History Meets Luxury at Carriage Way Inn

Located on Florida’s northeastern coast, St. Augustine’s history dates back to 1565, which means it is the oldest city in the United States. It is home to mythical relics and impressive structures like the Fountain of Youth and Castillo de San Marcos military fort, as well as dozens of modern bed and breakfast businesses – some of which, including Carriage Way Inn, have centuries-old histories of their own.

We spoke to owner and hospitality enthusiast Michaele O’Neill about Carriage Way Inn’s past and present, how her team keeps the inn running smoothly, and what to expect at a bed and breakfast as a first-time guest.

The Jewel of the Ancient City

Carriage Way Inn’s Victorian structure was first built in the mid-1880s as a private residence. After spending 50 or so years as an apartment building, it was ultimately converted to a bed and breakfast in 1984. Michaele O’Neill and her husband, Julio Torres, became the inn’s third owners in 2013.

“Hospitality is in my blood,” O’Neill says. “My mother was the director of sales and marketing for big hotel chains, so I’ve been running around them since I was five.”

O’Neill knew a bed and breakfast would give her the opportunity to offer guests personalized hospitality that isn’t feasible at larger operations. The couple found Carriage Way after spending two years looking for the right bed and breakfast in the right location.

Michaele and Julio, Owners of Carriage Way Inn

Michaele and Julio, Owners of Carriage Way Inn.

“We searched from Key West all the way into Georgia, and we landed in St. Augustine,” O’Neill says. “Both of us wanted to get out of corporate America, and we wanted a different lifestyle. We had been in major metropolitans such as the Ft. Lauderdale-Miami area for many years, and we were looking for a walkable, bikeable [town] with genuine people.”

St. Augustine, which has a population of around 14,000 people, gave the family the change of pace they wanted, and Carriage Way Inn – nicknamed “The Jewel of the Ancient City” – proved to be a great fit. The bed and breakfast has received recognition as the “Best of St. Augustine” two years in a row, but O’Neill says that connecting with every guest has been the real reward.

“Obviously we get tons of domestic travel [from] right here in the states, but then we get [guests from] all over Europe, and China, and Australia,” O’Neill says. “Because we are a small, intimate setting, you get to talk to them about their home food, their education system, and things that they like to do, so those personal connections have been a delight.”

What to Expect at a Bed and Breakfast

One of the biggest misconceptions many first-time guests have is that inn owners live on the premises, but O’Neill says that isn’t usually the case in vibrant markets such as St. Augustine. By her estimation, only one inn out of 26 has an owner living on-site.

Carriage Way Inn Exterior

The exterior of Carriage Way Inn.

“Most inn owners do not live on site [for a] couple of reasons,” O’Neill says. “Number one, to keep your longevity in owning your business [by having] separation between your business and personal life; and number two, you’re much better served if you convert those rooms that you might occupy into guest rooms to generate revenue for your business.”

Since each one is unique, choosing to stay at a B&B for the first time can be intimidating, but O’Neill enjoys being able to introduce new guests to the amenities provided at a modern bed and breakfast.

“We love having first-time B&Bers, because we get to open their eyes to a totally different experience from a box hotel,” O’Neill says. “We have on-site parking right in our back yard, which is highly unusual in St. Augustine. Another amenity is Chef’s Choice, a hot breakfast each morning when you wake up. Every afternoon, we put out a fresh-baked sweet treat [like] miniature homemade cupcakes, chocolate chip cookies, or brownies. Our bistro dining room is opened to guests literally 24/7, and it is fully stocked [with] Coca-Cola products, three kinds of wine, eight kind of hot tea, coffee, [and] bottled water.

“If you have all of those lovely amenities that are included in your rate, [it] does make it feel a little more at home. But I tell people we don’t aspire for guests to feel at home: Our ultimate goal is that we want you to feel pampered [by] superior, high-end accommodations.”

O’Neill describes Carriage Way Inn as “more like a boutique hotel” because it has 14 guest rooms that each include en-suite baths and five guest rooms with private entrances.

“Sometimes they might be concerned about seclusion or privacy,” O’Neill says. “If someone were a little timid about being in the main inn, we have nice options for them with private side entrances.”

A Room at Carriage Way Inn

A room at Carriage Way Inn.

The bed and breakfast is manned by hardworking part- and full-time staff members who have been a part of the Carriage Way team for years.

“There’s no divas at Carriage Way, and we do it all,” O’Neill says. “For example, staff comes in at 7 a.m. and they start making [our] fresh, from-scratch, Chef’s Choice breakfast every morning. Once we finish breakfast, we’re changing gears into checking guests out and checking guests in, and our check-in process is very personal. Then back-of-house switches from kitchen mode to housekeeping mode, and later on in afternoon you’re switching to laundry mode.”

That “very personal” check-in process includes aromatherapy towelettes, welcome drinks, restaurant and entertainment recommendations, and a customized map of St. Augustine to ensure guests know how to get to every item on their itinerary.

“I think our amenities, our personalized service, and the accommodations that we provide are top-notch, speak for themselves, and continue to help us grow and be very prominent in the market,” O’Neill says. “We aim to please, so come to the oldest city in the nation and let us pamper you.”

Ariana Keller
Ariana Keller

Ariana Keller was raised on the banks of the Chattahoochee River in south Alabama, where she learned to fish and love football. She moved to Knoxville with her family when she was 12 and later graduated from the University of Tennessee with a bachelor's degree in English. She spends her free time playing tabletop and video games and passionately rooting for mediocre sports teams. She is an advocate for animal rescue and lives in Knoxville with her husband and their two adopted pets: a hound dog named Beau and a Maine Coon mix named Vesper.