St. Augustine

St. Augustine, Florida – the nation’s oldest city

The oldest permanently occupied settlement in the continental United States.


Don Pedro Menéndez de Avilés first stepped on a sandy beach here August 28, 1565, the feast day of St. Augustine, and established a small settlement for the Spanish government. It was ruled for a very short time by the British in the 1700′s and became a United States territory (with Florida) in 1821 and part of the state of Florida in 1845.

Henry Flagler, real estate promoter and railroad developer, was a key figure in developing Florida’s eastern coast along the Atlantic Ocean, and founder of the Florida East Coast Railway. Flagler began his hotel and railroad development projects in Saint Augustine around the turn of the century (1900) and much of the current architecture is a result of the Flagler era.

Today St. Augustine retains the charm of all of its history from the Indians preceding the Spanish settlement to modern day shops and cuisines. One of the delights of this old city is its compact size, walkable from end to end in about 20 minutes. Narrow cobbled stone streets with quaint shops, inviting art calleries, fine restaurants and boutiques invite exploration.

Just 10 minutes over the Bridge of Lions is St. Augustine Beach, a delightful change of pace with its perfect white sand beaches, warm ocean waters and casual life style. More info here

Stimulating, interesting, surprising – fun!
Here are highlights of our visit – view each day and enjoy as we did!







day 1 fly to St. Augustine – arrive late afternoon

very special Welcome Dinner Raintree Restaurant go

with special guests/historic characters (portrayed by reenactors):
– Don Pedro Menendez de Aviles [founder of St. Augustine]
– Confederate General Edmund Kirby Smith
– Diamond Lil
– Mary Lily Keenan Flagler [Henry Flagler’s 3rd wife]

stay Carriage Way Bed & Breakfast Inn go


day 2

breakfast Carriage Way Bed & Breakfast Inn

historic tour with Sam West aboard St. Augustine Sightseeing Trains go – introduction to St. Augustine

tour Flagler College (Former Ponce de Leon Hotel) go

lunch with Henry Flagler (portrayed by reenactor), a very special St. Augustine resident, at 95 Cordova (Casa Monica Hotel) go

visit local artists on Aviles Street – painters, potters and cobblers at work. These artists create some of St. Augustine’s finest works of art in original art district of St. Augustine.

visit Gonzalez-Alvarez House (known as Florida’s Oldest House) – historic St. Augustine home, located at 14 St. Francis St. – U.S. National Historic Landmark go

late afternoon O.C. White’s Restaurant go – refreshments with a twist! and visit by Three Sheets to the Wind Pirates, followed by early dinner

take Ghosts & Gravestones night tour go 90 minute Trolley of the Doomed Frightseeing tour – visit Spanish Military Hospital (certified haunted building) and haunted Old Drug Store – meet spirits that live there. Then a short Trolley ride past graveyards, to frightening wind up in jail cell in Old Jail, next to the gallows

stay Carriage Way Bed & Breakfast Inn go





day 3

breakfast in Gazebo at Plaza de la Constitucion – special presentation by Marie Pacetti (portrayed by reenactor), a 1778 Menorcan settler

take St. Augustine Eco Tour by boat around St. Augustine Municipal Marina harbor with Zack McKenna go

visit St. Augustine Lighthouse LAMP program marine archeologists go followed by climb up 219 steps to tower top observation deck

lunch The Spanish Bakery go tucked away in out of the way garden in middle of St. Augustine Downtown Historic district

visit Panama Hat Company of St. Augustine go

relaxing St. Augustine Scenic Cruise on Victory III go

visit Inn on Charlotte go sit on “Coffee Cake Challenge” panel – help owner Lynne Fairfield determine best entries in nationwide contest for “best coffee cake recipe”

drive across Bridge of Lions to St. Augustine Beach

dinner Barnacle Bills go

stay Holiday Inn on St. Augustine Beach go






day 4

breakfast and tour Holiday Inn on St. Augustine Beach go

visit St. Augustine Florida coquina quarry go
presented by Spanish Soldier (portrayed by reenactor)

explore St. Augustine Alligator Farm Zoological Park go

see Fountain of Youth go

lunch Subway (final local color) go

leave St. Augustine for home on Tran Air





Thanks to all who helped create this fine experience

Raintree Restaurant

Carriage Way Bed & Breakfast Inn

95 Cordova (Casa Monica Hotel)

O.C. White’s Restaurant

The Spanish Bakery

Barnacle Bills

Holiday Inn on St. Augustine Beach

St. Augustine, Ponte Vedra & The Beaches Visitors and Convention Bureau
     Barbara Golden, Communications Manager

     Jay Humphreys, Communications Director

     Glenn Hastings, Executive Director