Expert-Curated Key West Itinerary – Best Things To Do in Key West

There’s no better way to enjoy summer than with a getaway to Key West – and no better island playmates than Sebago Watersports and Margaritaville Beach House Key West! From...

Expert-Curated Key West Itinerary – Best Things To Do in Key West

There’s no better way to enjoy summer than with a getaway to Key West – and no better island playmates than Sebago Watersports and Margaritaville Beach House Key West! From families to newlyweds, Key West welcomes a variety of visitors in search of its fun, funky, fabulous treasures. Anglers, artists, families, retirees, and everyone in between enjoy exploring the island’s rich history, music, food, and culture, along with an endless stream of summertime parties, parades, concerts, tours, and more.

Only have a few days to come and play? Here’s a suggested itinerary carefully curated to help you make the most of a 3-day getaway with expert help from Sebago Watersports.

Day One

Welcome to Paradise! You’ve arrived in Key West – now head straight to Margaritaville Beach House Key West (2001 S. Roosevelt Blvd), the perfect home base for your island adventure. If it’s before check-in time, store your bags with the amazing front desk staff and head to the resort’s Tin Cup Chalice Bar & Chill for a delicious lunch and a frozen concoction (or two). We recommend the fresh fish tacos or peel & eat shrimp with an Iguana Mojito or frosty Fins Up Margarita. Once properly fueled, change into your bathing suit for fun in the sun at Smathers Beach, the largest beach in Key West, located directly across from the resort. Feel free to splash, soak, or snooze, but Smathers also has tons of rental water activities available – paddle boards, kayaks, sailboats, jet skis, and more.

4 p.m. – Now that you’ve got some sun on your smiling face, it’s check-in time! Head to the front desk and get settled in your room, where you can refresh for your first night on the town.

5 p.m. – Grab your sunglasses, hat, and camera, hop aboard the resort’s free trolley downtown, and jump on board the Flyer for the Captain’s Choice Dolphin Watch & Sunset Sail with Sebago Watersports. Indulge in our chef’s selection of tapas and shrimp cocktail, boutique wines, champagne, water, and soft drinks. Toast to the up-close local landmarks, dolphin sightings, and renowned Key West sunset on this sail that has it all. 

Evening – Once you’re back on land, treat yourself to Florida’s freshest seafood at our award-winning favorites, including The Docks Restaurant + Raw Bar, Blue Heaven, and Louie’s Backyard. Insider tip – aim for a streetside table for some of the most entertaining people-watching you’ll ever experience. After dinner, head to the trolley stop for an easy ride back to Margaritaville Beach House for a good night’s sleep.

Day Two

Morning – Wake up, sleepy head! Time to refuel with breakfast al fresco (7:30 to 11 a.m.) at the resort. Go big with the Ultimate Breakfast, Huevos Rancheros, or Brioche French Toast, or keep it light with the Granola & Yogurt or Steel Cut Irish Oatmeal, fresh fruit, coffee, and juices. Then take the resort shuttle to the Seaport Harbor area for the Old Town Trolley Tour. This easy “hop on/hop off” tour is a great way to hit all the main sites, immerse yourself in the history of the area, and get a lay of the land. Popular sites and stops include Hemingway’s Home, the Lighthouse, Little White House, Mel Fisher’s Museum, the Southernmost Point, and more. Plus, you can scope out spots for your next drink, meal, photo op, or shopping excursion

Afternoon – Once you’ve seen it all, catch the shuttle back to the resort for some R&R at the lagoon-style pool, or see how far you can make it through the menu of margaritas before taking a siesta in one of our tucked-away hammocks. If you’re up for more adventure, call your new friends at Sebago Watersports and ask about putting together a private custom charter or jumping on an afternoon eco-tour. No matter how you plan on making the most out of Key West, Sebago has the activity for it! 

Evening – Tonight, hang out at Margaritaville Beach House to enjoy live music and dinner at Tin Cup Chalice Bar & Chill. Start with the Fried Calamari, savor an Angus Skirt Steak or Eggplant Rigatoni, or add fresh-caught Mahi to the Chickpea Curry. For a sweet ending, order up Guava Bread Pudding, Chocolate Mousse Torte, or the island’s preeminent pastry, Key Lime Pie. 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

Morning – After you’ve grabbed a bite to eat, it’s Snorkel Time! Join Sebago Watersports to explore an underwater paradise unlike anywhere in the world. Home to the only living coral barrier reef in North America, Key West is the go-to place for snorkeling among dolphins, sea turtles, and tropical fish. Whether you’re an expert or just earning your water wings, Sebago’s highly experienced captains and crew have your back. And don’t worry, you won’t leave hungry, as Sebago will have a full picnic lunch for you, too.

Afternoon – Rinse & Refresh. Head back to the resort for more R&R at the lagoon-style pool, or a walk (or rest) on Smathers Beach.

Sunset Hour – If you think the sunset from the water was great, just wait! Take the resort’s shuttle downtown and head to Mallory Square to join the happy crowds for the famous Nightly Sunset Celebration. Make sure your phone is charged to capture some great sunset pics.  

Last night – Nighttime is the right time to see Duval Street in all its summertime glory. Once the sun has set, follow the music across the square for a flip-flop foray past the most colorful collection of restaurants, bars, shops, attractions, and more along Key West’s most popular thoroughfare. It’s hard to believe, but this main drag is only about 1 mile long, running north and south between the Gulf of Mexico and the Atlantic Ocean. Crawl world-famous pubs and bars at your leisure before – and after – enjoying another fabulous Key West dinner. (The last shuttle back to the resort leaves at 10 p.m., so plan on Ubering if you’re staying out late.)

Day Four

Parting is such sweet sorrow! But don’t worry – checkout from Margaritaville Beach House Key West isn’t until 11, so you should have time for one last breakfast and a little more beach or pool time before heading out.

Pro Tip: As you plan your summer getaway, live like a local and mark these destination-wide event celebrations in your calendar: Key West PRIDE (June), Key Lime Festival (July), and Key West Lobster Fest (August).


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Custom Charter Options

  • Experience amazing Key West Sunsets with customized catering options
  • Morning or Afternoon Snorkels
  • All day adventures or eco-tours
  • Dolphin Watches
  • Parasailing


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