Cycling Tours Gray & Co
Credit: Radio

Back in 2005, Cari Gray took a two-wheeled detour from law school to guide cycling tours. After 14 years with Butterfield and Robinson, she struck out on her own, creating fully customizable bike trips for discerning clients. And in 2016, her eponymous company was rated the No. 1 Tour Company in Travel + Leisure’s World’s Best Awards for the first time. She shared some of her experiences—plus tips for getting the most out of a bike trip.

Anyone considering a biking tour should:

Definitely make sure they’re in some kind of shape for it. And a lot of people are good spinners but haven’t been on a real bike—they don’t know how to work the breaks or the gears. It’s crucial to know how to balance.

Before you sign up:

Make sure that the trip is consistent with how far you want to ride. Most people really appreciate 20 to 30 miles a day, with options to do more or less. After that you can go much higher. Also look at the general pace you want to have—most people don’t want to move every night.

The most involved trip I’ve planned was:

For just two people, a father and daughter who went over Australia. He’s a prominent businessman, and they had four security guards accompanying them. There were a lot of private planes and charters. He’s a really great dad—during the trip, he never looked at his phone.

I always pack:

Good sunglasses. I’m pretty fanatical about sunscreen; I use Anthelios by La Roche-Posay, which you can get in the U.S. now. Nowadays it’s so convenient to take puffy jackets everywhere, because they fold up to nothing. I have one as a blanket for my kid or just to sit down on. S’well bottles keep things really hot or really cold, whether you want hot coffee in the morning or cold water on a bike ride. And I always travel with a good camera.

The hot touring spot right now is:

Mallorca. It’s probably the best biking in Europe. There’s a highly developed tertiary road system because of the vineyards and olive groves. It has amazing hiking, great weather for much of the year, and beautiful places to stay. There has been a real surge in upmarket hotels. Some of my favorites are Castel Son Claret, Gran Hotel Son Net, and Son Brull.

My secret to traveling with children is:

Midday travel whenever possible. If you’re rested you can cope with anything.