Delray Beach, FL Itinerary + Travel Guide— Where to Stay + What to Do


If you are planning a trip to Delray Beach, Florida and are wondering where you should stay and what you should do while you’re there… then you’ve come to the right place! I will be breaking down our 4 day trip and posting our exact itinerary below in case you want to replicate it.

To those that aren’t familiar with Delray it’s a small charming beach town located in southeast Florida and it’s the perfect spot for a fun getaway in the sun. Whether you are traveling with friends, a significant other, or your family there are things to do for everybody! It is also conveniently located centrally to both PBI and FLL airports, so you have options when it comes to which airport you want to fly into and out of.

PS, if you’re new here my name is Stephanie and I am a wanderlustin, fashion obsessed, spicy margarita enthusiast. Follow me along on instagram @sugaredstilettos to see all that and a big dose of my daily life… I love new friends!

Here’s a summary of what you will find below in case you want to jump ahead!

  1. Avelo Airlines

  2. Where We Stayed — The Ray Hotel

  3. Best Places to Eat/Drink in Delray Beach

  4. What to Do

  5. Our EXACT Itinerary

  6. Outfits I Packed with links!


Before I get into the whole breakdown of our Delray trip below I want to take a second to talk about Avelo Airlines. I had the absolute pleasure of being able to partner with Avelo for our flights to and from FL and it was SUCH a seamless experience. If you are from CT like us Avelo is based out of Tweed Airport in New Haven, CT and if you haven’t tried flying with them yet I couldn’t recommend it enough. The airport is super small so it makes going through security a breeze and it’s so much less hectic than a larger airport (goodbye airport anxiety!) The airfare is also much more affordable compared to larger airlines, which is obviously a win in and of itself!

Avelo also gave me a discount code for $25 off your next flight, it’s “SUGARED25”!

Below is a map of all the places Avelo flies and as you can see even if you’re not from CT, you can still make use of my discount code if you’re flying to any of these destinations. Just an FYI they don’t have WIFI on the planes, so download movies ahead of time or bring a book!

If you are looking for an Instagram worthy hotel that has all the bells + whistles then The Ray Hotel (click here to book) is the place for you. This new addition to Delray’s hotel scene is absolutely gorgeous. From the moment you step onto the property and walk through the front doors you’re instantly transported to this modern bohemian tropical oasis. If you’re somebody like me who loves taking pictures then consider yourself in good hands because just about every square inch of this hotel is photo worthy. I did a full hotel tour on my IG if you want to take a sneak peek into what is awaiting for ya (tap to watch)!

The Ray Hotel is pristinely located within walking distance of Pineapple Grove, Atlantic Avenue, and the beach, so location wise it’s incredible. We literally were able to walk to 90% of the things that we did during our trip which was fantastic. The hotel also offers complimentary bike rentals which I highly recommend taking advantage of!! Easiest, quickest, and most fun way IMO to take a tour of the area.

On site you will find four dining options— the Rosewater Rooftop, Ember Grill, Akira Back, and Stinger’s Cafe — so you truly never have to leave if you don’t want too! We personally went to the Rosewater Rooftop pool + bar EVERYDAY on our trip and we did the happy hour at Ember Grill one night (more details in the “Best Places To Eat/Drink” section below).

Let’s talk about the rooms though because your girl was in HEAVEN. We stayed in one of their premier rooms with a private furnished terrace and it was honestly such a beautiful room. From the palm tree wallpaper in the bathroom and spacious + bright bedroom to the MASSIVE outdoor terrace that was just for us, it was PERFECT. We popped many bottles of champagne out there watching sunsets!


Before I get into the full breakdown below, I have a full Delray highlight on my instagram that showcases everything we did… forewarning you might get hungry watching it!


Located at the Ray Hotel this tropical rooftop lounge and pool is the perfect spot to soak up all the rays. As a guest of the hotel you get full access to the pool amenities and as I mentioned above we ended up coming up here every single day on our trip to lounge out on the chairs and drink some craft cocktails poolside. There is also a full food menu so you truly never have to leave if you want to just chill out one day and do absolutely nothing.

Even if you’re not staying at the Ray you can still enjoy the 360 degrees of Downtown Delray from the rooftop lounge and bar area where they offer half off drinks during their Golden Hour happy hour! Perfect spot for a cocktail before a night out on the town.


This is also located at the Ray Hotel and as with everything else within the hotel the decor at Ember was beautifully done. Ember Grill offers an innovative menu that serves up fun twists on classic dishes. There are both indoor and outdoor seating options, but we actually went for the happy hour which is available at the bar area only. It is WELL worth checking out because you get half off cocktails and $7 bites. We personally tried the Mac and Cheese Bites, Oysters, Jumbo Shrimp, and Charred Buffalo Cauliflower and every thing came out delicious. The Mac and Cheese bites were definitely my personal favorite though because you can’t quite beat that flavor combo!

