Multiple wine barrels stacked in a dark cellar.

SIP Bourbon Trail

October 15th - 17th, 2026

Passes & Rooms ON SALE SOON

Event poster for the 2nd annual Bourbon Trail festival featuring songwriter performances in Paradise, with dates October 15th to 17th, 2026. The poster includes simple line art of a landscape with hills, a large circle representing the sun or moon, and some birds, all in a monochromatic brown color scheme.
A person standing outdoors at dusk, holding a wine glass in one hand and a microphone in the other, with a dark mountainous landscape in the background.

Songwriters In Paradise began in 2013 when singer-songwriter Patrick Davis invited a small group of his closest songwriter friends to the Bahamas for a weekend of music, wine, and storytelling.

What started as an intimate gathering among friends quickly became one of the most unique music experiences in the world.

Today, SIP hosts curated events in Healdsburg, Napa Valley, Cabo and Bourbon Country.

Every SIP experience is intentionally intimate. World-class songwriters take the stage together in round format, sharing the stories behind the songs, and performing in a setting that feels more like a private gathering than a traditional concert.

Over the years, SIP has welcomed Grammy Award–winning writers, legendary hitmakers, and emerging artists—all performing just a few feet away from guests.

While each destination offers its own atmosphere and setting, the spirit of SIP remains the same:

Incredible music.

World class bourbon.

Stunning backdrops.

Welcome to SIP Bourbon Trail.

The Experience

  • 3 official shows at 3 different distillery partner venues
  • Music from over a dozen world renowned singer-songwriters
  • Intimate, almost back stage experience, with events capped at 150 people(some are even smaller)
  • GA, Single Day, VIP and SUPER VIP pass experiences
  • VIP & SUPER VIP only additional events

What’s Included

  • Entry to event (based on type of pass purchased)
  • Complimentary pours, cocktails & heavy Hors d'oeuvres at the show
  • Nightly shuttle service from host hotel to event
  • Commemorative SIP Bourbon Trail pass & lanyard
  • Downloadable photos from the event
  • Additional merch perks available for purchase

    *VIP passes have additional perks including VIP bars with elevated selections, VIP seating, VIP swag and VIP only events

Book Hotel

Want to stay close to the action? Book a room and pass package before they sell out!
Book Room

Purchase Passes

Explore your perfect SIP experience. We offer pass only options as well as room and pass packages.
Passes