The Walking Collection
Walking Retreats: Small-Group Walking Trips Abroad
A walking retreat is a small-group trip built around relaxed days on foot: easy-paced walks on beautiful footpaths, your bag sent ahead, and a good meal waiting at the end of the day. Our walking retreats follow England’s Cotswold Way through storybook villages, with bookish evenings along the way, and we take care of the hotels, luggage transfers, and every detail.
4 to 7 Miles a Day
Relaxed, Never Rushed
Villages, Fields & Footpaths
Why a walking retreat?
Walking is the best way we know to really see a place. You notice the stone walls, the sheep, and the bakery you would have driven right past. Our team walked the entire Cotswold Way before we planned a single retreat there, and we kept only the best stretches: the views, the villages, and the pubs worth stopping for.
Every walking day is relaxed, your bag goes ahead, and you can always transfer to the next village or skip a day. This is about enjoying the miles, not counting them.
What a day actually looks like
Every itinerary is different, and everything is optional. Here’s how most walking days go.
Cotswold Way
Who you’ll walk with.
Our walking trips are led by Away hosts who know these trails well, and one of them always walks the full day, so whether you go further or stop early, you’re never on your own.
Amy Heinemann
Away Host
Amy grew up on long family road trips through the national parks of the US and Canada, and she has carried that love of wide open spaces into adulthood. She has visited 142 countries, discovering each one through its food, markets, and landscapes, and this is her second time leading our Cotswold Way retreat.
Brittany Mora
Away Host & Founder, Silver Shuffles
Brittany founded Silver Shuffles, a movement company in Raleigh, North Carolina, that helps adults stay active, connected, and confident. A returning Away host, she loves experiencing new places at a slower pace, which makes the Cotswold Way a perfect fit.
Samantha Bahn
Bookstore Owner & Co-founder, Book Club Salida
Samantha spent more than 15 years as a public school educator and once worked as a whitewater rafting guide. She owns an independent bookstore, co-founded Book Club Salida, and helped create and lead our Reading Retreat in New Mexico.
Deb Bass O’Brien
Educator & Co-founder, Book Club Salida
With nearly 20 years as an educator, Deb loves the conversations a great book sparks. As co-founder of Book Club Salida, she curates reading lists and hosts literary events, and she helped create and lead our Reading Retreat in New Mexico.
Pick your dates.
Every upcoming walking retreat, soonest first. New dates show up here as soon as they’re announced.
Retreat
Collection
Destination
Dates
From
New Walking Retreats are on the way. Get first word in Lindsay’s Sunday email, or book a call to hear what’s coming.
Get first word on the next Walking Retreat.
We announce new dates first in our Sunday email, Sundays from Somewhere. Each trip includes airport transfers, boutique hotels, luggage transfers on walking days, and the group activities, in a small group.
What it’s really like.
“Best trip and experience for your money! … Immersive outings in the local villages for a well-rounded experience.”
– Anna H.
Walking Retreat FAQ
“The attention to detail in The Azores trip planning was impeccable and when hiccups with weather, etc occurred you pivoted with a smile.”
– Gwen R., Azores 2025
The “sheep hills”
Find your kind of retreat
Six ways to travel with us, all with small groups, a menu of choices, and every detail handled.
Not sure which retreat fits? Ask our team.
A quick call to talk through dates, rooms, and what each retreat feels like day to day. No pressure, ever.