Wine & Dine Pairing Tour (St. Augustine, Rolling) in St Augustine
St Augustine, United States

Wine & Dine Pairing Tour (St. Augustine, Rolling)

Outty Ranking 76 4.9 · 268 traveler reviews3 hoursFrom $155

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September 2026

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Adults

Age 13 and over

2

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Age 12 and under

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From, per person$155
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Outty Ranking

76/100

Strongly Recommended. Our proprietary evaluation. How we score

Traveler rating

4.9/5

Based on 268 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Wine & Dine Pairing Tour (St. Augustine, Rolling) worth booking?

Wine & Dine Pairing Tour (St. Augustine, Rolling) is a 3-hour experience in St Augustine, United States, from $155 per person. It scores 76 out of 100 on the Outty Ranking, which we label “Strongly Recommended, based on a 4.9/5 rating across 268 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
76 / 100
Rating
4.9/5 (268)
Duration
3 hours
From
$155 per person

A 'Progressive Style' Foodie Adventure (ROLLING): This unique food tour invites you to explore the vibrant neighborhoods BEYOND the historic core. Satisfy your appetite with four progressive style stops, each offering a

What you get

    About this experience

    A 'Progressive Style' Foodie Adventure (ROLLING): This unique food tour invites you to explore the vibrant neighborhoods BEYOND the historic core. Satisfy your appetite with four progressive style stops, each offering a seated tasting experience in one of our city’s hidden gems. From savory starters to sweet finishes, every course is paired with a boutique wine or artisanal cocktails. Bonus: arrive via the comfort of our chauffeured vehicle. Highlights: ELEVATED EXPERIENCE: Delve into St. Augustine's culinary scene with exclusive tastings at four (4) top-tier venues. LOCAL INSIGHT: Benefit from insider knowledge shared by a local culinary guide. CHAUFFEURED COMFORT: Explore the city's charm in comfort aboard our open-air electric vehicle. Note: Pairings are included. 24-HOUR ADVANCE NOTICE REQUIRED FOR ANY FOOD ALLERGIES. Age 21+ only. Sorry, NO pets of any kind. 4-person min to depart. Primary focus is on the culinary scene with a bit of history and sightseeing sprinkled in.

    What's included

    Included

    • Private transportation
    • Lunch
    • Alcoholic beverages
    • Dinner

    Not included

    • Tour Host gratuity
    • Sorry, NO pets of any kind are allowed.
    • 21+ and older only (no children or infants)

    What you'll see and do

    1. St. Augustine

      We offer local-neighborhood foodie tours and culinary adventures, entertaining everyone from lifelong locals to international visitors. Founded in 1565 by Spanish explorers, St. Augustine is the oldest continuously-inhabited European-established settlement in what is now the contiguous United States. Love historic cities? Then come explore the brick lined the streets and some of our favorite venues, in St. Augustine! Tour Includes: 3 hours of glorious food and wine pairings 4 to 5 fabulous venues Fully guided by a licensed and knowledgeable tour host Exciting, chauffeured city exploration on route to each amazing venue All-inclusive of food and wine (beer substitution available by request)

      Pass by without stopping

    Where it starts and ends

    Meeting point

    St Augustine

    Grace United Methodist Church (loading zone). No parking is provided. Your tour host will confirm, the exact meeting details, the day of your tour. VERY IMPORTANT: Make sure to include your CELLULAR number, in the contact information, so that we may reconfirm all tour and meeting details.

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    Grace United Methodist Church (loading zone). No parking is provided. Your tour host will confirm, the exact meeting details, the day of your tour. VERY IMPORTANT: Make sure to include your CELLULAR number, in the contact information, so that we may reconfirm all tour and meeting details.

