The Foundation for a Meaningful Life
Kindergarten - Grade 9 in Southborough, MA
Student Life
Upper School Trips

Fay Adventures

Ready for an Adventure?

For Upper School students looking to expand their horizons beyond the classroom, Fay Adventures offers optional travel opportunities during major school breaks, including Thanksgiving Break, Midwinter Weekend, and Spring Break.

These multi-day, immersive excursions are organized in partnership with trusted student travel organizations and chaperoned by Fay faculty and staff. Each itinerary blends educational tourism, hands-on activities, and cultural exploration to introduce students to the unique heritage of the region. Select trips also feature a service-learning component, providing students with a meaningful opportunity to engage with and support local communities.

Trips for 2026-2027
Questions?
    Contact Jill Anthony, Director of Equity and Inclusion, at janthony@fayschool.org.

Frequently Asked Questions

Tuition & Logistics

List of 3 frequently asked questions.

  • Are Fay Adventures included in tuition?

    While our signature seventh, eighth, and ninth-grade class trips are included in tuition, Fay Adventures are optional extensions of our core educational program and require an additional fee.

  • Can a student depart from a trip early?

    To ensure the safety and cohesion of the group, all participating students must depart and return together. The only exception is the Spring Break itinerary, where students may opt to remain in the destination to begin a vacation with their families, provided they are met directly by a parent or guardian.

  • Are these trips open to parents?

    Fay Adventures are designed specifically for student growth and independence; therefore, these excursions are open to current Fay students only.

Accommodations & Dining

List of 2 frequently asked questions.

  • Where do students stay?

    Students and faculty chaperones stay in thoroughly vetted, reputable hotels. Students are assigned to double or triple rooms and are welcome to submit roommate requests prior to departure.

  • What are the dining arrangements?

    Meals are designed to be both safe and culturally immersive. When traveling internationally, we prioritize local cuisine to deepen the cultural experience. Dining arrangements include a mix of sit-down group restaurants and curated food halls where students receive vouchers to choose their own meals.

    Dietary Restrictions & Allergies: We work closely with our travel partners and venues to ensure that ample, safe, and diverse options are available at every meal for students with specific dietary needs.

Safety & Eligibility

List of 2 frequently asked questions.

  • Who is eligible to participate?

    Fay Adventures are open to all Upper School students through an application process. To participate, students must demonstrate a consistent record of responsibility, maturity, and citizenship during their time at Fay, ensuring they can safely and positively contribute to the group dynamic.

  • How are students supervised during the trip?

    Student safety is our highest priority. All Fay Adventures maintain a strict 7:1 student-to-chaperone ratio. Students remain in small groups and operate in close proximity to Fay faculty and staff at all times.

Thanksgiving Break 2026: Fay Adventures in the Grand Canyon & Southwest National Parks

Fay Adventures is thrilled to announce our upcoming Thanksgiving Break expedition to the Grand Canyon and the Southwest National Parks.

Because Fay School dormitories are closed over the Thanksgiving Break, this multi-day excursion offers a spectacular opportunity for students. The trip will depart on Saturday, November 21, and return to campus on Monday, November 30, 2026.

We are proud to partner with Grand Classroom, a nationally recognized student travel organization, to deliver this adventure. The trip will be fully chaperoned by Fay faculty and staff, who will travel alongside expert Grand Classroom guides to provide a safe, educational, and awe-inspiring experience.


Itinerary Overview

Our nine-day journey takes students through some of the most iconic landscapes and national parks in the American Southwest:
  • Day 1: Flight from Boston to Las Vegas | Exploration of Red Rock Canyon and the Coral Pink Sand Dunes
  • Day 2: Zion National Park | Hike the historic Emerald Pools Trail
  • Day 3: Bryce Canyon National Park | Exploration of the unique hoodoo rock formations
  • Day 4: Escalante National Monument & Capitol Reef National Park
  • Day 5: Arches National Park | Discovering the world's largest concentration of natural sandstone arches
  • Day 6: Canyonlands National Park | Panoramic views from the "Island in the Sky" mesa
  • Day 7: Monument Valley Navajo Tribal Park | Guided tour of the red sand desert and iconic buttes | Visit to Glen Canyon Dam
  • Day 8: Grand Canyon National Park | Immersive exploration of the South Rim
  • Day 9: Journey through scenic Oak Creek Canyon | Return flight to Boston and transportation to Fay campus


Registration & Timeline

Due to strict airline requirements regarding advanced group travel booking, this trip operates on an accelerated timeline:
  • How to Register: Registration can be completed directly online via the Grand Classroom Registration Link or through the detailed information link above.
  • Registration Deadline: June 30, 2026 (Please note: Airlines require a minimum of 90 days advanced purchase for group travel).
  • Final Payment Due: August 2026


Informational Webinar

On May 19, we hosted a virtual informational meeting for interested families featuring a representative from Grand Classroom to review the itinerary, logistics, and safety protocols. Click here to see the slideshow from the presentation >>

Mid-Winter Break 2027: Fay Adventures in Maryland & Washington, D.C.