They also have extremely creative and IG worthy cocktails. My top recommendations are the Pineapple Smoke, South of the Rio, and the Garden of Eden which comes served in a flower pot!!


This is such a fun spot that’s located right on the water, so the views are on point. This was actually our first stop straight off the plane for lunch and it was the perfect way to start off our trip. We sat outside by the water and got to soak up some sun paired with some great food and much needed cocktails.

They have a large selection of items to choose from so you’ll be sure to find something you like no matter your food palette. They also have a great drink menu featuring some awesome summer cocktails— we loved the mango jalapeño marg and pool boy! AND if you have a dog they have a freaking doggy diner menu. My top food recommendations would definitely be the chicken empanadas, Baja fish tacos, and the Deck burger.


Located right on Atlantic Avenue, City Oyster is a fun, lively restaurant that’s known for their fresh seafood, full sushi bar, and a vast selection of oysters from coast to coast making it an awesome spot for lunch or dinner! The decor is also so on point and fitting for the space so it’s definitely an aesthetically pleasing dining spot.

We ended up going for lunch and opted to try out the sushi menu and OMG was it freaking good. If you’re a sushi lover then I highly recommend trying out at least one roll while you’re there and if you’re a spicy food kind of person then PLEASE do yourself a favor and try the Kamikaze roll because it was 20/10 good.

PS… if you are somebody like me who loves a good oyster shooter they offer two different kinds on their menu.


If you love authentic Mediterranean and Lebanese food then you need to add Amar to your list because everything here is made in house so it was as fresh as it gets. This cozy romantic restaurant is serving up some incredibly flavorful savory small plates that are perfect if you want to get a little taste for everything. They also have larger entree sized portions as well. The ambiance and dim light vibe makes this spot perfect for date night.

We decided to try out a variety of things and I can honestly say EVERYTHING was top of the line. Some of my top recommendations would definitely be the classic hummus, falafel, and the arnabeet mekle (fried cauliflower).

AND PLEASE… do yourself a favor and get dessert. I saw this melted cheese tart on the menu and to be honest was skeptical because well… cheese for dessert? But PLEASE order it, it’s called the Kanafeh for 2. I am not even kidding when I say this thing was DROOL WORTHY good.


We met friends that live in the area here for dinner one night and what a cool little spot! If you’re a wine lover then this one is for you because they have over 200 hand selected wines available that you can self dispense through the coolest dispensing system. So basically you can try a LOT of wine because you can do 1, 2.5, or 5 oz. pours— prepare to become a wine connoisseur.

The food was also so delicious. I definitely recommend ordering a cheese and charcuterie board because they pair fantastic with wine and the ingredients used were top notch. My husband ordered the steak for two and I got the halibut— YUM.


Located SUPER close to The Ray Hotel this is such a great brunch spot, but honestly the place is packed all hours of the day, so it’s safe to say they’re serving up some pretty dang good food no matter when you go. The vibe of this place is awesome, so it’s no surprise people want to stick around a bit sipping on some cocktails.

We opted to do brunch here and sat outside on their patio and it was wonderful. We started with the Lulu’s Irish basket which is a mixed basket of scones and house made jams and butters. I definitely recommend trying out the French toast and cold brew martini.

PS. we also tried the margarita picante because my husband and I are obsessed with spicy margs and it was bomb. Probably odd to try for breakfast unless you are equally as in love with margs as we are LOL.


If you’ve been following me along for a while then you know (as I just mentioned above) my husband and I are AVID Mexican and marg people. There is just no doubt that we will forever be finding a restaurant on vacation that fills that craving. In Delray, that spot was Rocco’s Tacos and YUM. First off, the decor inside this restaurant is so freaking cool, so even if you decide to sit outside like we did, do yourself a favor and go check it out!

Now on to the good stuff— the marg menu is VAST so prepare to want to try them all because there are just too many good options on there. I HIGHLY recommend the black diamond and the jalapeño margs though! We started off with guac, queso, and chips and then dove right in to some enchiladas and tacos— all so freaking good, consider that craving of ours satisfied…. immensely.


Such an eclectic little spot with the coolest outdoor dining setup Dada makes an awesome dinner spot to add to your list. They serve up some super unique dishes in a laid back and relaxing atmosphere.

My top recommendations are the bacon wrapped Dada dates, bolognese, and jalapeño glazed salmon!


Let me just preface this entire paragraph with… this place is so freaking cool. They have two locations— one located right in Delray and one located a short drive away in Deerfield Beach. GO TO THE DEERFIELD BEACH LOCATION and here’s why.

