Winding Roads & Historic Gems

A physical trip comes in the mail as 5 sealed envelopes: a "Before You Go" guide, plus 4 surprise stops you open one at a time as your day unfolds. Since it ships, it takes a few days to arrive.

A digital trip has the same 5 sections, sent instantly to your inbox after checkout. Since it's all one document, just go section by section and try not to peek ahead.

Plan for a full day of adventure! Most trips include 4–6 hours of exploring, plus the drive to and from your starting point. We recommend choosing a trip that's about 2.5–3.5 hours round-trip from home for the best experience.

You only need one trip per group. If more than 5 people are going, we recommend putting someone in charge of making reservations (they can peek at the trip by scanning the QR code in the Before You Go booklet).

Just below the trip description, you'll find the town/area where this trip ends. This will give you a good idea of how far you'll be from home at the end of the day.

No advance planning needed for your road trip itself - since it's self-guided, you can pick any date. We do recommend the best days of the week and seasons for each trip, so it's worth checking those before you go. Some stops recommend a reservation, and we'll flag those in your "Before You Go" guide so you know ahead of time.

Of course! After purchasing, you will find hotel recommendations in your confirmation email.