a beach attached, read Gulf Coast Florida’s Favorite Walkable Vacation Town: Pass-a-Grille

Voted One of the Most Walkable Small Towns in Florida: New Smyrna Beach

Bradenton Beach is Like the Youngest Brother of the Three Siblings on Anna Maria Island


The best Mexican meal we have ever had:  El Camino Mexican Soul Food & Tequila Bar





Anchor Park

340 S. Ocean Blvd.

With 3 miles of public beach, if you can find a parallel parking space on the main drag, any of the lovely beach paths will lead you to the wide sand and typically calm waters. As of our recent visit, parking along Ocean Blvd. was free, though we did see the beginnings of parking meters being installed. There are several parking lots with meters – $1.50/hr. – an easy walk just across the street: Sandoway Park Sarah Gleason Park,   Atlantic Dunes Park, and Anchor Park.  

Sandaway Park We chose Anchor Park because of its close proximity to Atlantic Ave. and its facilities.

  • PARK/WALK:  Anchor Park’s lot is just across the street from the beach.
  • GO/RINSE:  Restrooms are located within the park, rinse off right after you exit the beach path, before crossing the street to the parking lot.
  • CROWD FACTOR:  Delray Beach is wide and relatively uncrowded.
  • GUARDS:  Lifeguards are present from 9 am-5 pm.
  • IMBIBE:  Alcohol is not allowed on the beach.
  • BEST FRIEND:  Your dog is not allowed on the beach.
  • WE LOVE:  Delray Beach has received so many awards we hardly have room to write about them all (but we’ll try), including being designated a Blue Wave Beach by the Clean Beach Coalition, and awards from the American Shore and Beach Preservation Association. The city has contracted with a beach cleaning service which keeps the beach area pristine and gorgeous. A cabana rental service is also contracted so that you don’t even have to haul that beach chair and umbrella. Have the cabana boy set it all up for you and pretend you’re famous.


How cool is this bench made of coral? Sit here and brush the sand from your feet or watch all the runners and bikers go by. There are so many athletic, fit people in Delray Beach – even really old people – it was inspiring! Also made us feel like sloths…


The original pavilion was destroyed by hurricanes in 1926 and 1928, and a new one was built during The Depression with workers donating time and materials, and with  donations from businesses and locals – some as little as $6, but still! The community spirit was strong. Blown down by a hurricane in 1947, the whimsical design remained in the town’s memories and this current incarnation was built with fundraising – including talent shows – sponsorships and donations. Architect Bob Currie offered to draw the pavillion for free.




40 S. Ocean Blvd.


Open daily 11 am-11:30 pm

We joked that in this swanky town there might not be that classic basic we always seek out: a beach bar. But Boston’s on the Beach made sure Delray didn’t lack this Florida beach town must-have. You can dine more finely (think Freebird Farm Chicken or Tagliatelle) at their 50 Ocean, next door and upstairs, or medium-finely at Boston’s on the Beach, also next door, downstairs. This menu is HUGE, bring your appetite. Oh, and they have a POOCH MENU! Your well-behaved best friend can sit outside with you at Boston’s on the Beach.

But on to the Sandbar:

  • VIBE:  The most superlatively beach bar vibe ever. Tiki? Check. View of the beach? Check. Rustic/creative decor? Check. Waitresses in bikinis? Ugh. I mean, check. Happy people imbibing, music, roll-call of perfect bar food? Check check check.
  • ARRIVE:  By foot or bike is best, but if you drive there Sandaway Lot is close by for parking. Or take the free Downtown Roundabout Trolley. We also saw Valet parking at Burger Fi two doors down (and thought that sounded fun; valeting your car for a burger night out!)
  • SIT:  Outside, of course.
  • SIP:  Happy Hour is M-F 4-7. Check their website for daily specials including S & M Mondays (half price Sam Adams draft and Cazadores Tequila Margaritas.) You might also want to check their drink menu online before your visit – the drinks list is so long you might need that extra time to decide what you’ll choose.
  • NOSH:  Pub-grub but elevated with creative-chef touches. Try the Key West Conch Fritters with sweet pepper remoulade dipping sauce, or their Butcher Block Turkey Burger with avocado, chipotle aioli served on warm pita bread. Salads, a veggie wrap, sliders, and a Maine lobster roll are among the choices.
  • LISTEN:  DJs spin fun dance music.
  • WE LOVE:  Besides all the above-mentioned goodness, we love how the Sandbar looks. If you were just ambling past without a plan, you’d want to spend the rest of the evening here.

We’re wondering what the history and current use of that so very cool ramshackley building in the back is… let us know if you know!



We didn’t stay in a bungalow. Nor did we stay in a mom-and-pop or a B & B. Not even a locally owned boutique hotel, though the hotel we ended up in did have a distinctly boutique hotel look and feel. You know we’re all about guiding you to independently owned, family owned, locally owned. Anyone can decide to be a luxury travel writer, getting complementary stays at huge pampering chain resorts, but we’ve always had a heart for the small, hard working teams who go it on their own. The husband and wife team who clean the toilets and also make your breakfast (maybe I should place those two things into two different sentences… but you know what we’re trying to say.) The parents and kids who man the front desk, keep up the lush grounds and gardens, manage the social media and get involved in their town’s beautification and fund raisers.

