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St Augustine, FL- USA's Oldest City Weekend
40's - 50's and 60's+ Singles Weekend

April 13 - 17, 2022


St Augustine is America's oldest city, known for its rich heritage, beautiful shoreline, historical attractions andclaims to be one of the most haunted destinations in the United States. Sip from the Fountain of Youth, step back in time at the Old Jail and cruise along the shore of Matanzas Bay. Enjoy all this and more as you join a fun group of singles as we explore the Oldest City in the USA.

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St Augustine - The Oldest City in the USA Singles Weekend Itinerary

St AugustineVacation Day 1 - Wednesday - Jacksonville Airport - St Augustine
Upon arrival at the Jacksonville airport (airport code JAX) take the provided shuttle to St Augustine. The shuttle will run at 12:00pm, 2:30pm and 5:00pm. Upon arrival in St Augustine you will check into the group's hotel, Doubletree by Hilton St Augustine Historic District. The hotel is centrally located, about 1/2 mile from the Historic District, Castillo de San Marcos, and Ponce de Leon's Fountain of Youth so arrive early and enjoy the afternoon. Meet and greet with your group leader and other single travelers at 7:00pm for our first look at the oldest city in America.


Vacation Day 2: Thursday - Old Jail - Trolley Tour - Castillo de San Marcos - MOJO BBQ - Ghost Tour
Old JailAfter breakfast we will stroll, about a 1/3 mile to the first stop on the Trolley tour, the St Augustine History Museum and the Old Jail. The Old Jail gives us a glimpse into the daily lives of St. Augustine’s most notorious prisoners of the 19th and early 20th centuries. Costumed actors tell tales of the jail and its occupants, and can even book you as an inmate.
Visit the History Museum, divided into several galleries and see how tourism started with the arrival of the Cracker pioneers and their covered Conestoga wagons. Learn about the ‘Tin Can Tourists,’ known for eating canned foods, and the vehicles they drove like a fully restored 1927 Ford Model T pickup camper. Time to step onboard the Old Trolley RideTown Time Trolley for an overview of the historic center of St Augustine. The Trolley route encompasses seven miles of fascinating history as recounted by one of their highly-trained tour conductors. We will get off at stop 14 so we can walk, the famous St George Street, a designated walking mall, located in the heart of the historic district. With charming shops, museums and historic buildings on every corner, visitors from all around the world dine and shop on St George St. Enjoy free time for lunch and shopping as we stroll along this 11-block stretch of stores, restaurants and historic sites.
Castillo de San MarcosThis afternoon visit the oldest masonry fort in the continental United States, the Castillo de San Marcos. Sitting on the shore of Matanzas Bay, the Fort was constructed in 1672 to guard the coast of St. Augustine against foreign invasion. Take a self-guided tour of the historic National Monument and learn about its fascinating history. There are a variety of exhibits to view, daily Ranger Talks, a short video every hour that features cannon and musket firings and weapons demonstrations and presentations by costumed re-enactors.
Oldest School HouseThen we Trolley back to the Doubletree to relax and change for dinner. Put your walking shoes as on tonight we get to see the spooky side of St Augustine on our Walking Ghost Tour. First we walk the 1/2 mile back to St George Street to get our MoJo on at the MOJO BBQ, a premier barbecue, southern food, and craft cocktail destination. Locals say the historic buildings and cobblestone streets are filled with spirits who once lived in St Augustine hundreds of years ago. Tonight we visit historic cemeteries and other well-known landmarks, learning about spirits from the past, share paranormal investigations and St Augustine's most interesting haunted discoveries.


Vacation Day 3: Friday - Mission Nombre de Dios - Fountain of Youth - Winery - Cruise
Mission Nombre de DiosAfter breakfast we will walk to the Fountain of Youth, stopping at the Shrine of Our Lady of La Leche at Mission Nombre de Dios, located at the Great Cross on the way. It was on these grounds that Father Lopez celebrated the first parish Mass and began the work at America's first Mission. At Mission Nombre de Dios, we will find numerous artifacts, both sacred and secular, from the very beginning of the Spanish settlement in St. Augustine.
Fountain of Youth entryFountain of Youth Archaeological Park is a 15 acre waterfront Historical Site where St. Augustine was founded. Stroll through this waterfront park where peacocks strut and shady oaks beckon us to stay. This is the location where Spanish Explorer Pedro Menendez de Aviles, in 1565, established the first and oldest continuous European Settlement in the United States. For over 4000 years, Native Timucua Indians prospered on this land, hear their story, see Fountain of Youththeir skills for survival and learn their customs. Our exploration begins with a drink from the Legendary Spring and learn the history of Ponce de Leon's search and his Spanish claim for Florida. Then we will visit the burial grounds and explore the historical landmarks.After a wonderful morning we will take the Trolley to St George street for free time for lunch before we hop back on and hop off at Stop 12, the San Sebastian Winery. Enjoy at leisure a self-guided complimentary tour and wine tasting. A short audio-visual presentation in the upstairs theater explains the art of winemaking and the importance of the 5,000 gallon stainless steel tanks where the wine is fermented and stored prior to bottling.
cruise st augustineNext it's time to relax and cruise the waters of historic St. Augustine on an hour-and-fifteen-minute boat ride narrated by the captain. Enjoy picturesque views of historic Saint Augustine and dolphins and birds in their natural habitat, while cruising along Matanzas Bay to and from North Beach. Then we will leisurely walk back to the hotel stopping along the way for an optional dinner.

Vacation Day 4: Saturday - Alligator Farm - Farewell Dinner

Alligator Farm St AugustineAfter breakfast we will trolley to St George Street, where we will switch to the Beach and Alligator trolley. The Alligator Farm Zoological Park features a variety of animal species, including hundreds of native alligators. Exhibits include lemurs, Komodo dragons, toucans, and a sloth exhibit. The park is the only place in the world to see all 24 species of crocodilians in one place. The Alligator Farm offers an optional intriguing zip line and aerial adventure course called Crocodile Crossing. You can coast at eye-level with exotic birds and dangle above crocodiles on one of two courses that reach up to 30 or 60 feet St Augustine nighthigh. Visit the Park at your leisure as the rest of the afternoon is free.
Make your way back to the hotel using the trolley or hang out with our group leader as they spend the rest of the afternoon in the historic district. Tonight we will feast at our Farewell Dinner at one of St Augustine's seafood restaurants.


Vacation Day 5: Sunday - Depart St Augustine, Florida
Sad to say but our St Augustine singles weekend comes to an end today. Enjoy breakfast and then take the provided shuttle to the airport according to your flight schedule.


St Augustine, Florida Singles Weekend

April 13 - 17, 2022

Price: $1549*

Singles Getaway Vacation Includes
* 4 Nights Accommodations
* Breakfast Daily - Welcome Dinner & Farewell Dinner

* All Activities and Tours listed above

* Airport shuttles at specific times on tour days
* All Taxes and Surcharges

*The price per person is for a double room. Free roommate matching is available on all our vacations, so there is never a need to pay a "single supplement". If you wish to room alone it is an additional $750

Not Included

* Airfare
* Gratuities



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