Defining Success In Innkeeping

How many new Innkeepers have we seen enter the business with enthusiasm, confidence in their abilities and entrepreneurial spirits in our 36 years as Inn consultants? And how many have we helped to exit that milieu, once they had successfully built a viable business and desired to move toward true retirement, travel or other unfulfilled dreams on the horizon? The answer is, we’ve nearly lost count!

Life progresses and our aspirations become accomplishments. Over the years, we have witnessed rooms torn apart, public spaces transformed and, then, 10 years later, new owners follow the same path of renovation and renewal. Equally enthusiastic, dedicated and motivated to offer guests their taste, their generosity and gracious hospitality. The greatest Inns take on lives of their own, driven and revised by their Innkeepers, and always with an eye toward the future.

Photo of room at Chatham Inn at 359 Main
Guest room at Chatham Inn at 359 Main

Jeff and Kayla Ippoliti, owners of Chatham Inn at 359 Main in Chatham, MA, and the Regatta Inn and Centerboard Inn in Nantucket, MA, were a recent reminder of Inn owners who understand how to balance an Inn’s unique past with the need for change. Soon after their purchase of the Chatham Inn at 359 Main, Jeff and Kayla upgraded every guest room, while continuing to offer the extraordinary service and atmosphere that the #1 Cape Cod Inn was known for. World-class amenities, including luxurious Frette robes and slippers, Nespresso machines and Malin + Goetz bath products have also helped to solidify the Inn’s position as the #1 hotel in Chatham, MA. The Regatta Inn and Centerboard Inn have enjoyed similar success, with positions as the #1 and #3 Bed and Breakfasts in Nantucket, MA, respectively.

As Inns evolve and change hands, previous guests may move on, making way for new guests, your guests, who are drawn to the Inn, not only because of the experience that you have curated from dining room to sitting room to guest room, but because your hospitality continues to be genuine and heartfelt. Whether you are selling your Inn or buying into your dream lifestyle, it is all part of an evolution. Our greatest joy comes in helping to make that perfect match between buyers and sellers of Inns, Bed and Breakfasts, boutique Hotels and everything in between!

Photo of dining room at Chatham Inn at 359 Main
Dining at the Chatham Inn at 359 Main

All the best to all of you who are starting the process, those who are considering exit strategies and those planning the next renovation or re-creation of their Inn. It takes energy, imagination and drive to do your very best every day and that is the basis for success in our wonderful industry. For those aspiring Innkeepers in the Northeast, we will be hosting an iteration of our seminar at the Chatham Inn at 359 Main, with preferred rates for our attendees. We would love for you to take advantage of this opportunity to learn the ins and outs of Innkeeping at this one-of-a-kind property.

Otherwise, I would love to hear what you current Innkeepers have you done recently to keep on the cutting edge.

Best Wishes,


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