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Chapter Three: The Rock in Key West

$3,295.00

April 8–11, 2027

LIMITED AVAILABILITY

Reserve your place today with a non-refundable deposit of $1,600 per person.

Americana Trilogy is a journey through the people and places that tell America's story—not through monuments or postcards, but through vineyards, songs, island traditions, shared meals, and the remarkable people who keep those stories alive.

The journey concludes on the island known simply as "The Rock." At the southernmost edge of the continental United States, Key West has long welcomed dreamers, artists, writers, fishermen, cigar makers, musicians, and adventurers drawn by its independent spirit and unmistakable sense of place. Life here has always been shaped as much by the people as by the sea, creating one of America's most distinctive and enduring communities.

Over four days and three nights, you'll discover the authentic character of Key West through thoughtfully curated culinary experiences, guided walks through Old Town, fascinating museums, historic neighborhoods, hidden local treasures, and meaningful encounters with the people who continue to preserve the island's unique heritage. From exceptional seafood and island-inspired cuisine to evenings along the historic waterfront and a memorable sunset cruise across sparkling waters, every experience has been chosen to reveal the true spirit of Key West.

Designed for travelers who value authentic experiences and meaningful connections, this signature A Culinary Society journey goes beyond the familiar tourist attractions to uncover the people, history, and cultural influences that transformed a small island at the edge of America into one of its most extraordinary destinations.

Key West is the final chapter of Americana Trilogy—a collection of immersive journeys celebrating the people and places that define the American experience. From Oregon's vineyards to the legendary music of Muscle Shoals and the island spirit of Key West, each chapter reveals a different expression of America through food, wine, music, history, and the people who preserve those traditions for future generations.

We invite you to take your seat at the table.

Journey Investment: $3,295 per person (double occupancy)

April 8–11, 2027

LIMITED AVAILABILITY

Reserve your place today with a non-refundable deposit of $1,600 per person.

Americana Trilogy is a journey through the people and places that tell America's story—not through monuments or postcards, but through vineyards, songs, island traditions, shared meals, and the remarkable people who keep those stories alive.

The journey concludes on the island known simply as "The Rock." At the southernmost edge of the continental United States, Key West has long welcomed dreamers, artists, writers, fishermen, cigar makers, musicians, and adventurers drawn by its independent spirit and unmistakable sense of place. Life here has always been shaped as much by the people as by the sea, creating one of America's most distinctive and enduring communities.

Over four days and three nights, you'll discover the authentic character of Key West through thoughtfully curated culinary experiences, guided walks through Old Town, fascinating museums, historic neighborhoods, hidden local treasures, and meaningful encounters with the people who continue to preserve the island's unique heritage. From exceptional seafood and island-inspired cuisine to evenings along the historic waterfront and a memorable sunset cruise across sparkling waters, every experience has been chosen to reveal the true spirit of Key West.

Designed for travelers who value authentic experiences and meaningful connections, this signature A Culinary Society journey goes beyond the familiar tourist attractions to uncover the people, history, and cultural influences that transformed a small island at the edge of America into one of its most extraordinary destinations.

Key West is the final chapter of Americana Trilogy—a collection of immersive journeys celebrating the people and places that define the American experience. From Oregon's vineyards to the legendary music of Muscle Shoals and the island spirit of Key West, each chapter reveals a different expression of America through food, wine, music, history, and the people who preserve those traditions for future generations.

We invite you to take your seat at the table.

Journey Investment: $3,295 per person (double occupancy)

Key West, Florida is a sun-soaked island paradise where turquoise waters meet pastel conch houses, and every sunset feels like a celebration. This laid-back destination blends tropical beauty with a quirky, artistic spirit. Joins us for a long weekend excursion exploring and enjoying the best that Key West has to offer.

Experience Details

April 8-11, 2027

Dates

4 days, 3 nights

Trip Duration

$3,295/person

Pricing

What’s Included

  • Round-trip Main Cabin airfare from Charlotte is included in the package price. Guests wishing to upgrade their seats may do so directly with the airline at their own expense. Airfare is based on rates available at the time the package is published; significant increases in airfare prior to ticketing may result in a supplemental charge.

    All ground coordination throughout your stay

  • Boutique Old Town Hotel

  • Signature culinary experiences designed to foster connection and community

    • Walk through Hemingway’s Key West - with stories that stretch to Havana

    • Sunset Sail along the Gulf as the sky turns golden

    • Spend time with members of old Conch families whose roots on the island stretch back generations.

    • Time to Explore, Relax, and Discover at your own pace.

Frequently Asked Questions

  • You can reach us anytime via our contact page or email. We aim to respond quickly—usually within one business day.

  • Our prices vary based on cost of tickets, lodging, transportation, and included events and experiences on each trip!

  • Each retreat is an all inclusive experience - Let us take care of everything for you! The only time you will have to take out your credit card once is for souvenirs. From lodging in boutique accommodations, wine pairings with sommeliers, private ground transportation, trip hosts, all meals, and entry fees to planned events included in trip fees for any easy, relaxing retreat curated for your needs!