Pam Winterstein and Associates
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Fleming Island, FL - 888-319-3254
  Meet Our Team  

Lets introduce our team of Cruise and Vacation Specialists at Dream Vacations - Pam Winterstein & Associates.  We are your travel agents based in the North Florida area.  We take great pride in making your dream vacation become a reality.  We pay attention to every detail so you don't have to worry, and can have a hassle free, wonderful vacation.  We are able to help you with all kinds of vacations, whether it be a cruise, land based vacation, all inclusive, tour operater, guided vacation, have a group you need help with, or just want to travel alone, we are here to help.  We have many years of experience among us, so you can feel confident in our knowledge to be able to help you plan your best vacation!


The Team

Pam Winterstein - Franchise Owner/Vacation Specialist

Pam has been in the travel business for 9 years.  Prior to the travel business she was in management in the banking business.  She has an extensive customer service background.  So far she has been on 15 cruises, and plans on taking many more!  She loves to travel, which is what got her started in this career.  Beginning with Cruises Inc., which is affiliated with World Travel Holdings, just as Dream Vacations is, it gave her the knowledge and experience she needed in order to feel confident enough to become a franchise owner.  She hopes to continue to help many more clients make thier travel dreams come true!

Since starting her career as a travel agent, she have become Freestyle Certified with Norwegian Cruise Lines, became a Royal Caribbean Expert, achieved CLIA's  Accredited Cruise Counselor Certification as well as completed Disney's College of Knowledge.  She has obtained her Princess Commodore Status, as well as a Certified Five Star Travel Partner with Celebrity Cruise Lines.  She is also an AMResorts Master Agent (Zoetry, Dreams, Now, and Secrets resorts)


Terry Weems - Senior Independent Cruise Specialist

I fell in love with travelling when I was 14 years old and had the opportunity to be an exchange student in San Miguel de Allende, Mexico, and I have enjoyed travelling ever since.  Fast forward a few (okay, several) years (and trips) later … I took my first cruise in October, 2004, onboard Royal Caribbean’s Voyager of the Seas.  I was in awe and hooked from the moment I stepped onboard the ship – what an experience!  In fall of 2005 I took another cruise.   I was so hooked that in 2006 and 2007 I took a spring and a fall cruise.  No turning back, the addiction was real.  By 2008 I decided that I’d like to help others with planning and booking their cruise vacations, so I decided to become a “cruise specialist”.  I took a week of vacation time from the day job, went to Ft. Lauderdale, FL, and attended a very intensive, week-long training session with Cruises Inc., a sister company to Dream Vacations, and I became a certified cruise specialist for Cruises, Inc.   I still enjoy helping people plan cruise vacations, and I still enjoy going on cruises a couple times a year.  I have known Pam for a several years, we have covered for each other when we travelled.  My transition to join Dream Vacations, Pam Winterstein and Associates, is a natural progression of my passion for cruises and travel in general.  I’m excited to be part of Pam’s team.  I still work a full-time day job, but I am in my “cruise” office evenings and Saturdays, and I’m ready to help plan your dream cruise vacation.  Please let me know how I can help!  I can be reached at 904-236-5000 or toll free at 866-245-2405.  My email address is


Diane DiGuiseppe - Vacation Specialist


I was born and raised in the smallest state of the Unites States.  Since traveling as a teenager, I was fascinated on how large the world is compared to my hometown.  I fell in love with travelling, mainly, cruising, and have been on numerous cruises in my lifetime.  I’m at a point in my life where I can take more leisurely cruises, and have the opportunity to helps other make any travel vacations.  It’s an exciting part of life, and in my opinion, everyone should, at least, experience a cruise.  They will be hooked.  


My background has been in the legal field for the past 30 years as well as 4 years as a Social Worker working with abused children.  Even though it’s rewarding to help my clients in a different way, I would like to help families experience a lifetime of travel.  


I met Pam when we worked together in the same law firm, and she is an inspiration to me.  I now have the opportunity to work with her, and I am very excited to join Dream Vacations and be part of her team.  I work full-time, but in the very near future, my plans are to retire.  I maintain my “cruise office” during the evening hours and/or on the weekends.  I will make myself readily available to meet your traveling needs.  I can be reached at (904) 720-7969.  My email address is


Testimonials From Clients


My agent, Pam Winterstein, was extremelyhelpful during the entire process. She was very knowledgeable about shore excursions and helped us make the best decisions for our family.  She was also great about timely communication.  We would definitely use her again!  4/4/11


Thanks to Pam for going above and beyond for the arrangements 2/26/11




Agent was great,will use her again 3/24/12


Your job was excellent, whenever we cruise again we will contact you. Thank you very much!2/7/11


Pam was very knowledgeable and helpful throughout the entire process of planning
our family vacation.  1/4/13


Call Pam Winterstein for all your travel plans.  She is phenomenal - always going that extra mile.  When we are traveling, other (experienced!) travelers ask us how we know something (tour details, flight changes, etc.), and we tell them it is because of Pam!!!  She is the best because she cares!  6/15/17

Partnerships Awards Header
Carnival Cruise Line Supplier Award
Celebrity Cruise Line Supplier Award
Partnerships Awards Header
Norweigian Cruise Line Supplier Award
Royal Caribbean International Cruise Line Supplier Award
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