There’s no better way to enjoy summer than with a getaway to Key West – and no better way to get there than the Key West Express! Ideal for all travelers, 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 to make the most of a 3-day getaway, starting with a fun ferry ride on the Key West Express year-round from Fort Myers Beach or seasonally in the winter months from Marco Island.
Day One
7 a.m. – All aboard the Key West Express! Boarding starts at 7 a.m. for an 8 a.m. departure from the Fort Myers Beach terminal (1200 Main Street, Fort Myers Beach, FL 33931). The jet-powered catamaran ride usually takes 3.5 to 4 hours, depending on weather conditions. But with air-conditioned interiors, exterior sun decks, couches, tables, and reclining airline-style seating, it beats the long drive to Key West, hands down. Plus, there’s a full-service galley, bar, and flat screen TVs, if the gorgeous gulf views aren’t entertainment enough. There’s no Wifi on board, so plan on a few blessedly refreshing screen-free hours. Check the website for schedule updates, guidelines, and all the info you need to make the most of your trip.
Noon – Dock at the ferry terminal in Key West (100 Grinnell Street) and take a quick 10-minute ride to Margaritaville Beach House Key West (2001 S. Roosevelt Blvd), the perfect home base for your island adventure! The hotel’s complimentary shuttle picks up at the Historic Seaport Harbor (in front of the Waterfront Brewery at 201 William Street), which is near the Ferry Terminal. Just call the hotel to arrange for your pickup. 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). Try the fresh fish tacos or peel & eat shrimp with an Iguana Mojito or frosty Fins Up Margarita. Properly fueled, change into your bathing suit for some fun in the sun at Smathers Beach, the largest beach in Key West, located directly across from the resort. Feel free to just 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. Take the resort’s free 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 photos.
Evening – Nighttime is the right time to see Duval Street in all its 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 dining on fresh Florida seafood for dinner at an award-winning restaurant. Some of our favorites include, The Docks Restaurant + Raw Bar, Blue Heaven, and Louie’s Backyard. Get a streetside table for some of the best people-watching you’ll ever experience.
Day Two
Morning – Wake up, sleepy head! Time to refuel with breakfast al fresco (7:30-11 a.m.) at the resort before you take the resort shuttle and head to the Seaport Harbor area to catch the Old Town Trolley Tour. This easy “hop on/hop off” tour is a great way to hit all the main sites, learn some unique history, 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 much more. Plus, you can scope out spots for your next drink, meal or shopping excursion.
Afternoon – Once you’ve seen it all, catch the shuttle from the Seaport Harbor pick-up location and head back to the resort for some R&R at the lagoon-style pool or a siesta in one of our tucked-away hammocks. Drop by the resort’s concierge desk to make plans for Day 3.
Sunset Hour – If you think the sunset from Mallory Square was great, try one on the water! Just hop aboard a Sunset Sail with Sebago Watersports, which you can book through the hotel’s concierge. This 2-hour sailing adventure includes live music from local musicians and premium drinks and appetizers, as you tour Key West landmarks ahead of a dazzling sunset.
Evening – Make your way back to the resort for more 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. And for a sweet ending, order up Guava Bread Pudding, Chocolate Mousse Torte, or the island’s preeminent pastry, Key Lime Pie. The pool is open until 11 p.m. for a soak under the stars.
Day Three
Morning – How to spend your last day? The Key West Ferry doesn’t start boarding until 5 p.m., so you’ve got time to either hang out at the resort or get out and explore at your leisure. Check in with the concierge to confirm any plans you made – a fishing trip, bike tour, snorkeling excursion, shopping along Duval, a visit to Fort Zachary Taylor, whatever. Or ask about getting a late check out to get in more sunning and swimming time at the beach or pool. As you plan your getaway, make sure to note these destination-wide event celebrations: Key West PRIDE (June), Key Lime Festival (July), and Key West Lobster Fest (August).
Pro Tip: If you’d rather be out and about on your last day, you can leave your bags at the ferry terminal (see the hotel concierge) while you have fun on Duval Street and Old Town, which are just a few blocks away. Just hop aboard the hotel shuttle, which stops just a few steps away from the terminal. 5:00 p.m. – Time to board the ferry terminal for the return trip north to Fort Myers Beach. Whether you’re chilling at the resort or beach, or kicking around Old Town, make sure you’re on board no later than 5:30 p.m.
As an extra bonus, the Margaritaville Beach House Key West is giving you a 15% discount for your stay! What could be better than that? "Bubbles Up" and Save!
All resort photos courtesy of Margaritaville Beach House Key West