St. Augustine Guest Houses

Holiday in the Gardens
2019-12-08 10:00 - 16:00 (America/New_York) | Washington Oaks Garden State Park, 6400 N Oceanshore Blvd.,, FL
Take advantage of the crisp December air with a stroll through one of the area’s most charming state parks. Not only will the gardens be festively decorated, but the park will also be playing host to Mr. and Mrs. Claus as well as arts and crafts for the little ones and live entertainment all day. Bring the whole family along for some festive holiday fun and some beautiful Florida scenery.
Admission is free with the donation of toys or canned goods.

Toy Drive at Jacksonville Ice and Sportsplex
2019-12-08 12:00 - 15:00, 2019-12-13 19:00 - 22:00, 2019-12-14 12:00 - 16:00 | Jacksonville Ice and Sportsplex, 3605 Phillips Hwy, Jacksonville, FL, 32207
During select sessions in December, when you bring a new, unwrapped toy to Jacksonville Ice, you get $2 off Public Ice Skating Admission! The toys will benefit low-income children and families in the surrounding communities of Jacksonville.
Sessions:
Saturday, December 7th from 12 – 4 pm
Sunday, December 8th from 12 – 3 pm
Friday, December 13th from 7 – 10 pm
Saturday, December 14th from 12 – 4 pm

Christmas Tour of Homes
2019-12-08 12:00 - 17:00 | Downtown St. Augustine, 29 West Castillo Drive, St. Augustine
Now in its 50th year, the popular annual Christmas Tour of Homes is hosted by the Garden Club of St. Augustine. Guests will get a once-in-a-lifetime look inside some of the city’s most beautiful historic homes, all decorated for the holiday season. The walking tour can be taken at each guest’s own pace from 12-5pm. In addition to the tour, make sure to visit the Garden Club’s “Unique Boutique,” which offers delicious treats and many hand-made items created by the Club’s members as well as an Afternoon Tea.
Tickets are $30 per person and sell out quickly, to purchase click here.

St. Augustine Winter Spectacular!
2019-12-08 14:00 | Lewis Auditorium at Flagler College, 14 Granada St, St. Augustine, FL, 32080, United States
The St. Augustine Winter Spectacular is a family-friendly, entertaining holiday production that follows a young girl’s journey during the holidays.
Filled with a variety of dance styles, characters, and holiday scenes to kick off the season, the show offers an exciting and unique experience for St. Johns County residents and visitors. You can expect high-kick dancers, ballerinas, acrobats, actors, and more amidst dazzling costuming and props. The Dance Company’s elite Performance Ensemble comprises the majority of cast members as well as other dancers and performers who auditioned for roles.
Now in its 7th year, the St. Augustine Winter Spectacular has become a family tradition to celebrate in St. Augustine! Enjoy refreshments in the lobby, a silent auction with gift ideas, and more!

Menorahs and Merlot
2019-12-08 14:00 | St. Augustine Beach City Hall, 2200 A1A South, St. Augustine Beach, FL, 32080, United States
In honor of the upcoming holiday of Chanukah, the Jewish Women of St. Augustine are hosting the “Menorahs and Merlot event.” Inviting women to come together and design and craft their very own menorahs while sipping on wine and enjoying delicious latke treats.
This event is intended to bring the women of the community together while having fun and creating something beautiful!
This event is for women and girls 12 and older.
Admission
Tickets are $8 and RSVP required.
To RSVP to this event, please contact one of the organizers below:
Fraidy Vogel – Fraidyk@gmail.com
Karen Stern – Kstern426@gmail.com
Cathy Kasriel – Georgiagaiter@gmail.com

The Rescue of Santa Claus
2019-12-08 14:15 - 15:45, 2019-12-14 14:15 - 15:45 | Black Raven pirate ship, 111 F Avenida Menendez, St Augustine, FL, 32084
Every Saturday and Sunday on our 2:15 departure time, the crew of the Black Raven and her passengers will have to rescue Santa Claus from the Evil duo Captain Hook and Blackbeard! Santa joins the crew until he is kidnapped by those evil pirates! The kids will learn swordfighting and have their faces painted as we gear up for the big sea battle to save Santa and restore Christmas for all the children. Once saved, all the children will get a present from Santa. Pictures are welcome so bring your camera!

