Upcoming Events in Vilano Beach & St. Augustine
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― January to December (every Wednesday)
Wednesday Pier Farmers Market
St. Johns County Ocean Pier Park
350 A1A Beach Blvd. St. Augustine, FL 32080
Enjoy a refreshing morning at the Wednesday Pier Farmers Market, where oceanfront views meet a diverse selection of local produce and handmade crafts. It is the perfect spot to support small businesses and enjoy ready-to-eat bites in a relaxed coastal atmosphere.
Wander & Rest Tip
After your morning at the market, continue the coastal vibe by relaxing at the thoughtfully designed Saltwater & Sunset or Coast & Palms properties. It is the perfect setting to kick off your shoes, enjoy your fresh market finds, and ease into a slow, sun-soaked afternoon at your Wander & Rest retreat.
The Wednesday Pier Farmers Market offers oceanfront shopping at the St. Johns County Ocean Pier Park every Wednesday from 8… -
― May 8 (Friday)
Thick & Thin String Band at Marina Munch
Marina Munch
509 S. Ponce de Leon Blvd. St. Augustine, FL 32084
Catch the Thick & Thin String Band for a lively sunset performance at Marina Munch. With waterfront views, a variety of food trucks, and soulful acoustic music, it’s the perfect spot for a relaxed and flavorful St. Augustine evening.
Wander & Rest Tip
Arrive early to grab a front-row seat by the water or explore the unique shops along South Ponce de Leon Blvd. Afterward, return to your Wander & Rest sanctuary to unwind in the private infrared sauna or the heated saltwater pool.
Enjoy live performances from 5-8 p.m. Food trucks available. 509 S. Ponce de Leon Blvd., St. Augustine. www.facebook.com/MarinaMunch.904 Location Marina Munch… -
― May to February (Every Wednesday)
St. Augustine Weekly Farmers Market on Sundays
Classic Car Museum of St. Augustine
4730 U.S. 1 S. St. Augustine, FL 32086
Browse local produce and artisanal treasures at the St. Augustine Weekly Farmers Market held at the Classic Car Museum. It’s a must-visit Sunday destination for anyone looking to experience the city’s vibrant community spirit and handmade local goods.
Wander & Rest Tip
Bring a reusable tote from your Wander & Rest sanctuary to fill with fresh local ingredients for a farm-to-table snack later. After your market morning, head back to unwind with a rejuvenating session in the private infrared sauna or a dip in the heated saltwater pool.
The St. Augustine Farmers Market, open 10 a.m.-2 p.m., features local flavor, handmade goods, and community vibes every Sunday at… -
― January to December (Every First Thursday of the Month)
Nature Journaling at GTM Research Reserve
GTM Research Reserve
505 Guana River Rd. Ponte Vedra Beach, FL 32082
Connect with nature at the GTM Research Reserve’s free monthly journaling workshop, perfect for all skill levels. Meet at the Visitor Center at 10 a.m. to explore the scenic reserve through guided observation and creative expression.
Wander & Rest Tip
Pair your peaceful morning of nature journaling with a scenic coastal drive, stopping for a bite at local spots like Palm Valley Fish Camp or The Kookaburra. Afterward, return to your Wander & Rest property to completely unwind in the heated pool, sauna, or hot tub.
Join nature journaling instructor Elaine Bergstrom at GTM Research Reserve on the first Thursday of each month to explore the… -
― June to July 1 (Every Wednesday)
Beginner’s Wheel Throwing Series at The Art House
The Art House
3920 A1A S., Unit 8 St. Augustine, FL 32080
Master the fundamentals of pottery with The Art House’s beginner-friendly, four-week wheel throwing series. Meeting Wednesdays for $275, this hands-on course includes all materials and covers everything from shaping clay to final glazing.
Wander & Rest Tip
On your way back to Vilano Beach from the pottery studio, stop for a cocktail at 36 Granada or a hot slice at 180 Vilano Grill. Back at your property, soothe your creative muscles by relaxing in our heated pool, private sauna, or hot tub.
Learn the fundamentals of wheel throwing in this beginner-friendly pottery series at The Art House. Designed for those new to… -
― May 25 to May 31 (Monday through Sunday)
Art Collective St. Augustine May Feature Artist Jessica C. Smith
Art Collective St. Augustine
51 Cordova St. St. Augustine, FL 32084
The Art Collective St. Augustine proudly presents local artist Jessica C. Smith as their exclusive May Featured Artist. Guests are invited to browse her exceptional portfolio of work at the downtown gallery located on Cordova Street. The exhibition provides a sophisticated and inspiring cultural stop during your historic district travels, welcoming art enthusiasts daily starting at 11 a.m.
