How to Plan a Cycling Vacation

Rob Annis

For me, the only thing better than visiting a new place is seeing it for the first time from a bike saddle.

As a cycling fanatic, most of my trips involve a bicycle in one way or another. Whenever I’m heading to a new place, the first place I try to hit is a bike shop, whether it’s to rent a bike or just get recommendations for local routes. For the past few years, my bicycle has been a central part of my travel plans, whether it’s traveling to a far away city for a massive charity bike tour or renting a house and pedaling in every direction for a week.

Every travel website claims the journey is often as important as the destination, and that’s even more true on a bicycle. You’re traveling at slower speeds, and exposed to the elements and your surroundings much more than if you were in a car. In my opinion, there’s no better way to travel.

In San Antonio, a wrong turn led my wife and I down a maze of residential streets. As we attempted to find our way back to our hotel, we stumbled across a beautifully decorated gazebo, where moments before a deliriously happy couple had gotten married. As the mariachi band serenaded the crowd, we watched from afar, not wanting to intrude on the scene. The scene reminded us of our own wedding years before, and quickly eased any frustration that was building inside me after I got us lost.

So what’s the right bike tour for you? If you’re a first timer, going with an established tour company or tagging along with a more experienced friend will be your best bet. Bike travel has its own unique set of challenges – equipment failures, gear options and unforeseen physical limitations – that novice riders might not be ready for. The Adventure Cycling Association is an incredible resource for finding a bike tour or planning your own epic journey.

The one-day or weekend tour

Probably the most common bike tour is a short-term tour. Organized rides typically have multiple distance options, so you can ride 100 miles while your significant other does 30 at their own pace. Organizers will usually have support stations between every 15-20 miles, so you’ll be able to stop, refill your water bottles and grab a quick snack. Some of the better one-day rides have mechanics at most stops to quickly adjust your brakes or solve the mystery squeak coming from your bottom bracket.

If you’re looking for quiet and solitude in nature, this type of tour is not for you. The Hilly Hundred, a two-day autumn ride through the rolling hills and foliage of Southern Indiana, boasts more than 5,000 riders, so you’re never truly alone on the roads.

Guided group tours

Go to the back of almost any cycling magazine and you’ll see offers from multiple companies offering to lead you and a group of other riders in winding tours through gorgeous roads or trails here in America or abroad. Groups tend to be on the small side – expect about a dozen or so riders, depending on the operator – with a follow van filled with drinks, food and repair tools. Depending on the tour, riders will either camp or stay in hotels or inns along the way. Guides typically are extremely knowledgeable about the areas they ride, so be sure to spend some time pedaling next to them.

Be sure to study the routes and mileage before signing up for this type of tour and be honest about your skill level. There are few things worse than signing up for an expensive tour and spending large portions of it in the van because the route is more mountainous than you can handle.

Romantic couple pedal

This is definitely high on my list of to-do trips with my wife. Several tour operators specialize in scenic inn-to-inn trips through Vermont or other states. Each morning you depart from a different bed-and-breakfast, outfitted with a map and a snack. While you and your better half casually pedal to the next inn on your itinerary, your luggage is transported via van. Many of the tours offer different routes to make it as easy or as challenging as you want.

These are great tours, but make sure you know some basic bike repair skills, like changing a flat tire, before you go. Depending on the tour, the operator might not offer roadside assistance.

Self-supported bike packing

For riders interested in riding at their own pace and roughing it a bit, this is a great option. Your only limit is your imagination; some friends and I are currently planning a 3-5 day tour hitting Midwest microbreweries. If you want to camp at night, ultralight gear and food can be towed behind you in a trailer. Or you can try credit-card touring, where you stay at a hotel each night and carry extra clothing and gear in panniers strapped to your bike.

Try to pick friends who are roughly at the same cycling level and temperament as you. If you’re planning on riding mostly back roads, make sure at least one of your group members has the needed mechanical skills to do roadside repair work, like fixing a broken chain or spoke.

Fantasy camp for racers

In July, I’ll be riding part of the Tour de France with Sports Tours International, along with a dozen or more other cycling enthusiasts. For about nine days, we’ll be riding the same roads as the pros – albeit a lot slower. For amateur racers like me, the trip will be the closest I’ll ever come to the WorldTour peleton. During the ride, we’ll leave before the pros, stop for a bit to eat and watch as the real racers rocket past. Afterward, we’ll pedal our way back to the hotel. Most professional races, including the Amgen Tour of California and the US Pro Cycling Challenge in Colorado, have similar tours. For other pro cyclist wannabes, there’s the La Vuelta Puerto Rico, a three-day, 375-mile “pro-like experience,” according to the website.

Many of these trips are typically for more advanced and fit riders. Scan the tour operator’s website to get an idea of what to expect before typing in your credit card information.