Explore St. Augustine’s Holiday Sip & Shop Event: Festive Shopping and Wine Tasting in the Historic District
Difficulty
easy
Duration
2.5–3 hours
Fitness Level
Suitable for most fitness levels; expect easy walking with some standing during tastings.
Overview
Discover St. Augustine’s festive Holiday Sip & Shop Event—a guided tour through charming boutiques in the Historic District, capped with an exclusive wine and charcuterie tasting. Perfect for holiday shoppers looking to mingle and find unique treasures.
Holiday Sip & Shop Event
ST. AUGUSTINE
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Adventure Photos
About This Adventure
Embark on the ultimate holiday shopping adventure in St. Augustine's historic district! Enjoy a guided stroll through charming boutiques, discovering unique treasures. Conclude your experience with an exclusive wine and charcuterie tasting, making it a festive celebration with friends. This is more than shopping; it’s a memorable holiday tradition!
THE ULTIMATE AFTERNOON EXPERIENCE
Get ready to shop til you drop! This experience starts with a Chef's pairing lunch (2 to 3 courses). Then will launch into an exciting historic district exploration – filled with boutique shopping and a wine tasting event. The adventure finishes with a decadent dessert.
Tour Includes:
- 3 hour private and personalized experience – fully guided
- 3 fabulous venues (Wine pairing lunch, Wine tasting with charcuterie and Dessert)
- TTT SPECIAL: Souvenir canvas tote (shopping bag for your goodies) and etched wine glass (for sipping along the way)
- 4 or more fabulous boutique shopping opportunities. *shopping purchases are not included.
- Food, wine, additional sips & treats (rate does not include tour host gratuity)
Location
- St. Augustine, FL
Duration:
3 - 3.5 hours
Availability:
Call to book a date
Please note: Gratuities for your Tour Host are NOT included in the price of the tour, but can extended after the tour or can be added upon check out.
Meeting Location:
24 Cathedral Place Suite #401 St. Augustine, FL 32084
Your Tour Host will be in touch, the day of the tour, to confirm all details.
Adventure Tips
Wear comfortable, sturdy shoes
The Historic District’s brick-lined streets can be uneven and cobblestoned, so sturdy shoes will make your stroll easier and safer.
Bring a light umbrella or poncho
Tours go on rain or shine; be prepared for Florida’s unpredictable weather with rain gear.
Arrive early for check-in
Plan to arrive 15 minutes before the 10:30 am start to check in at Blot Lip Lounge.
Plan for an age-21+ event
This is an adults-only experience; please arrange childcare accordingly as guests must be 21 or older.
Local Insights
Wildlife
- Urban migratory birds like mockingbirds
- Squirrels commonly seen in shaded parks
History
St. Augustine was founded in 1565 and is the oldest continuously inhabited European-established settlement in the continental U.S.
Conservation
Local businesses emphasize sustainable shopping with many handmade or locally sourced products, supporting environmental responsibility.
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Adventure Hotspots in St. Augustine
Frequently Asked Questions
Recommended Gear
Comfortable walking shoes
To comfortably navigate uneven brick streets throughout the Historic District.
winter specific
Light rain poncho or umbrella
Florida weather can be unpredictable; these keep you dry during light rain.
all specific
Reusable tote bag
Perfect for carrying your holiday shopping finds, provided as a souvenir.
all specific
Light jacket or sweater
Evenings and early mornings can be cool, especially in winter months.
fall specific