Meet our Caribbean Service Adventure and Costa Rica Language and Service Leaders!

Hablas español? No? Well, no need to – these four leaders have got you covered! All four of them will be headed south this summer with Apogee students to make new friends, tackle community service projects, and soak up some Latin American sun. Jealous already? Read on… you’ll be even more jealous after you learn more about these awesome leaders.


Growing up on a vineyard north of Santa Barbara, California, Matthew Firestone worked hard to maintain and harvest his family’s grapevines. This summer, Matthew is looking forward bringing that same work ethic to Puerto Rico as he leads our Caribbean Service Adventure trips. The CSA itinerary should serve him well; not only is Matthew a hard-worker who loves to give back to the community, but he is also able to hang ten with the best of them. Matthew grew up spending weekends surfing on the coast of California, and as he grew older, he began leading surf-camping trips for his peers. A natural leader, Matthew was a tri-sport captain at his high school and was elected to be the student group leader on both of the NOLS wilderness trips he has completed. Matthew is a rising senior at Trinity College, where he is a Political Science major and plays on the varsity soccer squad. In addition to this mounting list of interests and hobbies, Matthew recently completed a summer working for a production company in Los Angeles where he was part of the team that produced “Duck Dynasty”! Matthew is excited to create new Apogee families through service, exploration, and a bit of surfing as he explores the Island of Enchantment with his students this summer.


We are excited to welcome Emma Westwater back to Apogee, this time as a leader instead of a student! Emma has been a student on our Maine’s Downeast Explorer and Maine Coast College Essay trips and we are pleased to announce that this summer she will be leading our Caribbean Service Adventure trips. A self-described Latin America-buff, it seems that Emma was tailor-made to lead CSA. Emma’s credentials include five trips to Ecuador (where she also lived for a year when she was ten), visits to Bolivia, Guatemala, Peru, Puerto Rico, and a planned semester in Chile next fall. While traveling throughout Latin America, Emma has engaged in a significant amount of community service work; she has worked on painting and refurbishing projects and has also volunteered her time as a tutor for elementary and middle school students. Based on her extracurricular interests it comes as no surprise that, as a rising junior at Bates College, Emma is studying Latin American Politics, Spanish, and Education. When she’s not volunteering as a tutor or honing her Spanish skills, Emma loves to run, cross country ski, and swim; this past summer in her hometown of Carlisle, Massachusetts, Emma swam across Walden Pond every day! Emma is looking forward to sharing her love for Latin American culture with her students this summer as they explore beautiful Puerto Rico together.


Growing up in suburban Washington, DC, with four siblings, Connor Chess was raised as a team-player with an eagerness to explore the world – and explore he has! While he flexed his chops as a thespian, Connor focused primarily on sports through high school, playing football and lacrosse. Connor continued his dedication to athletics by playing football at Washington & Lee University, where he is wrapping up his senior year. Over the past few years, however, Connor’s focus has expanded from athletics and acting to travel, working with kids, and playing in the outdoors. He’s traveled all over the world – to Northern Europe, Brazil, Bolivia, Costa Rica, Spain, and Peru – just to name a few locations on his impressive list! Through travel, Connor has realized how much he enjoys seeing the natural side of the places he visits – finding ways to see more through kayaking, hiking, biking, and surfing. He’s also made these trips more meaningful by making deep connections to the people and culture wherever he is. Connor spent the summer of 2015 teaching English at a high school in Costa Rica and spent last summer living and working in Argentina after finishing up his semester abroad there. Connor’s love of team-bonding and teaching, not to mention his boundless warmth and enthusiasm, make him the perfect fit for any Apogee family – and we’re excited to put his Spanish-speaking skills and extensive experience in Costa Rica to good use on our Costa Rica Language & Service trip this summer.


We’re excited to welcome Newton, Massachusetts native, Anna Clements, back to Apogee for her second summer as a trip leader! A seasoned traveler, Anna grew up exploring some of the most beautiful places in the world with her parents and brothers, including Alaska, South Africa, and various European countries. Leading our Vermont to Montreal trips last year, Anna also crossed the Canadian border not once, but twice. And, after whetting her appetite for Latin America with a service trip to Ecuador in high school, Anna spent this spring semester studying in Bolivia. Back in the US, Anna also has a great deal of experience working with kids; she has been a counselor at a softball camp for elementary and middle school girls, participated as a big sister in the Big Brothers Big Sisters program, and spent a summer working at a girls camp in Vermont. Anna continued to develop her leadership skills on a three-week wilderness leadership trip throughout Colorado, New Mexico, and Utah that included canoeing, hiking, and community service. A rising senior at Bates College, Anna plays club ice hockey, works in a homework help program for local immigrant students, and provides SAT prep assistance to underprivileged high school students. Anna is dedicated to community building and exploring the outdoors – and we’re thrilled to have her put these passions, along with her Spanish skills and unwavering energy, to use on our Costa Rica Language & Service trips this summer!