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The Oprah Cruise 2019: Our Experience and Favourite Memories

As many of you know (if you follow along with me on Instagram!) I recently took my mom on the Oprah Cruise and today I’m finally going to dish the details of our experience!! I also documented a good portion of the trip which we turned into a vlog for you to view below!!! Actually, some of you may know a little bit about the trip already as I briefly mentioned our cruise in my blog on pumping and storing breast milk while travelling (check out my 8 tips, here!). So today, I thought I would give you the low down on how everything went!!

My mom and I have ALWAYS been massive Oprah fans, since the time her talk show first aired back in the ’80s!! I’m sure many of you are very familiar with Oprah, so I don’t need to go on about how inspiring she is and why I love her so much! Needless to say, meeting her has always been a dream of mine! Back in 2009, I actually took both of my parents to see her last show in Chicago and while we didn’t get to meet her that time around, it was still such a cool experience as we have always been mega fans!

One day a few months back, I was cruising Instagram and I came across this cruise by Holland America … THE OPRAH CRUISE!! I was immediately intrigued and quickly checked out all of the details as I knew this would be so special for my mom. She has had a few tough years recently and we haven’t had much mother-daughter time lately so I didn’t hesitate to book the tickets. I purchased these back in July and kept them a secret until my mom’s birthday in November. Make sure to watch the video below as I got the whole surprise on camera … and there were a few tears!!

Jillian Harris 7 Tips for Pumping and Storing Breast Milk

Fast forward to February and this mama-daughter duo was OFF!! I had only ever been on one cruise before this and to be honest, I swore I would never step foot on another cruise again after my first experience because it was so terrible!! So, I was completely unsure of what to expect! Well, this cruise (as I mentioned above) was with Holland America (and no, this isn’t a sponsored post!! ? ) on their brand new ship, the Nieuw Statendam!!

The Nieuw Statendam was gorgeous and the colour scheme was RIGHT up my alley! We’re talking whites, and creams, with nice little pops of colour. The service and food were seriously INCREDIBLE!!! I couldn’t believe how may vegan and vegetarian options there were! My mind was totally blown!! The casino and the entertainment on board the ship were top notch as well!!

The cruise was seriously everything you would imagine it to be … other than the fact that I pictured mom and I sitting down with Oprah talking about life, with a glass of champagne in hand … and her inviting us to her vacation home in Hawaii … LOL!! While that didn’t happen … mom and I DID get to meet Oprah very quickly (and snag a photo!!) and we had the opportunity to hear her speak … which was nothing short of amazing!!!

Jillian Harris Oprah CruiseJillian Harris 7 Tips for Pumping and Storing Breast MilkJillian Harris Valentines DayI think mom and I would both agree that listening to Oprah speak was one of our favourite memories from the trip … she shared SO MANY valuable lessons (which I’m going to share with you in another blog post … coming soon!!) … and we left feeling totally invigorated. I felt (and still feel) so inspired … not only to be a better person myself but to read more and help OTHERS more. It was ridiculously inspirational and I can’t WAIT to share my favourite bits and pieces with all of you.

It was all such an amazing experience and on top of that, mom and I got to spend 5 full days together which was so overdue. We have the best time and were able to really bond on this trip. The last time we took a mother-daughter trip together it was a little bit chaotic and I wasn’t very relaxed and I felt a bit high strung. So this time together was needed. At one point I remember thinking how much I missed the kids and then it hit me … that I AM my mom’s little girl, HER baby … and it makes me emotional writing this because one day I know that Annie and I will be in the same situation. Annie will grow up and she will move out and start her own family and we won’t get the same quality time as we have now.

Jillian Harris Valentines Day
Jillian Harris 7 Tips for Pumping and Storing Breast Milk

When that hit me, I knew I had to be fully present with mom and to really take the time to connect with her. I think this is important for EVERYONE to do … and it doesn’t have to be going on a cruise with your mom … it could be going out for a drive … grabbing ice cream cones for the road while looking at houses … or, it could be going on a little day trip somewhere close.

So all in all, this experience was truly amazing. In fact, it was so amazing that it completely changed my view on cruises and Justin and I are thinking of planning a family cruise at some point. I think cruises are really one of those things that you either love or hate and this one was on for the books. It was so great! Thanks, Oprah!!! LOL!



