Are you looking for the very best bed and breakfast in St. Augustine? Established by Spanish explorers in 1565, St. Augustine is the nation’s oldest city. For a few hundred years, it commanded a wealth of incredible prominence as St. Augustine set down its fascinating past, including the bloody fight amongst the marauding natives and the ravage of the city by notorious pirates like Sir Francis Drake.
Over the following few centuries, St. Augustine had some notable sieges that occurred as the Americas were founded. If you love history, this city is simply a gem! St. Augustine has a varied culture, from the visible Spanish presence to hosting the first liberated Black settlement in the 1700s at Fort Mose to playing an important role in African American history as the original underground railroad led countless people to the city.
The city also has an impressive history going back to Minorca, where the indentured laborers were from the coasts of Greece, Italy, and Minorca, which run throughout the city. After escaping to the city of St. Augustine, the few survivors settled down, and their incredible culture and food have lived on through modern restaurants throughout the city. But it did not become the tourist destination it is today until an oil tycoon named Henry Flagler in the early 1900s built a sumptuous hotel for the rich in the center of town.
Luxurious in design, with no detail spared, it lured the rich and famous for the winter months to a balmy Floridian climate. St. Augustine—known for political activism since the establishment of Lincolnville after the Emancipation Proclamation—became a hotbed for the civil rights movement in the 1960s. Battles in the streets of St. Augustine resulted in street beatings and arrests of heroes of the civil rights movement, with rabbis standing up in the streets to defend them as they paved the way for what would become a watershed moment in our country’s history and the passage of the Civil Rights Act.
It is also an ideal haven for literary dreamers to spend hours dreaming up their next pages with the likes of Hemingway and Hurston exploring the narrow streets. Now St. Augustine sits as a bustling tourist town, locked into historic architecture, beaming with the very best holiday lights spectacular in the nation, and overflowing with an homage to its multicultural roots as the oldest city in the USA.
When to Visit
Coming to enjoy the very best bed and breakfast in St. Augustine has to offer? St. Augustine, like any coastal Florida city, is most enjoyable in the cooler months, from September to May, the very best time to visit. But the coast is beautiful year-round, and there is always something happening in this place. One of the prettiest cities to wander at sunset is St. Augustine, particularly when the pastel-hued skies wash the narrow streets and centuries-old facades with pastel light.
Thousands of bricks, not cobblestones, line the narrow streets of St. Augustine. From the live music throughout the city for the Sing Out Loud Festival in September to races, fireworks, and historic reenactments, to the millions of spectacular lights that adorn the city for the Nights of Lights from December through January, there is simply no question of sitting idle or getting bored.
Where to Stay
So, if you are looking for the very best bed and breakfast in St. Augustine, make sure to check out the Westcott House in the first place!
