Day Trip |The Signature Trail Tour
A concierge-style bourbon experience designed for groups who want a well-paced, engaging day without ever planning a single detail.
At a Glance
Duration
Evening Bourbon Social + full-day | 3 distillery experience + Lunch + Transportation + Expert Guide
Pricing
Starts at $450 a person (based on a minimum 4 guests; final pricing may very with group size)
Group Size
Up to 14 guests per booking
Availability
Tours operate daily
Start Times
8:00 AM–5:00 PM
9:30 AM–6:00 PM
Cancellation
14+ days in advance: eligible for partial refund or rebooking options
[View full cancellation and rebooking policy]
The Experience
The experience begins the evening before with a private welcome event reserved exclusively for Sipping in the South guests. It sets the tone, brings the group together, and quietly removes the pressure of “figuring it all out” before the day even begins.
The following day is built around your one must-do distillery, with two additional experiences thoughtfully selected to round out the day. These may include an interactive mixology class that invites participation, laughter, and a little friendly debate, a complementary distillery visit that adds contrast and depth, and a well-timed Southern-inspired lunch that gives the day room to breathe. Throughout it all, your guide manages the pace behind the scenes so everything feels easy and unforced. The result is a concierge-style experience built around connection and energy, where nothing feels scripted and no two tours are ever the same.
⸻
The Bourbon Social
Every In-Laws & Outlaws tour begins with a private welcome event known as the Bourbon Social. This relaxed gathering is designed to help guests ease into Bourbon Country, discover what they enjoy, and feel comfortable before the first distillery stop. It’s where conversations start, preferences emerge, and the tone for the entire experience is set. It’s social, welcoming, and exclusive to Sipping in the South, and it’s one of the reasons the following day flows so naturally.
⸻
What’s Included
Each experience is thoughtfully designed and fully managed from start to finish.
• Private Bourbon Social welcome event
• Three curated bourbon experiences, including guided tastings and Interactive mixology or barrel thieving session.
• Southern-inspired lunch
• Private transportation for the day
• Expert guide and host
• Dedicated Experience Coordinator
⸻
How Planning Works
This tour is pre-designed for flow, then refined around your group.
At booking, you’ll select your preferred region, your one must-do distillery from Maker’s Mark, Buffalo Trace, Woodford Reserve, or Heaven Hill, and your preferred timing for the Bourbon Social. You’ll also have the opportunity to share any food restrictions or special considerations so everything is thoughtfully arranged in advance.
From there, two additional experiences are carefully selected to complement your must-do stop, with each experience building off the other to create a day that feels cohesive, balanced, and easy.
Your Experience Coordinator handles all scheduling and logistics behind the scenes, ensuring everything aligns seamlessly. A detailed itinerary will be finalized and shared once booking is complete, so all you need to do is arrive and enjoy
⸻
Who This Experience Is For
This experience was designed for groups that don’t all show up the same way. For families, friends, or groups with strong opinions. For bourbon lovers and bourbon skeptics, sharing the same van. For those who care less about memorizing facts and more about how the day feels
⸻
Good to Know
Distillery visits are subject to availability, and timing may shift slightly to ensure the best overall flow of the day.
Special requests and mobility needs can be accommodated with advance notice.
Gratuity is not included and may be given directly to your guide.
⸻
Book This Experience
Reserve your date, choose your preferred start window, and let us take it from there.
• Preferred timing for your Bourbon Social.
