St. Augustine Beach Getaway: The Perfect Mini-Vacation from The Villages, FL
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One of the best parts about living in The Villages, Florida, is that we’re perfectly positioned for spontaneous road trips. In just a couple of hours, we can leave our golf cart bubble and dip our toes in the Atlantic—or hop on a cruise ship from Port Canaveral. On this particular trip, we headed east on a mini-vacation to St. Augustine Beach. If you're dreaming about living the retirement life in Florida (or already doing it), this getaway was made for you.
Let us walk you through why St. Augustine is the perfect day trip or weekend escape from Central Florida.
📍 Getting There: A Scenic Escape from The Villages
The road from The Villages to St. Augustine Beach is just over 100 miles and takes under 2.5 hours. We opted to take the backroads through the Ocala National Forest rather than braving I-95 or the turnpike. Not only was it a smoother drive, but the scenic views of Florida’s interior made the journey part of the fun.
Tip: Leave early in the morning to make it a day trip—or pack your bags for a few nights and make a real vacation out of it like we did.
🏨 Where We Stayed: Beachside Convenience & Hilton Points
We used our Hilton points and stayed at the Hilton Garden Inn, just a half-block from the beach. While not directly beachfront, it was incredibly close and more affordable than other options in the area. If you want to splurge, try the Embassy Suites on St. Augustine Beach!
🧳 Travel Tip: If you’re a Hilton member (or even if you’re not), this location is ideal for budget-conscious retirees who still want to enjoy the luxury of staying close to the ocean. Join Hilton Honors for free! Sign Up for Hilton Honors
Across the street, we found a handy pedestrian flag system that makes it safe and easy to cross A1A—something we’d love to see implemented back in The Villages!
🎶 A Concert to Remember: Ringo Starr and the All-Starr Band
The real reason we made the trip? To cross a major bucket list item off—seeing Ringo Starr live in concert at the St. Augustine Amphitheatre! The Amp is a great smaller venue. It is all outside, so be sure to take a personal fan if it is in the summer months.
Thanks to our friends and fellow Villagers, Don and Debbie, we got the VIP treatment, including backstage access, up-close views of Ringo’s drum kit, and some amazing stories from Don, who’s Ringo’s longtime tour manager (and has worked with Aerosmith, Bruce Springsteen, and Sammy Hagar).
🚗 Parking Tip: The amphitheater doesn’t have much parking, and spots sell out quickly. We parked at the nearby Elks Lodge for $20—super convenient and highly recommended.
It was a magical and memorable night. And yes, Ringo still has the energy of a 25-year-old at nearly 85!
🏖️ Beach Day at St. Augustine Beach
The next morning, we packed our beach gear and walked right over to the sand. Michael played beach pack mule while Tiffany waved the safety flags across A1A.
We set up our Sun Ninja shade (a game-changer—check it out on our Amazon shop) and spent the whole day swimming, reading, listening to music, and enjoying the perfect waves. Not too calm, not too choppy—just right.
🏄♂️ Water Tip: The beach between Hampton Inn and Embassy Suites is car-free, making it ideal for peaceful strolls and lounging without vehicle noise.
💡 Fun Fact: This was our first time to St. Augustine Beach despite having visited the historic district multiple times. Verdict? We’ll definitely be back.
St. Augustine Beach at the 16th Street Entrance
🍴 Local Eats: From Fried Seafood to Fine Dining
We love a mix of saving, splurging, and skipping. Here’s how we ate our way through St. Augustine:
🐟 Day 1 Lunch: Oasis Restaurant
Right off A1A, this classic beach shack serves fried seafood and beachy vibes—perfect for arriving hungry and soaking in the ocean breeze.
🍹 Dinner: Sunset Grille
Located literally next door to our hotel, this two-story gem serves up fresh seafood with coastal charm. Be prepared for a wait if you want a table on the upstairs patio (we waited nearly an hour). Shout out to Layla, our hilarious and helpful hostess!
🍳 Breakfast: Beachside Diner
Simple, fun, and classic. Open until 3 PM and perfect for fueling up before a day of sightseeing or beach-hopping. They have classic breakfast and lunch diner fare with friendly service.
🥘 Splurge Meal: Columbia Restaurant (Historic District)
A must-do in St. Augustine, even if you’ve been before. The 1905 Salad is prepared tableside, and the paella? Worth every bite. Bonus points for the gorgeous atrium setting and comforting café con leche. Be sure to make a reservation and ask for Bridgett to be your wonderful server. We have already made reservations to go to the original Ybor City location!
🥪 Hidden Gem: Little Margie’s FA Cafe
Our favorite meal of the trip. Owned by a mother-daughter duo, this tiny beachside shack offers incredible hospitality, great prices, and killer sandwiches. We shared a Reuben and soaked up the low-key vibes while chatting with Margie herself.
🛺 Exploring the Historic District: Trolley Tour Tips
You can’t visit St. Augustine without diving into its rich history. We took the Old Town Trolley hop-on hop-off tour—worth every penny. ($38–$40 per adult)
🚎 Pro Tip: The trolley has a beach shuttle that picked us up right across the street from our hotel. We didn’t move our car for days.
✅ The beach trolleys have vinyl windows you can unzip to enjoy the breeze.
✅ Jim from Philly, our driver, was a hilarious and knowledgeable guide.
✅ Buy your tickets online for easy check-in at the kiosk downtown. Old Town Trolley Hop On Hop Off Tour Tickets
We made sure to get on the first trolley of the day to beat the heat and the crowds. And it worked!
📸 Stops We Loved:
Castillo de San Marcos (The Fort) – Free with a National Parks Pass. Long line, but worth a look even from the outside.
St. George Street – Great for strolling, shopping, and people-watching.
Ripley’s Believe It or Not – Skip if you've been before.
Fountain of Youth – The peacocks were louder than expected!
Oldest House – Fascinating piece of early colonial life.
Make sure to catch the last beach shuttle by 4:30 PM—or you’ll be hailing an Uber!
🏁 Wrapping Up the Trip
We ended our last evening with a simple meal, packed up our stuff, and enjoyed one final walk along A1A. The drive back to The Villages was just as easy and scenic as the drive out.
💬 Final Thoughts (From the Bubble)
St. Augustine Beach was a perfect mini getaway. Whether you want to:
Check out a legendary concert at The Amp
Sip coffee by the waves
Explore Florida’s oldest city
Or just eat some amazing seafood
...this trip checked all the boxes.
Would we go back? In a heartbeat.
As more of our Villages neighbors retire or semi-retire, we hope this inspires you to turn your dreams into road trips. Whether you're in pre-tirement or enjoying full-on retired bliss, St. Augustine makes an ideal destination just a couple hours away from our doorstep.
💌 Stay Connected
We’re Michael & Tiffany—empty nesters, retirees, and adventure-seekers living in The Villages, FL. If you love fun travel, practical tips, and Florida life, join us:
📘 Facebook: @MichaelAndTiffanyTVE
📺 YouTube: Subscribe and share for more!
“It’s another awesome day to be in FLA.”
Let us know in the comments: Have you been to St. Augustine? What’s your favorite Florida beach? And where should we go next?