From flip flops and frozen drinks to salty tunes and celebrated sunsets, the best way to experience the Margaritaville lifestyle is with a trip to Key West, Florida – where it’s always 5 o’Clock and the ocean breeze carries a familiar tune. And the perfect island home base is Margaritaville Beach House Key West. 

Here’s a no-worries, all-fun three-day itinerary to soak in the iconic laid-back island vibes:

Day One: Welcome to Paradise

Land in Margaritaville – You made it! Step off the plane, breathe in that salty sea air, and slap on the sunscreen and sandals. First stop? Margaritaville Beach House Key West (2001 S. Roosevelt Blvd). If you arrive before check-in time, stash your bags with the friendly front desk team and enjoy a complimentary cocktail from the front desk – because vacation starts NOW.

Lunch & Beach Bum Bliss – Time to raise a glass (or two!) at Tin Cup Chalice Bar & Chill, where the Fins Up Margaritas and LandShark Lager flow like the tide. Pair it with fish tacos, peel-and-eat shrimp, or whatever floats your boat. Once you’re properly fueled, slide into your swimsuit and sashay over to Smathers Beach – Key West’s biggest and best stretch of sand. Swim, sunbathe, or rent a kayak, jet ski, or paddleboard if you’re feeling adventurous.

Sunset Sail & Dolphin Tales – At 5 p.m., grab your shades and salty sweet attitude, hop on the resort’s free guest shuttle to downtown, and set sail on the Captain’s Choice Dolphin Watch & Sunset Sail with Sebago Watersports. This dolphin-watching, tapas-munching, wine-sipping cruise serves up front-row seats to Key West’s epic sunsets. Raise a glass and toast to the pirate life.

Dinner & Nightcap – Back on land, treat your taste buds to a seafood feast at local favorites like The Docks Restaurant + Raw Bar, Blue Heaven, or Louie’s Backyard. Grab a streetside seat for some world-class people-watching. Then, catch the trolley back to Margaritaville Beach House or wander down Duval Street to see where the night takes you. (Spoiler: Probably somewhere with live music, happy people and tequila.)

Day Two: Chasing the Island Vibes

Breakfast & Story Time – It’s time for breakfast al fresco (7:30 – 11 a.m.) at the resort. Go big with Huevos Rancheros or Brioche French Toast, or keep it light with Granola & Yogurt if you’re still recovering from last night’s rum-run. Then, hop the resort shuttle to the Seaport Harbor for an Old Town Trolley Tour. This hop-on, hop-off adventure takes you past iconic landmarks such as Hemingway’s Home (because every island needs a resident genius); the Key West Lighthouse (great for working off that French toast); the Southernmost Point (snap a pic or it didn’t happen); and Shrimpboat Sound – Jimmy Buffett’s personal recording studio, where the magic happens.

Afternoon Poolside & Biking – Back at Margaritaville Beach House, cool off in the lagoon-style pool or find your favorite hammock for an afternoon siesta. Feeling sporty? Grab a bike and cruise the A1A Jimmy Buffett Memorial Highway, which runs right past the resort. Jam to your own Radio Margaritaville-inspired playlist and let the sea breeze do the rest.

Dinner & Dancing Under the Stars – Tonight, stay close to home at Tin Cup Chalice Bar & Chill for live music and a dinner to remember. Chow down on Angus Skirt Steak, Chickpea Curry with fresh-caught Mahi, and the island’s preeminent pastry, Key Lime Pie. Afterward, dance the night (and the calories) away – and remember the pool is open until 11 p.m. for a soak under the stars.

Day Three: One Last Splash

Lazy Mornings & Cheeseburgers in Paradise – Spend your last full day however the tide pulls you. Poolside lounging? Yes. Beach strolls? Absolutely. Local burger joints? Essential. Suggested stops are always the Margaritaville Restaurant, Sloppy Joe’s, Sunset Pier, or Frita’s Cuban Burger Café – each one a bite of pure happiness.

Afternoon Siesta or Sunset Prep – Before you head out for one final adventure, take a last lazy lap around the resort. Squeeze in some poolside daydreaming, a final margarita, or a quick shopping spree for souvenirs.

Mallory Square Magic – If you thought the sunset on from the water was great, just wait! Hop the resort shuttle downtown to Mallory Square, where sunset celebrations are a Key West tradition. Street performers, fire jugglers, and island musicians set the mood as the sun melts into the sea. Pro tip: Make sure your phone is charged to capture your awesome sunset shots.

Duval Street Nightcap – As the stars come out, follow the laughter, steel drums, and salty tales down world-famous Duval Street, home to a colorful collection of bars, restaurants, shops, attractions, and tropical shenanigans. Crawl your favorite pubs and bars before – and after – enjoying another fabulous Key West dinner, then let the night decide what happens next. (Just remember: The last shuttle is at 10 p.m. – or there’s always Uber.)

Day Four: Parting is Such Sweet Sorrow

Check-out from Margaritaville Beach House Key West isn’t until 11 a.m., sometimes even later for Margaritaville Perks members, so you should have time to enjoy one last breakfast, one last swim, and one last toast to the good life before heading home.

Pro Tip: If you fall in love with Key West (and let’s be honest, you will), plan your next trip around Key West Pride (June), Hemingway Days (July), or Lobster Fest (August).

Whenever you visit, Margaritaville Beach House Key West is where the sun is hot, the drinks are cold, and the good times never stop. Check out the special offers, and book your visit.  🦈🍹🌅