Weekend Trips from Delray Beach

Delray Beach is the kind of place that feels like a getaway in itself—sun-drenched mornings, walkable beach charm, and a breezy Atlantic backdrop. But what makes this vibrant town even more appealing to those who call it home is how perfectly it's positioned for quick and luxurious weekend escapes.

Whether you're looking to hop in the car for a one-tank road trip or prefer to fly somewhere fabulous in fewer than 90 minutes, Delray Beach makes both options effortlessly accessible. With Fort Lauderdale-Hollywood International Airport 30 minutes to the south, weekend adventures—whether Gulf Coast beaches, boutique islands, or cosmopolitan city stays—are always within easy reach.

Here's a curated collection of top weekend getaways that are perfect for Delray Beach residents and visitors alike.

Keep the car and your sanity with these short, luxury-laden South Florida road trips.

Drive time: 60 minutes

Sometimes, a dose of art, nightlife, and haute cuisine is just what the weekend calls for. Miami's Design District is an ideal destination for daytime inspiration, offering world-class fashion, contemporary art, and Michelin-starred dining. After a day in the Design District, options are aplenty, including a short drive to South Beach for late-night energy and beachfront hotels.

Where to stay: The Moore in the Design District or The Setai, Miami Beach

Don't miss: Visiting the inspiring Institute of Contemporary Art, shopping the district's more than 150 stores and designer boutiques, and vibrant dining at Michelin-starred COTE in the district, or at Havana Vieja or Ocean Enoteca e Forno in South Beach.

Drive time: 90 minutes

If you're craving a more relaxed, Old Florida vibe, Vero Beach delivers. It's a quiet, upscale coastal town where time slows down, making it perfect for a rejuvenating weekend.

Where to stay: Kimpton Vero Beach Hotel & Spa or Costa d'Este Beach Resort

Don't miss: The Vero Beach Museum of Art, oceanfront dining morning, noon, and night at Creperie at Maison Martinique Restaurant, and boutique shopping along Ocean Drive.

Drive time: 2 hours

Among the most underappreciated aspects of Delray Beach's location is the ability to quickly flip the waterfront script—from the Atlantic Ocean to Florida's equally spectacular Gulf Coast. Accessed via a straightforward trek south on Interstate 95, then west on Interstate 75, Naples is one of the state's most luxurious destinations, the kind of place where white-sand beaches meet European-inspired shopping promenades, well-preserved historic districts, and opulent accommodations.

Where to stay: The Ritz-Carlton Naples, Tiburón or LaPlaya Beach & Golf Resort

Don't miss: Spend the day at Vanderbilt Beach or Lowdermilk Park, then explore the boutiques, galleries, and fine dining of Fifth Avenue South and Third Street South. For golf lovers, Naples also boasts some of the state's most prestigious courses including Calusa Pines and Naples National. Other pursuits include the Naples Botanical Garden, and a stop at Seed to Table on the way into town.

Drive time: 2 hours 15 minutes

Islamorada offers the barefoot luxury of the Keys without the crowds of Key West. It's ideal for boating, diving, paddleboarding, and sunset dining on the water.

Where to stay: Cheeca Lodge & Spa or The Islander Resort

Don't miss: A sunset charter, dinner at Morada Bay, or the iconic Green Turtle Inn. Those with an affinity for underwater exploration will appreciate the lauded Florida Keys Dive Center as well as the island's History of Diving Museum.

Thanks to Delray Beach's proximity to Fort Lauderdale-Hollywood International (FLL), you're never far from a totally different scene. Here are a few high-end destinations accessible by flight in under 90 minutes.

Flight time: 50 minutes from FLL

Tampa's renaissance has made it a magnet for curated luxury. Nearby, St. Pete complements the city buzz with coastal beauty and a booming art scene. It's ideal for a weekend of exploring museums, enjoying rooftop bars, and staying in boutique hotels.

Where to stay: JW Marriott Tampa Water Street or The Saint Hotel on St. Pete Beach

Don't miss: The Salvador Dalí Museum, dinner at Bern's Steak House and cocktails at Bulla Gastrobar, and a stroll through Hyde Park Village.

Flight time: 60 minutes from FLL

If you're seeking an upscale escape in a familiar destination, Orlando has evolved into a world of high-end escapes well beyond the typical theme park fare. Consider booking a luxury suite, hitting a championship golf course, or dining your way through celebrity-chef restaurants.

Where to stay: Four Seasons Resort Orlando or Waldorf Astoria Orlando, both at Walt Disney World Resort

Don't miss: At the Four Seasons, indulge in Michelin-star dining at Capa, pampering at the on-site day spa, and golf at Tranquilo Golf Club. The Waldorf Astoria counters with dinner at the award-winning Bull & Bear, therapies and treatment at the Waldorf Astoria Spa, and golf at the on-site Waldorf Astoria Golf Club.

Flight time: 45 minutes to Freeport, 60 minutes to Nassau, both from FLL

With its turquoi00se waters at just under an hour by air, The Bahamas is the closest international destination to Delray Beach. Whether opting for Freeport on Grand Bahama Island or Nassau and Paradise Island, weekend travelers couldn't ask for a better, ultra-accessible tropical escape.

Where to stay: Private villas are plentiful across Grand Bahama Island, but for an all-inclusive experience, opt for Lighthouse Pointe at Grand Lucayan Resort in Freeport. For those choosing Nassau, resort options are endless, including some of the world's most celebrated waterfront accommodations, including Rosewood Baha Mar, SLS Baha Mar, and The Reef at Atlantis, Paradise Island.

Don't miss: In addition to golf, beach, and water-based excursions, you can enjoy shopping and dining at Port Lucaya Marketplace along the waterfront in Freeport, a deep dive into Nassau's history and culture at the National Art Gallery, or try your luck at the Atlantis Casino.

Flight time: 90 minutes from FLL

Charleston is an ideal weekend escape for those who crave cobblestone charm, antebellum architecture, and a world-class culinary scene. Rich in history yet thoroughly modern in taste, this coastal city brings timeless style and Lowcountry warmth.

Where to stay: Full of extraordinary downtown inns, The Dewberry, Hotel Bennett, or Zero George are among the best, most authentic Charleston experiences.

Don't miss: Sunset sailboat tours out of Charleston Harbor, dining at FIG or Iron Rose, and visits to the pastel-hued mansions of Rainbow Row and The Charleston Museum, considered America's first museum.

One of the hidden perks of living in Delray Beach is how effortlessly it connects you to the rest of Florida—and beyond. Whether you're after barefoot seclusion, cosmopolitan energy, or island tranquility, you can find it in just a couple of hours or less.

If you're ready to start searching for a Delray Beach luxury home—or interested in listing yours for sale—contact Lisa Wennick today to start your South Florida real estate journey. Allow Lisa's extensive experience and expertise to help you discover the best of  Delray Beach's extraordinary luxury lifestyle.