The “bungalow” that we wanted to stay in had no vacancy, so this time we’re going to tell you where we wanted to stay and where we did stay – both are worth talking about.

We really wanted to stay at

Crane’s Beach House Boutique Hotel & Luxury Villas

82 Gleason St.


As always when we recommend a place to you that we didn’t experience fully ourselves, we spent hours researching, reading reviews and talking to fellow travelers and locals, and Crane’s was the standout favorite for the kind of experience – peaceful, tropical, beautiful, off the beaten path, yet close to everything – that we, and you, seek. AND, get this:  Crane’s has its own, open to the public, Tiki Bar! Play where you stay, we say! Talk about walkability: tip back a few while listening to some chill live music, then toddle a few yards away to your room. Tipple, Then Toddle! (Sounds rather promising for a future blog post.)

From Crane’s Boutique Hotel and Luxury Villas website:

“This magical hideaway bristles with tropical Key West style beauty, barely visible through the perimeter treeline, earning its mystique as ‘Delray’s hidden treasure.'”

You could walk right past Crane’s without noticing it, the lush landscaping gives such privacy to the property, yet it is located just one block off of Atlantic Avenue and one block to the beach.

Other amenities besides the noteworthy Tiki Bar:

  • 2 tropical saline swimming pools
  • Large internal courtyard with lush, tropical greenery
  • Complimentary hotel guest parking
  • Gated security entrances
  • Lobby souvenir/gift shop
  • Guaranteed 12 pm checkout
  • Dog friendly rooms available


Our photos don’t do it justice, so click on their name above to visit their website and plan your visit!


Where we stayed, and ended up loving:


The Seagate Hotel & Spa

1000 E. Atlantic Ave.



Though we sound as if we were dragged unwillingly to the Seagate, it being a large property owned by a sophisticated Hospitality Group with a portfolio featuring luxury resorts, boutique hotels, select-service hotels and residential properties across the nation (no mom-and-pops visible on their website), truth to tell? We luxuriated in the ‘exclusive ambiance’ of this ‘getaway of luxury and leisure.’ For real. We didn’t hate it.

I was smiling the whole time. I swanned around in the plush white robe, stretched out on our spacious balcony with my wine and the current magazines they placed on our contemporary dark neutral wood coffee table, and had to be bodily heaved out of the ultra comfortable bed with its cool and crisp high thread count sheets because I never wanted to leave that cozy nest. The room was airy and huge. And the bathroom was large enough to live in.

  • VIBE: As described above. Luxurious, great attention to detail, and such a friendly staff at the ready we felt like celebrities.
  • WALK: The perfect location for walking everywhere. The beach is less than a block – a 3 minute walk – away. All the shops, restaurants and art galleries are right out the front door and down the street in both directions.
  • DECOR: Contemporary and sophisticated without feeling like you can’t put your feet up on the coffee table. Soothing neutrals with some beachy touches.
  • SLEEP:  One of those sleeping experiences that made us want to figure out how to replicate the entire set-up at home.
  • EXTRAS:  24-hour valet, twice-daily housekeeping, newspaper delivery, luxury courtesy car service, and more. Covered in your resort fee is the use of the Seagate Beach Club, a lovely, private oceanfront club with a swimming pool, towel service, chairs and umbrellas, ocean view casual and fine dining restaurants.
  • WE LOVE:  The perfect mix of exclusivity, comfort, and friendliness.


 In addition to the recognition for its clean beaches, Delray Beach has deservedly gotten these awards:


Makes you want to live there, doesn’t it?

In case you need more convincing:


City Oyster & Sushi Bar has its own bakery upstairs, and their wine list has been recognized by Wine Spectator as one of the premier wine selections in the country


Deck 84 overlooks the Intracoastal, and has the best Bar Bites menu for Happy Hour! 3-time winner Top 100 Al Fresco Dining Restaurants voted by Opentable


The Colony Hotel and Cabana Club was built in 1926, and has been owned and operated by the same family since 1935



Some photos of the cute cottages and bungalows around town:


This may be the “carriage house” to the larger pink one on its left, but wow, this is all you’d need! And right across the street from the ocean…


Multiple awards, friendly artistic climate, diverse and vibrant community, a million hip restaurants, and the cleanest beach around – oh, and a beach bar – make Delray Beach remarkable and worth putting on your Must Visit Soon list, don’t you think? Let us know in the comments if you’ve been here and agree with us!



Delray Beach is on Florida’s east coast, 20 miles south of West Palm Beach and 28 miles north of Fort Lauderdale.



  1. Neat post. Who wears black teva these days?

    1. Thanks! I know, regarding those shoes — I guess I should confess I have a pair! So comfortable when walking around beach towns, or on the beach for long walks. Just not out at night for a delicious meal with my handsome husband!

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