For many people, planning a vacation starts with excitement and quickly turns into a long list of tabs, decisions, and second guesses. That’s where Jill Schlofer, founder of JJS Travel Planners, found a need. Based in nearby Lakeville, Jill works one-on-one with clients to create trips that feel personal, thoughtful, and well-organized from start to finish.
Jill did not grow up traveling often, but once she had the opportunity to explore through her career, something clicked. Travel became more than a getaway. It became a way to explore new places, meet people, and experience life outside her everyday routine. That sense of curiosity and discovery stayed with her, eventually leading her to launch JJS Travel Planners in 2024.
“I realized I could turn something I love into a way to help others experience it, too,” she shares.
Meeting Clients Where They Are in the Travel Planning Process
Some clients arrive with a detailed vision and simply want help pulling it all together. Others come in with a destination and a loose idea of what they want to do. And some have no starting point at all. Jill adapts to each situation, offering as much or as little guidance as needed.
That flexibility is one of the biggest advantages of working with a travel planner. Instead of sorting through endless online options or calling a generic booking line, clients work directly with one person who understands their preferences, priorities, and concerns.
“I’m not just booking a trip,” Jill explains. “I’m helping you think through the full experience. What do you want this trip to feel like? What matters most to you while you are there?”
Her background in service and account management plays a big role. From coordinating flights and accommodations to preparing clients for what to expect, Jill helps remove the guesswork that often comes with travel planning.
Travel to Near and Far
Recently, a family of four came to her with a goal of visiting Norway and Sweden, but they were unsure how to bring everything together. Jill mapped out a multi-stop itinerary that included flights, excursions, and unique experiences such as dog sledding and fjord exploration. They even attended an NHL game in Sweden.
“It was a trip of a lifetime for them,” she says. “And hearing that they could not have done it without help was incredibly rewarding.”
Jill also brings her own travel perspective into her work. Tuscany remains one of her favorite destinations, and she is currently planning a milestone birthday trip to Nantucket, inspired in part by her love of Elin Hilderbrand novels. That connection between storytelling and travel has even shaped a unique offering within her business.
Through JJS Travel Planners, Jill creates book-inspired travel experiences for readers. These can range from local day trips to longer retreats centered on a favorite setting or a shared love of reading. She is also exploring future hosted trips, potentially in collaboration with local authors, giving readers a chance to connect in a new way.
Your Dream Vacation with Support Along the Way
While some travelers enjoy planning every detail themselves, others simply want support in filling in the gaps. Jill’s approach leaves room for both.
“I can step in wherever you need me,” she says. “Whether that is a small piece of the trip or the entire experience.”
For those ready to start planning, the process begins with a simple step. Visit her website, select the type of trip you have in mind, and complete a short intake form. From there, Jill takes the lead in helping shape a travel experience that fits your vision.
Because sometimes, the best trips start with having the right person in your corner.