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United States | A Romantic Weekend in the Florida Keys

Sample Itinerary


Key West, Florida

Trip Duration

4 nights / 5 days

Unwind with your loved one on the blissful sands of the Florida Keys, a place where history, natural beauty, cultural diversity and unique architecture come together to create a subtropical paradise.

Below is just a sample of the immersive itineraries our Destination Specialists can create. Our Destination Specialists are happy to book the hotel highlighted in the itinerary below, or let them know if you would like something customized. And, feel free to offer our non-hyperlinked suggestions to your clients to further explore the destination.


Day 1: Your Home Town / Key West, Florida

Board your short flight from Miami to Key West International Airport, or hop in your Hertz car rental with unlimited miles for a scenic three-hour drive on the Overseas Highway. Upon arrival in Key West, check in to your Oceanview guestroom at Hyatt Centric Key West Resort & Spa for four nights of tranquility with your partner. This waterfont resort offers island-style decor, oceanside pool, Jala Spa and a turtle sanctuary.

Sip a signature cocktail with private beach views of the Gulf of Mexico at Blue Mojito Bar. Begin with an olives and cheese platter before devouring their seafood sliders or pink shrimp fritters. Then toast to your romantic getaway with a sparking Pink Flamingo Rose or their famous Blue Mojito.

Day 2: 

The southernmost point of the continental United States, Key West is renowned for its beaches, watersports, lively nightlife, historic sites and pastel, conch-style architecture. Start your day with breakfast on Duval Street at one of the many cafes or coffee bars, then stroll hand-in-hand around its boutique shops, historic homes, high-end galleries and souvenir stores, enjoying the vibrant atmosphere. Visit Ernest Hemingway's home and museum, Kalypso Gallery or the botanical gardens.

Spend the remainder of your day at one of many pristine beaches, taking advantage of the multitude of watersports available including kayaking, fishing, parasailing, glass bottom boats, dolphin encounters, scuba diving, sailing and more. Then, retire back to the hotel and order room service for a relaxing evening.

Day 3:  Spa Replenishment

After breakfast, get ready for a new level of rejuvenation at Jala Spa. Together with your partner, enjoy the Couple's Duet experience. Begin with a hot oil scalp massage followed by a full-body deep tissue massage using therapeutic pressure to ease tension. Finally, an invigorating foot scrub melts your worries away with a blend of pineapple sugar scrub and fresh coconut milk soak.

This evening, toast to each other at SHOR American Seafood Grill. Delight in the dock-to-dish menu on the veranda with a soft breeze overlooking the gulf, and complete your evening with their signature Key lime pie.

Day 4:  Day at Leisure

Spend your last day at leisure, sunbathe at the resort's beautiful pool or on its private gulf beach. Learn about the incredible marine life at its turtle sanctuary or embark on a day around town. Take a bike tour learning of the island's offbeat charm, charter a boat for a sunset sail, enjoy the live entertainment at Mallory Square or discover the sunken treasure of Spanish galleons at the Mel Fisher Maritime Museum. There is no shortage of activities to peak your interest.

Tonight, hang out with the locals at Green Parrot Bar, enjoying the band's lively beats and sipping cocktails together.

Day 5:  Key West, Florida / Your Home Town

Stroll hand-in-hand along the stunning white sand beach before fueling up with a crab cake benedict or Cuban skillet breakfast. Then, hop in your car rental to head home or to the airport for your comfortable flight home and begin planning your next romantic vacation.

Distinguished Recognitions, Pleasant Holidays Family of Brands