Some vacations help you unplug. The best ones help you reconnect. Enter for your chance to win a getaway to St. Augustine Beach, Florida. From relaxing on the beach to exploring the charm and history of America’s oldest city, this unforgettable vacation is all about slowing down, making memories, and experiencing the very best of Florida.
Life’s too short for ordinary days. Live More Floridays.
Enter at the bottom of the page!
The vacation package includes:
- Three (3) consecutive night stay at Guy Harvey Resort St. Augustine Beach, including daily breakfast for two
- One (1) guided horseback riding beach tour for two (2) with Equestrian Adventures of Florida
- One (1) $100 gift card to the Columbia Restaurant St. Augustine
- Two (2) tickets for the Old Town Trolley Tour, including unlimited hop on, hop off privileges.
- Two (2) admission tickets to the St. Augustine Alligator Farm Zoological Park
- Round-trip coach class airline tickets for one (1) winner and up to one (1) guest to Jacksonville International Airport
- A midsize rental vehicle for four (4) consecutive days
Live More Floridays
Guy Harvey Resort on St. Augustine Beach
Come to paradise and stay at this boutique resort Guy Harvey Resort on St Augustine Beach. Guy Harvey Resort is located directly on St Augustine Beach, minutes away from the historic downtown area known as the oldest city in America. Guests can relax in the sun by the outdoor pool and enjoy food and beverage at the Surf Shack Tiki Bar. Santiago’s, a contemporary restaurant and bar is open for Breakfast, Lunch, and Dinner. The Guy Harvey brand resonates throughout the resort, bringing a strong connection to the ocean, marine life, fishing, and the Florida coastal lifestyle. Enjoy shopping for Guy Harvey merchandise onsite at our outfitters shop. Relax. Go with the flow!
Equestrian Adventures of Florida
There is no better way to experience Florida’s natural scenery than from horseback. At Equestrian Adventures of Florida, we take pride in our horses and what our experiences have to offer: A unique look at Florida’s amazing beaches, state parks, and preserves. Explore old Florida through oak hammocks, along bluffs and rivers, wide open spaces, and winding trails.
The Columbia Restaurant – St. Augustine
Family owned for more than 115 years, the Columbia has earned acclaim for old-world charm and award-winning Spanish/Cuban cuisine and wine. Enjoy century-old family recipes in our Mediterranean-style dining rooms, filled with hundreds of hand-painted tiles and Spanish-style fountains. The Historic St. Augustine location is a sister to the Columbia in Tampa’s Ybor City, Florida’s Oldest Restaurant founded in 1905.
Old Town Trolley Tours – St. Augustine
Discover St. Augustine aboard Old Town Trolley Tours, where more than 450 years of history, fascinating stories, and unforgettable sights come to life. Explore America’s oldest city while enjoying a fully narrated tour through the historic district and beyond. From historic landmarks and museums to charming streets, shops, restaurants, and waterfront views, Old Town Trolley Tours makes it easy to experience the best of St. Augustine. Hop on and off at convenient stops throughout the city to explore the attractions that interest you most, then continue your adventure when you’re ready.
St. Augustine Alligator Farm Zoological Park
The St. Augustine Alligator Farm Zoological Park’s diverse collection of inhabitants extends beyond alligators and is the only place in the world to see all 24 species of crocodilians. Thrill-seekers can zipline over the zoo, enjoying an aerial perspective of the park’s tropical birds and lemurs while alligators and crocodiles sun themselves below.
Heather Furr
Heather is the Colorful digital director of the Bob & Sheri Team, She helps out with our Video, Livestreams, Social Media, Tech issues, Podcasting and so much more! Heather is cat & lizard mom from North Carolina who whenever she's not fighting with the Facebook algorithm or bullying wordpress is probably gardening, reading or playing videogames!
Wanting a getaway with hubby after 17 years of wedded bliss. We are a family with 3 kids that are active in band, swimming and after school activities like a DnD club that our oldest started at school. We do have a camper that we visit almost every weekend and while that is our family getaway, hubby and I need a couple getaway.
How do we enter the contest? We love St. Augustine!
Well..this looks like an awesome vacation! And I could use one! Got my fingers crossed! Long time listener here. Appreciate all you guys do!