Wander & Rest Tip
On your way back to Vilano Beach after exploring the art gallery, stop for an afternoon refreshment at 36 Granada or grab a hot meal at 180 Vilano Grill. Once home, keep the luxurious vibes going by relaxing in our heated pool, private sauna, or hot tub.
Artist Jessica C. Smith will be the Art Collective May Feature Artist. Gallery is open daily from 11 a.m. 51… -
― October 24 (Saturday)
Jailbreak 5K
Old Jail Museum
167 San Marco Ave. St. Augustine, FL 32084
The unique Jailbreak 5K challenges runners to a one-way course from the St. Augustine Old Jail, over the bridge, and right onto the Vilano Beach ramp. Registration costs $25–$45, with all proceeds supporting St. Johns County public school students and teachers through the local non-profit INK.
Wander & Rest Tip
Celebrate your race finish right in Vilano Beach with a hot meal at 180 Vilano Grill or head toward 36 Granada for a premium afternoon drink. Back at your property, kickstart your muscle recovery by unwinding in our heated pool, private sauna, or hot tub.
Escape from St. Augustine! This one-way 5K takes you from the St. Augustine Old Jail across the Vilano Beach Bridge,… -
― October 10 (Saturday)
Donna 5K at TPC Sawgrass
TPC Sawgrass
110 Championship Way Ponte Vedra Beach, FL 32082
The Donna 5K invites participants of all fitness levels to historic TPC Sawgrass to celebrate breast cancer survivorship and support the life-changing mission of The DONNA Foundation. Registration for this officially chip-timed event costs $35–$45 and includes a finisher’s medal, t-shirt, and swag bag for a morning of community-driven impact.
Wander & Rest Tip
Celebrate your 5K finish with a premium afternoon drink near 36 Granada or a hot post-race meal at 180 Vilano Grill. Back at your property, kickstart your muscle recovery by unwinding in our heated pool, private sauna, or hot tub.
Lace up your sneakers for the Donna 5K to kick off breast cancer awareness month. This family friendly event celebrates… -
― September 26 (Saturday)
The 904 Redfish Tournament
Palm Valley Outdoors Bar & Grill
377 S. Roscoe Blvd. Ponte Vedra Beach, FL 32082
The 904 Redfish Tournament invites competitive anglers to Ponte Vedra Beach for an exciting weekend of sport fishing based out of Palm Valley Outdoors Bar & Grill. Following a mandatory Captain’s Meeting on September 24, the tournament day features official weigh-ins from 1–4 p.m. and an awards ceremony, with registration entry fees ranging from $175 to $200.
Wander & Rest Tip
On your drive back to Vilano Beach after the weigh-ins, stop for a premium drink near 36 Granada or grab a hot bite at 180 Vilano Grill. Back at your property, transition into total relaxation by unwinding in our heated pool, private sauna, or hot tub.
Reel in the excitement at The 904 Redfish Tournament in Ponte Vedra Beach. Anglers are required to attend the Captain’s… -
― August 21-23 (Friday through Sunday)
22nd Annual Jacksonville Tattoo Convention
Renaissance Resort at World Golf
500 S. Legacy Trail St. Augustine, FL 32092
The 22nd Annual Jacksonville Tattoo Convention is returning to St. Augustine, bringing together top-tier artists and enthusiasts from across the region for a spectacular weekend of body art. Featuring live tattooing, artist meet-and-greets, and specialized industry vendors, entry tickets range from $20 to $40 with kids 15 and under free.
Wander & Rest Tip
On your drive back to Vilano Beach after the convention, stop for a premium drink near 36 Granada or grab a hot meal at 180 Vilano Grill. Once home, completely refresh and unwind from a long day on your feet by spending time in our heated pool, private sauna, or hot tub.
The Jacksonville Tattoo Convention brings together tattoo enthusiasts, artists, and professionals from around the region. This event showcases a diverse… -
― October 24 (Saturday)
Jason Ricci & The Bad Kind perform at Cafe Eleven
The Original Cafe Eleven
501 A1A Beach Blvd. St. Augustine, FL 32080
Grammy-winning harmonica virtuoso Jason Ricci & The Bad Kind are bringing their high-octane mix of blues, funk, and New Orleans soul to The Original Cafe Eleven. Known for fierce live performances and deep storytelling, the St. Augustine Beach show runs from 8:00 p.m. to 10:00 p.m. with tickets starting at $26.58.
Wander & Rest Tip
On your way back to Vilano Beach after the concert, stop for a premium drink near 36 Granada or grab a late-night bite at 180 Vilano Grill. Once home, keep the relaxing vibes going by completely unwinding in our heated pool, private sauna, or hot tub.
