3-Day Key West Weekend Adventure: Sailing, Dining, and Island Exploration

Welcome Back!

As you may know, my journey from Fort Myers ended with the sail away on the Key West Express. Let me tell you a bit about this fantastic service. The Key West Express operates sleek catamaran boats from two convenient ports—Fort Myers Beach and Marco Island—straight to the vibrant island of Key West.

Key West Express: The Ultimate Relaxation

The Key West Express catamaran has three levels of comfortable indoor and outdoor seating. Inside, you'll find air conditioning, big-screen entertainment, and a full-service bar and galley. Now, if you've ever driven from Fort Myers to Key West, you know it takes about 5 hours and 15 minutes, assuming perfect traffic conditions. Want to fly? You could, but don't get me started on dealing with TSA, early arrival times, and cramped airplane seats. In contrast, the Key West Express whisks you away in just 3.5 to 4 hours of smooth sailing, offering blissful convenience and stunning ocean views.

Personally, I’m not a fan of long drives, so handing over the reins to the capable crew of the Key West Express was a no-brainer. It was a relief to let someone else take the wheel while I relaxed and enjoyed the journey. 

As promised, I wore a souvenir shirt from Panamá. After all, Key West is the perfect place to break out those Hawaiian shirts and fully embrace your inner tourist.

Onboard Dining and Tips

Key West Express Bar

The food on the Key West Express is reminiscent of a baseball game concession stand, with hotdogs, chicken tenders, pretzels, a few breakfast items, and more. If you have dietary restrictions or are watching your diet, I recommend bringing your own food. While coolers aren’t allowed onboard, you can bring a personal lunch box, which is exactly what I did. Also, as the ferry ventures farther from the shoreline, you might lose signal, so it's wise to bring cash for food, drinks, and tips for the crew.

 I spent most of the trip at the bar, happily chatting away with the friendly crew and fellow vacationers. We laughed, shared stories, and toasted to new adventures until we finally reached the magical island of Key West.

Day 1: Key West Adventure Awaits!

Navigating Key West is a breeze. You can rent a car, grab a Lyft or Uber, rent a golf cart or bike, or simply walk if you're close to the action. We arrived around 12:30 PM at the charming Grand Guest House Bed and Breakfast. Nestled in a quiet neighborhood, it's just a 10-minute walk from the bustling Duval Street. In true to Land with Dan fashion, we walked quite a bit!

The staff at the Grand Guest House were incredibly personable. As soon as we approached the stairs, I was greeted by name, given a quick property tour, and escorted to our cozy queen-sized room with a private patio. The Grand Guest House offers free coffee, a variety of teas, refillable water (bring a reusable bottle), and a complimentary continental breakfast in the morning. They truly know how to deliver great hospitality!

Lunch at Moon Dog Cafe & Bakery

First up on our Key West adventure was lunch at Moon Dog Cafe & Bakery, a whimsical spot next door to the Hemingway House. Moon Dog serves breakfast, lunch, dinner, and everything in between. The best part? They offer both vegan and non-vegan meals and desserts. Yum!

I asked our server for a drink recommendation and ended up with a refreshing Watermelon Sangria. My IPA-loving boyfriend ordered a local IPA. We shared spinach gyoza dumplings with a wasabi ginger soy sauce—delicious and perfectly balanced. For my meal, I ordered blackened tofu tacos with Daiya cheese, avocado, chimichurri, and pico de gallo. My boyfriend went for the Big Papa burger with Swiss cheese, caramelized onions, applewood bacon, and chipotle aioli. The tacos were a delight, especially since vegan blackened options can be hard to find. My boyfriend enjoyed his burger but wished it was cooked more Medium than Medium Rare.

Everyone raves about Moon Dog's Key Lime Pie, so I had to try it. I had the Mini Vegan Key Lime Pie with key lime coconut curd, toasted meringue, and a pâte sucrée shell. It was rich and delicious, perfect for Key Lime Pie lovers!

Exploring Key West with a Self-Guided Audio Tour

After lunch, we started our self-guided audio tour, booked through Viator for just 15 USD. This format allowed us to explore at our own pace, with the flexibility to stop for restrooms, snacks, souvenirs, and drinks. The tour, which starts at Mallory Square and ends at the southernmost point, takes about two hours and features an engaging storyteller.

Salty Frog Bar & Grill

Just as we were about to start, it began to rain, so we took shelter at Salty Frogs Bar & Grill near Mallory Square. We ordered drinks, and by the time we finished, the rain had subsided. The tour was fascinating—we learned about the origins of the Mallory Square sunset celebration, saw Hemingway's favorite bar, walked along the "Longest Street" in the world, and visited the southernmost point in the continental US.

