The charming and historic town of Delray Beach bustles with eateries, galleries, shops, live entertainment, and festivals. There’s always something happening along Atlantic Avenue, often referred to as “America’s Longest Main Street.”
There’s a reason this eclectic community was voted “Most Fun Small Town” by USA Today. Delray Beach hosts a variety of festivals, and events throughout the year. There’s something for every interest in this Atlantic coastal town. So get packing for your Delray Beach road trip.
How Gay is Delray Beach?
Delray Beach is sandwiched between West Palm Beach to the north and Fort Lauderdale to the south. Although far from a “gayborhood” like Wilton Manors in Fort Lauderdale, Delray’s laid back, hip vibe with stunning beaches makes the town an ideal place to eat, shop and stay on a gay Florida road trip.
Palm Beach County is home to several gay events, including PrideFest of Lake Worth and the annual Gay Polo Tournament.
Drive 15 minutes north, and find yourself in Lake Worth, just south of West Palm Beach. Lake Worth is extremely gay-friendly. Home to Compass, the gay and lesbian center of The Palm Beaches, Studio 205, the only gay themed retail store in the county, and Zoo Health Club, a gym owned by an LGBT couple, Lake Worth welcomes travelers from every lifestyle.
H.G. Rooster’s
H.G. Roosters is a staple of The Palm Beach’s gay nightlife. Located in West Palm Beach, H.G. Rooster’s offers daily specials, and hosts shows and events every night of the week. Check their website for COVID-19 updates.
The Mad Hatter Lounge
The Mad Hatter Lounge in Lake Worth is one of the area’s most popular gay bars. The friendly neighborhood lounge has a large patio, a pool table and video games, light food and a good mix of cocktails, beers, and wine. Again, check their website for calendar updates. They were closed during my visit, but hopefully they’ll be back up and running soon!
Where to Stay on Your Delray Beach Road Trip
Delray Beach offers a variety of sleeping accommodations. If you want luxury, head to Opal Grand Resort or the Seagate Hotel & Spa. But if you’re like me, and simply desire a place to crash with a comfy bed, modern amenities, and within walking distance of Atlantic Avenue, then check out the Aloft Delray Beach by Marriott.
Aloft Delray Beach
202 SE 5th Avenue
Ease on into paradise at the new Aloft Delray Beach by Marriott. Located in the heart of Delray, this modern hotel is just steps away from all the town has to offer. Start off at the lobby bar, WXYZ, before heading out to explore.
Choose from a variety of loft-inspired rooms and suites. Some feature balconies or terraces. All include free wifi, coffee makers, mini-fridges, and complimentary bottled water. For those who can’t leave work behind entirely there are even ergonomic workstations.
Traveling with your four-legged family members? Inquire about their pet-friendly rooms and suites. Start planning your stay here.
My Experience: I LOVED this hotel. The Aloft Delray Beach had a very cool vibe. The lobby was probably my favorite spot complete with oversized modern sofas and billiard table. It even had a feature wall showing off the “Dogs of Delray”.
Guest rooms were spacious and comfortable with a great use of space. I even had a gift waiting for me with a note from the General Manager! I also liked having a smart TV in my room. This was the first time on my Big Gay Florida Trip that I had a moment to sit and watch TV for a bit. I appreciated having access to my Prime movie account while catching up on emails.
Although the weather turned rainy during my stay, I do suggest taking a nighttime swim in the rooftop pool. In the morning, grab a breakfast bowl to-go on your way out of town.
Guest Room Bed 
Guest Room Living Space 
Super Cool Clock 
Dogs of Delray Wall 
Hotel Lobby
Other Accommodations
Where to Eat on a Delray Beach Road Trip
Although Delray isn’t one of the gayest towns in Florida, every cool town has drag queens. And Delray Beach is no exception! If you’re up for food and entertainment, then plan to go to the Tin Roof during a Divas Brunch. And if drag isn’t your thing, we’ll forgive you.
These are the two places that I visited during my Delray road trip:
Tin Roof
8 East Atlantic Avenue Jacqui
This entertaining venue is known for its eclectic crowd, casual comfort food and local entertainment lineup. Enjoy out their eats featuring new twists on old favorites. Don’t miss their Nashville hot chicken dip, taco combos, custom salads, and impressive wing selection.
When it comes to fun under the Tin Roof, there’s something for everyone. Dance the day, or night, away to a changing calendar of rock, Reggae or DJs. Get ready to cheer-on your favorite drag queen during Battle of the Divas Brunch on Sundays! Check out the menu and entertainment schedule here.
My Tip: The tacos are delicious! And there is entertainment nearly every night of the week, so make this a must-visit spot on your Delray Beach road trip!
Deck 84
840 East Atlantic Avenue
Watch passing boats from this stylish open-air restaurant and bar. Nestled on the waterfront under the Intracoastal Waterway Bridge Deck 84 is a casual spot to unwind after a day on the beach or wind-up before a night on the town.
