Meet The Super Travel Agent Who Takes U.S. Presidents To Remote Lands

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Sienna Charles

Jaclyn India of Sienna Charles, a travel firm for V-V-V.I.Ps

Ten years ago, Jaclyn India founded Sienna Charles, a boutique travel firm solely for ultra-high net worth individuals that routinely spend $500,000 on a single trip. At 35, she is a super traveler herself, logging more than 200 days a year on the road and with over 80 countries on her "been there" list.

The company personally vets every restaurant, spa, hotel and experience before offering them to clients (India once flew just to test out a masseuse for a client), which partly explains a customer pool that ranges from CEOs and bankers to George W. Bush and his family. On a 2015 trip to Ethiopia with the former president and family, India arranged for a private plane and seven helicopters to land in otherworldly Danakil Depression as well as remote tribal villages in the Omo Valley. I’ve been to the Omo. Trust me: It’s beyond imagining how challenging it would be to arrange a V.I.P. visit in that isolated corner of the world.

Sienna Charles

In Ethiopia in 2015 with former President George W. Bush

I’m fascinated by businesses that cater exclusively to the top of the top of the top, so I asked India for her greatest hits list of achievements for her guests. After all, mere upgrades to the Presidential Suite won’t cut it when you’re dealing with actual presidents. Here’s some of what she told me:

  • Asked by a wife to hire the New York Rangers for her husband for their anniversary.  Rented out a bar, and after he attended the game, took him for drinks as the team showed up to celebrate with him after their big win.
  • Arranged a private breakfast on top of the Arc D’ Triomphe.
  • Personally brought peanut butter and non-alcoholic beer into Ethiopia so President Bush could enjoy peanut butter & jelly sandwiches.
  • Arranged a fake car breakdown in Israel, where the guests thought they were stranded in the desert. But instead of actually being stranded, camels picked them up and brought them to a tent set up or a glamorous dinner.
  • Coordinated and received approvals to bring a personal yacht into the Galapagos, which has never been done, so that the guests could tour in comfort.
  • Regularly clears space in popular sold-out hotels, including Hotel du Cap, for clients who decide last minute they must be there over the peak period. This is generally true for any hotel.
  • Arranged Christmas trees to be flown in to make sure a guest’s trip in India felt festive in each of the four hotels they stayed in. Presents were personalized under each one for all 10 travelers.
  • Secured sumo tickets for guests wanting to see the matches (tougher than Hamilton tickets), as well as arranged for visits to their stables outside of Tokyo
  • Arranged for guest to meet with J Lo during her Las Vegas show last year.

You get it. It sounds like a cross between pure exhilaration and absolute exhaustion, but India appears to have been born for the job. She calls herself a workaholic who will "email you back in one second" no matter when the email comes in.

She got her start working at Le Bec Fin, the iconic five-star restaurant in Philadelphia. It was where she first observed service at the highest level. Sommeliers knew each producer and the provenance of the grapes. The servers could practically show you photos of where the beef and vegetables came from. A meal might run $2,000, and most felt it was worth the price.

After five years, India left to work in a luxury travel firm but was struck by how different the commitment was to customers. "People were spending ten times as much for a trip as they were for one meal at Le Bec Fin, yet nobody was looking at details in a start-to-finish way like they did at the restaurant," she told me. "I thought, ‘What if I could create the most amazing customized luxury service, but for travel?’"

Launched in 2008 in New York, Sienna Charles works with around 50 families, all of whom want to feel like India is working just for them–and they should. She charges $1,000 for a hotel reservation, which includes India’s selection of the property and room and any transfers needed. It’s $2,500 for more complex requests, and if clients need her full attention, they will put Sienna Charles on retainer for $36,000 a year.

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Sienna Charles

Jaclyn India of Sienna Charles, a travel firm for V-V-V.I.Ps

Ten years ago, Jaclyn India founded Sienna Charles, a boutique travel firm solely for ultra-high net worth individuals that routinely spend $500,000 on a single trip. At 35, she is a super traveler herself, logging more than 200 days a year on the road and with over 80 countries on her “been there” list.

The company personally vets every restaurant, spa, hotel and experience before offering them to clients (India once flew just to test out a masseuse for a client), which partly explains a customer pool that ranges from CEOs and bankers to George W. Bush and his family. On a 2015 trip to Ethiopia with the former president and family, India arranged for a private plane and seven helicopters to land in otherworldly Danakil Depression as well as remote tribal villages in the Omo Valley. I’ve been to the Omo. Trust me: It’s beyond imagining how challenging it would be to arrange a V.I.P. visit in that isolated corner of the world.

Sienna Charles

In Ethiopia in 2015 with former President George W. Bush

I’m fascinated by businesses that cater exclusively to the top of the top of the top, so I asked India for her greatest hits list of achievements for her guests. After all, mere upgrades to the Presidential Suite won’t cut it when you’re dealing with actual presidents. Here’s some of what she told me:

  • Asked by a wife to hire the New York Rangers for her husband for their anniversary.  Rented out a bar, and after he attended the game, took him for drinks as the team showed up to celebrate with him after their big win.
  • Arranged a private breakfast on top of the Arc D’ Triomphe.
  • Personally brought peanut butter and non-alcoholic beer into Ethiopia so President Bush could enjoy peanut butter & jelly sandwiches.
  • Arranged a fake car breakdown in Israel, where the guests thought they were stranded in the desert. But instead of actually being stranded, camels picked them up and brought them to a tent set up or a glamorous dinner.
  • Coordinated and received approvals to bring a personal yacht into the Galapagos, which has never been done, so that the guests could tour in comfort.
  • Regularly clears space in popular sold-out hotels, including Hotel du Cap, for clients who decide last minute they must be there over the peak period. This is generally true for any hotel.
  • Arranged Christmas trees to be flown in to make sure a guest’s trip in India felt festive in each of the four hotels they stayed in. Presents were personalized under each one for all 10 travelers.
  • Secured sumo tickets for guests wanting to see the matches (tougher than Hamilton tickets), as well as arranged for visits to their stables outside of Tokyo
  • Arranged for guest to meet with J Lo during her Las Vegas show last year.

You get it. It sounds like a cross between pure exhilaration and absolute exhaustion, but India appears to have been born for the job. She calls herself a workaholic who will “email you back in one second” no matter when the email comes in.

She got her start working at Le Bec Fin, the iconic five-star restaurant in Philadelphia. It was where she first observed service at the highest level. Sommeliers knew each producer and the provenance of the grapes. The servers could practically show you photos of where the beef and vegetables came from. A meal might run $2,000, and most felt it was worth the price.

After five years, India left to work in a luxury travel firm but was struck by how different the commitment was to customers. “People were spending ten times as much for a trip as they were for one meal at Le Bec Fin, yet nobody was looking at details in a start-to-finish way like they did at the restaurant,” she told me. “I thought, ‘What if I could create the most amazing customized luxury service, but for travel?'”

Launched in 2008 in New York, Sienna Charles works with around 50 families, all of whom want to feel like India is working just for them–and they should. She charges $1,000 for a hotel reservation, which includes India’s selection of the property and room and any transfers needed. It’s $2,500 for more complex requests, and if clients need her full attention, they will put Sienna Charles on retainer for $36,000 a year.

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