Board a comfortable, air-conditioned unit for a scenic journey through Montego Bay—Jamaica’s vibrant tourism capital. As you make your way through the bustling streets, your guide will share captivating stories about the city’s rich history and cultural significance.

Your first stop is Sam Sharpe Square, the historic center of Montego Bay. Named after National Hero Samuel Sharpe, a courageous Baptist deacon who led the 1831–32 Emancipation War, the square serves as a powerful tribute to Jamaica’s struggle for freedom. Here, you'll see the monument honoring Sam Sharpe and other heroes, and view an original 1806 iron cage once used to imprison enslaved people accused of defiance.

As you explore the square, you’ll gain insight into Jamaica’s colonial past and the resilience of its people. The square’s architecture, statues, and historical markers paint a vivid picture of Montego Bay’s evolution from a colonial stronghold to a symbol of national pride.

On this leg of the tour, you'll explore the journey through Jamaica’s vibrant history and culture and hear story of the island’s earliest settlers, Montego Bay’s rise as a major sugarcane port, and its darker chapter during the era of slavery. You'll also gain insight into the Rastafarian movement—its origins, beliefs, and lasting impact on Jamaican society.

To complement this cultural experience, guests will enjoy a freshly baked Jamaican patty—a popular local favorite. Far from bite-sized, these full-sized patties feature a flaky golden crust filled with your choice of flavorful options: traditional beef, spicy chicken, beef and cheese, vegetable or a hearty soy-based vegetarian patty.

A brief stop at the historic St. James Parish Church, a remarkable structure over 200 years old, designed in the shape of a classic Greek cross. This architectural gem stands as one of Jamaica’s oldest and most elegant churches, with its grand columns, stone walls, and serene courtyard. Inside, you’ll find a stunning stained glass window dating back to 1911, which serves as both a spiritual centerpiece and a tribute to prominent figures who played key roles in Montego Bay’s past. As you explore the church, your guide will share the stories behind its design, craftsmanship, and cultural importance.

After departing the church guests have the option to enjoy a 20-minute shopping stop. Browse local craft markets and souvenir shops offering handmade goods, Jamaican spices, artwork, and other authentic island treasures.

Let’s depart the St. James Parish Church, where history and architecture came together. From here, we journey to the majestic Rose Hall Great House—an 18th-century architectural gem high above the Caribbean Sea. Surrounded by beautifully landscaped gardens, this former sugar estate offers sweeping panoramic views and a glimpse into the island’s colonial past.

Be guided through the haunted halls of the mansion as you uncover the chilling legend of Annie Palmer, the infamous "White Witch of Rose Hall." With gripping detail, your guide will recount how Annie, known for her beauty and dark mysticism, allegedly murdered her three husbands and took numerous enslaved men as lovers—many of whom met tragic ends. The tale reaches its haunting conclusion with her own mysterious death, said to be at the hands of the man she truly loved.