Multiple award winning jazz, funk and blues harmonica player, singer, songwriter Jason Ricci has played with, toured and recorded with… -
― April to November (Fridays through Sundays)
Spring Menu — Sunset Tasting Tour
St Augustine Sailing
3076 Harbor Drive St Augustine, FL 32084
Indulge in a luxurious two-hour sunset cruise featuring a sommelier-curated wine flight paired with gourmet seasonal appetizers. This exclusive experience offers a sophisticated way to unwind while taking in the stunning golden hour views of St. Augustine’s historic coastline.
Wander & Rest Tip
After your cruise, grab a quick bite at Odd Birds Café or enjoy a scenic riverside nightcap at Cap’s on the Water on your way back. Once home at your Wander & Rest retreat, fully unwind in the private sauna or with a tranquil late-night dip in the heated saltwater pool.
Set sail on a luxurious 2-hour Sunset Tasting Cruise with St. Augustine Sailing, where gourmet cuisine and fine wines meet… -
― April to November (Every Third Saturday of the Month)
Yoga in the Garden at Lightner Museum
Lightner Museum
75 King Street St. Augustine, FL 32084
Find your zen during an outdoor all-levels yoga session in the beautiful Radzinski Family Garden at the Lightner Museum. This donation-based class is the perfect way to combine wellness with the historic charm of St. Augustine’s most picturesque gardens.
Wander & Rest Tip
Enjoy a healthy brunch at The Corazon Cinema and Cafe or take a quiet stroll through the Villa Zorayda Museum grounds after your practice. Afterward, return to your Wander & Rest sanctuary to keep the wellness vibes going in the private infrared sauna or the heated saltwater pool.
Join the Lightner Museum for an early morning outdoor yoga session for all-levels in the Radzinski Family Garden. Participants should… -
― May (Every Saturday)
Hand Sewing and Crochet Class at The Art House
The Art House
3920 A1A S., Unit 8 St. Augustine, FL 32080
Master the basics of crochet and hand sewing in this beginner-friendly workshop at The Art House. With all materials included, you’ll learn to create beautiful, practical items in a supportive and artistic beachside setting.
Wander & Rest Tip
Take a peaceful walk along St. Augustine Beach just minutes away to find inspiration for your next crochet project. Upon your return to your Wander & Rest sanctuary, continue the relaxation with a session in the private infrared sauna or the heated saltwater pool.
Learn the basics of crochet in a relaxed weekly class, starting with foundational skills and progressing to simple projects like… -
― May to June 7 (Every First Thursday of the month)
The Honey Knots at Marina Munch
Marina Munch
509 S. Ponce de Leon Blvd. St. Augustine, FL 32084
Enjoy a lively afternoon on the waterfront with live music from The Honey Knots at Marina Munch Waterside Food Truck Park from 2–4 p.m. It is the perfect opportunity to relax by the river, sample delicious local food truck eats, and experience local St. Augustine talent.
Wander & Rest Tip
Pair your waterside music experience with a drive back past local favorites like Bog Brewery or The Blue Hen Cafe. Afterward, head straight back to your Wander & Rest property to unwind your muscles and relax in the heated pool, sauna, or hot tub.
Live music from 2-4 p.m. at Marina Munch. Enjoy live music and savor some delicious eats than at Marina Munch… -
― June 13 & October 31 (Saturdays)
Tangled Orchid performs at Colonial Oak Music Park
Colonial Oak Music Park
21 St. George St. St. Augustine, FL 32084
Experience free live music with Tangled Orchid in a family- and pet-friendly outdoor setting at Colonial Oak Music Park. Running from 7 to 10 p.m. on St. George Street, it’s the perfect casual night out to enjoy great local talent under the oaks.
Wander & Rest Tip
On your way back to Vilano Beach after the show, stop for a cocktail at 36 Granada or a hot slice at 180 Vilano Grill. Once home, keep the relaxing vibes going by soaking in our hot tub, unwinding in the sauna, or swimming in the heated pool.
Enjoy free live music in a family- and pet-friendly setting from 7-10 p.m. 21 St. George St., St. Augustine. www.thecolonialoakmusicpark.com Location… -
― May 25 to May 31 (Monday through Sunday)
P.A.St.A. May Feature Artist Svetlana Shorey
PASta Fine Art Gallery
214 Charlotte St. St. Augustine, FL 32084
Discover the original fine art of Svetlana Shorey, celebrated as P.A.St.A. Gallery’s featured artist for the month of May. Located at 214 Charlotte Street, the gallery is open daily from 11 a.m. to 5 p.m., offering an excellent opportunity to experience premier local craftsmanship.
