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Our Story 

We believe it’s important to know who you work with, so we’d like to introduce ourselves.  We’re Jim and Judi Drennan. Also known as Mr. & Mrs. D.  Jim moved from Chicago to Cleveland in 2017 and we were married on Valentine's Day 2018. 


We are a multi-generational home with 4 generations ranging from a teenager to our Mom in her 80s.  Jim is a retired software engineer and Judi just retired from financial services to work full-time with Jim. 


Jim was an avid cruiser before we married, having been on almost 50 cruises.  He always told Judi “I can get on a ship, unpack my bag, take a couple of deep breaths of sea air and I know I’m on vacation.” Judi understood in theory – but having never cruised, it wasn't personal. On their honeymoon in 2018, Judi understood! Jim looked at Judi on the first sea day and said, “I’ve never seen you this relaxed”.  Judi, lying on a deck chair with a hat covering her face, lifted the hat, looked at Jim and said, “No one has”. She put the hat back over her face and continued to enjoy that feeling of complete relaxation. 


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Our personal passion is cruising. It’s where we disconnect, renew and refresh. We understand cruising is not everyone's perfect vacation. We focus on helping our clients find where they can renew and refresh – whether that is a cruise ship, an all-inclusive or an adventure vacation. We believe making memories is most important. Vacation time spent by yourselves, or with family and friends, is for creating memories that will last a lifetime.  


The venue and the destination are important – however the memories you make over drinks, dinners, or adventures are what will stay with you. Our most memorable vacation to date was a multi-generational cruise to celebrate Mom’s 80th birthday.  That time was extremely special and one we are so grateful to have captured as a family. 

We would love the opportunity to share our travel services and expertise with you and your guests. To start planning your next trip with Cruisin' with the Drennans, please schedule a quick chat with us. In 15-30 minutes, we can get to know a little about you and begin to create your next vacation!

Our Personal Travel Gallery

A picture’s worth a thousand words, but the memories they hold are worth a million. We invite you to see some of the adventures and memories we've made at Cruisin' with the Drennans. Explore our personal photo gallery below.  

Cruisin' with the Drennans is proud to be partner with top travel suppliers worldwide.

Our Industry Affiliations

We continue to expand our knowledge through a certifications, courses, and in-person seminars. We are also proud to be members of ASTA and CLIA.  Jim has earned his Master Cruise Counsellor accreditation with CLIA.


We invite you to experience travel with Jim and Judi taking care of the details. Our proven process makes travel planning fun, smooth, and easy! We're here for you from planning phase until the time you return home! Learn more about why Cruisin' with the Drennans is the right agency for you!

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