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  1. You rock Jillian!!! What an awesome trip for you and your mom. I love your positivity and passion.

  2. So glad for you both. Jillian. I too went on a cruise with my daughter recently. I have to confess I’m not the one originally booked to go but due to some marital issues my daughter asked me to go. It may not have been under ideal circumstances but we made the best of our trip and I feel so very grateful for time we spent together.

  3. Your mom is so sweet. Both of your parents are. Not hard to see where your kindness comes from. So nice you were able to do that for your mom. I enjoyed watching the video.

  4. This video makes my heart so happy! I am Carly Waldron- I work for HAL and I sent you the wine and chocolates. (Sorry if the wine was mediocre, my options were so limited!! I tried to request sandhill of course, but it wasn’t an option) nonetheless, the relationship you have with your mom reminds me of that of mine with my mom (who you also met and took a photo with onboard!!!) and it is inspiring! The way you were talking about how Oprah made you feel is how you made me feel in your Instagram shoutout! I’m so glad you had a great cruise and I hope the memories last forever. Thanks for being you!!

  5. This video was amazing! Thanks for sharing Jillian :). My mom and I just went to Hawaii and did a cruise together! It was the best! I love that you are so real ❤️

  6. I was not a cruise person at all either. But now I’m totally hooked!!!! We have gone on 3 as a family and have booked another one for Christmas! I highly recommend Disney Cruise Lines if you are taking the kids. (Not sponsored ?)
    I love your stories and blog. What and adventure to meet Oprah! Amazing! Whenever I take a selfie now with friends I tell them to say Yay like Oprah does!!!

  7. We just went on our first cruise also Jillian, a Western Caribbean cruise. We sailed with Princess Cruise Lines on the Regal Princess which is the Love Boat,…OMG, amazing!!!! We were treated like royalty, food, entertainment, everything was so amazing!!! We will definitely do it again, such a good holiday for families!!

  8. It looks like you and your mom had a wonderful trip. I am so jealous. We have been on 6 cruises and have loved 4 of them so it can definitely be hit or miss even on the same cruise lines.

    It would be so great if you would do a post on what you wore on your cruise. I love your outfit your wearing when you are headed to the airport leaving your cruise and your sweater at the airport looks so comfy.

    Also, the few times I have flown in and out of Kelowna, I am always on the lookout to see it you are there.

    Keep up the great posts.

  9. Thanks for sharing! I think all girls and their moms watched Oprah after school in the 90s. She was such an inspiration as you also are Jillian! I really appreciate watching you connect with those around you and use your charm and fame to better the lives of others! What a great trip! Xo

  10. Love loved your blog! What an amazing experience with your Mom. Thanks for sharing!! I never did see the photo of your Mom alone with Oprah. Did you ever share it and I missed it?

  11. So cute thanks for sharing -I too am a huge Oprah fan and have seen her speak and she is so inspirational.
    My Mother and my daughter trips are my favorite – -and when Annie gets older she can go too!
    Ox? Jillian I just saw you speak at the International Wonen Day in Edmonton and you are funny, entertaining and inspirational too. I laughed , cry and cheer. Thank you for being you!

  12. This post made me tear up. It’s so nice that you made time for just you and your mom ? Quality time with our moms is so important. I’m an only child and have always been really close to my mom. Now that I have my own little family, we rarely get one on one time together. I’m really looking forward to my bday weekend in early April when just the two of us are going to P! NK together and spending the night in Vancouver. I think it’s the first time we’ve spent a solo weekend together since I had my first daughter 4 years ago! This post inspires me to make more mom and me dates in the future!

  13. Hi Jillian,

    Wonderful vlog! Thank you for this glimpse into the cruise but mostly, thank you for showing your vulnerability! We’ve all felt like a “dweeb” (cute word) at some point and I think that feeling vulnerable is one of the things that unites us in our humanity. Thank you again for sharing and wishing you much continued success! xx

  14. Hi Jillian…just watched your beautiful. Video of your cruise with your Mom…It was so lovely, and I know you really cherish this forever. My sis and I went on an Alaskan cruise with my Mom when she was fighting breast cancer…I will never forget our special time together….keep making more memories with your mom when you can….Loved you and the Bachelor and still love you now….keep well and all the best with your career and family…you are amazing ! Deborah xo.


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