Conversation with Oprah and Gayle Alaska cruise

Every Photo has a Story to Tell – My Photo with Oprah in Alaska

Posted on Posted in Activities/Experiences, Alaska, Cruise
Glacier Bay Alaska view with Holland America Eurodam
Glacier Bay Alaska was a fantastic day on Holland America Eurodam

Leave it to my eleven (going on thirty) year old precocious niece to burst my Oprah bubble.  I was showing my sister and mom my photo with Oprah  from the O Magazine, Share the Adventure cruise to Alaska on Holland America’s Eurodam.  My niece said “did you meet Oprah…and she knows your name?  Or did you stand next to her for the photo?”  Um, let’s look at photos of Glacier Bay…

As part of the “Oprah cruise” which is what we were calling it, there was a private fundraising dinner with Oprah to benefit the National Parks Alaska program “Return to the Homeland”.  How I got my ticket is a hilarious (now) story.  I wanted to sail the inaugural Holland America Eurodam Alaska cruise with Oprah and O Magazine to see how the newly announced partnership was going to work with wellness programming for cruises in 2017 & 2018.  And Oprah was a bonus, on the ship for two days, for a free afternoon talk and an evening fundraising private dinner (extra cost).  I was keen to get that private dinner ticket, it helped that it would be a charitable donation.


Advanced Planning – the Oprah Dinner Ticket

I was on the Disney Magic Cruise in the Southern Caribbean in April with my family to celebrate my Mom’s 75th birthday (yes, I know didn’t we already celebrate her birthday in New York, Paris & London last year? That was her 75th pre-celebration).  The tickets for the private dinner would go on sale at noon EST on a Tuesday.  I checked the cruise itinerary and breathed a sigh of relief that I would not be out at sea that day subjected to dripping slow (and expensive) internet.  I would be on land in Barbados and scheduled to be at the plane geek’s nirvana, the Concorde Museum.  So I brought the phone number and internet information ready to buy my ticket at noon.

Barbados Catamaran El Tigre Snorkeling
El TIgre Catamaran Cruise in Barbados on a lovey April day

Unfortunately, I hit a bit of turbulence in my plans, the cruise line canceled my tour to the Concorde museum because there were not enough plane geeks onboard to do the tour.  With that, my friend canceled her day at the beach and we found a catamaran tour to go snorkel and swim with turtles.  Hmmm, now I was a bit apprehensive.  Would my cell service work out at in the water?  How far from the shoreline would we be?

Booking my Oprah Dinner Ticket from Barbados

Barbados Catamaran Snorkeling
Barbados Catamaran site of the Oprah dinner ticket incident

As we set sail for our second stop to snorkel and see some wrecks, I still had bars on my phone so I was pretty happy.  My friend, “country mouse”, put her flippers on and joined the rest of the boat to go into the water and snorkel.  I stayed onboard and at noon, called (rather than internet) into the private dining line and was easily buying my dinner ticket (is it really this easy?).  I didn’t care that I was reading my credit card information aloud with others still on the boat.  I was happy that I secured a dinner ticket and unaware that only 80 tickets were being sold (on a ship of 2,500 guests!).  Happy it didn’t take too long, I asked if I could go in the water and catch up with the group.  The crew said yes and I climbed down the stairs with my flippers on and facemask ready.  I was told to swim straight ahead to the white boat and make a right in front of it to join the group.  Got it! With that I began to swim in the warm, clear water looking down every few minutes at the wonders below the surface. The waters were a bit choppy but I wasn’t fazed.  At one point as I swam toward the white boat, I thought “this seems further and more work than I anticipated”.  I looked back at our catamaran and decided to keep swimming to the group rather than give up and go back.

