A Bike Tour of the Florida Keys
- nocellajoe
- 1 day ago
- 7 min read
718 Outdoors is a 1-person operation that has remained small, local and independent by design since 2008. If this resonates with you, your support is welcome and greatly appreciated! If not, that's cool too.
A New Job (in addition to my existing job!)
Finally ready to make this big announcement…I got a new/another job as a Tour Manager for Wilderness Voyageurs.
Since the close of our retail space at the end of 2024, I’ve been looking to supplement my bike touring gig with something related and meaningful. I will be remotely managing multiple departures of the following tours:
The 6 best things about this opportunity are:
1. I am able to continue to develop and lead my full 718 Outdoors Tours Schedule.
2. I will pick up more skills in becoming a better guide.
3. After leaving architecture, I finally found a job that I am 100% qualified for!
4. Wilderness Voyageurs is a National Leader when it comes to bike tours. Since 1964!
5. I can do it remotely
6. I get to work in the same organization as @kingsburyscyclery
In 2025, when not on a 718 Tour, I had a lot of downtime. I'm very excited to fill in the blanks!
The Florida Keys Bike Tour:
The Florida Keys Tour is a new tour in the WV lineup, so this was it's first go. As a newly minted Tour Manager, it is part of my training to head off and tag along on the tours I will be managing. Pretty much the best on-boarding of a job I've ever had!
I left NYC, bound for Miami on the night before a major snow storm hit.
"Mama, I'm freezin' (mama, I'm freezin'), I wanna go to the sun (to the sun)
These icy winter breezes (winter breezes) are chillin' all my fun (all my fun)
I'm headin' for Key-ey-ey West, the key to happiness"
-Village People, 1978 (please watch the video..the song is a deep cut classic!)
Day 0: Saturday, January 24, 2026
The aforementioned travel day. After my arrival, I stayed at a hotel in Miami that was basically attached to the airport (although a 20 minute drive away). This was, coincidentally, my birthday, and I was reminded of when I spent my 40th birthday in an airport as an architect.
I have never been on a bike tour that I wasn't leading, and this was the job of Tour Guides Jeremy and Tom. I was able to meet with them the night before the tour started, and update the route a little but as they had been out scouting this new route that afternoon. They also prepared me as to what to expect.
The Tour Manager role that I stepped into basically supports the Tour Guides, getting all the details (accommodations, routes, meals, excursion, etc.) squared away months before the big ride, and being an on-call resource while the Tour is out.
Day 1: Sunday, January 25, 2026
To get one big thing out of the way, Wilderness Voyageurs Bike Tours are very different than the Tours I create and lead here at 718 Outdoors. WV creates all-inclusive adventures, where high-quality meals, accommodations and support are provided. Sometimes called "inn-to-inn" or "credit card touring", this method of touring takes the pressure off of the riders so that they can enjoy the experience without worrying about crazy campsites, wet tents, climbing big elevations or wielding a fully loaded bike. It takes all kinds, right? For me, it's been eye-opening to lean more about the touring industry, as 718 Outdoors certainly occupies one end of the spectrum (the "un/self-supported" end).
OK, so jumping back into Day 1. This was an introductory ride of sorts, heading out to the Cape Florida Lighthouse on Key Biscayne. After a trailside lunch provided by our guides, we were shuttled a few miles down the road to avoid some pretty rough stretches of highway. We were then unleashed to ride the final 13 miles to the Amara Kay Resort in/on Islamorada.
We were able to unwind with a great group dinner at the Resort, while (unfortunately) back home, NYC was getting battered by a huge snow storm and subsequent cold front.
Day 2: Monday, January 26, 2026
The prep work that the guides do every day really blew me away, as they really take care of everything a guest might need (just like me on 718 Tours, right?). I got thrown right into the mix, fixing a flat tire during the morning set-up period. We were then off for only 3 miles, stopping for breakfast at Robbie's for breakfast. This place is a local institution; an outdoor/covered eating area right on the water. After breakfast, we were able to feed the tarpons.
