Slipping out of Matanzas Harbor at no-wake speed, it felt odd to be on the water looking down at a familiar landmark, Bowditch Point. Beachcombers looked up, startled at the size of the Key West Express, the high-speed ferry that zips between Fort Myers Beach and Key West daily. We weren’t at a high speed, yet, but with blue skies and sunshine, we expected smooth sailing.

Bowditch Point from the Key West Express
Bowditch Point from the Key West Express

Thankfully, we were right. One of the biggest variables in ferryboat travel – that will make or break your experience – is how rough the seas are. The Gulf of Mexico is shallow and frequently smooth, making this connector by water a compelling way to get to bustling Key West.

On a map of Florida, it’s obvious that it’s far shorter between Fort Myers and Key West by water than by highway. So it made sense while we were in Southwest Florida to try a trip on the Key West Express, our goal an overnighter with on-foot exploration of one of Florida’s oldest and best known outposts. We’d considered carrying our bicycles along, but for an overnight stay, it wasn’t worth the extra logistics and cost. One thing about Key West being so small and so visitor-focused: we could always rent bikes or scooters upon arrival if we needed to.

Savoring the Seas

I hadn’t been on a passenger ferry in years, but ferry culture is familiar. Some folks stay close to the bar, nursing their drinks. Others go topside and let the wind blow their hair around as they hang out on the sun deck, savoring the views.

In the main cabin, booths with comfortable chairs beckoned, so we claimed one with the friends we were traveling with. That gave us a place to sit and write. We aren’t television watchers, but with big screen TVs in the corners catching our attention, it wasn’t hard to sit back and enjoy a screening of one of the Pirates of the Caribbean movies that I hadn’t see before.

Mainly, my eyes were on the coastline, which took a couple of hours to vanish entirely. Eventually I went above deck, entranced by the strange stillness of the sea. Every ferryboat ride I’d taken in the past had rollicking waves. This was the first truly glassy sea I’d ever sped across, almost surreal. And pure luck.

Key West Express
Seas so calm that sky and water merged at the horizon line

Key West Ahead

After nearly three hours on the water, the seascape changed. Islands – and massive floating mats of seagrass – began to appear in the greenish seas. We knew one of those islands out there was Key West, but which?

We could see a cruise ship at Key West as we came into port

It took getting much closer to be clear: Mallory Square up ahead, and then the historic Key West Seaport, where we would disembark. About that time, the announcements included information on how you could purchase discounted tickets for the Key West Old Town Trolley as well as arrange scooter rentals.

Savoring Island Time

We were in no hurry once we arrived in Key West, but we were hungry. The ferryboat has a small snack bar, but we disembarked at a perfect time to grab a decent lunch. A short walk up Grinnell Street led us to Azur Restaurant, a cozy spot to share a unique Mediterranean brunch of braised beef rib hash and eggs. As we waited outside for the Old Town Trolley to come around on its route, a curious rooster and his buddies decided they wanted to mooch off us. They’d be the first of many we’d see throughout the city over the next day.

Key West rooster
A young rooster followed us around outside the restaurant

On the trolley, our guide made a point of pointing out some of the more unique architecture in Key West, including some of the older homes. This was a part of town well away from what we’d walked in the past, so it was nice to learn its backstory. Reaching the beach at the end of White Street, I was surprised to see the grand banyan tree gone from the West Martello Gardens, a bowl of botanical beauty cradled in a historic fort. That meant I’d need to revisit to see what other changes hurricane season had brought. Although it was obvious some of the tree canopy of the city had vanished, there were no other signs that, nine months before, Hurricane Irma had slammed into the Florida Keys. Key West took only a glancing blow and healed quickly.

Key West Trolley passing the West Martello Tower

After depositing us at the Casa Marina Resort, the trolley continued on. We walked into Key West’s past. This grand hotel opened in 1920 as one of Henry Flagler’s destination hotels, although he never set foot in it. Eight years before, when “Flagler’s Folly,” the Overseas Railroad, was completed, he envisioned a destination to lure wealthy northerners. This Mediterranean fantasy was the carrot at the end of the line, reflecting the tastes that those who basked in the Gilded Age would expect. Rich architectural details, tropical gardens, and a beach.

