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.

Mountains & Sea Explorer

Explore the trails of New England and get on the water on Martha's Vineyard!

Two Weeks of Adventure and Friendship

Mountains & Sea Explorer begins in southern Vermont, with a series of short hikes. From Vermont we’ll head south and east, to Martha’s Vineyard. There, we’ll explore historic coastal towns, and play on some of New England’s most famous beaches. We’ll also spend two days learning the basics of kayaking. Towards the end of our trip, we’ll tackle our final challenge: Franconia Ridge in New Hampshire’s White Mountains. It’ll be the longest hike of our trip, but also the most rewarding. On the top, we’ll celebrate together, and enjoy mountain views, as we reflect on two amazing weeks with new friends!

Download the
Mountains & Sea Explorer Itinerary
for all of the details!
"My leaders were a great duo. They were super supportive and brought a great enthusiasm to the group. I loved them!"

Caroline H.

New Jersey

"This trip was a great way for me to step outside of my comfort zone and try something new. I'm so glad I did this because I made lots of new friends and awesome memories."

Ayla K.

New Jersey