Wander & Rest Tip
On your drive back to Vilano Beach after visiting the P.A.St.A. Gallery, stop for an afternoon refreshment near 36 Granada or grab a hot meal at 180 Vilano Grill. Back at your property, transition into total relaxation by unwinding in our heated pool, private sauna, or hot tub.
Artist Svetlana Shorey is the Professional Artists of St. Augustine’s (P.A.St.A.) May Feature Artist. Gallery is open daily from 11… -
― June 5 & October 23 (Saturday)
One Good Ring performs at Colonial Oak Music Park
Colonial Oak Music Park
21 St. George St. St. Augustine, FL 32084
Catch local Grateful Dead tribute band One Good Ring performing live under the majestic trees at Colonial Oak Music Park. Blending veteran musicians with a new generation of talent, this energetic act delivers a refreshed, crowd-driven live experience packed with classic rock nostalgia.
Wander & Rest Tip
On your way back to Vilano Beach after the concert, stop for a premium drink near 36 Granada or grab a late bite at 180 Vilano Grill. Once home, keep the relaxing vibes going by unwinding in our heated pool, private sauna, or hot tub.
One Good Ring is a tribute act out of St. Augustine, Florida, that channels the sound and spirit of the Grateful… -
― October 10 (Saturday)
67th Annual Cracker Day
St. Johns County Fairgrounds
5840 SR 207 Elkton, FL 32033
The St. Johns County Cattlemen’s Association invites families to the 67th Annual Cracker Day at the county fairgrounds for a full day of horse games, local vendors, and authentic barbecue. General admission to this historic, day-long celebration runs from 8 a.m. to 6 p.m. and costs $5 in cash, with participant registration for the arena games ranging from $5 to $15.
Wander & Rest Tip
On your drive back to Vilano Beach after Cracker Day, stop for a premium drink near 36 Granada or grab a hot meal at 180 Vilano Grill. Once home, completely refresh and unwind from the outdoor festivities by spending time in our heated pool, private sauna, or hot tub.
The St. Johns County Cattlemen’s Association hosts this event at the St. Johns County Fairgrounds featuring horse games, a vendor… -
― September 25 (Friday)
Flipturn with special guest Winyah at The AMP
St. Augustine Amphitheatre
1340C A1A S. St. Augustine, FL 32080
Jacksonville’s own indie rock powerhouses Flipturn are bringing their Burnout Days tour to the St. Augustine Amphitheatre with special guest Winyah. Famous for their explosive live energy honed on the national festival circuit, the band will showcase their signature blend of New Wave nostalgia and modern alt-pop starting at 8 p.m.
Wander & Rest Tip
On your way back to Vilano Beach after the Flipturn concert, stop for a premium drink at 36 Granada or a late-night bite at 180 Vilano Grill. Once home, keep the relaxing vibes going by completely unwinding in our heated pool, private sauna, or hot tub.
For Flipturn, success didn’t arrive overnight. The band, comprised of Dillon Basse (lead vocals, guitar), Tristan Duncan (lead guitar), Mitch… -
― July 20 (Monday)
Lindsey Stirling performs at The AMP
St. Augustine Amphitheatre
1340C A1A S. St. Augustine, FL 32080
Platinum-selling electronic violinist and dancer Lindsey Stirling is bringing her visionary and sonically daring Duality tour to the stage. Fusing grandiose Celtic-inspired compositions with high-energy modern pop choreography, this spellbinding live performance delivers an empowering journey through Stirling’s chart-topping musical catalog.
Wander & Rest Tip
On your way back to Vilano Beach after the concert, stop for a premium drink at 36 Granada or a late-night bite at 180 Vilano Grill. Once home, keep the relaxing vibes going by completely unwinding in our heated pool, private sauna, or hot tub.
Lindsey Stirling’s seventh full-length album, Duality, showcases her genre-bending virtuosity as an electronic violinist, dancer, and visionary songwriter. Produced alongside…
*(extra charge)
☀️ August in St. Augustine:
Music, Art & Coastal Thrills Await
As summer winds down, St. Augustine heats up with culture, music, and seaside adventure—and there’s no better place to experience it all than from the comfort of Saltwater & Sunsets, your luxury escape in Vilano Beach. Whether you’re planning a romantic weekend, a family getaway, or a friends’ retreat, August offers the perfect blend of events and exploration. Here’s your guide to the best happenings this month.
Friday, August 2
First Friday Art Walk 🎨
Our Pro Tip
Start your evening with dinner at Michael’s Tasting Room, then stroll to Butterfield Garage or Aviles Street. Don’t forget your camera—the colonial architecture and golden hour lighting are pure magic.