Casa Marina key west
Poolside at the Casa Marina

When the Labor Day Hurricane of 1935 destroyed the Overseas Railroad, and hundreds of lives, it disrupted travel to Key West for a very long time. Like many of Florida’s historic hotels, the Casa Marina languished, empty, for decades, a ghost along the Atlantic. It wasn’t until 1978 that a complete restoration was undertaken, with additional wings added to expand its guest capacity. Now part of the Waldorf Astoria brand under Hilton, it’s on the National Register of Historic Places.

We relaxed and savored the sound of the waves until it was time to ramble back into town and hop on Fury Water Adventures for one of their signature ecotours that was also a sunset cruise. After boarding, we found out that we’d be taking a different route than usually. The Atlantic was getting rough and the captain felt we wouldn’t see much over the reefs due to sediments in the water. So we headed out into the Gulf instead.

Some of the islands we recognized from our ferryboat trip, but some of the stops over the rock reefs were new and interesting. Like the glass-bottomed boat at John Pennekamp Coral Reef State Park, this one also offered inside viewing of the undersea world. But like most folks on the cruise, we spent a lot of it out on the deck, savoring the views. Especially the sunset.

An iconic stop along Duval Street after dark

Idling back into port, we saw the crowds at Mallory Square watching performers, and here we were watching the same shows from the water, a snippet at a time. Our dinner, as it turned out, was to be a performance too. Sitting at a bar at dinnertime isn’t a strange thing in Key West, but sitting at a bar while your chef uses a hibachi and a blowtorch to cook your dinner in front of you is another thing entirely.

Serving up a series of small plates at the Raw Bar, Henry Christian at Smokin’ Tuna simply asked what what we liked, and crafted each delightful dish – some oysters, some beef, some sashimi – like edible works of art. Add in the banter you’d expect when watching an artist at work, and it was an evening to remember.

The Wild Side

While it was hard to pry ourselves out of bed early on island time, John had a paddling tour booked with Key West Eco Tours and they were swinging by the hotel to pick him up. He’d never paddled in the Keys, and so was grateful for the opportunity. While he was being surprised by iguanas in the mangroves, I was rambling on foot to visit gardens.

First stop was Bahama Village, where I was meeting friends for breakfast. Despite my many visits to Key West, I’d never ventured into this corner of town; it took a local to point me in this direction. What a gem! The tropical canopy above Blue Heaven – a bustling art-meets-gardens eatery that sprawls open-air through an urban forest – had me delighted. Add in live music and Blue Heaven Benedicts with fresh Key West shrimp, and John didn’t know what he was missing.

Blue Heaven
Blue Heaven had interpretive signs for its tropical plantings. Bliss!

Walking up Whitehead Street afterwards, I was relieved to see the tropical canopy unsullied. It’s the garden atmosphere that I’ve always loved about Key West, and I’d feared the worst from Irma. It was good to see the kapok tree still standing in front of City Hall, and, up the street, one of the largest banyans in Key West looking none the worse for wear. My friend Carol laughed when I pointed it out. “Would you believe someone climbed into it, dropped down inside, couldn’t get out, and had to call the fire department for a rescue?”

At the Audubon House and Tropical Gardens, a personal favorite on the island, I focused on photographing the plant life. As lush and vibrant as it was, it was a good sign. Notable as the home of Captain John Geiger for whom the Geiger tree was named, the house is both a museum to his family’s past and a gallery honoring John James Audubon, whose painting of the white-crowned pigeon of the Florida Keys features a flowering branch of a Geiger tree. In all, Audubon painted 22 of the birds of the Keys in 1831 and 1832.

My next focal point was the West Martello Gardens, or more properly, the gardens within the historic West Martello Tower, built in the 1860s by the Army Corps of Engineers. This free (donations appreciated) attraction is a must-see for anyone who appreciates botanical beauty. Spilling across several acres inside the historic fortress, the gardens were established in 1955 by the Key West Garden Club and include thematic rooms and plantings. Since the interior of the fortress is surprisingly hilly, ocean views are framed by tropical forest.

This is one of those quiet spots where you can bring a notebook or a sketchpad, find a nook, and disappear for hours into your own creativity. While the impressive banyan that once shaded much of the garden was indeed a victim of Hurricane Irma, the lack of its canopy opened up different views and exposed more of the crumbling fortress walls.

As I left the gardens, John texted me. He’d met Carol for lunch at Salute!, a beachfront restaurant just around the corner. Checked out of our room, we were free to roam for a few more hours until it was time to board the ferry back to Fort Myers. We just had that suitcase to deal with, which Carol was happy to hold for us. But she had a surprise for us, first.