I am a listener and I simply love your show!!
I would love to win this trip.
I’m a long time listener and love your show.
Been listening for years. I love you guys!!!!!!
Love the show
I am a daily listener and love your show!
I’ve been listening since Sheri was pregnant with Caramia. You are all my family now and I do let people know that. Have a wonderful day.
I’ve been a long time listener since the beginning! So happy that Lamar has become a permanent host on the show too! Love all you guys so muc
We are long time listeners and love the show. Our grown children appreciate that we still listen, they have fond memories.
It has been a rough year with a need for a getaway. A moment to reset, take a breath and enjoy the St. Augustine would be appreciated.
Cool!
This would be such a great trip! I have visited, but never stayed in St Augustine fingers crossed!🤞
So excited to even be considered to win this amazing get away! I am a teacher beginning much 33th year in Elementary Education and began listening when my now 27 uear old daughter was born. Love your show and each of you through all the changes!!
I would be thrilled to get away with my husband! We haven’t gone on a trip like this, so it would be pretty amazing!
Never been to St. Augustine! I love people, travel, food, new experiences! This would be awesome. I have been a nurse for over 40 years and am hoping to retire in the next year or so! This trip would be a fantastic Segway to retirement!
This would be amazing!
Well..this sounds like a wonderful vacation! And I sure could use one! I got my fingers crossed! Oh..and I’m a long time listener. Thanks for all you guys do to entertain us and make us feel like we’re family:)
Get away? What is get away ???
Yes I’m that lost and it’s been that long
With twin girls who just stared middle school, and parenting our 19 year old nephew through the beginning years of young adulthood, my husband and I are exhausted. This would be the perfect way to celebrate our upcoming 20th wedding anniversary.
PICK ME! PICK ME! PICK ME! ☀️🏝️🐚
I have teenagers and pets. I’ve been a nurse for 28 years. This economy is killing me. What more can I say!? Please pick me!☀️😵💫❤️
I love St. Augustine and the Bob & Sheri Show!
Would love to win!!
Y’all bring normalcy to my crazy retirement in paradise. I moved here 5 years ago. 2 of my 4 children followed. I spend my days fostering puppies and kittens and love it!! I may not have house beautiful but I love it here. But sometimes, ya just need to get away!!
Could certainly use this vacation and visit with my daughter.
In the past year I’ve retired as a teacher (30 years), missed the last step coming out of the camper and dislocated my shoulder (surgery to repair), been hospitalized twice it’s where I am now) with diverticulitis and the home i was in the process of buying fell through. I need a fun getaway to ease my troubles!
I am single and work 2 jobs; listening to Bob and Sheri is what helps me make it through my 14 hour shifts!!! I haven’t been on vacation for YEARS, so this would be a welcome and much needed break! A trip with my bestie and some much needed girl time!
We would love this getaway!!
Would love a getaway . Never been out of my hometown .
I would love to win. I’ve never been to Florida.
I’m in the middle of a divorce and yall are my sanity (insanity?) every morning. Nothing would make me happier than a beach getaway. 🩵 Thank you for always being there for us!
This is my go to for podcast daily. Long time listener.
Also love STA my favorite beach and town.
I would absolutely love to win this trip!
Would love to win this. And if I do, hopefully I can talk the husband into going with me. Thank y’all for the opportunity!
HEY YOU GUYYYYYS!!!
Designer of the “Are you there Doc” merch ❤️ My daughter and I would be thrilled to spend a few days in St. Augustine 🙏 We love historical places… were down for a spookable hunt too 😁
Hoping to go for the Billy Strings shows in April!!!
Pick me… pick me PLEASE!!! 🙂
Would love to win this for my 10 yr wedding anniversary! Love listening to you guys every morning!
I’ve heard so much about how beautiful St. Augustine is. Would love to see the history there.
With everything we are going through, this would be a blessing.
This trip sounds amazing! Thank you all!!
Absolutely love you guys. Longtime listener. Would love to spend this time with husband. Looking forward to hearing about it from whoever wins this fabulous trip!!
Thanks for the opportunity. Fingers crossed!
Have been a fan of your for years. Love the show! St Augustine has been on my bucket list of places to visit.