Deck 84’s diverse menu has something for every diner including vegetarians and those avoiding gluten. Favorites include house-smoked fish dip, meatloaf, and their signature chopped salad. Weekly specials include Taco Tuesday and Sunday Brunch includes a bloody Mary bar!
Bring the whole family to this off-the-beach beach bar. Well-behaved leashed canine companions are welcome in the outdoor area. There’s even a “Doggie Diner” menu!
Make a grand entrance and arrive by boat. Forgot your boat? Valet parking is also available. Get all the details here.
My Tip: If you’re looking for an outdoor water view, this is it! I also highly recommend the Brussel sprouts. Can you say “addictive”?
More Restaurant Suggestions
For a full list of Delray Beach restaurants, click here.
Things to Do on a Delray Beach Road Trip
I spent one night in Delray Beach during my Gay Florida road trip, although I wish I had extended my stay. I’m a shopaholic! And If you love to shop, Delray Beach is the place to be! Downtown Delray Beach and the Pineapple Grove Arts District will more than scratch your shopping itch.
If you’re an art and museum enthusiast, you’ll find that here, too, in the Old School Square. And for our beach lovers – we haven’t forgotten about you either. What I loved the most about this area is that everything is fairly walkable.
Read more on my suggested must-visit places below.
Shopping in Downtown Delray Beach
Atlantic Avenue and surrounding blocks
Stroll the charming streets of Delray’s downtown to explore the eclectic mix of shops and boutiques. Shoppers of all tastes and budgets will discover unique treasures of this inviting, walkable “Village by the Sea.”
For a list of local merchants, specialty shops, and service providers visit here.
My Tip: Visit the Blue Gallery while strolling along Atlantic Ave. I’ve never seen so much color and love in one space! Here are just a few of my favorite pieces from this gallery.
Sculpture by Joel Amit 
Sculpture by Marc Lipp 
Sculpture by Niso Maman 
Work by Joel Amit 
Sculpture by Niso Maman 
Work by Joel Amit 
Work by Joel Amit
Pineapple Grove Arts District
Northeast 2nd Avenue
Observe artists in action at various galleries and studios in Delray’s Pineapple Grove Arts District. Visit the many eclectic boutiques and cafes of this vibrant enclave.
Be sure to check out the outdoor art including sculptures and numerous murals that tell the story of this diverse and welcoming community. I was a bit obsessed with the pineapple murals, as seen below.
Stroll the seasonal farmers market on the weekends for unique crafts and fresh produce. For all the details of Pineapple Grove’s events, artists, merchants, and other businesses visit here.
Old School Square / Delray Center for the Arts
51 North Swinton Avenue at Atlantic Avenue
Satisfy your art and culture cravings at Delray’s Old School Square complex. Housed in what were once, you guessed it, the town’s old schools, these historic buildings now serve as a cultural hub.
Visit the Crest Theater for concerts, dance performances, plays, and other events. The surrounding Town Square is home to the Cornell Art Museum, the Creative Arts School, and an events stage/pavilion. Find out about upcoming events here.
Morikami Museum and Japanese Gardens
4000 Morikami Park Road
Take a day trip to Japan! This world-class museum features a fascinating collection where visitors can learn about Japanese customs, history, and culture.
Enjoy lunch at the waterside cafe. Wander the 16 acres of traditional Japanese gardens, including a tea house, sand garden, and bonsai tree collection. Check the Morikami’s calendar for upcoming exhibit info, tea ceremonies, and cultural events.
Hit the Beach
State Road A1A at Atlantic Avenue
Head east on Atlantic Avenue to one of southeast Florida’s best beaches. This hidden gem is a great spot for relaxing, people-watching, or getting out into the water. Take a surfing lesson or rent a paddleboard from one of the beachfront concessions.
Metered parking is available along State Road A1A and in five designated lots. In addition to the beach itself, there several nearby parks and natural preserves to explore.
Sadly, my phone died at the very moment I stepped foot on this beach, or I’d have a photo to share! See the article cover image for a sneak peak of this beautiful beach.
Other Things to Do
For more ideas on what to do during a Delray Beach road trip, check out our South Florida travel guide.
COVID Updates
As the Delray Beach and Palm Beach County areas reopen, information is frequently being updated to best meet the needs of the community and ensure safety for residents and visitors.
Delray Beach, specifically, has signs posted, like the one below, to make sure people are mindful of social distancing.
During this unusual time please travel safe. Check with your hosts, restaurants, and other venues in advance to learn their current plans and regulations.
Links to local resources:
City of Delray Beach: https://www.delraybeachfl.gov/our-city/safety/coronavirus
Palm Beach County: https://discover.pbcgov.org/coronavirus/pages/updates.aspx
Plan Your Delray Beach Road Trip
Plan your Delray Beach road trip for a taste of small town America set in the Tropics. There’s something for everyone in this unique east coast “Village by the Sea.”
