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United States | Family Escape to Key West, Florida

Sample Itinerary


Key West, Florida

Trip Duration

7 nights / 8 days

A welcoming beach getaway awaits as you reconnect with your family and build cherished memories.

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

Just a short flight or a scenic drive from your home town, arrive in Key West with your immediate and extended family, where you will continue on to your premier resort or pick up your three full-size Hertz rental cars with pre-registration and unlimited mileage. Settle into your three, one-bedroom suites with balconies at Casa Marina, A Waldorf Astoria Resort as you begin reconnecting with your loved ones. With more than 1,100 feet of secluded beach, this legendary resort offers the ultimate sun and sand getaway.

This evening, dine at HMF Sidecar, where you will learn fun facts about the resort's rich history and founder, railroad tycoon Henry Flagler. Listed in the National Register for Historic Places, the resort has been hosting dignitaries and artists since its opening on New Year's Eve, 1920. After dinner, enjoy an ocean water martini as you listen to the restaurant's live music and toast to the fun in the sun that awaits.

Day 2: Beach Fun & Exploration

Begin the morning with a scrumptious breakfast on your balcony. Afterwards, head to the beach for hours of activities for the entire family. Snorkel or scuba dive as you explore the only living barrier reef in the United States.

After lunch, try your hand at parasailing over the crystal clear waters of Key West.

This evening, head to Sun Sun restaurant for toes-in-the-sand dining. Delight in Bahamian conch fritters with key lime Creole mustard, followed by your main course, Gulf shrimp and scallop fettucine in a chardonnay cream sauce with caramelized fennel, pancetta and fresh basil. For dessert, indulge in your choice of pineapple upside down cake with caramel sauce or key lime pie with raspberry coulis.

Day 3: Dolphin Encounter & Resort Relaxation

Spend the day enjoying the marine life of the Florida Keys as you and your family embark on a Dolphin Encounter to see firsthand some of the world's most beautiful sea animals. Snorkel with the dolphins in backcountry reefs, with instruction from expert guides, and enjoy refreshments on this family-friendly excursion.

After your dolphin encounter, laze at one of the resort's two oceanfront pools, and then grab a sandwich and locally crafted gelato at Rambler's, named after the famous private railcar of Henry Flagler.

Day 4: Spa Indulgence & Sand Art

Enjoy another cozy morning in the comfort of your suite with breakfast in bed as you prepare for a day of ultimate spa experience.

Indulge in the Spa al Mare's Ocean Breeze massage on the beach as you listen to the gentle waves of the ocean. Then, gather the kids for a sand sculpture workshop, where professionals will assist your family in building your own sand sculpture. Snap a picture of the entire family in front of your work of art with the blue water of the Atlantic in the background.

Conclude your day with a catamaran sail sunset cruise, complete with beer, wine and champagne for the adults.

Day 5: Golf & More

Marvel at the beautiful sunrise with your toes in the sand as you indulge in an a la carte breakfast at Flager's Terrace at the resort's Sun Sun restaurant.

After your delectable meal, enjoy 18 holes of championship golf at the Key West Golf Club, offering a Par 70 course. Discover Key West's most exclusive rum collection at RumBa, which also features a local cigar maker.

Then, spend a leisurely afternoon together at the pool, followed by a night in savoring Black Angus prime skirt steak with yucca fries, chimichurri, sauteed brocolini and caramelized balsamic cipollini onion, followed by an indulgent Valrhona Chocolate Mousse.

Days 6 - 7: Days at Leisure

Enjoy your days at leisure at this exquisite iconic resort. Rejuvenate with a hatha yoga class or explore paradise by scooter with your loved ones. For your more adventurous family members, spend the day on a private charter wreck and reef fishing, reeling in fish such as snapper, grouper, shark, king mackerel amidst the wreck sites and coral reefs of Key West.

Day 8: Key West, Florida / Your Home Town

Rent a bicycle to immerse in the beauty of the beach one last time before flying or driving back home. Reminisce about the delightful memories and connections of the past week as you begin planning your next multigenerational vacation.

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