Barbados Snorkeling Catamaran Flippers
Big feet = big flippers to snorkel with in Barbados

As I moved slowly forward, I stopped to clear my facemask and looked back again at the boat to see a crew member jumping in with an orange lifesaver.  I thought “surely, he’s not coming to save me, I’m fine” but sure enough he was swimming toward me to save me.  Geez, now I’m feeling old and embarrassed and as he neared I said “I’m fine, don’t you know fat people float pretty well?”  He didn’t laugh and said “the white boat was drifting and you veered way off course instead of going straight toward the boat you were swimming on an angle away from the group”.  Ok, not all my fault.  He then told me to use the flippers on top of the water and swam me to the group.  My friend saw me coming and wasn’t surprised that I was “being saved”, she just laughed and asked “did you get the Oprah ticket? Was it worth it?”  I said I got the ticket but maybe I should have stayed on the boat to drink the rum punch and dance to the music.  But the water was amazing, the views and experience of sailing on the water exhilarating even before my need to be saved.


Surprise! It’s Oprah

Oprah Winfrey photo on Eurordam
Pushed out of the way but I still got the photo of Oprah

Fast forward to July when I’m on the Oprah cruise.  I arrived for dinner and joined the snaking line halfway down the hallway across from the elevator bank. I started talking to a woman from Atlanta behind me who told the story of her dream board and that “she would have dinner with Oprah and Gayle someday in the future”. She didn’t realize the future was now when she heard about the cruise. And definitely didn’t imagine meeting Gayle during the cruise to tell her the dream board story.  As she’s telling me this, the elevator opens and to the shock of the women in the back of the line who all yelled at once,  Oprah and Gayle emerge (with bodyguards) and Oprah walks right over to this woman and says “I heard all about you and your dream board”, Oprah was right in front of me and before I could say “Hi, I was rescued in Barbados, it’s a funny story…” an older woman in front of me pushed me out of the way to lunge at Oprah to hug her (calm down crazy lady! She then proceeds to rattle off all of the Oprah events she’s attended as a superfan). So I just took a photo (downside of celebrity for me are all the folks invading your space and touching you without your permission) so I didn’t get to introduce myself to Oprah.

I didn’t get to mention that earlier in the day, Gayle read the first question during the Oprah Q&A from me. My Oprah moment was gone.  I’ve worked with celebrities in the past at film festivals and they are inundated with people in their face and rarely remember them in the sea of people so I wasn’t too upset, a bit disappointed of course but there really were superfans who worship Oprah so let them have their moment.

Conversation with Oprah and Gayle Alaska cruise
Conversation Q&A with Oprah and Gayle – my question was first!

Oprah Dinner in the Pinnacle Grill on Eurodam

As we entered the Pinnacle Grill restaurant, an aide took my handbag and jacket, another walked me to stand next to Oprah, I said “Hi” and she smiled for the camera, that big Oprah smile, and I was moved along like a conveyor belt of people.  I was handed off to a staff member to guide me to my table. I found my assigned table but my name wasn’t there (did someone move me so they could sit with a friend or celebrity?).

Oprah fundraising dinner Pinnacle Grill view
Sneak peek at the lovely place settings for the Oprah dinner in Pinnacle Grill

I found my name on the end of another table and sat with five other women. Each place setting had our name and a gift (sadly not “you get a cruise, you get a cruise….”) but a leather jewelry case from the onboard vendor, Roberto Coin.  Each table had an Oprah SuperSoul100 celebrity featured on the cruise or one of the O Magazine staff to dine with.  India.Arie was at the table behind me and a my new friends were seated with Adam Glassman, O Magazine’s resident fashion expert.

India.Arie Glennon Doyle Oprah Cruise Live Your Adventure
India.Arie and Glennon Doyle, special guests performing on the Oprah cruise

Private Fundraising Dinner with Oprah

As we introduced ourselves, I realized that I was seated with author, O Magazine contributor and motivational speaker, Glennon Doyle Melton, known for her Momastery blog and New York Times bestseller, Love Warrior. She introduced us to her wife, Olympic Gold Medalist & former US Soccer player, Abby Wambach, who is also an author and motivational speaker. To be honest, at the time, I had no clue who either of them were but I was interested to learn more about them as well as the other ladies at our dinner table (retired teacher, her cousin the banker and a new mom from Anchorage who won the Holland America employee contest).