Every Wednesday through August | ⏰ 7–9 PM
Music by the Sea 🎶
Our Pro Tip
Grab takeout from Salt Life Food Shack on the way, bring chairs or a blanket, and enjoy a laid-back evening under the stars. Great for couples and families alike.
Every Thursday in August | ⏰ 6–8 PM
Concerts in the Plaza 🎸
Our Pro Tip
Arrive early and explore historic sites nearby like the Cathedral Basilica or the Lightner Museum. Pack drinks and snacks or enjoy dessert after the show at The Hyppo (try their mango habanero popsicle!).
August 22–24, 2025
Florida Skimboarding Pro/Am Tournament 🏄
Our Pro Tip
Start your morning with a coffee from Vilano Coffee Spot, walk to the beach, and claim your front-row seat in the sand. You’ll be amazed at the athleticism and beachside buzz.
Explore in Style: Slingshot Rentals 🚗
Our Pro Tip
Book your rental in advance through companies like St. Augustine Slingshot Rentals. Early morning or golden hour drives are best for cooler temps and dramatic views.
Why August Guests Love Staying
at Wander & Rest
Location
Perfection
Steps from Vilano Beach and a short drive to downtown
Luxury
Comforts
Stylish interiors, premium linens, chef’s kitchen, and serene
outdoor seating
Event
Access
Easy to attend concerts, festivals, and beach competitions without the hassle of downtown parking
Adventure
Ready
Beach chairs, towels, and even space to park your Slingshot rental
Ideal Itinerary
for Your August Stay
Day |
Activity |
Wed |
Check in → Dinner → Music by the Sea at the beach pier |
Thu |
Explore downtown → Concert in the Plaza with a picnic |
Fri |
Sleep in → beach time → First Friday Art Walk & dinner |
Sat |
Skimboard tournament watching → shopping & dining in Vilano |
Sun |
Early Slingshot cruise → brunch → check-out |
Ready to Book
Your August Escape?
With art, music, sunshine, and coastal thrills, August is one of the best times to experience St. Augustine—and Wander & Rest makes it unforgettable. Whether you’re catching concerts, beachside competitions, or simply enjoying luxury by the ocean, this month’s lineup is your invitation to indulge in adventure and unwind in style.
Book your stay today!
and start planning your perfect August getaway.
☀️ September in St. Augustine:
Sun, Songwriters & Scenic Lunches
From Beach Bash to Art Walk—Your Month of Music, Events & Relaxation Starts
at Wander & Rest
As summer fades into fall, St. Augustine comes alive in September with art strolls, songwriter showcases, dog-friendly festivals, and waterfront concerts. Whether you’re drawn to music in the plaza, sipping wine in art galleries, or relaxing poolside after a beach bash, this month is the perfect blend of energy and ease.
At Wander & Rest, your luxury retreat in Vilano Beach, you’re just minutes from the action—but with the serenity of a saltwater private pool, hot tub, and your own golf cart* to cruise to local favorites and hidden gems. Let’s map out a month of unforgettable moments.
Friday, September 6 | ⏰ 5–9 PM
First Friday Art Walk 🎨
Wander & Rest Tip
Park near the Vilano Bridge and enjoy golden hour views before walking into the gallery scene.
Wednesdays, through mid-September 24, 2025 | ⏰ 7–9 PM
Music by the Sea 🎶
Our Pro Tip
🧺 Pack dinner or stop by Salt Life Food Shack for island-inspired eats with a view before heading to the pier for live tunes and a beachy sunset.
Saturday, September 6, 2025 | ⏰ 12-4 PM
End of Summer Beach Bash 🎉
Our Pro Tip
🔥 Post-bash relaxation? Head back to your private patio and unwind in the heated pool or hot tub under the stars.
Sunday, September 14, 2025 | ⏰ 12–5 PM
Art & Bark in the Park 🐾
September 26–28, 2025
St. Augustine Songwriters Festival 🎤
Wander & Rest Tip
Spend your day at the beach, then catch a songwriter set at Prohibition Kitchen, followed by a late-night soak in the heated pool or hot tub to end the day.
All Month Long | Headliner Showcase Sept 21–22
Sing Out Loud Festival 🎶
VIP idea 🎟️
Grab tickets for the Live Wildly Showcase, and use your Sunday to cruise riverside, grab a waterfront lunch, and unwind poolside before another night of music.
