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Itinerary for the Perfect Key West Getaway

If you’re looking for an escape from the hustle and bustle of everyday life, Key West makes for an ideal travel destination. With its white sand beaches, vibrant nightlife, and exciting outdoor excursions, there is truly something here for everyone. In fact, it can be difficult to narrow down the list of activities to fit just a few days – that’s why we’re here to help! 

Looking for a tropical adventure in Key West? Margaritaville Beach House Key West is the ideal hotel for your Key West getaway. Read below for a sample itinerary for 3 days in this paradise.

Before You Leave:

Packing can be the hardest part of any trip. Fortunately, you’ll find that Key West has a refreshingly relaxed, casual vibe, one that can easily accommodate any wardrobe. Here are some must-haves for your packing list:

Straw hat with a book and sunglasses and hotel room key

  • Flip-Flops/Sandals

Flip-flops are known as the unofficial shoe of the Florida Keys. They are necessities for beach days and lounging by the pool. Keep in mind, though, that Key West’s beaches are very sandy, with few rocks, so you may be able to go barefoot as well).

  • Swimsuit

If you want to take a dip in the pool or ocean, or try a snorkeling excursion.

  • Sunscreen & sunglasses 

The sunlight here is very strong – and plentiful! – so make sure you protect your eyes and skin while you’re by the pool or ocean. There is also sunscreen at the Margaritaville Beach House Key West gift shop if you need to resupply.

  • An outfit for when you aren’t lounging by the water 

For going out to dinner downtown and/or bar hopping on Duval Street.

  • Shorts and T-shirts 

For exploring the downtown area and perusing local shops.

  • Sneakers & athletic clothes

If you want to explore downtown via bike or scooter!

Key West Itinerary Day 1: Explore Margaritaville Beach House Key West, Grab a Drink, and Relax by the Water

After you check into Margaritaville Beach House Key West, get settled into your room and explore the grounds. Breathe in the ocean air as you take in the sights of palm trees, blue skies, and the hotel’s tropical-chic decor. Enjoy a complimentary welcome drink, smoothie, or popsicle with fellow guests.

If you’re feeling peckish, head to Tin Cup Chalice Bar & Chill, conveniently located by the pool, to enjoy the best of Key West’s seafood – the fish tacos are especially tasty! Then, grab a refreshing margarita, pina colada, or soft drink and relax by the lagoon-style pool.

A Woman Sitting On A Lounge Chair By A Pool

Next, walk across the street to Smathers Beach – lucky for you, the island’s largest and most beautiful beach is just across the street. Before heading out, be sure to pick up beach chairs and coolers at the front desk. Find a quiet spot to relax and take in the breathtaking views. You’ll see pristine blue water and pelicans soaring inches above the surface. In the distance, windsurfers and jet skiers can be found riding the waves. Feel free to take a dip, as the water is relatively warm year-round, as well as clean and safe. 

A Beach With Many People On It

Back at the hotel, freshen up and head back to Tin Cup Chalice Bar & Chill to enjoy a quintessential Key West dinner. If you have a sweet tooth, be sure to try the island’s famous key lime pie. All meals are made with fresh ingredients and have a tropical, Key West flare – you can’t go wrong with our delicious menu! 

Key West Itinerary Day 2: Explore Town, Do Some Site-Seeing, and Experience the Nightlife

After coffee and a bite at Tin Cup Chalice Bar & Chill (which has an impressive array of breakfast options), catch the shuttle downtown. Margaritaville Beach House Key West provides a free shuttle for guests into downtown Key West, running every hour on the hour. This is a unique offering that you should definitely take advantage of whether you rent a car or travel without your own transportation. En route, your shuttle driver may give a mini history lesson of Key West, pointing out the many writers, politicians, and celebrities who have found a home here. The shuttle will drop you off at the Historic Seaport Harbor, an ideal spot to begin exploring the town. 

If you’re a literature fan, take the 18-minute walk to The Hemingway Home and Museum. There is an entrance fee, but the price for admission is well worth it for the beautiful setting and informative guided tour. Learn about “Papa” as you peruse his rooms, gaze upon his writing studio, and meet the 60+ six-toed cats roaming the grounds. 

On your way back downtown, observe the quirky architecture of surrounding houses. Stop by Blue Heaven or Moondog for some lunch before dropping into one of the town’s famous rum distilleries. 

If you have kids in tow and you’re looking for family-friendly activities in the Keys, be sure to check out the Key West Aquarium, or Mallory Square – this is a beautiful spot to hang out at sunset, and it features a diverse array of street performers. 

A Man And Woman Standing In Front Of A Sign

For dinner, we recommend A&B Lobster House for seafood (be sure to make a reservation in advance), or Amigos Tortilla Bar if you’re looking for something quick and cheap. For more affordable options, wander downtown on and around Duval for other eateries. There is something for everyone. 

You can’t visit Key West without getting a taste of its nightlife. Head over to the landmark bar “Sloppy Joe’s” for a drink or to the “La te da Hotel” for a cabaret performance. Duval Street is the hub of nightlife in Key West and is a great place to bar-hop if you’re up for a late night. Just be sure you catch the last night shuttle (at 11 pm) back to the hotel unless you plan to take alternative transportation.  

Key West Itinerary Day 3: Take an Outdoor Excursion

Margaritaville Beach House Key West has a wonderful concierge service where you can book a variety of excursions operated by Sebago Watersports – from sunset cruises to dolphin tours, to parasailing and snorkeling excursions. Sebago Watersports offers several outdoor adventures, including guided parasailing trips, private boat charters, and reef snorkeling. Choose an excursion that appeals to you and take the free shuttle downtown to Sebago Watersports. Enjoy a few daytime hours of watersports before returning to Margaritaville Beach House Key West for some R&R. Or, alternatively, spend the day napping in a hammock or playing cornhole at the hotel before heading into town for a sunset cruise. Sebago’s evening cruises offer stunning views of Key West’s one-of-a-kind sunsets, all while you enjoy live music and an open bar. After your excursion, grab dinner in town or at Tin Cup Chalice Bar & Chill.  

A Group Of People Sitting At A TableOur knowledgeable concierge can arrange one-of-a-kind excursions for the whole family.A Group Of Boats In The WaterEnjoy a snorkel trip to one of Key West's picture-perfect reefs with Sebago Watersports.A Group Of People On A BoatA sunset sail is the perfect memory-making experience with friends old and new.

The Island With it All

Two People Riding BikesRent bicycles from Margaritaville Beach House Key West and roam the island with the wind at your back.

You might be surprised to know that despite its size, Key West has so much to offer visitors. Margaritaville Beach House Key West is the perfect place to explore the island, from its beautiful pool to gorgeous beach views to great eats at Tin Cup Chalice Bar & Chill. Are you ready to start planning your Key West getaway? Take advantage of one of our special offers here to book the perfect Key West vacation. 

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