Wanderbrush

Our second day of our Florida trip and first day in Key West started out bright and early. My parents had been to Key West a couple of times in the past, and if there is one thing my dad loves more than traveling, it is watching livestreams on YouTube. I made the short walk over to the Southernmost Point Buoy to get our photo op and wave to my parents virtually.

This spot fills up quickly. Even at 7:30am a small line had formed for everyone to get their classic picture in front of the landmark. At this point, you are the furthest south you can be in the continental United States – and also 90 miles from Cuba! This makes it quite a popular spot in Key West. It was convenient having this so close to our hotel, and this allowed us to experience it before the swell of the crowd.

This morning was also when we had our first spotting of the chickens that roam the island. These chickens have become a tourist attractions of sorts for the island and will just freely roam around all areas. It never got old seeing them casually strolling by throughout our adventures on the island.

By now, the caffeine cravings had hit. Duval Street—the heart of Key West—is packed with art galleries, cafés, and Cuban-influenced coffee stops, but we decided to level up our exploration: we rented scooters! A&M rentals, right next door, offered a full-day ride for about $80. There was a bit of a learning curve, but once I got the hang of it, zipping around the island felt like the purest Key West experience: sun, salt air, and the wind in your hair.

I pulled up and parked my scooter right next to Keys Coffee Co., a local favorite tucked off Duval Street. The iconic Cuban Coffee Queen—renowned for its iconic café con leche—is just a few blocks away. However, it was on our Day  3 agenda, and today called for something cool, so we opted to try Keys. Instead of their rich espresso drinks, I opted for an iced matcha latte, the perfect antidote to Key West’s tropical heat. The service was quick, the matcha pleasantly smooth without any chalky aftertaste. It was the perfect treat to kick start the day.

After I had got my morning drink, I set my sites on my favorite vacation activity, souvenir shopping. There were a handful of shops close to our hotel, so I scoured through them. I delighted in browsing shelf after shelf: picking out a commemorative magnet here, a vibrant sticker there—small treasures to remember the trip. Meanwhile, I couldn’t help but admire the pastel-hued homes and rainbow-colored storefronts. Key West’s candy-colored architecture wasn’t just a backdrop—it was part of the souvenir experience itself. The mix of AC, shopping, and whimsical colors felt like hitting the perfect trifecta: a welcome escape from the heat, a souvenir hunt with purpose, and a wander through an island that feels as much art gallery as town.

Around this time, we were getting hungry. As we strolled, we spotted a little restaurant just steps away from our hotel, The Lobster Shack Key West. Ever since our Maine trip last year, we have been craving lobster rolls ever since the start of summer. Mason got the Diablo roll that had a touch of sriracha mayo while I got the Key West roll, a classic buttered lobster roll topped with a touch of fresh key lime juice. This tiny but mighty stop packed a punch. Both were just what we needed to refuel for the day.

After recharging in the air conditioned comfort of our hotel and enjoying a complimentary drink at the bar, we hopped back on our scooters to visit one of Key West’s crown jewels—Ernest Hemingway’s House.

Just a short ride away, this iconic Spanish Colonial-style mansion dates back to the 1800s. With thick limestone walls built to withstand hurricanes and just steps away from the Key West Lighthouse, the house’s beauty instantly captivated you. We purchased our tickets at the gate and chose a self‑guided tour, intrigued by the promise of exploring Hemingway’s personal world at our own pace. Stepping inside, we wandered among Hemingway’s antique furniture, the sunlit writing studio above the carriage house—where he penned some of his most famous work—and the surprisingly luxurious in-ground pool.

But the real stars of the afternoon? The resident felines. We enjoyed their company as we wove through the property and spotted as many as we could taking an afternoon nap. Some lounged on the porch, others sprawled inside the house—even on Hemingway’s bed! It was an unique twist to the history he left behind at this estate.

After bidding farewell to Hemingway’s cats, we hopped across the street to the Key West Lighthouse & Keeper’s Quarters, a much quieter oasis than the bustling museum across the way.

Arriving just an hour before closing, we had the lighthouse pretty much to ourselves. We climbed the 88 iron steps to the top of the iconic white tower—built in 1848 after a hurricane destroyed the original and later raised to help its beam reach further out to sea. At the summit, we were rewarded with sweeping, unobstructed views of Key West’s pastel rooftops, swaying palms, and glittering ocean beyond—an unforgettable panoramic moment.

Downstairs, the museum told a rich tale of the keepers who resided here in decades past. We wandered through historic rooms dedicated to 19th-century keepers—many of them women, including Barbara Mabrity, who held the post for over 32 years, photos and artifacts that spoke of shipwrecks, storms, and the quiet heroism that lit the way for mariners. Lighthouses are one of my favorite landmark’s to visit; however, this one was definitely a magnificent one that further colored the history of Key West.

After we finished up with these two historic and iconic sites, our friends M&K were just about to arrive on the island. With M & K arriving just in time for dinner, we headed to the highly‑lauded Blue Heaven, famed for its laid-back Bahama Village vibe and irresistible seafood fare. Fortunately, we snagged a table right away. No sooner had we sat than I spotted the legendary Key Lime Martini—apparently, it’s so beloved, some say it takes three days to prepare! My waitress confirmed the hype, and I couldn’t resist. We started with a shared appetizer of golden crispy calamari, just enough to tease our taste buds. For my entrée, I chose the Yellowtail Snapper, served over a bed of silky angel‑hair pasta drenched in a creamy sauce. As you can tell – I am still thinking about this meal. Mason got the Black Grouper special and we all savored our meals, getting increasingly more excited about our Day 3 adventure.

We got the Key Lime Pie to share to finish off our meal. Blue Heaven’s pie is topped with a mound of meringue, and we all enjoyed our bites before heading off.

Before we retreated to our hotels, we made one last stop. We took a group trip to Publix to grab groceries and ice for our coolers for our next day adventure – camping at Dry Tortugas.