Where to Grab a Great Lunch
With a View
St. Augustine and Vilano Beach are packed with great spots for a scenic, laid-back lunch. Here are our favorites:
Caps on the Water
(Vilano Riverfront)
🟐 Gorgeous intracoastal views, local seafood, and southern charm
🟐 Sit on the dock, sip a cocktail, and savor the blackened mahi tacos
The Reef
(Oceanfront, Vilano Beach)
🟐 Steps from Wander & Rest with ocean views and an unbeatable beach breeze
🟐 Don’t miss their crab cakes or the grilled shrimp salad
St. Augustine Fish Camp
(Downtown/Riverside)
🟐 Waterfront lunch with fresh catch daily, shrimp & grits, and a craft cocktail list
🟐 Dockside seating right off the Matanzas River
Beachcomber Restaurant
(On the Beach, A Street)
🟐 Flip-flops welcome! Fun spot for beachside burgers, fried shrimp, and cold beer
Crave Food Truck
(San Sebastian River)
🟐 Colorful health-forward bowls and wraps with picnic seating along the water
🟐 Perfect quick bite after the art walk or before an amphitheater show
Why September Guests Love Staying at Wander & Rest
Location Perfection
Peaceful Vilano Beach, minutes from downtown and events
Amenities
Private saltwater pool and a hot tub for relaxing between outings
Golf Cart* Available
Zip to lunch, river views, or pack it for an easy beach trip
Luxury Comforts
Crisp linens, spa-worthy soaks, and breezy beach vibes
Sample Itinerary
for Your September Weekend
Day |
Activity |
Fri |
Check-in → Cruise to the beach → First Friday Art Walk → Late night soak |
Sat |
Art & Bark → Lunch at Caps → Pool nap → Songwriters Festival downtown |
Sun |
Morning beach walk → Lunch at The Reef → Sing Out Loud at Francis Field |
Ready to Book
Your September Escape?
There’s no better way to say goodbye to summer than with music-filled weekends, art walks, and scenic lunches by the sea. At Wander & Rest, you’ll experience it all in luxury, with space to relax and amenities that make every moment feel like vacation.
Book your September escape now!
and get ready to soak up the best of September in St. Augustine.
🎃 October in St. Augustine:
Ghosts, Greek Food & Sweet Treats by the Sea
Spooky Adventures and Cozy Nights Await at Wander & Rest
October in St. Augustine is a magical blend of old-world charm, spine-tingling legends, cultural festivals, and fall sunshine. Whether you’re into ghost stories, cultural eats, or just a relaxing evening by the pool under the stars, this month offers unforgettable experiences for couples, families, and thrill-seekers alike.
At Wander & Rest, your luxury beach retreat in Vilano, you’re just minutes from downtown St. Augustine’s eerie alleyways and festive events—but worlds away in terms of peace, privacy, and indulgent comfort. With a chef’s kitchen, hot tub, and private saltwater pool, you can soak, steam, or cook up something cozy after a night of spooky exploring.
Here’s your complete guide to everything October has to offer in St. Augustine.
October 11–12, 2025
St. Augustine Greek Festival 🔱
Wander & Rest Tip
🍳 Bring home a few festival goodies and reheat them in your chef’s kitchen—they’re just as delicious the next morning with coffee on the patio.
👻 Halloween Haunts & Ghost Tours
All Month Long
St. Augustine is America’s oldest city—and one of its most haunted.
October is the perfect time to take a step into its eerie past.
St. Augustine Ghost Tours 👣
Our Pro Tip
🎃 Choose from family-friendly versions or scarier adult-themed tours.
Friday to Sunday, October 24-26, 2025 | ⏰ 5:30–8 PM
Creatures of the Night at the Alligator Farm 🦇
Wander & Rest Suggests
🐊 A perfect stop before heading back to Wander & Rest for movies and s’mores.
Desserts on a Dime:
Sweet Treats That Won’t Break the Bank
Because no October evening is complete without something sugary, here are the best budget-friendly dessert spots in St. Augustine:
ChocoLattes
(Downtown)
🟐 Local gem for $2–$3 cake pops, cookies, and chocolate bites
🟐 Pair it with their house coffee or grab a few to go for a cozy night in
Borrillo’s Pizza & Subs
(West King Street)
🟐 Surprisingly delicious homemade cannoli and zeppoles (Italian fried dough)
🟐 Under $5 and worth the stop—even if you don’t get a slice
Mayday Ice Cream
(Aviles Street)
🟐 Artisan ice cream shop with generous scoops and creative flavors
🟐 Try the seasonal pumpkin spice or bourbon pecan—small cup starts around $4
The Donut Experiment
(St. George Street)
🟐 Custom-topped donuts starting at $2 each
🟐 Open mornings—great for a sweet brunch sidekick or afternoon treat
Or make dessert yourself
🟐 Pick up local ingredients at the St. Augustine Farmers Market on Saturdays and bake something warm in your chef’s kitchen at Wander & Rest while the ocean breeze floats in.
