Private tours are one of the things we do best. Your group, your date, your own guides, and a route through the oldest city in the country built around what you want to see, eat and drink.

We take up to 60 guests on the St. Augustine History Tour and up to 30 on our food and drink tours. The streets here are narrow, so each guide leads 8 to 15 guests and larger groups split across several guides. Nobody strains to hear. Nobody waits on a crowd.

We’ve led walking tours since 2010, starting with Manhattan Walking Tour in New York, and we’ve hosted groups in St. Augustine since 2019.

Groups we host

Corporate outings, team building, holiday parties and conferences

Weddings, rehearsal dinners, bachelor and bachelorette parties

Family reunions and milestone birthdays

School and university trips

Church and seminary groups

Military groups and reunions

Cruise passengers with a few hours in port

Clubs, associations and convention breakout groups

Pick your tour

Our St. Augustine History Tour, St. Augustine Sweets & History and St. Augustine Food Tour welcome all ages. Our St. Augustine Historic Bar Crawl, St. Augustine Bourbon Whiskey & History and St. Augustine Wine, Cocktail & Food Tour are 21 and over, no exceptions.

St Augustine Old City Gates
St. Augustine Historic Walking Tour
$30 (90 minutes, All Ages)
donuts-and-coffee
Sweets & History Walking Tour
$79 (90 minutes, All Ages)
Barbequed meat and sauces
St. Augustine Wine, Cocktail, and Food Experience
$139 (3 hours, 21+)
4 flights of beer
St. Augustine Historic Bar Crawl
$119 (3 hours, 21+)
Polish and Greek Food on plates
St. Augustine Food Tour
$119 (2.5 hours, All Ages)
Whiskey-Glass-Square-convert.io_
Bourbon, Whiskey, & History Experience
$189 (3.5 hours, 21+)

8 to 15 guests per guide

Up to 60 guests walking, 30 on food and drink

One firm price

Build your own

We can blend tastings from different tours into one private experience, like St. Augustine Sweets & History paired with St. Augustine Bourbon Whiskey & History. Any blend that includes a 21+ tour is 21 and over.

Small party?

Any public tour can run as a private tour with a minimum of 4 tickets. A party of three can book four tickets and have a guide to themselves. This depends on guide availability. In the busy season, when every guide is out on public tours, we can’t offer it.

Not sure which fits? Tell us about your group and we’ll recommend one.

What it costs

Private tours start at $20 per guest for a walking tour and run to $250 per guest for a high-end food and drink experience, with top-shelf pours at every stop. Every private tour is built around your request, so you get one firm price for your group before you book.

Evenings

Evening St. Augustine History Tours run all year.

Evening food and drink tours run Sunday through Thursday only. Our restaurant partners can’t guarantee seats or quick service on Friday and Saturday nights, so we leave those nights to them. Evening food and drink tours also pause during Nights of Lights (November 21, 2026 to January 18, 2027).

How it works

Send us your date, group size and the kind of day you have in mind.

We reply with the tour we’d recommend and one firm price.

We send an invoice through Square to save your date:
-Tour within a month: full amount due at booking.
-Tour further out: 50% deposit at booking. Final headcount and balance due 1 week before your tour.

See what our guests say

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Questions groups ask

It depends on the season. For November through January, reach out three months ahead. Nights of Lights fills our calendar and guides book up early. For the rest of the year, one month is usually enough. Summer is our quietest stretch, so we can often accommodate shorter notice. If your dates are tighter than that, call us anyway at 904-599-7391. We would rather tell you no than have you assume it.

Vegetarian options are available. We’ll go over dietary needs with you before we send your invoice, and please remind your guide at the start of the tour. Guests with other dietary restrictions or food allergies (gluten free, dairy free, kosher, vegan) are welcome to join the tour but should expect a more limited selection of tastings compared to other guests. While we do our best to accommodate, substitutions are not always possible.

Yes, on the St. Augustine History Tour, St. Augustine Sweets & History and St. Augustine Food Tour. If they can walk, they need a ticket, and a child in a stroller counts as a guest. A child in a body carrier does not. Bar, bourbon and wine tours are 21 and over with no exceptions.

Our streets were laid out in the late 1500s. A group of 50 on one guide means 40 people hearing nothing. At 8 to 15 per guide, everyone hears every story.

PLAN YOUR PRIVATE TOUR