Lori Chesloff
She/Her
Based in Boston
English
Road Trip to College
Ask us about
Our Story
I take the stress out of college planning with custom itineraries that allow families to discover their student’s future campus without the logistical headache. When we’re not on the admissions trail, I’m crafting adventurous trips focused on local experiences, fabulous restaurants, and breathtaking views.
Travel Style
As a travel planner, I offer a unique service planning college tour road trips. You provide me with the list of colleges that your student wants to visit, and I will schedule the tours, map out the itinerary, book the hotels and provide helpful information such as local restaurants and attractions to visit with the goal of helping students to find their perfect fit schools.
In addition to my work planning college tour road trips, I offer vacation planning, specializing in curating unforgettable experiences that allow my clients to immerse themselves in the local culture. With a deep love for breathtaking views and authentic travel, I believe in exploring each destination as a local, uncovering hidden gems, and embracing unique cultural nuances. Whether it’s dining at a Michelin-starred restaurant in Paris or discovering the perfect roadside empañada stand in Isla Mujeres, I craft journeys that go beyond the surface, offering luxury and local immersion in perfect harmony.
Reviews (2)
Rosemary F.
travel to Portugal and Spain
over 1 year ago
Lori was amazing! We planned a week-long trip to Portugal and Spain. Not only did she help with the practicalities like hotel reservations, she also suggested tours and activities for each of our planned stops and let us know about a few other beautiful spots that we would not have found on our own.
Elissa S.
travel to Louisville
over 1 year ago
Lori did a phenomenal job finding and booking the 21c Museum Hotel for us. I provided her with the general area that we wanted to be in as well as our budget and she quickly gave us a few excellent options, including the 21c Museum Hotel that I never would have found on my own. She was extremely responsive when I had questions and provided us with all of the details that we needed. Thank you, Lori!!
Rosemary F.
travel to Portugal and Spain
over 1 year ago
Lori was amazing! We planned a week-long trip to Portugal and Spain. Not only did she help with the practicalities like hotel reservations, she also suggested tours and activities for each of our planned stops and let us know about a few other beautiful spots that we would not have found on our own.
Elissa S.
travel to Louisville
over 1 year ago
Lori did a phenomenal job finding and booking the 21c Museum Hotel for us. I provided her with the general area that we wanted to be in as well as our budget and she quickly gave us a few excellent options, including the 21c Museum Hotel that I never would have found on my own. She was extremely responsive when I had questions and provided us with all of the details that we needed. Thank you, Lori!!
Travel ideas (1)
Ohio & Pittsburgh Colleges: 6 Visits in 6 Days
Searching for the right college can be overwhelming! This road trip is a fantastic way for families to explore six outstanding schools—Case Western Reserve, Oberlin, Kenyon, Denison, Carnegie Mellon, and Pitt—while seeing the full range of life in Ohio and western Pennsylvania. Along the way, you’ll experience lively urban campuses in Cleveland and Pittsburgh as well as charming college towns and rolling rural landscapes, giving students a real feel for how different settings shape daily campus life. Beyond official tours, the route is designed to include local neighborhoods, restaurants, and downtime spots so students can imagine what it’s like to live and study at each school. I can fully customize the itinerary based on your priorities—academic interests, travel pace, lodging style, or adding cultural stops and outdoor experiences along the way.
Ohio & Pittsburgh Colleges: 6 Visits in 6 Days
Searching for the right college can be overwhelming! This road trip is a fantastic way for families to explore six outstanding schools—Case Western Reserve, Oberlin, Kenyon, Denison, Carnegie Mellon, and Pitt—while seeing the full range of life in Ohio and western Pennsylvania. Along the way, you’ll experience lively urban campuses in Cleveland and Pittsburgh as well as charming college towns and rolling rural landscapes, giving students a real feel for how different settings shape daily campus life. Beyond official tours, the route is designed to include local neighborhoods, restaurants, and downtime spots so students can imagine what it’s like to live and study at each school. I can fully customize the itinerary based on your priorities—academic interests, travel pace, lodging style, or adding cultural stops and outdoor experiences along the way.
Ohio & Pittsburgh Colleges: 6 Visits in 6 Days
Searching for the right college can be overwhelming! This road trip is a fantastic way for families to explore six outstanding schools—Case Western Reserve, Oberlin, Kenyon, Denison, Carnegie Mellon, and Pitt—while seeing the full range of life in Ohio and western Pennsylvania. Along the way, you’ll experience lively urban campuses in Cleveland and Pittsburgh as well as charming college towns and rolling rural landscapes, giving students a real feel for how different settings shape daily campus life. Beyond official tours, the route is designed to include local neighborhoods, restaurants, and downtime spots so students can imagine what it’s like to live and study at each school. I can fully customize the itinerary based on your priorities—academic interests, travel pace, lodging style, or adding cultural stops and outdoor experiences along the way.
Ohio & Pittsburgh Colleges: 6 Visits in 6 Days
Searching for the right college can be overwhelming! This road trip is a fantastic way for families to explore six outstanding schools—Case Western Reserve, Oberlin, Kenyon, Denison, Carnegie Mellon, and Pitt—while seeing the full range of life in Ohio and western Pennsylvania. Along the way, you’ll experience lively urban campuses in Cleveland and Pittsburgh as well as charming college towns and rolling rural landscapes, giving students a real feel for how different settings shape daily campus life. Beyond official tours, the route is designed to include local neighborhoods, restaurants, and downtime spots so students can imagine what it’s like to live and study at each school. I can fully customize the itinerary based on your priorities—academic interests, travel pace, lodging style, or adding cultural stops and outdoor experiences along the way.
Travel photos
