Enjoy your relaxing ride down the scenic Jamaican coastline on the way into town. When you disembark in Montego Bay, follow your guide on a 1-hour sightseeing tour that takes you through the city highlights. Visit the St James Museum and Sam Sharpe Square, named after the slave who led the 19th-century Christmas Slave Rebellion. Walk through the neighborhood's blocks of impressive colonial buildings and learn about Jamaican history from your guide. Back on the bus, drive through some of the residential neighborhoods featuring stately Georgian homes funded with money from the island's once-thriving sugar trade. Stop by St James Parish Church, the home of stained glass pieces by English sculptor John Bacon.

At the conclusion of your tour, spend about 45 minutes perusing Rainbow, a local shop selling local Jamaican goods like coffee, rum and jerk seasoning. Pop out to a local restaurant for dinner (own expense), before continuing on to Rose Hall.