    Before you book

    Cancellation
    For a full refund, cancel at least 24 hours before the scheduled departure time.
    Languages
    en, es
    Ticket
    Mobile Only
    Runs on
    Wed, Thu, Fri, Sat, Sun
    Group size
    Up to 8 travelers per booking
    Operated by
    The Tasting Tours

    Know before you go

    • Not recommended for travelers with poor cardiovascular health
    • Not recommended for pregnant travelers
    • Suitable for all physical fitness levels
    • 24-HOUR ADVANCE NOTICE REQUIRED: When making your reservation, please note any severe, LIFE-THREATENING food allergies (IE: nut or shellfish). We CANNOT guarantee accommodations for: special dietary requests, vegan, kosher, dairy allergies, sugar, soy, gluten-free restrictions, pescatarian, etc.

    Photos

    Wine & Dine Pairing Tour (St. Augustine, Rolling) in St Augustine, photo 2Wine & Dine Pairing Tour (St. Augustine, Rolling) in St Augustine, photo 3Wine & Dine Pairing Tour (St. Augustine, Rolling) in St Augustine, photo 4Wine & Dine Pairing Tour (St. Augustine, Rolling) in St Augustine, photo 5Wine & Dine Pairing Tour (St. Augustine, Rolling) in St Augustine, photo 6Wine & Dine Pairing Tour (St. Augustine, Rolling) in St Augustine, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 268 traveler reviews. Written by us, not quoted from reviewers.

    Food and drink

    7 mentions

    The tastings and food stops are a highlight for most reviewers.

    The guide

    4 mentions

    Travelers single out the guide as the reason the experience works.

    Knowledge and storytelling

    3 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Traveler reviews

    268 verified traveler reviews for Wine & Dine Pairing Tour (St. Augustine, Rolling). Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    250
    4 star
    9
    3 star
    4
    2 star
    2
    1 star
    3
    Sort
    45billied · August 2026

    St Augusrine wine and dine

    If you are ever in St Augustine this is definitely something to book. Katie made our experience the highlight of our trip! Well worth the money. Kudos Katie for a wonderful time

    via Tripadvisor

    Steven_O · July 2026

    Anniversary trip

    Amazing from Start to finish, Ira was fantastic. Every place we visited was awesome. This is a must when visiting St Augustine

    Response from the operator: What a wonderful review - thank you for sharing your experience! We're so glad Ira made your visit to St. Augustine such a memorable one. From the first stop to the last, our goal is to introduce guests to the very best local flavors, and we're thrilled to hear every venue exceeded your expectations. Your "must-do" recommendation is one of the greatest compliments we could receive. Thank you for choosing The Tasting Tours, and we hope to see you again the next time you're exploring the Nation's Oldest City!

    via Viator

    Robin_I · July 2026

    Excellent

    Molly was awesome! Establishments visited were interesting and fun. Food and wine was delicious. Enjoyed the others on the tour with us. Just a lot of fun!

    Response from the operator: Thank you so much for the wonderful review! We're delighted to hear that you had such a fun experience with Molly. She has a fantastic energy that makes every tour enjoyable, and we're so glad you loved the restaurant selections, delicious food and wine, and the opportunity to meet and share the experience with your fellow guests. One of our favorite things about our tours is seeing strangers become friends over great food and conversation, and we're thrilled that was part of your day. Thank you for joining us, and we hope to welcome you back for another delicious adventure soon!

    via Viator

    Gsxrboy73 · June 2026

    Good times had by all

    My wife and I aren’t really into wine, but that didn’t matter. The food, cocktails and company made for a great time. Rob was an outstanding host and went out of his way to make everyone comfortable, and by the end, a St. Augustine history buff. Highly recommended!

    Response from the operator: Thank you so much for the fantastic review! We love hearing that you had such a great time—even if wine isn't usually your thing! One of our goals is to create an experience that's about so much more than what's in your glass. Great food, handcrafted cocktails, fascinating history, and wonderful company all come together to make for a memorable afternoon. We're especially glad to hear that Rob made everyone feel welcome and comfortable. His passion for St. Augustine is contagious, and it's always fun to hear when guests leave with a newfound appreciation for the city's rich history. Thank you for your recommendation! We hope to welcome you and your wife back for another delicious adventure soon.

    via Tripadvisor

    frankdU7849DR · May 2026

    Terrible people working in this venue

    This trip was cancelled. The day prior to the event I contacted the venue and confirmed the event. They never said that it was short of customers. That evening at 5:45 thay sent a cancellation text. I called them to discuss but they just sighted policy and hung up the phone on me. Since my day was around this tour I was left without anything because at this late hour, I could not get in another tour. If they told me in the morning that there might be a problem, I could have cancelled and gone elsewhere. This is no respect for the customer and extremely poor customer service.