Why Stay at Wander & Rest in October?
Comfortable space
Perfect for chilly nights after ghost tours
Heated
Saltwater Pool
Take a dip no matter the weather
Chef’s Kitchen
Ideal for cooking cozy fall meals or reheating festival eats
Quiet Location
Peaceful Vilano Beach retreat, just 5–10 minutes from downtown
Walk or Cart to
Restaurants & Beach
Use our golf cart* or walk to local spots with ease
“Our October guests say the best part is returning to a warm saltwater pool, a hot tub, and a starry sky
after hearing ghost stories in the oldest city in America.”
Sample Spooky Weekend Itinerary
Day |
Activity |
Fri |
Check in → Sunset walk → Greek Festival dinner → Ghost Tour downtown |
Sat |
Breakfast at home → Farmers Market → Lighthouse Ghost Tour → Late night soak |
Sun |
Coffee & pastry → Creatures of the Night → Homemade fall dessert & movie night |
Ready to Book
Your Haunted & Happy October Escape?
Between baklava, beach days, ghost tours, and gators in costume, October in St. Augustine is as playful, mysterious, and delicious as it gets. At Wander & Rest, you’ll have the space to unwind, the amenities to indulge, and the location to explore it all with ease.
Reserve your stay now!
and treat yourself to a spooky-sweet October escape in St. Augustine.
🍷 November in St. Augustine:
Lights, Local Art & Sips by the Sea
Explore, Indulge, and Unwind with Luxury Comfort at Wander & Rest
As fall settles over Florida, St. Augustine comes alive in November with crisp ocean breezes, glowing lights, and events that combine food, drink, and art with historic charm. Whether you’re sipping wine on the waterfront, browsing local art by the dunes, or watching the city twinkle to life for the holidays, November is a picture-perfect time to visit.
At Wander & Rest, our luxury short-term rental in Vilano Beach, you’re tucked just far enough from the crowds to relax, but only minutes from everything. Cruise to the beach or river in your golf cart*, take a dip in the private pool, soak in the heated saltwater pool or in the hot tub, and unwind after a day of exploring.
Let’s dive into what makes November magical in the Nation’s Oldest City.
November 6-9, 2025
Whiskey, Wine & Wildlife Festival 🥃
Wander & Rest Tip
🥂 Wander & Rest Tip: No need to drive—walk or golf cart* over in minutes, and return for a post-festival dip in the saltwater pool.
Saturday, November 29, 2025 | ⏰ 1 PM – 6 PM
6th Annual Beach Art Walk 🎨
Our Pro Tip
🎨 Bring a tote, grab a coffee nearby, and let the art walk set the tone for a laid-back, creative weekend.
November 15, 2025 – January 11, 2026
Nights of Lights ✨
Wander & Rest Recommends
Head into town early for dinner with a view, then experience the lights on foot or from the water. End the night in the pool or in the hot tub with a glass of wine under your own private stars.
Where to Enjoy a Fabulous Dinner with a View
St. Augustine offers no shortage of scenic places to dine—whether you’re overlooking the Atlantic, the Matanzas River, or tucked under oak trees glowing with lights.
Caps on the Water
(Vilano Riverfront)
🟐 Upscale seafood and steakhouse vibes
🟐 Dine outdoors at golden hour for views of the intracoastal
🟐 Must-try: Buttermilk fried oysters + a glass of Sauvignon Blanc
The Reef
(Oceanfront, Vilano Beach)
🟐 Right on the sand with panoramic views of the Atlantic
🟐 Perfect for romantic dinners or sunset cocktails
🟐 Must-try: Lobster ravioli + Key lime pie with a view
Kingfish Grill
(Vilano Marina)
🟐 Casual coastal dining with riverfront breezes
🟐 Great for lunch or a laid-back seafood dinner
🟐 Must-try: Ahi tuna nachos + mango mojito
The Raintree Restaurant
(Historic District)
🟐 Elegant setting in a Victorian home with courtyard dining
🟐 Especially charming during Nights of Lights
🟐 Must-try: Filet mignon + crème brûlée
Local Pro Tip
🛺 Use your Wander & Rest golf cart* to reach some of Vilano’s best restaurants quickly and enjoy dinner without the parking hassle.
Why Wander & Rest Is the Ideal November Getaway?
Hot Tub
Lounge and relax after cool coastal evenings or a dip in the ocean
Heated
Saltwater Pool
Perfect for relaxing after festivals or exploring downtown
Chef’s Kitchen
Host your own wine + cheese night or prepare market-fresh meals
Golf Cart*
Cruise to the beach, restaurants, or riverside in style
Peaceful Vilano
Location
Quiet nights just minutes from all the action
“There’s nothing better than ending the day with a local dessert in hand, stars above, and a warm soak just outside your door.”