I’m a tired health care provider who has been a listener for almost 30 years and haven’t been on vacation for a very long time. A vacation would be wonderful! 😊
This would maybe be the trip to “reconnect” for me and my husband,we are possibly losing our house to foreclosure and we are becoming more distant in our marriage because of it.
Kids are almost completely out of the house and doing great,we on the other hand ehh.
So good luck to everyone but just a little more luck for us though! Love the show,you guys are all amazing!😼
We will celebrate our 55th anniversary in February 2027. I’m still in awe that she has put up with my antics for so long. A sunny retreat in St. Augustine would be the cherry on top of the sundae since we stopped there on our honeymoon in 1972!!!
St. Augustine isn’t just a vacation destination to me.. it’s a piece of my childhood. ❤️ Growing up, I visited every year to spend time with my grandparents, and so many of my favorite memories are tied to those trips. There’s something incredibly special about returning to a place that once felt so magical as a child and now getting to experience that same magic through the eyes of my own children.
Winning this trip would give us the chance to make a new chapter of family memories in a place that already holds so many old ones. I would love nothing more than for St. Augustine to become one of those special places my children grow up remembering, too. It would truly mean the world to our family. ❤️
St. Augustine is beautiful! I was lucky enough to visit last December for 3 days to view the Christmas lights. I want to go back and see more!
Never been to St.Augustine, but have heard a ton about it. My boyfriend tells me about it all the time. (He lives in Florida and I am in NY.)
Love the show!
My hubby and I listen to your show and podcast all the time. Sending our last baby off to UNC Charlotte today. I will be clutching my emotional support car condiment box all the way home.
Love your show and podcast!
I’m a longtime listener and would love to win this trip! Everyone has been to the beach this year except me.
The memories that could happen with a trip like this!!
What a fantastic trip! Thank you for planning things like these for your listeners!
Never been to St. Augustine but my his dad and I have wanted to for years. We will be married 33 years in November and this would be an awesome gift for us.
Never been to St. Augustine but my husband and I have wanted to for years. We will be married 33 years in November and this would be an awesome gift for us.
Long time listener!! I’m ready for a getaway please send me!!!
My 16 year old daughter would love this the horses alone the beach the trolleys she must be an old soul but man it would be a dream come true. The food the atmosphere the getaway it all would be a blessing.
I love St. Augustine so much! Thanks for the opportunity to win. You all crack me up!
I have the St. Augustine Lighthouse tatted on me 🖤 This town is my absolute favorite. From Potter’s Wax Museum, to Ripley’s Believe it not, to the cobble stone road ways. I would love to win this and take a friend.
Never won anything before and always wanted to get a paid vacation. Love your morning show. Been a fan for as long as you been on air. The crew you have is fantastic and very interesting topics.
Thank you for your humor. Sometimes you are the only laugh i get all week.
I really need this getaway!!!!
Love the show and winning stuff is fun!
Sounds Awesome
I listen to your show every morning on the way to work. It is what got me through losing my son last year. I love you guys!!! And did I mention that I have not had a vacation since 2019!!!!! 😂😐😂
My husband and I are retired teachers. This would be an awesome getaway!!
The trip sounds phenomenal! Only thing that would make it better – a dog friendly hotel :).
MEMEmemememe!!
my anniversary is today August 13th. married in 1972. it would be a nice surprise for my husband. He would love it thanks so much ❤️
I love you guys! I do miss Bob’s little bits of wisdom though. But I have the book of Bob if I get too desperate. 🤣 I’ve listened to your show since 2000 when I worked the midnight shift at a distribution warehouse. One of my favorite Lamar stories is the one about his mom sitting by the window hoping to see them pull up. 🤭
I’ve listened to some of your “Weird” podcasts too. ♥️
My husband and I haven’t been on a vacation since we got married in 2007. 😲 He and I both retired this year and this would be so amazing to win!!
You guys are great! Never stop making the world laugh!
This would be a great getaway. Much needed.
I love you all. I loved meeting you all in Maine! John and I . We have pucs of all of us together. John is no longer with us. He was brutally attacked in December of 2025. He had a successful surgery, but , unfortunately did not survive. I am heartbroken. To say the least. It is a long story.
