Jeff the Planner
I have an MBA and a background in manufacturing and operations planning, so I know how to build a plan, manage a timeline, and execute with precision. But my heart has always been in wild places. Long days in the office left me thinking about alpine trails, coastlines, and small villages full of life and history.
Eventually I stopped just thinking about it and started planning. First for myself, then for others. What began as my own trips grew into itineraries for travelers who want more than a vacation. They want journeys that feel personal, active, and worth remembering.
My love for travel started with family road trips across the United States. We explored Yellowstone, dug for fossils in South Dakota, camped in the Painted Desert, hiked in Glacier, and watched orcas off the coast of British Columbia. I’ve taken a train from New York to Colorado to see the Rockies, hiked in the Adirondacks, the White Mountains, and the Smokies, and even chased two total solar eclipses.
International travel became a passion when I studied abroad in Ningbo, China. Navigating an unfamiliar culture challenged me to grow and gave me a deep respect for the ways people around the world live and connect. A countryside Buddhist temple, a solo night in Shanghai, even a hotel breakfast in Hangzhou, those moments still come back in full color.
In 2021 my wife and I took our first trip to Europe. We hiked in the Swiss Alps, wandered Tuscan hill towns, explored Florence and Siena, and ended on Lake Como. We learned how to balance adventure with rest and found what kind of travel truly fulfills us.
In 2024 we returned for an adventure honeymoon through the Italian Dolomites, Slovenia, and Croatia’s Istrian Peninsula. We explored castles, alpine meadows, glacial lakes, Roman ruins, and medieval villages. We hiked, biked, kayaked, and made space to reflect and recharge. That trip was the result of months of planning and years of dreaming. It reminded me how rewarding it is to create a journey that fits who you are.
That same planning mindset is what I bring home to the Berkshires. I’ve lived here for a decade, and my appreciation for the area keeps deepening. I love the layers of history, from Revolutionary War stories to literary giants who made these hills their home. I love the Gilded Age mansions and the landmarks that still carry a sense of time and place.
I also love how the Berkshires make nature feel close. I’ve hiked extensively across the region, and what many people overlook is how quickly you can shift from trail to town. You can stand on the highest mountain in Massachusetts and be sitting down to a great Italian dinner about an hour later. That mix matters: real outdoor access without giving up the comfort of a good community center, a cozy main street, or an easy place to land at the end of the day.
And the culture here is not a side note. The museums are genuinely world-class, the art scene is deep, and Tanglewood is a treasure. The food is better than people expect, with enough options to keep things interesting, plus plenty of familiar comforts when you just want something easy.
My thesis is simple: the Berkshires are worth traveling to not because they are a “top destination,” but because they are an ideal getaway. This is a place where the perfect weekend exists. It’s also a place you can visit to imagine living here, even if only for a few days.
Now, as a travel planner, I bring that same care and creativity to every trip I design, whether you’re heading abroad or coming to the Berkshires. I help curious, active travelers pursue authentic adventures, respect cultures and landscapes, and come home with stories that feel like their own.
Santa Maddalena, Dolomites, Italy
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