Star Gazing at TrailMark
2019-12-08 18:00 - 20:00 | TrailMark, 805 TrailMark Drive, St. Augustine, FL, 32092, United States
Come join the TrailMark Community for a night of stars with the Ancient City Astronomy Club
Telescopes Available OR Bring your own Telescope
Come for the stars, stay for the hot cocoa bar!
Open to the Public – Free Event
Sunday, December 8, 2019
6 – 8 PM
***WEATHER PERMITTING***

Star Gazing Event
2019-12-08 18:00 - 20:00 | TrailMark Community, 805 TrailMark Drive, St. Augustine, FL, 32092
Looking for a free event this weekend that’s family friendly? Come out to TrailMark (right off Pacetti Rd) to do some star gazing! We’re partnering with the St. Augustine Astronomy Club to get en even more in depth look at the stars. Bring your own telescope if you have one, if not no worries! The Astronomy Club is setting up theirs as well. We will also be setting up a Hot Cocoa Bar in the Welcome Center. Parking on site. Hope to see you there! Please RSVP! ***WEATHER PERMITTING***

Old Town Trolley Nights of Lights Trolley Tours
2019-12-08 18:00 - 21:00, 2019-12-09 18:00 - 21:00, 2019-12-10 18:00 - 21:00, 2019-12-11 18:00 - 21:00, 2019-12-12 18:00 - 21:00, 2019-12-13 18:00 - 21:00, 2019-12-14 18:00 - 21:00 | Visitor Information Center, 10 West Castillo Drive, St Augustine, 32084
he holidays are popular for enjoying time-honored traditions like gift-giving, bonding with family, and decorating your home in the spirit of the season. Here in America’s Oldest City, we take the latter to a whole different level. Inspired by an ancient holiday practice brought here by the Spanish of displaying lit candles on window sills, The Annual Nights of Lights is set to brighten up the holidays in The Ancient City once again! To experience the glow of the season and the more than 3 million lights adorning every corner of the city’s historic district, take a ride on Old Town Trolley’s Nights of Lights Tour!

Wednesday Pier Farmers Market
2019-12-11 08:00 - 12:00 | St. Augustine Beach Pier, 350 A1A Beach Blvd, St. Augustine Beach, 32085
The market is a destination, a place that serves as a setting for the community and visitors to the area to gather and learn something new from a farmer, grower, producer or local artist. To build a community where we work and live. We support local economy, increase market opportunities for farmers and small businesses, and provides access to an assortment of local and regional sourced products.

World Golf Village Night Market
2019-12-11 16:00 - 19:00 | World Golf Hall of Fame, One World Golf Place, St. Augustine
On the second Wednesday of each month, World Golf Hall of Fame holds a night market from 4-7pm.
The market offers farm fresh produce, homemade and handmade products of all kinds, and food and beverage trucks. It also features a bounce house for the kids.
Admission to this event is free.

Dickens Illuminated Procession at Amelia Island
2019-12-12 17:00 - 20:00 | Downtown Fernandina at Amelia Island, 102 Centre Street, Amelia Island, FL, 32034, United States
Northeast Florida’s Amelia Island’s tradition of transforming downtown Fernandina Beach into a festive Victorian Christmas village will take place once again this year! This free event takes visitors back in time to experience Charles Dickens’ early Victorian era Britain, with themed characters and entertainers, festive lights and holiday décor, period vendors, exciting seasonal entertainment, a petting zoo and tastes of the holidays. This year, they will be introducing a brand new event, the Dickens Illuminated Procession will be a unique walking lantern parade of glowing holiday cheer. Other returning annual favorites include photos with St. Nick, Tiny Tim’s Kids Zone, the adults-only Dickens After Dark, and the Christmas Wish booth. Downtown restaurants, shops, art galleries, and other local businesses will be participating, along with period street vendors selling handmade crafts and special holiday treats. Don’t miss out on this festive event and get ready to celebrate the season!

Owl Prowl
2019-12-13 17:15 - 19:45 | Vaill Point Park, 630 Vaill Point Road, St. Augustine, FL, 32080, United States
Learn all about these big-eyed creatures at this educational event. Park Naturalist, AyoLane Halusky will take you on a tour to explore our county parks at sunset in search of our resident owls who live inside our parks.
Bring your questions and curiosity for this nighttime event that will have you leaving with plenty of knowledge regarding these creatures of the night.
Admission
This event is FREE and open to all ages, but you must register to attend. To register for this event, click here.
For more info, contact AyoLane Halusky at ahalusky@sjcfl.us or 904-209-0348.

