Cruising the Coast: A 10-Day Journey Through Florida’s Most Stylish Waterfront Resorts

In a state that thrives on contrasts—sunrise over the Atlantic, sunset in the Keys—a new kind of Florida getaway has emerged. Davidson Hospitality Group has teamed up with four of its top-managed properties to offer a 10-day luxury road trip that connects elegance, culture, and curated local immersion across the Sunshine State’s East Coast.

This exclusive multi-stop itinerary brings together The Singer Oceanfront Resort, Eden Roc Miami Beach, Baker’s Cay Resort, and Three Waters Resort & Marina for one seamless experience. Each destination offers more than just a place to stay—it’s a story, a setting, and a chance to live like a local with all the perks of five-star hospitality.

The journey begins on the quiet shores of Singer Island. At The Singer Oceanfront Resort, guests are welcomed with chilled rosé, a fresh fruit plate, and a private poolside cabana that sets the tone for a refined yet relaxed stay. The two-night minimum package includes a $50 daily resort credit, complimentary watersports and bike rentals, and a keepsake branded tote to take home. A curated insider map guides guests through the best of Singer Island and West Palm Beach, ensuring you experience the local character beyond the shoreline.

Next stop: Miami Beach. At the iconic Eden Roc, nostalgia and modern energy blend effortlessly. The resort’s Miami by Day & Night experience includes a private cabana, a $100 food and beverage credit, and a signature happy hour mixology session at Ocean Social. Guests also enjoy a “Stars & Bubbles” night under the cosmos—an intimate stargazing evening led by an expert astronomer—and additional $100 credits for both Esencia Wellness Spa and Ocean Social dining.

Eden Roc’s thoughtful offerings balance indulgence and introspection. Whether you’re people-watching from your beachfront lounger or recalibrating with a spa ritual before dinner, the resort invites you to slow down and take it all in.

As the drive winds into the Florida Keys, Baker’s Cay in Key Largo offers a deeper connection to nature and sustainability. Set within a 15-acre oceanfront sanctuary, the resort introduces guests to its eco-forward mindset through a multi-part experience that includes a Sunset Tiki Cruise with lite bites and beverages, followed by a private “Dock to Dish” boating adventure. Here, guests learn sustainable fishing practices firsthand before sitting down to enjoy a beachfront dinner featuring the day’s fresh catch.

It’s a return to simplicity—but with thoughtful luxury built into every moment.

The finale unfolds in Islamorada at Three Waters Resort & Marina, the newest gem in the Florida Keys and flagship of the Islamorada Resort Collection. Spread across 15 acres of oceanfront, the property combines a barefoot-casual vibe with elevated design and service. Guests receive a generous $500 F&B credit and can explore the water via the resort’s signature Rum Runner Water Taxi. A visit to the Rum Library for a private tasting adds a flavorful (and educational) twist, capped off with branded keepsakes that recall the spirit of the trip.

With 214 island-inspired guest rooms and nine distinct dining concepts, Three Waters is poised to become a new classic in the Keys—where you can sip, sail, and stay with effortless ease.

What sets this road trip apart isn’t just the picturesque destinations—it’s the intention behind each stop. From laid-back luxury to immersive experiences, Davidson Hospitality Group has designed the itinerary to feel as curated as it is customizable. Each property delivers a city-specific perspective through handpicked activities, regional flavors, and high-touch hospitality that doesn’t overreach.

Whether you’re traveling solo, with a partner, or bringing the entire family along, the 10-day journey strikes a rare balance between movement and stillness—rooted in local culture, elevated by world-class service.

It’s not just a road trip. It’s a reset.