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 Walking Romantic Castles of Romagna, Italy

September 28 - October 6, 2018

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Created Just for VagabondGALS !!!

The REAL Heart of Italy

May 11 - 19, 2018

(other dates available for men and women)

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Vagabond Agents


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For our GALS only !!!

Experience Bologna, Italy

May 11- 19, 2018

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Kristen Orlando

Kristen’s passion for traveling really began when she was a child.  Her parents took her on numerous vacations creating lifelong family memories.  Some of the places her parents have taken her include the Caribbean Islands of St. Thomas, St. Johns, The Cayman Islands, Cozumel, and Jamaica.  She has also traveled the European countries of France, Belgium, Switzerland, Germany and England.  And let’s not discount the states and cities throughout the US and countless trips to Walt Disney World.   Now, as a mom herself, she likes to travel with her husband and three sons, creating those same life long memories.    

 She was blessed to be able to stay home with her children until her youngest son went to kindergarten.  Now it was time to start to think about re-entering the work force.  Having the love for travel, she couldn’t think of a better career choice than to become a Travel Agent.  Over the years, she had booked several vacations with Vagabond Tour & Travel and now she is excited to be a part of their team.

Kristen has since become a Certified Sandals Specialists, visiting many of the Sandals and Beaches properties, and is also a Wedding Moons Specialist.  She is a Disney Travel Professional, Hawaii Destination Specialist, and a Royal Caribbean Cruise Line Expert.  She is constantly looking to gain more knowledge by attending various courses and visiting different destinations.  Kristen can give you the inside tips and advice using her personal experience to guide your vacation decisions in a way that provides you with the best vacation possible.

2016 travels:

Sandals Grande Antigua / Sandals Barbados / Port St. Lucie, FL

Stone Harbor, NJNassau, Bahamas & Castaway Cay with Disney Cruise Line  / Sandals Regency La Toc

Sandals Halcyon  / Sandals Grande/  St. Lucia  Chicago, IL  / Walt Disney World

2017 plans to travel to Beaches Turks and Caicos /  A Royal Caribbean 7 Night Western Caribbean Cruise / Host the Beach Turks and Caicos Girls Weekend Getaway September 28-October 2, 2017

To contact Kristen via email 






We enjoyed our stay at the Divi all Inclusive in Aruba. It was very nice to be able to go between the Divi and Tamrijn to eat, drink, swim, or just hang out. We had a very nice and relaxing stay. Everyone made us feel comfortable and they were very friendly. My only criticism would be that being our first time when we first got to the hotel and checked in no one at the resort told us how anything worked. Being an all inclusive resort we did not know that we had to make reservations for all the different restaurants except for the two dinning halls. Also at check in they gave us towel cards but again no one at the resort explained how they worked. We did eventually figure it all out on our own, but just feel as if that should have been things they tell you at the time of check in. Other than that we had a great time and would definitely go back to Aruba! Thank you to Kristen Orlando for taking the time to help us plan our honeymoon and making it go so smoothly :)

-Alexis D


My children and I just returned from their first trip to Disney World. I couldn't be happier with the travel arrangements! I was overwhelmed with trying to plan a trip with such a short amount of time (I had about six weeks to figure everything out). Vagabond Tour & Travel put together a travel package for me in only a few hours, and covered everything from flights to accommodations to park tickets. When I met with Kristen, she gave me tons of useful tips for visiting the Disney Parks, which were very handy. Overall, we had a very enjoyable experience, and I would highly recommend Vagabond! They took the stress out of planning a vacation and allowed me to enjoy myself instead of worrying about the small things. I can't wait to use them again for my next vacation!


Another wonder trip plan by our travel agent Kristen. We just returned from a Western Caribbean cruise on Royal Caribbean. We went with 31 people total and it went smoothly every second from pool side fun and excursion to dinner for 31 and party's afterwards. Our kids had a blast and can't wait to return and make more memories. We can't wait to book another . Thank you Kristen!

-Brenda J

Just got back from an awesome vacation at Beaches Ocho Rios . Our children (ages 5,10,13) had the time of their lives. We loved the ease of booking excursions and the kids loved the kids clubs so much they begged to go every day. The food and drinks were great, and the people couldn't be more friendly if they tried. Our travel agent Kristen prepared us for our trip with a wealth of information. From landing at the airport and taking advantage of Club Mobay, to which room she thought we would like best from her personal experience. Her continued contact leading up to the trip was exceptional. It was just the relaxing trip we needed. Thank you again Kristen!

-Erin G

Kristen Orlando made our Disney trip perfect! I told her what we were hoping to do and she made it all happen! Not only did Kristen make all of our reservations, but she also helped me with our daily itinerary so that we were able to fit everything in. We are excited to work with Kristen again as we plan our trip to Beaches!


Thank you so much Kristen! You did a great job planning the perfect vacation for our family. You helped in every area of our trip and even had great suggestions for making it more special. You made yourself available whenever I had questions and always got back to us quickly. I loved how the guess work was taken out and Kristen walked me through the whole process.



I have used Kristen for a number of trips. She is very knowledgeable and caring. We have done a couple of Sandals trips and are looking forward to the next one in late January. She is always up to date on the latest sales and promotions that are being offeerd. We are also currently booked in June on an Alaskan Cruise and land tour. She returns calls/ e-mails efficiently . She is a pleasure to work with and I would Highly recommend her for any of your trips.



Kristen made our honeymoon travel easy and special! With wedding planning.. you don't have as much time to plan out an itinerary for your honeymoon. I gave her some ideas and a budget and she made a wonderful honeymoon happen! Even hand delivered an itinerary before we left AND made us a honeymoon website (BEST idea EVER). We couldn't have been happier with her services!



Vagabond Tour and Travel was fabulous. Kristen sent us on 2 wonderful trips this year. One was a Mexico all inclusive and I highly recommend getting the info from Kristen. She picked a perfect place for us. Also beaches Jamaica couldn't have been any better. Kids can't stop talking about it. Kristen set everything up and made the trip so enjoyable for us. We will work with her any day! We are already having her work on our next trip! Can't wait! She is so knowledgable and cares about her clients. That's everything you want in a travel agent!



Thank you so much to Kristen! My husband and I were inexperienced travelers and she helped us to make an unforgettable trip!