For families in New York City sending a child to boarding school in New England, transportation logistics come up constantly — the start of every term, long weekends, holiday breaks, parents' weekend, and the countless smaller trips in between. This guide covers what parents need to know about arranging reliable, comfortable transportation between NYC and the region's boarding schools.
Why Parents Choose Private Car Service Over Driving Themselves
Many of these schools sit two to four hours outside the city, often down winding rural roads that aren't well served by rideshare apps and can be genuinely difficult to navigate for a first-time visitor, especially after dark or in winter weather. A private car service with a driver who already knows these routes removes the stress of the drive — and lets you spend the time in the car actually talking with your child instead of watching for the next turn.
Schools We Regularly Serve
MyNYSUV provides scheduled and on-demand transportation to boarding schools across Connecticut, Massachusetts, Rhode Island, New York, and Pennsylvania, including:
| School | Location |
|---|---|
| Phillips Academy Andover | Andover, MA |
| Deerfield Academy | Deerfield, MA |
| Cushing Academy | Ashburnham, MA |
| Berkshire School | Sheffield, MA |
| Westminster School | Simsbury, CT |
| Canterbury School | New Milford, CT |
| South Kent School | South Kent, CT |
| Millbrook School | Millbrook, NY |
| St. George's School | Middletown, RI |
| Portsmouth Abbey School | Portsmouth, RI |
If your child's school isn't listed here, reach out directly — we regularly add new routes and are familiar with most private schools throughout the Northeast corridor.
Planning Around the School Calendar
The busiest travel windows are predictable: the opening week of each term, Thanksgiving break, winter break, spring break, and parents' weekend. Booking these trips a few weeks ahead — rather than the day before — gives you the best chance at your preferred pickup time, particularly around major holidays when demand across the entire Northeast spikes at once.
Unaccompanied Minors
We're experienced in transporting students traveling independently, with clear communication to parents before and after each trip, and direct coordination with school staff for pickup and drop-off confirmation.
What a Typical Trip Looks Like
Most families book a direct trip from a Manhattan or Brooklyn address straight to the school's main entrance, drop-off circle, or dormitory, depending on the school's specific arrival procedures. Return trips work the same way in reverse — your driver arrives at the scheduled time, helps load luggage (which, for boarding school students, is often considerable), and drives directly back to NYC or connects to an airport for a flight home.
Choosing the Right Vehicle
A single student with standard luggage travels comfortably in a Luxury Sedan. Families traveling together for drop-off or pickup day — often with a full term's worth of belongings — typically choose an SUV for the additional cargo space. For multiple students traveling together, or a family with several children, a Sprinter Van keeps everyone in one vehicle.
Booking Your School Transportation
You can book a one-time trip or set up a recurring arrangement for the school year at mynysuv.com/reserve/. For recurring bookings — like every long weekend of the semester — contact us directly and we'll set up a schedule in advance so you're not rebooking each time.