Soaring Tortoise

A hot afternoon on bikes led us from Casa Marina's pool bar to an ocean-view margarita, Japanese small plates, and a familiar cocktail favorite in Old Town Key West.

One advantage of staying at Fitch Lodge, a historic inn near the Key West harbor, was how easily we could wander around the seaport and the northern end of Duval Street. The downside was that we had spent most of this visit doing exactly that. By Saturday, it was time to give the southern end of the island some attention.

Unfortunately, Saturday was brutally hot. Rather than spend the afternoon walking in the sun, we climbed onto our bikes and put together a loose plan: work our way from the south side of Key West back toward Old Town, stopping wherever a cold drink or something good to eat sounded appealing.

Casa Marina: A Beer and a Look Around

Our first stop was Casa Marina, one of the few full-scale beachfront resorts on Key West. We had considered using hotel reward points to stay here, so stopping for a bite gave us a chance to see the property without committing to a room.

The setting is noticeably different from the small inns and old wooden houses that make up so much of Key West. Tall palms, a broad stucco facade, and reflecting pools give the entrance a more formal feel. The resort also has an interesting place in the island's history: conceived as a luxury destination for travelers arriving on Henry Flagler's Overseas Railroad, Casa Marina opened on New Year's Eve in 1920. The hotel's history page tells more of that story.

We headed to the pool bar and shared a plate of delicious conch fritters over a cold beer. Our bartender was talkative and entertaining, and we found ourselves laughing through much of the stop. It was a relaxed start to an afternoon that had no real schedule. We didn't settle the question of whether we'd want to spend our hotel points here, but we enjoyed having a look around.

Open-air pool bar at Casa Marina in Key West, with palm trees, lounge seating, and the ocean in the background — Casa Marina’s pool bar gave us a shady place to cool off with a beer and conch fritters.

Sky Bar: Margaritas Above the Southernmost Point Crowds

From Casa Marina, we meandered toward the southern end of Duval Street and Sky Bar at the Mansion, perched beside the historic Southernmost House. The colorful old mansion and its seaside setting are a sharp contrast to Casa Marina's grand resort architecture.

We climbed the metal stairs to the elevated bar and ordered a cold margarita. From our seats, we had two very different views of Key West. In one direction was the steady line of tourists waiting to pose beside the Southernmost Point marker. In the other were the mansion, palms, and open Atlantic Ocean.

View from Sky Bar across a turquoise swimming pool, palm trees, and the Atlantic Ocean beside the colorful Southernmost House — An ocean view from Sky Bar, above the grounds of the Southernmost House

It's an entertaining vantage point, particularly if you've already taken your own obligatory photo at the buoy. We were content to watch the activity from above while enjoying our drinks.

Atlas Izakaya: Something Different for Dinner

By this point we were ready for more substantial food. We had noticed Atlas Izakaya, a relatively new addition to the Key West dining scene that had been appearing on plenty of restaurant recommendation lists, and decided to give it a try.

An izakaya is a Japanese-style gathering place built around drinks and small dishes to share. That sounded about right for an afternoon when we'd already been grazing our way across town. Arriving before the dinner rush worked in our favor, and we were able to get a table without much fuss.

We ordered several small plates and a glass of white wine. The food was thoughtfully prepared and nicely presented, with flavors that offered a welcome break from the familiar rotation of seafood sandwiches, conch fritters, and other Key West staples. Nothing we tried completely won us over, but it was a pleasant meal and a useful reminder that the island's dining options extend well beyond its traditional tourist fare.

Glossy grilled vegetable pieces in a speckled ceramic bowl, garnished with toasted nuts, sesame seeds, and small greens — One of the Japanese small plates we tried at Atlas Izakaya

A Miss at The Saint Hotel

We had one more potential stop in mind: Tempt, the dimly lit restaurant and bar inside The Saint Hotel. On a previous Key West visit, the bar had been a favorite, largely because of an excellent bartender who made the experience memorable. We were hoping for a repeat.

It didn't happen. We took seats and waited while the bartender devoted her attention to a small group nearby. After about 15 minutes without so much as an acknowledgment, we decided there was little reason to linger.

Every bar can have an off day, and this was only one visit. Still, it was a disappointment, especially given how much we'd enjoyed the place before. We got back up and headed for somewhere we knew would treat us well.

The Roost: Ending on a Better Note

That somewhere was The Roost, a compact cocktail bar and bottle shop on Fleming Street, not far from Duval. Its shelves of spirits, dark woodwork, and glowing sign felt familiar as we settled in for a nightcap.

Wooden shelves stocked with liquor bottles and hanging glasses behind the bar at The Roost, with a green neon sign above — Behind the bar at The Roost, our reliable Old Town cocktail stop

The Roost has become one of our favorite places for a well-made cocktail in Key West, and this visit reinforced why. After the indifference at our previous stop, its attentive service was especially welcome. We were happy to sit for a while, enjoy a drink, and let the afternoon wind down.

Pale yellow cocktail topped with foam and a dried citrus wheel, resting on a dark coaster on the bar at The Roost — A final cocktail at The Roost

Travel Tips for a Key West Bar Crawl

Start with a loose route. The south end of the island, Duval Street, and the Old Town side streets each have a different character. Leaving room for an unplanned stop is part of the fun.
Take the heat seriously. On a hot afternoon, even a short bicycle ride can feel longer than expected. Bring water and build in time to cool off indoors or in the shade.
Plan for the stairs at Sky Bar. We reached the elevated seating by a metal staircase. If stairs are an issue, check with the venue about other seating options.
Keep cycling safe. Lock your bikes at each stop, use lights if you'll be out after dark, and don't ride impaired. Walking or arranging a ride home is the better choice if you've had too much to drink. The Florida Department of Transportation has bicycle safety guidance.
Check before heading out. Menus, opening hours, and access policies can change, especially at hotel bars. The venue links above are the best starting point for current details.

A Good Way to Explore Beyond Duval Street

Our half-day crawl was a mix of old Key West character, resort polish, a little culinary variety, and one disappointing stop. We got to explore a part of the island we'd largely neglected during this stay, and we learned a bit more about where we'd like to return.

The best stop wasn't necessarily the fanciest one. After an afternoon of trying different places, ending at The Roost with a good drink and good service was exactly what we wanted.