Near the southernmost point, you'll find the Seaside Cafe at the Mansion. The bar is located right on the water and playfully called "the closest bar to Cuba." From this point, Cuba is only about 90 miles away, so if you have time and a passport, you could potentially plan a day trip to Cuba. I ordered the strawberry mansion margarita with a tajin rim, while my boyfriend opted for the strawberry lemongrass mojito with rock sugar for a little added sweetness. Seaside Cafe uses fresh ingredients and muddles all the fruit for cocktails made to order. The drinks were delicious, and our very hospitable bartender ensured we got our money's worth with a generous pour.

Shortly after we got our drinks, it started pouring rain. Luckily, we took this detour to grab a drink, or else we would have gotten drenched. We wanted to join the Mallory Sunset Celebration, a daily event on Mallory Square featuring local vendors and performers, but due to the rain and cloudy weather, we decided to skip it and grab dinner instead, after the rain stopped, of course.

Dinner and Nightlife on Duval Street

After the rain, we planned to visit the daily event on Mallory Square featuring local vendors and performers, but due to the rain and cloudy weather, we decided to skip it and head to dinner at China Garden West Downtown. You all know, I love trying Chinese food in any new city and country I visit. Often, the Chinese food in other places tastes much better than what I can find in my own town. So of course, Chinese food was on my list of places to eat. We shared spring rolls, I had General Tso's tofu, and my boyfriend ordered Happy Family. The food was standard American Chinese fare—good but not exceptional.

After dinner, we took a leisurely 15-minute walk back to the Grand Guest House to freshen up for the evening. Excitedly, we hailed an Uber to Duval Street, the epicenter of Key West's nightlife. If you're unfamiliar, Duval Street features a plethora of bars including iconic spots like Captain Tony's Saloon, Sloppy Joe's, Green Parrot (a Dive Bar with Free Popcorn), Hog's Breath Saloon, and Hemingway Social Club (a speakeasy), among others.

Original Sloppy Joe's

We went to the famous and infamous Original Sloppy Joe's, which has been a fixture since the 1937 prohibition era at its current location. A live band was rocking the house with classic pop and rock tunes like Bruno Mars' "Locked out of Heaven". Sloppy Joe's exuded a lively atmosphere reminiscent of a classic college house party, attracting a diverse crowd ranging from young bachelorettes to middle-aged revelers and seasoned empty nesters. It was a blast, and the unique vibe made it clear why Sloppy Joe's is an authentic Key West experience.

After Sloppy Joe's, we strolled down Duval Street to take in the scene. While some had warned us of a Bourbon Street-like experience, we found it to be more subdued than expected, likely due to our visit during the off-season in June. If you're curious about Duval's livelier side during peak season, let me know!

Seeking a change of pace, we discovered Rick's Bar, a multi-venue hotspot with eight distinct spaces:

1. Rick’s Downstairs (Karaoke Bar): Live music during the day, karaoke at night.
2. Durty Harry’s (Live Rock Music): Rock out seven nights a week with sports events on 15 TVs.
3. Rick’s Tree Bar (Rooftop): Enjoy drinks with a view of Duval Street, featuring famous Bloody Mary's made from scratch.
4. Rick’s Upstairs: High-energy atmosphere with a balcony overlooking Duval Street and the largest dancefloor in the Florida Keys.
5. The Red Garter Saloon (Gentlemen’s Club): VIP area, Champagne Rooms, and live performances.
6. The Crow’s Nest: Hidden retreat with balcony views of Durty Harry’s stage.
7. Mardi Gras Bar: Chill with frozen treats from the daiquiri bar overlooking Durty Harry’s courtyard.
8. Rick’s Loft: Alongside the cocktail bar, part of the complex's vibrant nightlife experience.

At Rick's Upstairs, we enjoyed a bird's eye view of Duval Street opposite Sloppy Joe's, complete with a DJ spinning early 2000s hip-hop and a lively dance floor where we even witnessed a dance battle—a first outside of movies! After a few hours of music, socializing, and soaking up the vibrant atmosphere, we headed home for some well-deserved rest.

Day 2: Exploring Key West by Bike and Sunset Sail

Morning: Brunch at The Cafe

After a long and enjoyable day yesterday, we decided to sleep in a bit this morning—it was much needed. With a leisurely start, we rented bikes from our B&B for 15 USD each and biked to brunch. The Cafe, a short ride away, continued the theme of quirky Key West restaurant names. It offers fresh, healthy, and globally inspired dishes in a laid-back setting complete with local art and a unique beer and wine selection.

This was our first visit to a fully vegan and vegetarian/pescetarian restaurant, and it turned out to be a delightful experience. I started with a seasonal sangria, while my boyfriend opted for a local IPA, a Civil Society Fresh IPA. We shared generously stuffed spring rolls, a delicious start to our meal. For brunch, I ordered the Flax French Toast with fresh fruit, toasted almonds, and maple syrup, and my boyfriend enjoyed the Veggie Scramble, a hearty dish loaded with veggies, served with grilled bread and breakfast potatoes. The food at The Cafe was superb, and I look forward to returning on my next visit to Key West.

