When a well-known former talk show host hired a ship from Crystal, she wanted every guest to take a gift home from the trip. The solution: For mementoes, travelers' initials were embroidered onto pillowcases in their staterooms.

Milestone birthdays inspire many private charters. Setloff cited the 60th-birthday celebration he oversaw for another wealthy client. The birthday boy wanted the ship festooned with his family crest. It flew from the mast and appeared on the staff 's custom polo shirts (which read "Happy 60th") and even on a custom decal placed along the bottom of the swimming pool. “Every day was 'Happy Birthday' on board,” said Setloff.

Windstar relies on landmark birthdays for much custom business. Conover confided that a client from London takes a weeklong, private, birthday trip most years; in 2016, the woman plans to celebrate year 75 by cruising the Mediterranean with 200 close pals on a custom itinerary of private islands and coves that are generally off-limits to commercial sailings.

“She rolls out everything: They have high tea every day at her request, and there’s a theme dinner every time, with customized menus,” Conover said, flagging an additional bonus for any private sailings. “She drives the ship every day, too.”

Most cruise experts credit Larry Pimentel, an industry legend who is currently running Royal Caribbean’s upscale subsidiary Azamara Club Cruises, with having originally conceived the idea of private charters. Pimentel spent three decades atop several companies, including stints as chief executive officer at Cunard Line and Seabourn Cruise Line. He identified the opportunity for private charters when tasked with launching a newly refurbished, 50-stateroom ship right around the time of the Sept. 11 attacks. 

“When the truly wealthy are looking to charter a yacht, most of them are too small for what they want–just 10 or 12 people,” Pimentel said via phone from Azamara's Journey as it was emerging from dry dock in the Bahamas. “They love the notion of wealthy, privacy, exclusivity, and freedom.” One of Azamara’s midsize ships, with space for 686 guests, was recently chartered for an on-board wedding; the covered pool served as a dance floor and entertainers boarded the ship to play during stops in Corsica and Sardinia.

Nothing, though, tops the largesse of a recent Azamara booking by a client who was eager to celebrate his father’s 70th birthday on a certain date. The ship was scheduled to make a glorious journey from Venice to Athens via the Croatian coast and Greek islands such as Santorini. Pimentel had to tell him that many of the vessel's staterooms had already been booked.

“He came to me and said: ‘I know your ship is full, but I’m prepared to give everyone who booked that week not one but two free cruises, whatever it takes to get that voyage.’ So he spent over $600,000 to buy them out—he had to handle some of the nonrefundable air tickets, too, of course—before he even got to the cost of the cruise.” 

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