Fay Adventures is pleased to announce our Mid-Winter Break service and leadership trip to the Eastern Shore of Maryland and Washington, D.C., departing Thursday, February 11, and returning to campus on Monday, February 15, 2027.

For this excursion, we are partnering with the World Leadership School, a highly respected student travel organization dedicated to meaningful community engagement and leadership development. The trip will be led by Christina Berthelsen, Director of Community Engagement, alongside Fay faculty, staff, and expert coordinators from the World Leadership School.


Itinerary Overview

This five-day program blends hands-on community service, environmental science, and historical exploration:
  • Day 1: Flight from Boston to the Maryland/D.C. area | Orientation and service/leadership activities at the Pecometh Retreat Center
  • Day 2: Environmental science and research exploration at the Horn Point Laboratory
  • Day 3: Local history and justice immersion with the Eastern Shore Network for Change | Visit to the Harriet Tubman Underground Railroad Visitor Center
  • Day 4: Cultural and historical exploration of the museums and monuments in Washington, D.C.
  • Day 5: Capstone service and leadership activities at Pecometh | Return flight to Boston and transportation back to Fay campus


Registration & Next Steps

Registration is now open. To secure your student's spot and select your preferred payment schedule, please use the link below:

Post-Registration Note: Once your initial registration is complete, you will receive a follow-up confirmation packet from the World Leadership School with instructions on completing your student's required travel forms through their secure portal.

Upcoming Informational Webinar: We will host a virtual informational meeting via Zoom in early September. This session will feature a representative from the World Leadership School to discuss the itinerary, service projects, and logistics in greater detail. Look for the meeting link and schedule in your inbox as the academic year begins.

Spring Break 2027: Fay Adventures in Ireland

Fay Adventures is excited to announce our upcoming Spring Break trip to Ireland, departing Friday, March 5, and returning Saturday, March 13, 2027.

We are partnering with Grand Classroom, a nationally recognized student travel organization, to deliver a deeply immersive and educational itinerary. The trip will be fully chaperoned by Fay faculty and staff, who will work alongside expert local guides from Grand Classroom to ensure a safe, enriching, and unforgettable experience.


Itinerary Overview

Our eight-day journey spans the rich history, vibrant culture, and breathtaking landscapes of Ireland:
  • Day 1: Arrival in Dublin | Journey to Cork via the historic valley of Glendalough
  • Day 2: Coastal town of Cobh | The Titanic Experience | Cultural exploration of Cork
  • Day 3: Return to Dublin for an immersive city tour
  • Day 4: Trinity College & The Book of Kells | The Irish Emigration Museum (EPIC)
  • Day 5: Travel to Derry | Guided tour of the historic Bogside Murals
  • Day 6: Belfast | Exploration of the geologic wonder, Giant’s Causeway
  • Day 7: Kayaking/boating on the River Lagan | Traditional Irish Céilí music and dance celebration
  • Day 8: Departure from Dublin | Return flight to Boston


Important Logistical & Travel Details

Break Logistics & Airport Pickup Please note that Fay School dormitories are closed during Spring Break. Parents must arrange to pick up their students directly from Boston Logan International Airport upon the group's return on Saturday, March 13.

International Student Travel: For international students who wish to fly directly home from Ireland for the second week of Spring Break, please note that you must still register for the full tour. Fay administration will work with families individually during the fall term to coordinate these specific outbound flight arrangements.

Registration & Next Steps

Registration for the Spring Break 2027 trip is officially live. Space is limited, and placement is determined through the Fay Adventures application process.
  • How to Register: You may register directly online through the Grand Classroom Registration Portal or by following the instructions in the detailed information link above.
  • Registration Deadline: September 24, 2026
  • Final Payment Due: November 2026
Upcoming Informational Webinar: We will host a virtual informational meeting via Zoom in early September, featuring a representative from Grand Classroom to answer specific questions about the itinerary, safety protocols, and travel logistics. Keep an eye on your inbox for the date and Zoom link as the school year begins.
48 MAIN STREET
SOUTHBOROUGH, MA 01772
main number 508-490-8250
admission 508-490-8201