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Our Story

Bill Johnson was a general manager for a western wear manufacturer and his wife, Diane owned a bed, bath, and gourmet kitchen store in Woodward, Oklahoma. Diane's dream of inn ownership made her begin searching for a perfect location in 1987. Three years later, Bill joined in the search. They both knew that they had to be able to make a living out of the business and that it could not be just a hobby.

In the early part of 1992, their son, John, came to St. Augustine, Florida from Bradenton for a business conference and stayed out on St. Augustine Beach. After the conference, John chose a route home that took him across the Lions Bridge from Anastasia Island into the Downtown Historic District of St. Augustine and immediately called mom to tell her all about the quaintness and beauty of the town, ideal for her innkeeping dreams.

Diane called Bill at the golf course and told him of her idea to "kill two birds with one stone" by traveling to Florida to visit John's family and to check out the area. By the time Bill had returned from golf, Diane had already called the travel agent and booked the flight.

Bill and Diane arrived in Jacksonville in the summer of 1992 on a Sunday. After a short trip to Amelia Island to look for inns, they drove down to St. Augustine and were charmed by this beautiful city full of historic tourism and romance.

Once Diane saw St. Augustine’s Historic Carriage Way Bed and Breakfast inn, the decision was all but made. This city was less seasonal than any of the other cities they had considered, and even though the inn was more than what they wanted to pay, Bill thought that they could make a Florida bed and breakfast work. By that Tuesday they had made their decision and signed a contract to purchase the Carriage Way after five long years of searching.

That is how it all went down!

An Addition to Our Historic St. Augustine Inn

In 1998, Bill and Diane purchased "Our Cottage" three doors down from the main house. At the time of the purchase, the cottage was being used as Betty's Books and Bobbles, an antique store. Diane envisioned that it would be the perfect place for family getaways, girlfriend getaways, and for couples traveling together. Considering Diane's retail background, she knew what 50% off meant and stopped in for a visit with Betty. Betty explained that she would be relocating her business closer to her sister and with that news, Diane told her to take it off the market and that they wanted it. This was before the realtor was even able to put a sign in the ground. Diane and Bill thought that this Florida cottage would be a place for them to eventually move, and then the children could manage the inn. A year later and after a short illness, Diane passed away before that plan had come to fruition.

The Carriage Way did call the children to innkeeping, just as Bill and Diane had hoped. Larry, the oldest son, came to help Bill continue the family business after Diane's passing. 2004 saw John move from Brandenton to join the team once his daughter left for college. In 2009, Jeanie left her sales position to help John and Bill, so that Larry could travel and see the country.

Bill passed away in January of 2011 after a three-year battle with brain cancer. But 19 years of innkeeping experience did not go to waste, and the Johnson family continues to provide St. Augustine hospitality and that home-away-from-home experience to this day, just as Bill and Diane first envisioned.

About the Inn

A vernacular Georgian four-square structure with Victorian features was built between 1883 and 1885 by Edward Masters: a lead carpenter for Henry Flagler's first Florida resort hotel, the Hotel Ponce de Leon. Mr. Masters built the home for his wife, Rosalie, and his family, putting the attention into the bones of the house. Mr. Masters chose the very best structural woods for building: cypress, cedar, and heart of pine.

The original home was built before the presence of electricity and did not have any bathrooms or a kitchen inside the home. The tall windows on the front of the house with its southern exposure captured the warmth of the sun during the winter months. In the summer, when the sun was higher in the sky and over the roof line, the oversized windows provided filtered light, helping to keep the home cooler.

The home stayed in the Master's family until the 1940s, when it was converted into an apartment building with four efficiency units. In 1984, the home was extensively restored to its original grandeur, and central heat and air were added, fulfilling a dream of creating what is now the Carriage Way Bed and Breakfast.