Go Big or Go Home

The race begins at the Duffy Square portion of Times Square in New York City, New York, United States.

Teams must search for the location of where the first Finish Line of The Amazing Race took place, the Unisphere at Flushing Meadows–Corona Park, for their next clue..

Teams must fly to Saint Thomas, United States Virgin Islands. The first flight on American Airlines can only accommodate five teams, while the second flight on Delta Air Lines departs 40 minutes after the first flight, carrying the six remaining teams. Upon arrival, teams must head to the Vendors Plaza, where they must sign up for one of six chartered flights on seaplanes destined for Lovango Cay.

Once at Lovango Cay, teams must travel by boat to Carvel Rock, where they must climb around and through the Carvel Rock, then jump once they have reached end of the islet. After both members have jumped, they'll retrieve their clue located in a series of floating bottles.

Teams must travel by boat to Hans Lollik Island, and find a pirate ship named Blackbeard's Revenge, a replica of Blackbeard's flagship Queen Anne's Revenge. Once found, they must search for a Blackbeard impersonator, who will hand them their next clue.

Teams must pull themselves to the shores of Lovango Cay, where they must search for their next clue.

The team member assigned to perform this Roadblock would have to use a traditional liquid compass, a shovel marked 1 yard, and a unique set of directions, in which they must start off in one of four landmarks on the beach (an anchor, a set of barrels, a ship's bell, and a ship's wheel). Starting from their assigned landmark, teams must locate the beach for a treasure chest, containing their next clue.

The Roadblock performers per team are underlined:

• Adam & Bethany
• Amy & Maya
• Brooke & Robbie
• Dennis & Isabelle
• Keith & Whitney
• Kym & Alli
• Lisa & Michelle
• Michael & Scott
• Misti & Jim
• Shelley & Nici
• Tim & Te Jay

Keith, Lisa, and Michael quit the Roadblock and opted to take the 4-hour penalty. Keith & Whitney and Michael & Scott's penalties were issued at the Pit Start of the next leg, while Lisa & Michelle arrived last and were eliminated.

Teams must travel by boat, then taxi to Fort Christian to check in.

For coming in first place, Misti & Jim won the Save.