St. Augustine Guest Houses

Taste of St. Augustine
2021-04-25 11:00 - 17:00 (America/New_York) | St. Augustine Amphitheatre, 1340 A1A South, St. Augustine
This signature food festival at the St. Augustine Amphitheatre serves up tastes from St. Augustine’s famous restaurants. From 11 a.m.-5 p.m., the area’s best restaurants will offer samples of their signature dishes. Restaurants will compete for the prestigious TOStA (Taste of St. Augustine) awards, with categories including Best Family Dining, Best Ethnic, Best Upscale and Best Dessert, as well as the ever-popular People’s Choice. Everyone gets to vote. There will be children’s area with fun activities including crafts and face-painting as well as live music throughout the day. Admission is $5 and taste tickets are $1 each with restaurants charging between 1-5 tickets per taste. 1340 A1A South, St. Augustine 904-829-3295

Lady’s Day at the Raintree
2021-05-01 13:00 - 16:00 | Raintree Restaurant, 102 San Marco Avenue, St Augustine, FL, 32084, United States
Join us for an afternoon of fun, fizz and fashion on Saturday, May 1st.
Fluff up your finest Derby Hat and celebrate the Kentucky Derby with Hopefull Handbags at the Raintree Restaurant in uptown St. Augustine!
After some welcome champagne on arrival, you will be treated to a Raintree favorite, their Salmon baked with a Lobster Champagne Cream Sauce, followed by their classic brownie bites dessert. You can continue in celebration mood during the afternoon with bottomless champagne on hand. Mint Juleps will, of course, be available (pre order please)
for just $5.
But hold your horses, there so much more! Everyone who wears their most imaginative millinery will be in the running for the first prize in the Best Hat Stakes. Trot around the vendors’ stands and peruse everything from jazzy jewelry and stylish apparel. There will also be fine fillies parading chic fashions. It will be an afternoon of galloping fun with your best girlfriends!
All net proceeds go directly to Hopefull Handbags which provides support and help to those who have suffered domestic abuse. In addition to giving them hope, we also give every victim a handbag filled with essential items.
If you care to bring a new or gently used handbag, we will pass it on to HH. For your kind donation, you will receive an arms’ length of tickets for our sensational prices.
Don’t be saddled with the shopping on Saturday, May 1. For just $75 our Ladies’ Day wins hoofs down! Join the winning connections at the Raintree on Saturday, May 1st. Everyone’s a winner.

Announcing the Ninth Annual Derby Run, a Benefit for Community Hospice & Palliative Care
2021-05-01 17:00 - 20:00 | St. Augustine’s Tringali Barn
Celebrate the 147th Kentucky Derby at St. Augustine’s Tringali Barn on May 1, 2021, from 5 to 8 p.m., with food, fashion and fun at the ninth annual Derby Run, a benefit for Community Hospice & Palliative Care. Derby Run proceeds support quality, compassionate Community Hospice care for St. Augustine and St. Johns County residents.
We are making necessary adjustments to enjoy this event in a safe fashion. For more information, contact Community Hospice & Palliative Care Foundation at 904.886.3883.

Humane Society Pin Up Paws Calendar Contest
2021-06-01 08:00 - 2021-08-07 20:00 | online
Calling all pets from sea to shining sea: the 11th Annual Pin Up Paws Calendar Contest awaits!
Your pet has the chance to be featured in the St. Augustine Humane Society’s 2022 “Paws Across America” Pin Up Paws Calendar. Snap an adorable photo of your pet, and enter our contest today! Be sure to add a fun description letting people know why they should vote for your pet.
For every $1 raised, your pet will receive one vote. All money raised will directly support the Humane Society’s lifesaving programs and resources. By participating in the contest, you are helping the many pets who would otherwise not receive the care they need.
The pet with the most votes at the close of the contest on Saturday, August 7th, will receive the coveted cover spot for the 2022 “Paws Across America” Pin Up Paws Calendar Contest. The 12 pets with the next highest number of votes will be our Second Place Winners.
All First and Second Place Winners will be a part of a special photoshoot with award-winning photographer, Addison Fitzgerald. Each month will feature winning pets in front of classic American images, such as the Redwoods, Statue of Liberty, Grand Canyon, and more, along with classic Americana props. For a full list of all the prizes, be sure to check out our “Prizes” page!
We will reveal the 2022 “Paws Across America” Pin Up Paws Calendar at our Pin Up Paws Party on Thursday, October 21st! Our PUP Party is always fun, and this year will be no exception. Look forward to a delicious dinner, live music, silent auction, wine pull, and more!
We are so excited for this year’s contest, and hope you are too. For more information and to enter, please visit www.PinUpPaws.com
