Anthony Clarke is traveling to Montego Bay, Jamaica from Toronto via Philadelphia. Some key points of the trip include staying at the Riu Montego Bay for $128 per night, and participating in activities like ATV tours, zip lining, and boat safaris. The itinerary provides details on Jamaica's geography, history as the second largest city founded by Europeans in 1494, and its diverse culture influenced by the Spanish, English, and African peoples who have settled there over time.