Gather. Savor. Celebrate together.

A spacious modern lounge with a circular leather sectional sofa surrounding a fireplace with a black hood and chimney. The room features wooden flooring, exposed brick walls, and a geometric patterned accent wall. There are various pillows on the sofa, a mounted TV on the patterned wall, and a railing with an open loft area above.

Group Retreats

A modern dining room with a long wooden table, blue upholstered chairs, exposed brick walls, and contemporary lighting fixtures.

What We Offer

At When in Roam, we create luxurious escapes that let you and your group focus on what truly matters: connection, indulgence, and unforgettable memories. Our spacious, beautifully appointed suites in Frankfort and Shelbyville, Kentucky, provide the perfect home base for couples or friends seeking a curated Bourbon Country experience.

Every detail—from the comfort of your accommodations to the moments you’ll remember long after checkout—is designed to inspire, delight, and bring your group together.

We liaise your ideal elevated retreat

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Private bourbon tours and tastings at local distilleries

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Bourbon cocktail sessions and mixology experiences

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In-suite chef-prepared meals tailored to your group

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Couples’ massage therapy and wellness experiences

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Local excursions, curated activities, and group experiences

Meet.
break away.
Stay close.

Exterior of a building with a black sign reading 'The Gatsby' in gold letters, featuring large windows and an entrance with glass doors.
Close-up of a modern chandelier with multiple small light bulbs on black and gold rods, against a textured, warm-toned ceiling.

When In Roam’s private suites are located within walking distance of The Gatsby, our expansive event venue designed for workshops, creative retreats, leadership offsites, and group experiences. The seamless proximity allows your group to gather with intention—then retreat into quiet, comfortable spaces without losing momentum.

EXPLORE THE GATSBY
Group of people in a wine cellar, tasting and discussing whiskey from glasses, with barrels in the background.
Close-up of stacked vinyl records on a shelf.

The Orphan Barrel Experience

A limited selection, thoughtfully chosen, available as part of your curated retreat.

Learn more

Book Your Group Retreat

Gather your friends, plan your escape, and let us bring Bourbon Country to life for your retreat.