Midday: Back Roads and Beaches Bike Tour

Feeling satisfied, we hopped on our bikes and embarked on a self-guided Back Roads and Beaches of Key West Bike Tour, booked for just 10 USD through Viator. This scenic tour began at the USCG Ingham Coast Guard Cutter Maritime Museum and was intended to end at the Green Parrot bar. 

The tour took us through lesser-known parts of Key West, revealing its rich history intertwined with Cuban influences, its thriving economy during the 1800s, and numerous nature preserves teeming with wildlife. Along the way, we learned that most of Key West's beaches are naturally composed of tiny bits of crushed coral and stones, giving them a unique texture and appearance. Smathers Beach, however, stands out as it imports white sand from the Bahamas each year due to the lack of natural wave action to create sand.

Despite the beautiful weather—clear blue skies and warm sunshine—the strong winds posed a challenge as we pedaled against them. The wind, blowing directly against us, made the biking more strenuous than anticipated. When doing this tour, I recommend renting an e-bike for better enjoyment, as it would provide assistance against the wind and allow for a more leisurely exploration of the island's hidden gems.

After pushing through for about two hours, battling the headwinds and taking in the sights, we decided to cut our tour short. We ended our bike adventure at Smathers Beach, having covered a little less than half of the tour route.

Afternoon: Happy Hour at Mac's Place

With the wind to our backs and just a short bike ride from Smathers, we arrived at Mac's Place, an ocean-side sports bar and restaurant renowned for its inviting atmosphere and great happy hour deals from 3 PM to 6 PM. The menu boasted a variety of options with small bites and plates priced between 5 USD to 10 USD, including BBQ Chicken and Gringo tacos priced at just 5 USD each. They also offered beers, wines, wells, and seltzers for only 5 USD, making it a budget-friendly choice.

Mac's Place pleasantly surprised us with its ample vegan options, ensuring we could enjoy our time cheering for our favorite golfers and baseball teams without worry. I opted for the happy hour special, Chips & Pico, a generously sized drink made with dark rum and pineapple juice. Meanwhile, my boyfriend indulged in two BBQ chicken tacos, which though not vegan, were aromatic and surprisingly large for their price.

Seated on the patio, we had a picturesque view of the water, enjoying the ambiance as large screens played Rory McIlroy and Bryson Dechambeau competing in the US Open. As we finished our snacks and drinks, a live band began setting up, promising an evening of lively entertainment. Unfortunately, we had to depart before the band started, needing to prepare for our Sunset cruise.

Unforgettable Sunset Champagne Sail

The Cubed

I mentioned Mallory Square and the Sunset Celebration, but due to the weather, we sadly didn't attend. Nevertheless, the weather was perfect for watching the sunset. We had booked an all-inclusive Catamaran Champagne Sunset Sail through Viator, hosted by Sebago Water Sports. Boarding the sailboat named Cubed, we sailed along the Key West coast in the Gulf of Mexico.

Now, while Mallory Square would have been great, being aboard the Cubed was an incredible experience. We enjoyed 80's hits by artists like Cyndi Lauper and Whitney Houston in a comfortable setting with a limited number of people. The bottomless drink options including champagne, beer, wine, sangria, soft drinks, and water were a great bonus. The sailboat offered a unique perspective to witness a beautiful sunset up close and personal as it dipped below the horizon on the Gulf. We also had stunning views of Mallory Square, Sunset Pier, Sunset Key (home of the restaurant Latitudes known for its elegant beachfront dining with fresh seafood and Caribbean flavors), and more.

The crew of Cubed did an excellent job not only ensuring our safety and
navigating smoothly but also providing great entertainment and ensuring our glasses were never empty. This Sunset Sail was an unforgettable highlight of our trip, and both my boyfriend and I highly recommend it.

Evening Plans

After our amazing sail, we had plans to dine at Flaming Bouy Filet Co. because my boyfriend loves a good steak. Unfortunately, our sail ended at 8 PM, and we wouldn't make it to the restaurant before it closed at 9 PM. Considering another look at Duval's nightlife or perhaps visiting:

• Lazy Gecko
• 2 Cents Restaurant & Pub
• The Marker (Hotel Bar)
• Don's Place
• Galleon Tiki Bar
• Bobby's Monkey Bar
• Hank's Hair of the Dog Saloon

However, I started to feel unwell, so we decided to head back to the Grand Guest House to rest up for our last day in Key West.

Day 3: Departure and Last Adventures in Key West

Departure from The Grand Guest House

Morning arrived, signaling our farewell to our home away from home, The Grand Guest House. We made our way to the Ferry Terminal, where Paradise Porters offered a convenient service to store our bags for 12 USD per bag. With our luggage safely stored until our departure on the Key West Express in 6 hours, we were free to explore a bit more before leaving.

