Drew and The Woo is a regular Pineapple series that follows two young professionals as they look for the perfect night out in Delray Beach. They’ll need a happy hour, a sub-20-buck dinner, some live music and a late-night hot spot. Call it a scavenger hunt, bar crawl or even a mild bender. Either way – you’re going to want to follow in their footsteps. At the end of the year, Drew and The Woo (Drew Tucker & Ryan Boylston) will select their top choice for each category and invite the whole city to come out and join them for “The Best Night Out In Downtown Delray.” HAPPY HOUR TRYST
When coming from the West, the first restaurant visitors pass as they enter “Restaurant Row” also known as Atlantic Ave is Tryst. Like most gastropubs, Tryst is inspired by the rich bar culture of Europe. Expect “bar food” with a gourmet twist coupled with an impressive list of craft brews. Ryan: Welcome back, Tryst. Drew: What do you mean “welcome back?” Ryan: Welcome back to my top three list of places I frequent the most. Since bringing back their legendary “half off any draft beer” happy hour – they have reclaimed their spot, listed right after home and work. Drew: We are here an awfully lot. Regularly meeting with family, associates and clients. If our readers really want to know what happy hour we personally frequent the most, they do not have to look any farther than Tryst. Agree? Ryan: Agree. Lee: Agree. Drew: Wait. When did Lee Cohen of Frankel Cohen Law join the conversation? Ryan: When we chose Tryst. The guy knows the menu, the beers and the scotches almost as well as the bartenders. Oh…he’s clearly here ALL the time. Drew: Well, I think that says a lot about Tryst. It is the only bar in Delray Beach that makes me feel like I am back in New York. Its like a white collar “Cheers”. I can see why a professional like Lee Cohen (Co-Founder of the professional group, Delray 21) and so many others would choose Tryst as their downtown bar of choice. Ryan: It’s probably why Delray Beach won Most Professional Small Town in America. Drew: I don’t think that’s quite the title we won….wasn’t it most fu…
Ryan: Either way – here is what really puts Tryst at the top for me. The well-versed culinary team at Tryst carefully chooses 12 diverse beers to keep on tap. They always keep the season in mind and there’s always something for everyone. Each bartender takes the time to understand and know the beers inside and out. Every customer that walks in the door (beer aficionado or not) feels right at home. Drew
: Then from 4-7 Monday through Friday – THEY OFFER THEM ALL AT HALF PRICE! Pair that with an astounding bar menu including Smoked Fish Dip, Pretzel Bread, Prime Pub Burgers, and Oysters – and you have a happy hour that truly can’t be beat. Lee
: Agree. DINNER FOR UNDER $20 ANTHONY’S COAL FIRED PIZZA
Anthony’s Coal Fired Pizza is one of South Florida’s biggest restaurant success stories in last decade. After introducing South Florida to a “well done” coal fired menu, Anthony’s quickly spread to over 30 cities in 4 states. And luck for us, Delray Beach is one of those cities. Ryan: Hands down the best smelling parking lot in Delray Beach. Drew: That’s your opening comment about Anthony’s? Ryan: Hey, when it’s true, it’s true. They’re probably the main reason we won Most Aromatic Small Town in America. Drew: Once again – that last part was incredibly inaccurate. But, Anthony’s really does entice you from the second you get out of your car, especially with the recent addition of an outdoor lounge and additional seating under the stars. Ryan: Dinner under the stars is cute, but I want the “Sinatra Table” you told me about. Drew: No worries buddy. I called ahead and ensured it’s availability for our group. Ryan: Excellent. Lets try to taste everything on the menu so that our readers can understand all the different ways you can eat for under $20 per person at Anthony’s. Drew: Well let’s do a quick rundown of our findings. You could, of course, go with a personal 12-inch pizza (we suggest the “Paul and Young Ron”) paired with two draft beers and call it a day. But Anthony’s has way more to offer than just pizza combinations under $20 at Anthony’s: – 10 Coal fired (delicious) wings served with roasted onions, a side salad and a glass of wine. – 6 Pork Ribs, two gourmet meatballs and a soda. – Roast Beef Sandwich, cheesecake and an espresso.
Ryan: And that new eggplant panini sandwich thing they tested on us, INCREDIBLE! Drew
: With all these amazing choices, Anthony’s service is probably overlooked. Their staff is always professional, pleasant and inviting. From the second you walk in the door. And don’t be surprised if a manager greets you at some point in your night. Ryan: Of course – after all it is Italian. You’re like family. LIVE MUSIC BOSTON’S ON THE BEACH
Open for over 32 years and nationally recognized – the legendary Boston’s is known for its beachside location, Florida style seafood heavy menu, multiple seating options and of course, great live music. Locals will tell you – they’re ain’t no place like Boston’s! Ryan: Why? Because we walked in? Drew
: No. Well, yes, but no. It just got better because the quality of the bands they book are now equally matched with the quality of the venue. Ryan: What do you mean? Boston’s has always been awesome. In fact, they’re for sure one of the main catalysts for us winning Most Awesome Small Town in America. Drew
: You’re getting closer. Yeah Boston’s was always entertaining, but the setup for musicians was nowhere close to what it is today. The new stage at Boston’s includes a very sophisticated sound system with drum shields and proper lighting that won’t roast the performers. Ryan: And toss in that sweet electric red lit Boston’s sign as a backdrop and it feels like the Rolling Stones could take the stage. I definitely see what you mean. The sound quality of the band on stage is completely different from any bar I have ever been to. Drew
: Well give credit where credit is due. We are here with Bounce
playing, one of the premium cover bands in South Florida. Not only do they know how to play, word is they know how to party. Regularly grabbing audience members to sing along with their multi-generational playlist.
Ryan: Its safe to say the “new” Boston’s has everything the “old” Boston’s had and much more. Drew
: Speaking of more… have you looked outside? LATE NIGHT SPOT THE SANDBAR
The latest edition to the Delray Beach coastline and an extension of the infamous Boston’s – The Sandbar is an establishment with a physical presence usually reserved for Disney World or Vegas. A huge tiki bar, a pirate village backdrop, a 15 foot hammer head shark, giant outdoor televisions and corn hole are just a few of the many features you will find here. Drew
: Wow. I didn’t even realize The Sandbar was open this late. Ryan: Excellent place to get a mixed drink after visiting the beach on a Sunday afternoon or after eating dinner on a Friday night. The Sandbar is a wonderful blend of Delray day and Delray night. It’s a perfect example of why Delray Beach won Most Fun Small Town in America. Drew
: Finally you got it right! The award bestowed on Delray Beach by “USA Today” and Rand McNally is finally revealed. I don’t know why it took you so long to remember after the 8 celebratory parties we have attended. Ryan: Hey, can you blame everyone for celebrating? We’re excited! In fact, Boston’s and The Sandbar hosted the official viewing party of the Travel Channel special a few nights ago. Even featured fireworks and drink specials. Drew
: I can’t think of a better place. Ryan: I also can’t think of a better place to end your night if you’re looking to dance in the sand to a live DJ and enjoy fresh ocean air with a few friends and a few drinks. Taxi.
A few bites of leftover Anthony’s.
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