At Penny Sheldon Travel we offer you a full range of travel services to any destination in the world.

 We specialize in all locations in paradise!

After 25 years as the owner of Penny Sheldon Travel I only recommend properties that will offer you the best vacation in Paradise based on my personal experience!  I am more than familiar with the finest beaches that have the most beautiful turquoise waters—waiting just for you.  Plus, I distinguish the difference between the best resorts for you as well as where NOT to stay. Which is equally as important!


My vacations are spent doing sight inspections so that I can better serve my clients. I stay and experience the destinations that I recommend and make it a point to inspect as many resorts as I can when I travel to a country. You work hard, you take care of your family—you deserve someone to take care of you.  Where else would you spend thousands of dollars of your hard-earned money without using a professional? Remember our service costs you NOTHING— so why not let us do the work for you!

Let me tell you how we got started in the travel business...

Many years ago, I was going out with a gentleman who wanted to take me to an all-inclusive resort in Jamaica for my birthday. I had traveled over most of the world and was quite the travel snob. I asked him why he thought I would want to go on such a vacation. After all I had been to the finest places and mixed with locals in London, Istanbul, Prague, Italy, Austria, Germany, Greece, and Mexico.

I'm surprised that he took me anywhere after the way I acted . . . however, we did go to Sandals Ocho Rios and fell in love with it. So much so that we went to six different all-inclusive resorts over the following few years. I was Executive Director of the Cystic Fibrosis Foundation for two states at the time. Yet I was so taken with the concept of helping others expand their world with adventures to far off lands, so I decided to leave my job and start my own travel agency. At the time that I opened Penny Sheldon Travel, the home-based travel agent community that is around today did not exist. I was truly a pioneer in this area of the travel business. It was a grass-roots effort to follow my vision and launch my one-woman office. My daughter, Ashley joined the agency in 2004 and with the arrival of three boys she has made her area of expertise in family resorts. 



  • Preferred Sandals & Beaches Agency

  • Certified Destination Wedding Specialist

  • Inaugural Member of Sandals Chairman’s Royal Club

  • Inaugural Recipient of Sandals Lifetime Achievement Award

  • ‘Best of the Best’ Agency for 18 years

  • Lifetime Platinum Member Since 1997

  • Top 10 Travel Agents Worldwide

  • Creativity Award for Outstanding Commitment and Dedication

  • Sandals Extreme Travel Agent


Chairman Gordon ”Butch” Stewart unveiled the Sandals Extreme Travel Agent Grand Prize winner of  a Sandals inspired Honda Element at the annual S.T.A.R. Awards.  The award was for the travel agent who had over exceeded his expectations.  Penny of Penny Sheldon Travel was awarded for her lifelong commitment and ingenuity.

Caribbean Tourism Organization


  • Renee’ Di Giulio-Naismith Caribbean Creativity in Travel Award
  • ‘Best of the Best’ Agency for 17 years

  • Globe Award

St. Lucia Piton Award – Top 25 Agents

Jamaica’s Top 50 Agents

I would like to say how helpful, experienced, informative, approachable Penny is. Nothing is too much trouble for her to help with in a friendly and unflappable way. Highly recommended for your holiday needs.

Dawn Kidd East - Sussex, England

Hear what they say about Penny:

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