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Grassy Flats

Winter Getaway Guide: A Perfect 2-Night Escape to Grassy Key

Updated: 54 minutes ago


When the winter blues start setting in, there’s no better cure than a tropical escape to the Florida Keys. Grassy Flats offers the perfect setting for a quick yet unforgettable two-night getaway. Whether you’re looking to unwind by the beach, try a thrilling water sport, or indulge in delicious food and drinks, Grassy Flats has something for everyone. 


Here’s a guide to making the most of your winter retreat on Grassy Key.




Day 1: Arrival & Relaxation


Check-in and Settle In

Your winter getaway begins as soon as you arrive. Nestled in the tranquil seclusion of Grassy Key, the resort provides a welcoming atmosphere and stunning views that make it easy to forget about the stresses of daily life. Check-in, drop off your bags, and take a moment to soak in the beauty of the resort’s tropical surroundings.


Lounge by the Pool or Beach

After settling in, it’s time to fully embrace island time. Head to the pool or stroll over to the beach where you can enjoy a leisurely day of sunbathing or take a refreshing dip in the water. With the winter winds gently swaying the palm trees and the soft sound of waves in the background, this is the perfect opportunity to unwind and soak up the Keys' signature laid-back atmosphere.


An aperol spritz on the Palm Deck rooftop bar in Marathon, Florida.

Cocktails & Tapas at the Palm Deck Rooftop Bar

As the afternoon turns to evening, head up to the Palm Deck for cocktails and tapas. With panoramic views of the Atlantic, this is the ideal spot to catch a stunning sunset while sipping on a refreshing drink. The bar features a great selection of craft cocktails and a unique tapas menu perfect for sharing. And with live music every night, nothing beats the vibe at this laid-back, open-air bar.


The Palm Deck is open Wednesday, Thursday & Sunday 4 - 9pm, Friday & Saturday 4 - 10pm.





Day 2: Adventure & Exploration

Kiteboarding lessons in the Florida Keys

Kiteboarding on Grassy Key

The Florida Keys are known for their ideal conditions for water sports, and Grassy Key is no exception. If you're feeling adventurous, day two is the perfect opportunity to try kiteboarding. The winter winds create excellent conditions for both beginners and experienced kiteboarders alike. Sign up for a kiteboarding lesson with one of our instructors who can get you up and riding in no time. 




Alternative Adventure: Rhum Runner Aqua Park or Wakeboarding

If the winds are not cooperating or you’re looking for something a little different, there are other exciting options available. Visit The Lagoon at Grassy Key, where you can test your skills at the Rhum Runner Aqua Park—a floating obstacle course that's perfect for those who love a fun challenge. For an extra adrenaline rush, try wakeboarding at Keys Cable. Either way, you're guaranteed to have a blast.


Poolside Lunch & Drinks at Bales Away

After a busy morning of adventure, head back to the resort and relax by the pool. Bales Away serves up delicious drinks and lunch options, making it the perfect spot to cool off and refuel. Order your favorite tropical cocktail, snack on fresh seafood, and enjoy the peaceful ambiance of the resort’s lush grounds. 


A rum flight at The Rhum House in Marathon, Florida.

Dinner at The Rhum House

After a day full of activity, treat yourself to a spectacular dinner at The Rhum House, our premier dining venue. The menu is a celebration of fresh local seafood and bold island flavors. Start with the Roasted Woods appetizer or the Coconut Rhum Oysters. For your main course, we recommend the Iberico Secreto—a tender, flavorful cut of pork that will have your taste buds dancing. End your meal with a rum flight, sampling some of the best rums the Keys and Caribbean have to offer, each one more exquisite than the last.



Day 3: Farewell to Grassy Key


Bongo's Botanical Beer Garden in the Florida Keys.

On your final day, enjoy a relaxed morning before checking out. Head over to Bongo’s for a laid-back brunch. Located at The Lagoon, Bongo’s offers a variety of delicious breakfast and brunch options, from the Lobster Benedict to a Chimichurri Steak Bowl. Pair your meal with a mimosa or one of their 20 beers on tap as you reflect on your memorable getaway.


Pick Up Souvenirs at the Saloon Surf Shop

Don’t forget to stop by The Saloon Surf Shop at The Lagoon. Whether you're looking for a keepsake to remember your trip or some local island goods, the shop offers a great selection of souvenirs, clothing, and water sports gear. Grab a t-shirt, a locally made piece of art or jewelry, or some sunscreen for your next adventure in the sun!



A Winter Getaway Like No Other


Whether you’re seeking relaxation, adventure, or a mix of both, Grassy Flats Resort & Beach Club offers everything you need for the perfect two-night getaway this winter. From tranquil beach days to thrilling water sports, world-class dining to unforgettable sunsets, your time at Grassy Flats will leave you feeling refreshed and recharged. So pack your bags, grab your sunscreen, and get ready for a winter escape you won’t soon forget!

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