    Response from the operator: Thank you for your feedback. We are sorry that we were unable to host your tour as planned. We would like to clarify a few details regarding the circumstances of this cancellation. Contact was made the day prior to your scheduled tour to advise that the experience had not yet met the stated minimum number of guests required for departure. As outlined in our booking terms, a minimum of four guests is required for our public tours to operate. We understand that the cancellation impacted plans you had arranged around the tour, and we certainly appreciate that this was disappointing. However, the tour did not meet the required minimum participation level, and we communicated this as soon as that determination was made. At that time, options were provided, including rescheduling, joining another available tour, or receiving a full refund, all in accordance with our published policies. We would also like to respectfully clarify that our customer service representative remained professional throughout the conversation. While we understand that emotions can run high when travel plans change unexpectedly, our team strives to treat every guest with courtesy and respect and expects the same courtesy in return. At no point do we intentionally disconnect calls with guests. Our representative's goal was simply to explain the available options and policies while assisting with a resolution. While we regret that the tour did not depart as scheduled, we appreciate the opportunity to clarify the facts surrounding the cancellation for future readers.

    via Tripadvisor

    Good to know

    Duration
    3 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Wed, Thu, Fri, Sat, Sun
    Price range
    $155 to $165
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    94
    Verdict
    Strongly Recommended

    Why this scores 76

    The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

    Traveler sentiment (30% weight)92
    Review evidence (18% weight)72
    Booking momentum (14% weight)68
    Value for money (12% weight)31
    Listing quality (10% weight)85
    Local standing (8% weight)70
    Booking flexibility (8% weight)100

    Wine & Dine Pairing Tour (St. Augustine, Rolling): questions travelers ask

    Practical detail on this experience, plus the wider planning questions for St Augustine.

    How much does Wine & Dine Pairing Tour (St. Augustine, Rolling) cost?

    +

    Prices start at $155 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in St Augustine usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does Wine & Dine Pairing Tour (St. Augustine, Rolling) take?

    +

    Plan for about 3 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in St Augustine is not rushed.

    Is Wine & Dine Pairing Tour (St. Augustine, Rolling) worth it?

    +

    It holds an Outty Ranking of 76 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.9/5 across 268 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in St Augustine, and how flexible the cancellation terms are.

    Can I cancel or reschedule Wine & Dine Pairing Tour (St. Augustine, Rolling)?

    +

    Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.

    Is Wine & Dine Pairing Tour (St. Augustine, Rolling) suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 3-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Wine & Dine Pairing Tour (St. Augustine, Rolling)?

    +

    Around 94 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in St Augustine can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.

    What should I bring or wear?

    +

    Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in St Augustine and add a light layer if any part of the 3-hour experience runs outdoors or after sunset.

    Where does Wine & Dine Pairing Tour (St. Augustine, Rolling) start and how do I get there?

    +

    The exact meeting point and directions are on your voucher once you book, and they sit in central St Augustine within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.

    What are the best things to do in St Augustine?

    +

    St Augustine is walkable history: Castillo de San Marcos, Spanish quarter walking tours, trolley loops, lighthouse climbs and some of the best-attended ghost tours in the country. Guide storytelling quality is the main variable. On Outty we rank every St Augustine experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Medieval Torture Museum with Ghost Hunting and Tiny Art Gallery, St. Augustine's Wine, Cocktail and Food Experience, Dolphin and Wildlife Adventure of St. Augustine. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.

    When is the best time to visit St Augustine?

    +

    February to May and September to November. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.

    How many days do you need in St Augustine?

    +

    Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.

    Do I book through Outty or through the operator?

    +

    Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.

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