Pinnacle Grill Holland America Eurodam dinner
Pinnacle Grill steak on Eurodam dinner with Oprah

Sharing a meal on a cruise is always a special experience to meet others from around the world and listen to their life stories.  My life hasn’t been as dramatic as Glennon and Abby’s (check out their inspirational tour Together Live in a city near you) but that doesn’t make it any less worthy.  In my circle, I’ve led an adventurous life traveling the world solo for the past twenty years. We are each on our own path and that’s what the Oprah cruise was all about – finding your own path, listening to your soul and learning how to be more authentic you.  If you’re not an Oprah fan, that’s ok, the messages are all about finding the best you and really who doesn’t want that?  To live your best life and know when it’s all over you really gave all of yourself to your passion, to your family, to your friends to yourself.

Glacier Bay National Park Holland America Eurodam
Cruise ships open the front viewing decks in Alaska when cruising in Glacier Bay National Park

Dining and Toasting with Oprah

Before and after dinner, Oprah would speak and the President of Holland America, Orlando Ashford would also speak about the beneficiaries of our dinner – the National Park System.  They would talk to the motivation of the collaboration of Holland America and O Magazine to bring new programming to a select number of cruises in the future.  It’s an interesting partnership and I was keen to join this cruise to see how it would be received and rolled-out.  Are cruisers ready to embrace new programming on meditation, book chats, fashion shows and motivational speakers to focus on being a better you?

Oprah fundraising dinner National Parks
Welcome to the Oprah fundraising dinner on Eurodam


Before dessert, Oprah would talk about her love of tequila (low points on the Weight Watchers program which made me laugh).  It was then that the staff brought around Holland America tall shot glasses with tequila for us to toast with.  To add to the cache of the event, it was her friend George Clooney’s special tequila, Casamigos that was just sold for almost $1 billion!  I expected nothing less from an Oprah event. We were toasting the wonderful day we had in Glacier Bay and the fantastic restaurant staff that made a wonderful multi-coursed meal.  The kitchen staff lined up with the chef and were also handed tequila shots. When it comes to tequila, I could easily do the salted shot with a lime but it was a bit more than a double shot so I toasted with a few sips.  It was really good (expensive) 80 proof tequila that can easily be enjoyed by sipping.

Oprah Cruise Casamigos Tequila George Clooney
The 80 proof Casamigos Tequila to toast with Oprah on Eurodam
George Clooney Tequila Casamigos on Eurodam Oprah dinner
George Clooney’s Luxury Tequila Casamigos because Oprah loves tequila!
Pinnacle Grill chefs on Eurodam
Pinnacle Grill chefs and kitchen staff toasting the Oprah dinner

The dessert arrived after the toast(s) were done, there were more toasts and free flowing refills of tequila (I was still sipping so I wouldn’t be drunk before the Rita Rudner comedy show).  I was excited by the chocolate dessert and the tree of mini chocolates (no one at the table had a sweet tooth so more for me!) which paired well with my glass of red wine.

Pinnacle Grill Eurodam dessert
Save room for this tasty dessert in the Pinnacle Grill at the Oprah private dinner
Pinnacle Grill Eurodam Chocolates
A tree of homemade chocolates – yes please!

My Photo with Oprah from the Oprah Dinner

As we left the restaurant, we were given our photo with Oprah in a special frame to commemorate our special night (mine was put into the frame wet so I have a blemish but oh well).  Did I meet Oprah? Yes.  Does she know my name?  Nope. Did I just stand next to her for the photo? Yes.  My niece may be technically correct, Oprah doesn’t know my name and won’t be calling me anytime soon.  But what my niece is too young to understand is that I don’t care, I had a special experience that night, meeting incredible women, sharing stories and laughing especially about my rescue at sea –  it’s in my memory and in my Barbados story. Life is an adventure and everyone has a story to tell about that vacation photo – that’s the fun of it all – the crazy stories behind the photos.

Philatravelgirl photo with oprah on alaska holland america Eurodam cruise
My Photo with Oprah – the story behind it was so fun and adventurous


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