James Lilla
646-354-3370
james@outandaboutholidays.com
Chicago, IL
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James Lilla

Travel Advisor

“Adventure may hurt you, but monotony will kill you.”

I realized my dream of traveling the world solo for a year after walking away from my 15-year Advertising Sales career that spanned from New York to Chicago. What started as one year turned into two, and what started as a passion turned into a career.

So far, I visited over 30 countries throughout Europe, Asia, Africa and South America and have no plans to stop! While traveling, I love finding off-the beaten-path restaurants and bars to mix with the locals.

My specialization is in Beach & Sun; Food & Wine and LGBTQ travel, both for individual travelers and groups. Most of my clients are successful professionals who entrust me with making the most of their vacation time, as they have the means, but not necessarily the time or expertise, to plan their travels.

Favorite Travel Memories

  • Visiting Greece five times and yachting off Mykonos with six of my best friends.
  • Cliff diving off Hvar, Croatia with friends while chartering a “James Bond”-style cigarette boat.
  • Spending a summer in Europe, including getting to know all the ins and outs of Ibiza, Spain.
  • A South African safari through Kruger National Park, including a too-close-for-comfort encounter with a young aggressive elephant!
  • Paragliding off Table Mountain in Cape Town, South Africa.
  • Exploring the Stellenbosch wine region in South Africa, including the most beautiful stargazing I have ever seen.
  • Eating cockroaches on the streets of Bangkok, Thailand.
  • Relaxing on car-less Railay Beach in Krabi, Thailand, in time for the most amazing sunset in the world, while taking in a Muay-Thai kickboxing match.
  • Feeding and bathing elephants at a sanctuary in Thailand
  • Renting a villa in Palm Springs, California with a group of friends once a year.
  • 4-wheeling through the Arabian Desert sand dunes outside of Dubai.
  • Fulfilling a childhood dream: watching the early morning fog lift off Machu Picchu!
  • Taking in the famous Nazca Line drawings in Peru via private plane.
  • Enjoying the food, wine and people of Buenos Aires, Argentina!

Interests: Beach & Sun, LGBTQ Travel, Food & Wine, Family Travel, Honeymoons

Destinations: Greece, Italy, Spain, France, Mexico, Ireland, Croatia, Costa Rica, South Africa, Peru, Saint Lucia, Portugal, Turks And Caicos Islands, Dominican Republic, United Kingdom