Our boomer travel readers love visiting Florida. And who can blame them? From spending a weekend on Amelia Island to a panhandle road trip, there’s so much to do!
If your Florida travel plans include “spend a day in Key West,” I might as well warn you—that’s not enough time.
With a vibrant waterfront playing host to a killer sunset, colorful historic homes to explore along tree-shaded side streets, and an energetic vibe emanating from local restaurants and bars, you’ll be crying in your margarita because you didn’t allot more time to explore the southernmost city in the continental United States.
How to spend one day in Key West
When the folks at The Florida Keys and Key West invited me on a Florida Keys road trip, I found myself in the same dilemma. How do I make the most of one day in Key West?
Armed with a ticket for the hop-on hop-off for Old Town Trolley, it can be done. So let’s get started with my tips for visiting Key West in a day.
Boomer Travel Tip
Save time. Purchase Old Town Trolley tickets online before leaving home.
Start With Breakfast at Blue Heaven
You’ll probably encounter a line while waiting to enjoy breakfast in the tree-shaded courtyard at Blue Heaven on Thomas Street, one of the best places to eat in Key West. But that’s okay because the local cats and roosters will keep you entertained until it’s your turn to order Lobster Benedict with Key Lime Pie for dessert.
Dessert for breakfast? Of course, we’re spending the day in Key West!
Located in historic Bahama Village, the building at Blue Heaven, which is listed as a National Historic Landmark, has seen almost as many lives as the cats that roam the grounds. From dance hall to bordello to playhouse to pool hall and ice cream parlor, they’ve all played a part in Blue Heaven’s colorful history.
Not to mention the gambling, cockfights and Friday night boxing matches in the courtyard. It’s said that Ernest Hemingway refereed those Friday night fights.
But you’re here for breakfast. So stroll across slate stones requisitioned from the tops of pool tables, to a table beneath an almond tree. Then order up a delicious breakfast.
Did you sleep in? That’s okay because Blue Heaven serves breakfast until 2 p.m.
Blue Heaven also serves lunch and dinner with live entertainment providing the ambiance from 11 a.m. to 1 p.m. and 7 p.m. to 9 p.m.
Boomer Travel Tip
Want to stay longer than one day in Key West? Book your accommodations here.
Visit Literary History at Ernest Hemingway Home & Museum
It’s a four-minute walk through historic Old Key West from Blue Heaven on Petroia Street to the Ernest Hemingway Home & Museum (official website) on Whitehead Street. And since this is one of the most popular things to do in Key West, it’s best to arrive early, so don’t dawdle too long over breakfast.
At the main entrance to the Hemingway Home, purchase a cash-only tour ticket for a 30-minute guided tour of the house that hosted Hemingway’s most prolific writing years. The tour includes a knowledgeable guide.
On my visit, Stan guides a group of 25 to 30 people (too many in my opinion), through the home filled with original furniture and personal touches before showing us the pool area, Hemginway’s studio and the lovely gardens.
Along the way, Stan regales us with stories and tidbits from Hemingway’s life. And, of course, we are introduced to some of the 40 to 50 six-toed cats living at the home, some of whom are the original descendants of Snow White, Hemingway’s first polydactyl (six-toed) cat.
Be Kissed by a Butterfly at The Key West Butterfly and Nature Conservatory
Hope you packed an energy bar in your purse or backpack because we’re skipping lunch. And who’s hungry after the Blue Heaven breakfast anyway?
We’re waiting by the Old Town Trolley sign for the hop-on hop-off trolley that will take us to the Key West Butterfly and Nature Conservatory (official website). Sure, we could walk, but riding on the trolley gives a good overview of the town.
Visiting the Key West Butterfly and Nature Conservatory makes a quiet escape from busy Key West. Although the glass-enclosed habitat is on the small side, it’s packed with tropical pants, a gurgling stream and hundreds of butterflies.
During my day trip to Key West, butterflies float around me, land on my shirt—eliciting a giggle or two—and twitter around my head. All the while, two flamingos squawk and prance in a small pond. The challenging task of taking butterfly photographs at just the right moment is part of the fun.
The conservatory exits into a gift shop filled with butterfly items if you’re looking for gifts or souvenirs.
Party at the Sunset Celebration at Mallory Square
After that quiet break with the butterflies, it’s time to board the Old Town Trolley for the Sunset Celebration at Mallory Square. We have a party to attend.
Each day, two hours before sunset, tourists and locals gather to watch street performers, browse arts and crafts booths, and indulge in tasty treats from the food carts before oohing and ahhing as a fiery sun dips behind Sunset Key. You’ll marvel at the crazy stunts, find a few souvenirs to bring home and wonder if there ever has been a more beautiful sunset.
Going Cuban at El Meson de Pepe
Has this Key West day trip made you hungry? It’s a three-minute walk to the authentically prepared Cuban food at El Meson de Pepe. For over 30 years, Chef Pepe Diaz and his family have served delicious dishes in the Cuban-Conch tradition at this historic Key West restaurant.
I recommend the Ropa Vieja, “traditional Cuban shredded beef stewed with fresh tomatoes, green peppers, onions and red wine.” And no day in Key West should ever end without a slice of Key Lime Pie.
Boomer Travel Tip
Traveling to the Florida Keys? Check out our Florida Keys road trip articles.
More things to do in Key West
It’s easy to build a Key West itinerary that fits your interests. Here are a few more ideas. Of course adding another day or two to your visit is a good way to see everything that Key West has to offer.
Fort Zachary Taylor State Park (official website) has plenty of firsts to explore. Located on the southern edge of Key West, Fort Zachary Taylor houses the largest cache of Civil War armament in the world. It’s also the southernmost state park in the continental U.S.
Don’t miss the beautiful beach at the park’s southern end. It’s very popular for swimming, snorkeling, paddling and fishing. Bring a picnic lunch with you!
Are you fan of found treasure? A visit to the Mel Fisher Maritime Museum (official website) is a must. Discover the maritime history of Florida and the Caribbean through artifacts including those from 1622 shipwrecks. Although small, the fully accredited museum is well worth your time.
If you have longer than one day to spend in Key West, I recommend a real adventure at an off-the-beaten-path national park! Read our tips for a Dry Tortugas National Park day trip.
The perfect do-it-yourself Key West cruise excursion
For those arriving by ship, this Key West itinerary, minus breakfast and dinner suggestions, makes a fun-filled do-it-yourself Key West shore excursion. So save yourself a little money.
Explore Key West on your own. This is one port where you don’t need to purchase the ship’s cruise excursion.
Disclosure: The Florida Keys and Key West provided this travel experience. However, as always, the opinions are strictly my own.