Family Night D&D with Artist Ron Vellucci
2019-12-13 19:00 - 20:30 | Butterfield Garage Art Gallery, 137 King Street, St. Augustine FL, 32084
Go Art offers a variety of art tours and events around northeast Florida. Tours are scheduled from St. Augustine through the Beaches and around Jacksonville. Go Art curates tour and experience options to offer some of the strongest most engaging art from this area.
Ron Vellucci is a sculptor of elegant yet playful mixed media sculpture. When he won first place at a Florida Artist’s Group annual exhibition, the judge, Stephen Knudsen, of Savannah College of Art And Design commented, “Clearly the piece is a signifier of a stainless-steel portal. If the door opened its moving panels would be as complicated as gears in a clock. A bit of Zoomorphic looking slice of wood and found ammonite seemed to me to be signifiers of the natural world in relationship with the polished, the artificial, and the future.”
This out-of-the box event is for families to enjoy the art gallery through an evening of games inspired by art. Ron Vellucci. These works will invite families to share their imaginations through looking and creating storylines inspired by the art. At the same time, the grownups will appreciate the quality and depth of content present in these sculptures.
Go Art will be cooperating with Emerald Dragon Games of Fleming Island to bring a memorable family night of art and games to Butterfield Garage Art Gallery.

Bed & Breakfast Holiday Tour
2019-12-14, 2019-12-15 | Downtown St. Augustine, 29 West Castillo Drive, St. Augustine
The 26th Annual Bed and Breakfast Holiday Tour is back once again for another year. This event features a tour of over 20 bed and breakfasts located in the heart of downtown St. Augustine. Multiple museums and historical sites will be open to participate with the tour on both days and on the bonus day of Monday, December 16, 2019. This year’s theme is “The Movies of Christmas” and guests are invited to enjoy the tours alongside festive presentations. Take part in this walking tour and even enjoy some delicious food at the bed and breakfasts catered by some of the best restaurants in town.

Visit here to purchase tickets.

Santa Suits on the Loose 5k 2019
2019-12-14 08:00 - 10:00 | St. Augustine Beach Pier, 350 A1A Beach Blvd, St. Augustine Beach, 32085
ST. AUGUSTINE YOUTH SERVICES (SAYS) is celebrating 30 years of serving children in St. Johns County! Help us continue our celebrations at the 8th Annual Santa Suits on the Loose 5k.
Santa Suits on the Loose 2019, will be held on Saturday, December 14, 2019 beginning and ending at the St. Augustine Beach Pier. There will be a choice of Santa Suit or Shirt to wear during the walk. 100 Santa Suits will be available.
SAYS, a non-proﬁt, shapes the future of Florida’s at-risk youth by providing coaching, counseling and care in family style therapeutic group homes and outpatient community services. Race proceeds, thanks to the help of many volunteers and sponsors, help us to provide therapeutic services and ‘normal’ life experiences for foster kids and youth with mental health diagnoses, especially during the holiday season.
Early Bird Price (Open Now!): $20
October 1st: $25
November 1st: $30
Packet Pickup & Race Day: $35

St. Augustine Amphitheatre Farmers Market
2019-12-14 08:30 - 12:30 | St. Augustine Amphitheatre, 1340 A1A South, St. Augustine
Fresh food, artisan goods, local arts and music, and community from vendors that set up each Saturday outside of the St. Augustine Amphitheatre. Come out to do your weekly shopping or just to explore everything that’s offered by area artisans and growers. No pets please.

St. Augustine Flea Market
2019-12-14 09:00 - 16:00 | St. Augustine Flea Market, 2495 FL-207, St. Augustine, FL, 32086, United States
Come shop and enjoy yourself with an array of booths and vendors, fun things to do, fresh food, and plenty more at the weekly St. Augustine Flea Market.

Hastings Hometown Christmas Parade
2019-12-14 10:00 - 13:00 | W.E. Harris Community Center, 400 E. Harris Street, St. Augustine, FL, 32084, United States
Sponsored by Friends of the Hastings Library, Rotary Club of Hastings, and Team UP Hastings, this year’s annual Hasting’s Hometown Christmas Parade will take place on Saturday, December 14 at 10am. Enjoy the beautiful procession that will take place on Main Street and enjoy the company of local vendors and residents who participate in the event.
For more info, contact the Hastings Library at 904-827-6970.

Regatta of Lights on Tall Ship Freedom
2019-12-14 17:00 - 20:00 | Schooner Freedom, 111 Avenida Menendez Slip 86, St. Augustine
Join the 2018 Grand Prize Winner as we parade in the annual regatta of lights for our 19th year in a row!
CALL (904)810-1010 TO MAKE RESERVATIONS
Join us this year for the lighted boat parade as the Freedom competes in this yearly event hosted by the St. Augustine Yacht Club. See all the decorated boats from the water and wave to the crowds as we pass by the fort on this fun night of holiday fun! The Freedom is decorated to a different theme every year, dress up and have fun participating in our themed cruise!
Time of departure to be determined closer to date. Reservations are highly recommended.
Duration: ~2 hours
Rate: $65 Per Person
There is a $5 per person cash discount
Includes complimentary soda, water, beer, wine, and hot chocolate.
Blankets provided for chillier evenings, but be sure to dress warm!