Sample Long
Weekend Itinerary
Day |
Activity |
Fri |
Arrive + Settle In → Dinner at The Reef → Saltwater Pool + Early Night |
Sat |
Breakfast in the chef’s kitchen → Art Walk → Lunch at Kingfish Grill → Whiskey, Wine & Wildlife Festival → Hot Tub or Saltwater Pool wind-down |
Sun |
Poolside morning → Brunch → Downtown stroll + Nights of Lights → Dessert + late-night soak |
Ready to Book
Your November Escape at Wander & Rest?
With fewer crowds, gorgeous weather, and a calendar full of flavor, art, and twinkling charm, November is one of the best-kept secrets in St. Augustine—and Wander & Rest is your gateway to it all.
Reserve your stay today!
and discover a month of light, local flavor, and luxury in Vilano Beach.
🎄 December in St. Augustine:
Coastal Cheer, Christmas Lights & New Year Nights
Celebrate the Season in Style with Wander & Rest
December in St. Augustine blends coastal charm with timeless holiday magic. From millions of twinkling lights and festive fireworks to seaside holiday markets and outlet shopping sprees, this historic city knows how to celebrate the season—without the snow boots.
And at Wander & Rest, our luxury short-term rental in Vilano Beach, we’ve transformed our space into a holiday haven. With tasteful Christmas decor, a heated saltwater pool, a hot tub, and golf cart* rental to cruise to the beach, riverside, or neighborhood restaurants, you’ll experience the holidays wrapped in style and comfort.
Here’s your festive guide to spending a magical December with us in the Nation’s Oldest City.
November 15, 2025 – January 11, 2026
Nights of Lights ✨
Wander & Rest Tip
Head downtown just before sunset for drinks and dinner with a view, then enjoy the lights as the city comes to life. Wrap up the night in the hot tub or n the heated saltwater pool with a holiday cocktail in hand.
Saturday, December 13, 2025 | ⏰ 3–7 PM
Holiday Market at the Pier 🎁
Wander & Rest Tip
🛍️ Arrive early, grab a hot cocoa, and support local artists while soaking up ocean breezes.
Saturday, November 15, 2025 | ⏰ 4-7:30 PM
Light Up the Night: Holiday Fireworks Show 🎆
Wander & Rest Tip
🔥 Return from the fireworks to your Christmas-lit rental, light up the fire pit, and enjoy the cozy glow of the season in peace.
December 31
New Year’s Eve in St. Augustine 🎆
Wander & Rest Tip
Top NYE Picks:
🍾 Or keep it luxe and low-key: prepare a gourmet dinner in your chef’s kitchen, soak in the hot tub or in the heated saltwater pool, and toast the new year in your private, decorated holiday escape.
Holiday Shopping at the St. Augustine Outlets
Wander & Rest Tip
Bring your finds back to Wander & Rest and enjoy a private fashion show, fireside dessert, or spa night with your new favorites.
Local Pro Tip
🛺 Use your Wander & Rest golf cart* to reach some of Vilano’s best restaurants quickly and enjoy dinner without the parking hassle.
Why Stay at Wander & Rest This Holiday Season?
Fully Decorated
for Christmas
From the glow of twinkle lights to a tree trimmed with care, the holiday spirit fills every room.
Heated
Saltwater Pool
Unwind after a festive day out—or skip the crowds and soak under the stars.
Golf Cart*
Zip to the beach, local markets, or riverside for lights and fireworks without the hassle.
Perfect for Couples,
Families, or Small Groups
Space to gather, cook, celebrate, and relax in style.
“Guests say they come for the events—but stay for the warmth, comfort, and
unforgettable memories made here.”
Sample Holiday Itinerary
Day |
Activity |
Fri |
Arrive + Explore Decorated Rental → Dinner in Vilano → Nights of Lights Stroll |
Sat |
Morning coffee in the pool → Holiday Market at the Pier → Light Up the Night Fireworks |
Sun |
Outlet Shopping → Poolside lunch → Fireside dessert + movie night |
New Year’s Eve(Optional) |
Gourmet dinner at home → Toast in the hot tub or in the heated saltwater pool → Watch fireworks from the bridge |
Ready to Book
Your Festive December Stay at Wander & Rest?
From Christmas markets to sparkling city lights, holiday fireworks, and luxury comforts, December in St. Augustine is a season you’ll never forget. Whether you’re escaping the cold or planning a peaceful end-of-year reset, Wander & Rest is your perfect holiday home base.