A getway woukd be nice. ❤️
I love St Augustine! This would be an amazing trip!
This would be a great getaway with my hubby! Thank you for the chance to win this! I love your show!
Love the whole gang!
The ONLY thing that would make this trip better would be for y’all to go too! I’ve been listening since 1995, but first met y’all on the Paris trip in 1996!
What a great trip to escape the daily stresses of life. Thanks for all you do. Been a listener for many years. I was pregnant with my girls the same time as Sheri was. I went through many of the same challenges as Sheri did with her girls. Especially with COVID, with high school kids and one in college made if very challenging. It was nice to hear others were going through the same issues. Thanks again!
PICK ME! NO WORDS JUST NEED A BREAK!
Our family’s been through such challenges. I getaway is long overdue & would be so greatly appreciated.
Thank you for the chance to win this wonderful trip! Love the show ❤️
Hi, I am a retired teacher. Have 2 cats. Love reading and traveling. I have a beautiful 16 month old granddaughter!
I wish Kevin a speedy and full recovery! ❤️🙏🏻
Would love a quick trip with the hubby to the sunshine state. 37th wedding anniversary this month would be fun to win.
My youngest daughter just got married to an amazing guy I get to call ‘son’ now. But this mama’s heart is still heavy knowing she’s not completely and solely ours anymore. My hubby and I could drown our tears (while celebrating her new life) with a few glasses of wine in St. Augustine. Mornings with the Bob and Sheri gang helps ease the pain. 🙌🏼👌🍷🍷👰🤵
Long, long, loooong time listener and fan of all things Bob & Sheri, including True Weird Stuff, The Oddcast, and Talking Lamar. On our last trip to St. Augustine, my child (who is two years from completing their PhD in Oceanography) actually swam with a sea turtle in the wild! It was an incredible experience we will never forget and we would love to take a trip back. St. Augustine is lovely!
Would love to take my daughter and do this for her 17th birthday. What an awesome gift for her. She loves Florida and someday we hope to move there so she can pursue her career becoming a Marine Mammal Trainer.
WOW such a wonderful and generous gift. We are all lucky to be in even with a single chance.
I have been to Florida, but never gone on an actual vacation and with the way the crazy world is right now I sure could use a mental health break.
Long time listener ~ love you guys 🏝️ ❤️☘️☘️☘️☘️☘️❤️ 🏖️
Love listening to the podcast and would love to go to St Augustine! Have never been there, sounds like such a fun adventure!
Husband just lost his job…. First and only grandchild on the way… would love a getaway to relax and refuel…
My father and grandfather were born in st Augustine and after doing some deep dives on ancestry sites, my family goes all the way back to the early 1700s there. I will try to find all the old cemeteries they’re buried in, if I happen to win! Fingers crossed!
I’ve been listening to the Bob and Sheri show since my local radio station in central Michigan began airing the show, which must be almost 30 years! I now listen to it through Spotify. I miss Bob and his antics but hearing more from the other boys has been great! Sheri can make anyone shine – she’s a rockstar warrior!
I love the beach
Winning this vacation would be a absolute lifesaver! Having survived paying for back-to-back weddings in 10 months—our son last October and daughter this August—our remaining travel budget covers a 5-star trip to the backyard plastic kiddie pool with PB&J sandwiches made on cheap white bread and a tall glass or cold water. We’re ready for a upgrade!
Been listening for forever! Sheri you don’t know it but we are besties! Would love this vacation for my husband & I!
We love listening to y’all. You make our commute to Charlotte for doctor appointments enjoyable even in all the traffic. We absolutely would love to win this trip.
I met my forever soul mate and I just got diagnosed with a Brain Anurysm and I would love to take my wife on a nice vacation.
This would be a wonderful anniversary get away.
I would love to take my wife on a wonderful honeymoon that we didn’t get to take due to the reason that I was diagnosed with a brain aneurysm and I have spent a lot of time dealing with that.
Thank you for this opportunity!!!
St. Augustine has been on my bucket list for YEARS!! And I’m definitely not getting any younger at age 70!!!😂🤞🤞🤞🤞
My wife and I had hip and knee replacement. I would love to take her on a trip before the end of the summer and school starts.