Alumni
Creating Community in Deer Isle: Andrew Schapiro ’95
Andrew Schapiro ’95 has always been drawn to places with a strong sense of community, and today, he’s helping create one of his own. As owner and innkeeper of The Ark in Deer Isle, Maine, Andrew welcomes guests into a thoughtfully designed space that blends modern hospitality with a nod to the inn’s history.
Deer Isle is meaningful to Andrew, who grew up visiting family on the island. Its natural beauty, close-knit spirit, and vibrant creative culture made it the perfect place for his young family to put down roots after living in the San Francisco Bay Area. Community driven, Andrew and his husband Bosco value the deeply engaged local culture, where neighbors come together, and there is a shared sense of pride in the town. “People really care about this place,” he notes.
That spirit is part of what makes both The Ark, formerly Pilgrim’s Inn, and Deer Isle so special. Built in 1793, the inn is a cherished place for generations of guests. As Andrew embarked on this new adventure as innkeeper and steward of The Ark, he set out to create a place where the community could gather and guests could make memories for years to come.
Andrew credits his time as Creative Director at Airbnb with sparking an interest in the hospitality industry. “Hospitality is multifaceted,” Andrew shares. “You get to design an entire experience.” The opportunity for creativity is one of the aspects he enjoys most, from designing the feel of the 15 guest rooms and cottages to curating the overall rhythm of a stay.
Running an inn also has its share of complexities. “There is an extraordinary learning curve,” Andrew notes. He is grateful to learn from others throughout this process, adding that he feels “lucky to connect with talented and experienced people in the industry.”
The Ark is open to guests May through October. Andrew and Bosco began welcoming visitors for the 2025 season with a clear vision: to create a deep, meaningful connection between their guests and Deer Isle. The inn quickly gained national recognition. TripAdvisor recognized The Ark as the top inn/bed & breakfast in Deer Isle. A guest’s trip is only complete with a visit to the on site Tavern and Dining Room. The seasonal chef-in-residence program brings a unique and delectable twist to the menu. The dining experience is so spectacular that the New York Times ranked it as one of its top 50 restaurants for 2025.
Reflecting on his journey, Andrew’s advice to fellow alumni is to stay curious and don’t be afraid to follow your gut even if it leads you down an unexpected path—at any point in your career. From the familiar hallways of Calvert to Maine's quiet coast, Andrew is creating something special, one guest and one memory at a time!
Visiting Maine? Stay at The Ark in Deer Isle and experience it for yourself!
Website: www.arkdeerisle.com
Calvert School is a coed independent lower and middle school.
