Florida Keys Family Multi-Adventure Trip: Bike, Paddle, and Cruise

For New Year’s 2019 we enjoyed the winter sunshine from the Everglades all the way to Key West. We selected worldwide trip leader Backroads as our Florida Keys outfitter and let them do all the heavy lifting and planning. Fresh air, wide-open landscapes and off-the-beaten-path trails are what Backroads is known for. If you are an extrovert you can go as a group and meet fellow outdoor enthusiasts; if you want something more intimate, you can make the entire trip private for the right price or if you have ten people in your group.

We did a group experience for our first Backroads excursion because that is the cheapest way and we have always enjoyed making new friends on our travels. Having similar-aged kids in our group was just the icing on the cake for our boys. When booking your trip with an outfitter, you can always ask what the age makeup of your group is.

Starting Out

We flew into Miami for our first night’s stay where we tried some authentic Cuban food at Versailles followed by a car tour of The University of Miami. Early the next morning, we met up with our group leaders and headed to Everglades National Park, the largest tropical wilderness in the country. If you prefer to stay closer to the Park, consider Flamingo Lodge, the only air-conditioned lodging within the Everglades.

Everglades National Park

To begin our tour of the Everglades, we did the 15-mile Shark Valley Bike Loop. You can rent bikes at Shark Valley, but they go quickly. Backroads provides you with your own high-end bike that you use throughout your trip. We saw our fair share of alligators (made me happy to not be on foot!). It was a great flat ride to get comfortable being back in the saddle before tackling the longer rides planned near Key West. You also have the option to join in on an airboat tour at Everglades Safari Park just outside the park. It’s a great way to see the wetlands but bring ear protection because those giant fans are loud!

Islamorada

From there we went to Islamorada (home of The Moorings Village and the Postcard Inn Beach Resort and Marina) and stayed at the popular Cheeca Lodge. In our downtime, we enjoyed walking along the resort’s private palm-lined beach. Snorkeling wasn’t great around the resort because of the weather, but we were able to drive to Robbie’s Marina to go kayaking among the mangrove trees where we spotted a crocodile sunning on a dock, much to my children’s excitement. I was more worried about the noticeable number of jellyfish in the water, but it was a fun, unique experience. When you are done, enjoy some lunch at the Hungry Tarpon Restaurant and feed the tarpon. Another worthy kayak excursion is Toilet Seat Cut. No joke! Finally, if kayaking is not your thing, check out Islamorada Coastal Adventures. They have something for everyone.

Key West

After a couple of nights on Islamorada, we moved on to Key West. It was a little touristy for my taste, but I had some family staying at the marina and enjoyed catching up with everyone. And yes, I did indulge in some local Key Lime Pie on my way to Mallory Square! If you have been to New Orleans and enjoy the entertainers in Jackson Square, check out the nightly arts festival right by the water at Mallory Square. It begins nightly two hours before sunset. Similar to Jackson Square, hold on to your wallet! If Mallory Square isn’t of interest, consider a private or group sailing excursion from the marina with Sunset Sail Key West. This was a trip highlight for my family. We didn’t bother with the incredibly long wait to see Ernest Hemingway’s home.

Cycling in Key West:  

While based in Key West, we biked part of the Florida Keys Overseas Heritage Trail. The FKOHT currently boasts over 90 miles of paved pedestrian and cycling trail that will eventually stretch 106 miles, all the way from Key Largo to Key West. We started our ride at Baby’s Coffee at mile marker 15 on the Overseas Highway. The coffee here is fantastic, and Baby’s works to serve bicyclists by offering an air pump and locks.

Another great route is to bike through Fort Zachary Taylor. You can start on Fort Trail and enjoy a short ride that takes you to the southern tip where visitors are sunbathing, fishing, and snorkeling. You can hop off, tour the fort, then get back on your bike and ride past a wooded area and along the seawall with gorgeous water views.

Backroads

What really made Backroads stand out from other operators in this area is how simple they make the biking, the quality of lodging, and the quality of the guides. They map out the routes (getting lost was one of my concerns going in, but it was never remotely an issue), drop off your bikes and pick you up when you are done. They give you options for longer or shorter routes based on what you are in the mood for and on your physical abilities. Electric bikes are available for those who need additional assistance (helpful if doing a multi-generational trip). Backroads has also vetted all the activity providers they use to ensure your satisfaction. The sailing operator they used on one of our afternoon excursions was top-notch.

My only issue with this Florida Keys trip was the lack of downtime. Evening meals were with the group. You could go off on your own, but then you were paying out of pocket whereas the group meals were all covered under the package rate. I guess it all depends on what you are in the mood for. We are always exhausted by the end of the year and would have enjoyed a few quiet dinners but, all in all, it was a great trip.

This post was updated on March 20, 2022.