Most Presidential

Over lunch, John had mentioned an old Scouting friend of his to Carol, a fellow who was involved with the operation of the Conch Tour Train for many years: Bob Wolz. Carol pulled out her phone, pressed a number, and made arrangements. She knew exactly where to find Bob, but she wanted to surprise him.

Harry S. Truman Little White House
Harry S. Truman Little White House

Being a local, she pulled into a “no parking” zone at the Harry S. Truman Little White House Museum to drop us off, and asked the guard if he could scare up Bob. It took a few minutes for the director to peel away from the group he was talking to, but when he turned around and saw John, the look was priceless. Two old friends had a lot of catching up to do.

Bob Wolz Truman Little White House John Keatley
Bob and John

Of course, Bob insisted we take the tour, which we did. While the 33rd president served before I was born, I remember learning a lot about him while I was a kid and he was still around. Truman’s presidency was an accident of fate, as he was vice-president when Franklin D. Roosevelt died in office. While he had to make tough decisions – using nuclear weapons on Japan, airlifting supplies to Berlin, engaging in the Korean War – he came from humble Missouri roots as a farmer. That humility is reflected in the simplicity of this getaway established for him in an older home at the Naval Air Station in Key West. This was not just a place for Truman to escape the stress of Washington, but it was a working winter White House where where Harry Truman met with admirals, generals, and world leaders on comfy couches, a poker table hidden under a more formal tabletop in one corner. Renovated to how it looked and felt in 1949, this presidential home is both warm and welcoming while unassumingly average and all-American, a real contrast to the other presidential homes we’re visited: George Washington, Thomas Jefferson, and Theodore Roosevelt. If furnishings and art set a tone for his international visitors, it was Harry S. Truman as everyman.

Key West Seaport
Roaming the old Key West Seaport

Our afternoon ticked away quickly, so after another visit with Bob after the tour, it was time to regroup with our friends over an early dinner at the Key West Seaport. I was a kid the first time I walked these docks, when the turtle kraals were just that – corrals with sea turtles about to be slaughtered for meat, and a cannery to process them – before the Endangered Species Act existed. Thankfully, this business went out of business once sea turtles were protected by federal law (and almost extinct in the Keys), and the old docks now house the Key West Turtle Museum to tell the story.

After poking around some of the shops along the waterfront, we found Carol and the others piling on the seafood at the Half Shell Raw Bar, and we joined in, picking up our suitcase from her so we could head back to the Key West Express.

A Sunset Return

Our return trip was much rougher, more of what I was accustomed to on a ferryboat ride. Perhaps it was the time of day – being early evening – or a change in the weather. I lurched around the cabin, grabbing for a means of support, grateful that I don’t get seasick. But I couldn’t miss the above-deck show of sunset.

Key West Express sunset
One final Key West sunset on the Key West Express

Afterwards, I joined John and the others in conversation in the main cabin, which was more densely packed than on the outbound trip. With our friends scattered to the four winds, we ended up sharing a big table with strangers and learning their stories as we sped into the night.

Planning Ahead

Round-trip fares start at $125 for a nonrefundable weekday ticket bought at least eight days in advance. Parking costs $13 a day if you depart from the dock on San Carlos Island at Fort Myers Beach; it’s free if you leave from Marco Island. While your departure day is set – and you’d better show up an hour before sailing for check-in – you can return at your leisure. So if you extend your stay in Key West, no problem, and no need to let them know. Just be sure to show up in plenty of time for a seat on the return trip!

Dining area inside the Key West Express
Dining area inside the Key West Express

We pack light and we only stayed overnight, so we put everything in one small carry-on. Each passenger is permitted two before there are additional luggage charges. If we hadn’t known we had a ride to our hotel, we would have piled what we needed in a backpack for simplicity of getting around town.

Key West pink taxi
If you don’t want to walk everywhere, hail one of those pink taxis

One of the biggest challenges in Key West is parking. It was blissful being without a car. Having a pass for the Key West Trolley meant we could hop on and off around town while learning from the guide. We also did a lot of exploration on foot. While we only had time for an overnight visit, taking the ferry makes it economical to spend a few days to a week. And for those considering riding the Florida Keys Overseas Heritage Trail north from Key West, here’s a unique way to do it! Get to Fort Myers, grab a one-way fare for you and your bike, and start heading north at your own pace after you arrive on land.

Learn more about the Key West Express