The season begins in Malta where Paul and Sheryl prepare their 37-foot sailboat, Two-Step, for a westward passage out of the Mediterranean. They are there in time for the start of the prestigious Rolex Middle Sea Race where mega- and maxi-yachts from around the world compete on a circuit of destinations in the Central Mediterranean. Following the race they make the emotional decision that after 18 years of sailing aboard Two-Step it's time for a new boat. Their search for a new boat begins at the London Boat Show in England where they investigate the latest yachts and participate in activities there. While in London they stay with friends living on a sailboat on the Thames River.