The Delray spot is awesome if you’ve already experienced the Deerfield location and are just CRAVING some of their unreal coffee concoctions and food because they have one located right downtown. However, since it’s located in the market the food/drink is served in plastic and the setup is a bit different, but nevertheless if you don’t have a car and can’t make the drive to Deerfield STILL GO because you won’t be disappointed I promise.

BUT if you can make the drive or even uber go to the Deerfield Beach location. The experience is so cool and the inside is like an antique masterpiece of the coolest decor and vintage coffee cups and plates. I mean just look at the photos, this place is decked out!

We tried out a TON of different things and everything was honestly incredible. My top recommendations would definitely be the lavender honey cold brew, coconut creme colada, avocado toast, and my absolute favorite— the modern egg sandwich make it spicy style.

I am still dreaming about being able to indulge in their coffee/food again. The owners are also from CT, my home base, so that’s pretty cool too!


Batch is a short drive from the Ray Hotel but WELL worth it. If you’re looking for some seriously creative cocktails and INSANELY yummy pub food look no further. I would also like to say that the service was over the top good. Our waiter was so knowledgeable about the entire menu and he was able to give us some great recommendations.

For starters, we had the duck pot stickers and the pub house tater skins and then for dinner I personally devoured the honey hot fried chicken sandwich and my husband had the hot pepper cheese steak. If you’re somebody that enjoys a good cocktail and I mean a REALLY good cocktail then you will love their selection. We tried the Agave Fizz, Gunpowder Dram, and the Toasted Pecan Whiskey Sour— again ALL so great.

PS… there is also an arcade and movie theater in the same parking lot, so it’s a win win because now you have something to do after dinner!


Common grounds is technically not in Delray, but again it’s only a short drive in Boynton Beach. I actually got to meet their social media coordinator, Jeanette, on my visit here and she was the freaking sweetest human. Common grounds is BIG on music and art and upon walking through their doors you immediately realize that. They have a piano that’s covered in philosophical quotes and messages from their patrons, local art displayed on the walls, and a bookshelf for those that want to bury their noses in a book with their coffee for a bit. Not to mention they host so many events at their various locations, I wish I could of went to one of the stand up comedy ones!!

Both the food and coffee here are so well done, but it’s no surprise as they actually roast their own beans which is so cool! We tried the lavender cold brew, dirty chai, prosciutto cream cheese toast, blueberry pastry, and açaí bowl. EVERY single thing would definitely be my top picks! I am not kidding when I say they have the best açaí bowl I have ever had in my life and I have since been trying to master it at home, but can never get it to taste the same. Common grounds do you deliver to CT LOL?



Beer lovers add this one to your itineraries. This brewery features a great variety of beer that they brew on site, has local food trucks parked outside for when you get hungry, and has live outdoor music on occasion! I personally LOVE a good sour beer, but I never end up finding them on the menus where I go… to my surprise they actually had a few different options and all were great!

They do beer flights too, so you can try out a nice variety! We also got to do a tour of the brewery (they don’t offer this to the public anymore) and let me just tell you their equipment is no joke. Such a cool spot!


This long strip also known as “The Ave” is a one stop shop for all things food, cocktails, live music, and shopping. It is jam packed with so much to do so it’s the perfect spot for a long stroll outside because there is a huge selection of incredible restaurants to satisfy any and all cravings and tons of local shops for all price ranges. The pineapple grove area is nearby too and has so many fabulous art galleries and a farmers market on the weekends!


I am dubbing this the best mini golf spot that my husband and I have ever been to thus far. Why? Well for one the courses are awesome— there is an easier one for kids, but there is also a more challenging one for adults which you don’t always find! Second, they serve beer/wine and have scan codes at every hole so if you need a refill they will deliver it to you. My husband and I had so much fun here. It’s only about a 10 minute walk from the Ray Hotel too!


As you can imagine Delray Beach is home to some beautiful beaches. Delray Municipal Beach is one of the top recommended beaches because you can rent chairs and umbrellas right on site and take a full day to just lounge out and do nothing if you prefer the ocean to the pool! They also have water sports that you can take rent as well!


If you’re a gamer like my husband and I the Silver Ball Museum is such a cool and unique spot. They have over 100 pinball machines dating back to the 50s which you get unlimited play with when you pay for a pass ($15 for an hour or $20 for a day pass). There is also a full bar on site so it’s the perfect recipe for a good time!



OUTFIT 1 (tap to shop)

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OUTFIT 6 (tap to shop)

OUTFIT 7 (tap to shop) (SUGARED20 for 20% off)

OUTFIT 8 (tap to shop)

OUTFIT 9 (tap to shop)

OUTFIT 10 (tap to shop)

OUTFIT 11 (tap to shop)

With Love Always,

Sugared Stilettos

(By Stephanie)


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