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Road Trip: St. Pete-Miami-Key West

Wheeling Warriors - Smart Ride - Florida Smart Ride- Chuck Hinchliffe - Mark and Chucks Adventures - Key West Florida - bicycle

Very shortly, Chuck and I will be making what has become an annual road trip.


Chuck is getting ready to participate in his third SmartRide, a 165-mile charity bike ride from Miami to Key West, benefitting AIDS Service Organizations across the state of Florida.

Wheeling Warriors - Smart Ride - Florida Smart Ride- Chuck Hinchliffe - Mark and Chucks Adventures - Key West Florida - bicycle

My job is to get him and the bike to Miami and back from Key West. I’ll get him to the starting point the day of the ride at some un-Godly hour before sunrise and take some photos of the journey along the way.

Mark Time

After the start of the ride, I generally get some client work done and find someplace for breakfast or coffee. I’m a bit of a junky for good café con leche, and after all, we are in Miami.

Cuban Coffee - Miami - Cuban Restaurants - Cafe Versailles - cafe con Leche - The Worlds Most Famous Cuban Restaurant

Cafe Con Leche

Empanada - Beef Empanada - Baked Empanada - Cafe Versailles - Versailles Restaurant - Miami - Cuban Restaurant - The Worlds Most Famous Cuban Restaurant - Cuban Food

Beef Empanada- baked, not fried!

The 500 riders will be leaving the University of Miami, in Coral Gables, and this year we’ll be staying at the Hampton Inn, Coconut Grove. This is even closer to the famous Versailles Restaurant where I stopped last year, but I’m open to other suggestions.

Exploring The Florida Keys

I start out a few hours after the riders are on the road, as they wind their way through Miami and down through Homestead to Key Largo. They keep to back roads, and once they are onto US -1, I generally get ahead of them and shoot some photos of riders along the way.

Last year I drove down through to Islamorada to Mile Marker 84.5 and spent some time at the Theater of the Seas. It was a great afternoon, beautifully kept gardens and amazing animals.

Theater of the Seas - Islamorada - The Florida Keys - mile marker 84.5 - dolphin show - Mark and Chucks Adventures

Dolphin Show


What are some attractions between Key Largo and Marathon that I don’t want to miss?

Day One

Day one ends with the riders finishing 100 miles and staying overnight at Duck Key, just above Marathon.

As the facilities are pretty much taken over by the 500+ riders and crew who get massages, dinner and get some rest, I typically drive on through to Key West for the night.

Skipping Lunch

Last year I crowdsourced on social media and took suggestions for lunch. An overwhelming recommendation was stopping for the ‘world-famous’ Lobster Reuben.

While I’m not a fan of mixing seafood and cheese {it’s something I picked up from the Italians I grew up with}, I went out on a limb and had what ended up being a VERY expensive sauerkraut sandwich with very little lobster. #EPICFAIL

This year, I’m skipping lunch and heading right into Key West. I’ll probably be making a quick pit stop at Baby’s Coffee right outside of Key West.

They are a pit stop sponsor of the SmartRide and the Saturday morning pitstop. I made the mistake of trying to stop there on Saturday morning last year, and it was packed with locals, crew, and riders who arrived early.

It’s too good to skip, and I need to stock up on some coffee, so I’ll get there on Friday afternoon.

Hanging in Key West

I’ve booked myself the afternoon Southernmost Food Tasting & Cultural Walking Tour with Key West Food Tours!

This tour celebrates everything Key West and the Cuban and Caribbean influences. We like to book food tours everywhere we travel, and even though we’ve been to Key West several times, the Vloggers and Bloggers we follow had an excellent experience.

After the food tour, I’ll be able to check into the 24 North Hotel right at the point of entry into Key West. It looks beautiful, has an awesome pool and a shuttle downtown.

Wrapping Up The SmartRide

The riders leave Duck Key and head to Key West in the morning. I typically drive back up US-1 and look for Chuck and his team coming across the 7 Mile Bridge before heading back into Key West.

The riders stop for a break and lunch at Key West High School and then ride as a group through the streets of the town, ending in a fantastic closing ceremony at the Truman Pier.


Asking The Experts

  • Where is the best place near Coral Gables for Cuban coffee?
  • What are the MUST DO attractions along the Oversees Highway between Key Largo and Key West?
  • I’ll have the evening free in Key West after my fantastic food tour, what do I want to see that I may have missed in the past?

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