Lunch at Old Town Tavern & Beer Garden

For lunch, we chose the Old Town Tavern & Beer Garden on Duval Street. I selected this spot not only for its prime location but also because my boyfriend, an amateur IPA connoisseur, was intrigued by its reputation. The tavern offered a menu typical of its genre: Scotch Eggs, Pork Belly, Flatbreads, and Shepherd’s Pie, alongside vegan and vegetarian options. It boasts the largest beer assortment in Key West.

I grabbed the veggie Bahn Mi with fries, while my boyfriend enjoyed the Shepherd's Pie. During our meal, a rooster casually wandered into the restaurant, surveying the scene. Key West is known for its population of roaming roosters and chickens. Why?  A legacy from their origins in Cuba and the Caribbean Islands, Chicken & Roosters were originally
brought over for food and cockfighting. However, once cockfighting became illegal, chickens became protected. It was a surprising and memorable sight—a testament to the island's unique charm.

Visit to Key West Butterfly and Nature Conservatory

After our meal at Old Town Tavern, we made our way to the Key West Butterfly and Nature Conservatory. Initially, my boyfriend was a bit hesitant when I suggested it, envisioning a typical outdoor butterfly garden under the hot Key West sun—landscaped gardens with a few butterflies fluttering about. To his surprise, the conservatory offered much more.

Imagine stepping into a rainforest-like habitat, teeming with 50 to 60 butterfly species from around the world. The air was warm and fragrant, filled with the gentle fluttering of vibrant butterflies. Exotic birds, cascading waterfalls, and tropical blooms enhance the enchanting atmosphere. Butterflies gracefully danced in flight around us, some even landing delicately if you were calm and patient.

Despite a cruise ship in port that day causing a slight delay in entry, the increased number of visitors didn't detract from our experience. It was truly a magical sight—one that I wholeheartedly recommend to anyone, including families looking for a memorable and educational outing.

Exploring Duval Street 

Today, our agenda was light—just a leisurely exploration of more of Duval Street. Duval isn't just bars and clubs; it's also lined with clothing stores, souvenir shops, coffee shops, and historical sites along its seemingly endless stretch. We strolled down Duval, popping into a few shops until we found ourselves back at The Cafe. It's just that good! This time, I indulged in some Carrot Cake (one of my favorite types of cake) and a Sichuan veggie noodle stir fry to enjoy aboard the Key West Express.

Happy Hour at the Boat House Bar & Grill

From The Cafe, we took an Uber over to Grinnell Street near the Ferry Terminal, where we docked for a while until it was time to catch our ferry at 5 PM. Currently, we're at the Boat House Bar & Grill, a waterfront restaurant on the docks. This place has been nominated for Best Happy Hour and Best Restaurant Service & Staff this year, and it was voted Best Happy Hour in both 2022 and 2023. The Boat House Bar certainly lives up to its reputation with a fantastic happy hour offering half-priced drinks and small plates that are hard to beat.

Earlier in the day, my boyfriend had mentioned he wanted to try Conch Fritters if he came across them. Lo and behold, The Boat House had them on their menu, and they were half off for happy hour. After years of his brother and sister-in-law encouraging him to try conch, he finally did. He found them quite good but noted their chewy texture, which was unexpected.

Departing Key West: Reflections on the Return Journey

At 5 PM, it was time to head to the terminal to collect our suitcases and board the Key West Express. The ferry was scheduled to leave at 6 PM, but we took off 30 minutes earlier because everyone was already on board. Remember to arrive at least an hour early to secure good seats; unfortunately, most people arrived at 4:30 PM and claimed them all. However, all was well, and we were back at the bar again. Only water for me, as I'd had my fill of alcoholic beverages for the weekend.

Heading back to Fort Myers was not the same experience as coming to Key West. The waters were rough, and you could feel it. Moving around the ferry or going to the restroom was quite the feat as people swayed back and forth. With the rough seas, many were seasick, and barf bags were being passed out left and right. If you're prone to seasickness, bringing medication like Dramamine is highly recommended to make the commute more comfortable.

Despite the challenging seas, I couldn't help but feel happy about my visit to Key West. I learned a lot of history and had a wonderful time making memories with my boyfriend. This trip is one I'll remember for a while. I can't wait to return and explore more of what Key West has to offer, perhaps even do a Jimmy Buffett tour next time.

Where would you like to Land with Dan?

Whether you're seeking vibrant nightlife, tranquil beaches, or rich history, Key West has something for everyone. I hope my travel adventures have inspired yours. Let me know where to Land with Dan next and where you plan to explore next. Until next time, safe travels, and may your journey with Land with Dan lead you to your own unforgettable experiences in Key West and beyond!