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Obviously, here at inGamba, we believe that the best time to go on a bike tour is anytime or all the time. 

But on an individual level, planning out when you’ll finally check off a major bucket list item like an inGamba trip through small towns on the coast of Italy or a five-day exploration of California wine country by bike can feel daunting.

Here, we’re looking at a few of the most important things to consider when you’re looking at the year ahead and trying to figure out the optimal time to take your trip.

What’s your fitness like?

We’ve written about how to know if you’re fit enough to have a great time on a bike trip, and while you don’t need to be a Tour de France hopeful to have a phenomenal riding experience, you do want to come into a bike trip feeling comfortable with the ride distances and durations. So, if you tend to spend most of the winter enjoying an offseason and only start pedaling when the weather warms up in April, you may not want to book a trip for March, since you’ll likely feel slightly out of shape and enjoy those long climbs a bit less than you would after a month or two of training.

What’s your motivation like?

On the flip side, a bike tour on the schedule can be the boost you need to stay in cycling shape! Will having a bike tour scheduled for May be enough motivation to keep you on the trainer a few days a week in the winter, building fitness so that you can climb mountain passes with ease?

Having a trip booked as a reward or motivator to stick to a training plan can make it much easier to do those trainer workouts early in the morning on dark February days. If this is the case for you, look for a tour that’s a few months away from a time of year when you traditionally struggle to ride but know you want to.

What’s the weather like?

Some people love vacationing in the summer and taking in the hot sun of Tuscany, while others prefer to book a trip to get them out of the winter doldrums. Some people love to focus on winter sports and keep their cycling to the summer months—know which weather you prefer to embrace, and which you prefer to avoid.

Your dream cycling destination also has optimal riding seasons, though many inGamba destinations are ideal almost year-round. But November is a great time of year to head to California or Arizona if you live in a chillier part of the world since the sunshine can provide a welcome respite before a long winter. And very few things beat the Italian countryside in summer. 

What’s your work/family life like?

Have a huge work conference scheduled for August? July probably isn’t the best time to go on a bike tour if you’re the kind of person who will end up obsessively checking emails and prepping their presentation instead of sitting around the patio after dinner swapping stories with fellow cyclists from the day’s ride.

It’s better to save the bike tour as a celebration of completing your big report or presentation rather than trying to cram it in beforehand. Look at the calendar for work and with your spouse/kids to see where there are blank spaces before committing to a tour—you’ll enjoy it more if you’re not stressing about home responsibilities. 

What’s your dream tour?

We have to admit, every other consideration gets tossed out the window when faced with the opportunity to sign up for our longtime bucket list bike tour.

If you’ve been saving images of coastal Italy, the Le Marche tour in May is the chance to make the ride of a lifetime fit into your schedule. Or maybe you had a poster of Eros Poli in your trainer room and want a chance to ride with the greats—head to California in November to get the chance to pedal with Poli. Perhaps you live for Classics season—the Strade Bianchi Experience in March is your chance to ride like the pros.

Molly Hurford

Molly is the author of Fuel Your Ride, and a Precision Nutrition-certified coach. Her writing has appeared in many leading publications, including Bicycling Magazine and Outside. When she's not writing or coaching, she loves ultra-running and racing on trails, riding bikes, or hiking with her mini-dachshund DW.