Day 2 was by far the hottest day we had on the road, topping out at 87 degrees while riding westward. We rode off from breakfast, getting treated to a snack stop about 14 miles into the ride. The last 18 or so miles brought us through Marathon and onto the Old Seven Mile Bridge to visit Pigeon Key Wildlife Refuge.
After another incredible trailside lunch, we were then shuttled to the western extent of the Florida Keys, Key West. We arrived at the Blue Flamingo Resort mid-afternoon, and went out to dinner in Old Town Key West at Nine One Five on Duval Street.
Day 3: Tuesday, January 27, 2026
Day 3 was the first of 2 full days exploring Key West. The weather got a little windy and slightly unseasonably colder (65 degrees) during our stay...but there was still tons to see and do. First up, was a 3 mile ride to the Southernmost Point in the Continental United States buoy. Then, it was breakfast at the iconic Blue Heaven in Bahama Village.
The group (which, I should mention was 12 riders and 2 Tour Guides) then had a free afternoon to explore the island. I hit the waterfront for pics, then rode back to the Blue Dolphin to chase roosters (and potentially photograph them).
Day 4: Wednesday January 28, 2026
Our Day 4 excursion on a boat out to a sand bar was unfortunately cancelled due to the weather. However, the Tour Guides had a great Plan B in their back pocket. After breakfast at the Blue Flamingo, we went to the Key West Aquarium, Ship Wreck Museum, and The Waterfront Brewery for Lunch. The day was capped off with an outdoor yoga session led by Tom (check out his Tomfoolery Outdoors). It was a nice release to have some "down time" at this mid-point of the trip, and a good chance to recharge for the final 2 ride days.
Day 5: Thursday, January 29, 2026
Day 5 saw us leave Key West and get back on the road east on the trail that parallels US Route 1, after another breakfast at the Blue Flamingo. We stopped at the Sugar Shark for a snack break 13 miles in, then rode about 18 miles to a trailside lunch on Big Pine Key at the Key West Visitor's Center. After a quick 7 mile bike hop to the southern end of the 7-Mile Bridge, we then got shuttled to Key Largo and stayed at the (pretty sweet) Holiday Inn, with dinner at Skippers Dockside. This was your classic 2 story motel, right out of the 60's. The inner courtyard with pool, hot tube and palm trees was quite cool!
Day 6: Friday, January 30, 2026
We woke to rain on our last day, so it was decided to cut the ride down a little bit for those who wanted to brave the weather. After breakfast at the hotel, we jumped on our bikes for an 8 mile run while there was a slight clearing in the forecast. The big treat, after lunch, was a Glass Bottom Boat Ride at John Pennekamp Coral State Park, out to Molasses Reef. It was actually a blast, as Sharks, Stingrays and Loggerhead Turtles were spotted.
This excursion brough the trip to an end, and we were then shuttled to the airport/hotels for our respective departures. We got to trade our favorite stories on the ride into Miami, and I will genuinely miss these folks.
I've been a part of A LOT of Tours, and this one really struck me as the riders has such a great sense of adventure while keeping open to the almost daily changes the weather threw at us. What also blew me away was the amount of prep work and support the Tour Guides (Jeremy and Tom) provided. This is the standard level of service at WV, and I have never seen anything like it.
More Info:
If you’re looking to broaden your bike touring horizons (and sleep in a hotel on tour for once!), check out the 49 Tour Destinations and over 250 Tour Departures that Wilderness Voyageurs has to offer each year.
For those of you on 718 Outdoors Tours this season...don't get any ideas, I wont be cooking you meals!
Final Note:
For better or worse, I do not use AI to create my posts. This is all me, with my misspellings, questionable grammar and tangential thoughts. I didn't get into this line of work to hand over my thoughts, expertise and experience to AI to spit out blog posts.
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