We Welcome Your Application to Join Us!

We build each of our groups with care, keeping the groups small (no more than twelve students), and paying close attention to age, grade, gender, and the mix of hometowns and schools. Our goal is to put together great groups — groups where nice kids thrive in a supportive, wholesome, and caring environment. Please note: availability as shown is based on students traveling without a friend; if your child is interested in traveling with a friend, please call our office for availability.

Important Information about Availability


This departure of this trip has good availability. Apply as soon as possible since availability changes quickly.


This departure of this trip has limited availability. Apply as soon as possible, and on receipt of your application, if space is still available, we’ll confirm a spot for you. If all of the spots are taken, we’ll call you to discuss options.


This departure of this trip is currently full — please call us to discuss options.

How to Apply

Apply online using a credit card for the $795 deposit (your card will not be charged until we confirm a spot for you). Applications are reviewed in the order in which they are received (we do not hold spots over the phone).

When to Apply

The flow of applications starts in July and peaks in January/February. Some groups fill by the December holidays, and others will have space into the late spring. Our advice? Apply as soon as possible — it only takes a few minutes — and we’ll get to work right away to find a great spot for you.


Call (413.458.9672) or email (info@overlandsummers.com). We look forward to hearing from you.

Sam Sayer Banner

Samantha Sayer

Hometown: San Francisco, California
College: University of Vermont

Since seventh grade, I have found my passion in the outdoors through the world of biking, completing self-supported trips across the Northwest and Pacific Coast.

Originally from San Francisco, California, I graduated in 2019 from the University of Vermont where I studied exercise science. As a Division 1 cross country and track and field athlete, I competed all over New England. I also worked for the library, volunteered at the campus bike co-op, and guided Special Olympic athletes through varying exercise routines. I have made the Dean’s List multiple semesters, and I am currently conducting research on exercise volume for people with multiple sclerosis. In my free time, I enjoy eating pie, reading, and Salsa dancing.

In 2018, I led Cape Cod & the Islands, and in 2019, I led Swiss Alps Explorer. Throughout my summer with Overland, I learned just as much from my students as they learned from me. Overland trips provide the opportunity to have adventures that create lasting memories and friendships. Empowering people to travel by bike is one of the most rewarding experiences a person can have, and Overland provides that opportunity wholeheartedly to each group member.