3-Day Travel Itinerary to Delray Beach, Florida

Delray Beach, Florida is located in Palm Beach County in Southeast Florida. It’s a small, charming beach town with a lively nightlife scene. This, combined with its walkability to the area’s best restaurants, bars and beach, make it a great destination for a 3-day trip. While there are endless activities to discover in Delray Beach, you can easily explore the area’s highlights in a long weekend trip.

Where to Stay: The Ray Hotel

Nestled in the heart of Delray Beach, and steps from all the action, is The Ray Hotel. This hotel has a tropical modern sophisticated design aesthetic that perfectly complements the beach town it’s located in. The Ray offers a rooftop pool and a variety of dining options, including the chic Rosewater Rooftop.

Outside of the hotel, The Ray is located in the hip Pineapple Grove Arts District. It’s steps from the bustling Atlantic Avenue where you can find a plethora of dining, drinking and shopping opportunities. The hotel is also one mile from the beach. The Ray provides complimentary transportation to and from the beach as well as local restaurants.

Day 1: Waterfront Dining and Rooftop Cocktails

Morning: Coffee and a Neighborhood Stoll

Start your day with a coffee and light bite from Stingers, the artisan coffee shop located in the lobby of The Ray. Stingers is known for its delicious, handcrafted espresso drinks and pastries. You can enjoy your coffee in the palm tree lined cafe seating outside of Stingers.

After you’ve fueled up for the day, take a stroll around the Pineapple Grove Arts District. Grab a selfie in front of the famous pineapple mural that can be found at 135 E. Atlantic Avenue. Work up an appetite exploring this colorful neighborhood and going into shops and art galleries.

Afternoon: Waterfront Dining and Live Music

Take a leisurely walk to Deck 84, an iconic Delray Beach restaurant that’s located on the water. Deck 84 is a casual restaurant where diners can take in the intracoastal views while enjoying American cuisine, specialty sushi rolls and fresh seafood.

Deck 84 offers live music Friday, Saturday and Sunday, and is also known for their fresh and handcrafted cocktails. The restaurant has a large back deck that is dog friendly and has boat docking availability right in front. Diners can spend hours at Deck 84 soaking in the waterfront atmosphere, dancing to the live music and sampling the restaurant’s food and cocktails.

Evening: Rooftop With a View

As the sun starts to set, head up to the top of The Ray for sunset cocktails at Rosewater. The rooftop bar and restaurant offers views of downtown Delray and the candy colored sky as the sun dips below the horizon.

Rosewater is known for their menu featuring a melting pot of cuisines and small plates that are perfect for sharing. The Bang Bang shrimp is always a spicy favorite! Drink wise, Rosewater has a creative mixology and craft cocktail program. Accompanied by a variety of tropical flowers and fruits, the drinks are as beautiful as they are tasty.

As the sun sets, the energy at Rosewater rises and patrons enjoy an electrifying entertainment experience. The venue has different DJ sets weekly as well as exclusive VIP tables and bottle service for those looking for a more elevated evening.

Day 2: Lawn Games and Beach Days

Morning: Tropical Party Brunch at Throw Social

Head to Throw Social, located a short walk from The Ray, for a unique brunch experience. Throw Social has a fun tropical theme with a retro 1960’s Palm Beach aesthetic. It’s part bar, part gaming venue. The space is huge with 11,000 square feet of flexible indoor and outdoor space. There is also a stage with a DJ spinning music.

Throw Social is a great destination for a group, and private cabanas are available to provide guaranteed seating and space away from crowds. Order one of Throw Social’s signature cocktails, like the floral drink tree or the Patron margarita tree – the drinks are served in mini Patron bottles!

Feast on brunch favorites like avocado toast, maple bacon stuffed french toast and loaded egg sandwiches. Challenge your friends to a round of darts or corn hole and soak in the fun, party atmosphere.

Afternoon: Hit the Beach

You’re in Delray Beach, so you have to spend some time oceanside. The Ray offers complimentary transportation to and from the hotel and the beach, which is a short one mile drive away.

Delray Municipal Beach spans approximately two miles and accommodates around 3.2 million visitors each year. Beach goers can enjoy powder white sand and the Atlantic Ocean’s surf. The Ray offers guests complimentary beach loungers, umbrellas and tote bags with towels.

The beach in Delray is located across the street from a variety of restaurants, cafes and vendors. There’s everything that one would need to have a perfect day enjoying Delray’s pristine coastline.

Evening: Dinner at Akira Back

Take The Ray’s complimentary shuttle back to the hotel and rest up before heading to dinner at Akira Back. Akira Back is led by the Michelin-starred chef of the same name. The restaurant draws inspiration from the chef’s Korean heritage and global travels with a menu of innovative Asian and American dishes.

Arika Back is a great restaurant to enjoy with friends. The restaurant serves a variety of hot and cold small plates that are ideal for sharing multiple courses. There are a variety of signature sushi rolls and robata which is a call back to the chef’s start of his culinary career working at Japanese restaurants.

Day 3: Pool Vibes and Coastal Cuisine

Morning and Afternoon: Rooftop Pool Day

Plan to relax at The Ray today and enjoy the hotel’s amenities. The Ray’s rooftop pool offers a luxurious tropical oasis, right in the urban center of Delray Beach.

The pool is seasonally heated. The lush rooftop patio area has a variety of comfortable lounge chairs and cabanas to provide shade from the Florida sun. Poolside snacks and cocktails are available throughout the day and patrons can indulge in bites while they relax.

Evening: Atlantic Avenue and a Locally Sourced Dinner

After a relaxing day at The Ray’s rooftop pool, gear up for dinner in Downtown Delray. Take a stroll from the hotel to Atlantic Avenue, the main street in Delray Beach. You’ll pass a variety of boutiques, galleries and restaurants as you walk through the heart of town.

When you’ve worked up an appetite, head to Costa by OK&M. This contemporary American restaurant specializes in healthy coastal cuisine and the food is sourced from local purveyors. Costa is located on a bustling corner of Atlantic Avenue and has a chic outdoor seating area that’s perfect for evening people watching.

The menu at Costa focuses on sustainability and organic and locally sourced ingredients. The cocktails are all created with cold pressed juice that the staff create daily. The food is fresh and flavorful. The tuna crisp appetizer is a favorite!

As your 3-day adventure in Delray Beach comes to a close, you’ll leave with memories of sun-soaked beaches, unique dining experiences, and lively nightlife. Whether you’re strolling along Atlantic Avenue or unwinding by the rooftop pool, this charming beach town provides a getaway that is both rejuvenating and unforgettable. We hope this itinerary helps you make the most of your visit to Delray Beach!

Caitlin Palumbo

Caitlin Palumbo is a New York-based content creator and freelance writer. She is a contributor to Forbes.com where she covers dining and drinks stories with a focus on trends, news and experiences worldwide. She also writes about luxury travel and has written for publications including Barron’s, Tastemade and Elite Daily. Caitlin creates travel and dining content on social media where she has amassed a following of over 240,000. Follow her on Instagram and TikTok @mydarlingpassport and check out her blog, My Darling Passport, for more travel tips. Caitlin graduated from Columbia University Graduate School of Journalism and started her career at NBC News.