Necker, British Virgin Islands: Harry first visited the Caribbean as a young boy with his mother and brother, and since returning as an adult for his first royal tour, he has also taken a few vacations there. Shortly before his second trip to Afghanistan, he enjoyed a trip with his new girlfriend Cressida and a mixed group of their friends.
Jamaica: There aren't many who would pop to Jamaica for a long weekend, but when Harry's best friend Tom Inskip got married there earlier this year, Harry was there to celebrate with him. Not only that, but the prince was accompanied by his globe-trotting girlfriendMeghan Markle, and after staying with the rest of the wedding party at the Round Hill Hotel and Villas and enjoying a little beach life there, the couple slipped off by themselves to a hotel called The Caves, which features candlelit private dining rooms in the caves themselves.