Cruise Of A Lifetime: Our Olivia Travels Experience

We were at the top of the rollercoaster, that slow, heart-pounding moment right before the drop. Our first Olivia cruise felt exactly like that––the unbridled joy of being surrounded by thousands of queer women, trans, and nonbinary folks as far as the eye could see. As we stepped aboard, nervous but ecstatic, we were swept up in the warmth of what instantly felt like a big, chosen family reunion.

Once on deck, we took off exploring the ship like giddy teenagers at summer camp. Darting past canoodling couples, packs of women in matching T-shirts, and solo travelers a few cocktails deep, we were greeted with open arms and a genuine eagerness to connect. 

Then came the champagne-fueled “sail away” party where Olivia founder Judy Dlugacz took the stage. She told us how she never felt safe being herself on traditional cruises in the ’80s, so she built something better. Since launching its first cruise in 1990, Olivia has made a name for itself as a cruise line “for us, by us.” The crowd roared with approval. The dance party that followed was part liberation rally and part skinny-dipping fever dream. That’s when we knew we were in for the ride of our lives.

The Generational Bridge

We kicked off our first full day at sea with an early morning workout and were surprised to see so many people awake and sweating with the sun considering how packed the dance floor had been late into the night at Club O. We wrapped up just in time for room service and had a slow morning acclimating to life at sea.

After breakfast, we headed up to the Lido deck for our pool party meet-and-greet with copies of GO Magazine featuring us as the cover models (no big deal!). A stream of incredible people stopped by our table, and we had many opportunities to ask queer elders about their experiences building community and fighting for our rights. 

We got firsthand accounts of what coming out was like in the ’70s, ’80s, ’90s. We heard the stories of the “late in life lesbians” who had only come out in the last decade. We heard about the summer flings at Woodstock, the comical breakups, the family members who finally came around (or never did). We made so many new friends and realized this kind of intergenerational mingling doesn’t happen often enough. There’s so much we can learn from people who have decades ahead of us, but we also have a lot we can teach them. 

Prom and Olivians Who Out-Party Everyone

Time flew by poolside, and soon we rushed off to shower and get ready for Prom, an event that felt like the lesbian version of heaven. Sapphics of every size, shape, and color showed up and showed out. We dove right into the gorgeous, glittery chaos. A Prom Parade invited singles and couples to strut down a red carpet while the crowd cheered them on with love. 

When it came time to crown the Prom Queen and Queen, a few couples (us included) had supporters in the crowd. But one couple in their 80s stole the show. We later spoke with them and learned they had been together for over 40 years. Both beautiful, Black women, they radiated a love that had weathered decades of challenge and change. We could only imagine the hurdles they encountered to make their love last. But boy did it last, and you could see it all over their faces. 

Themed nights like “Under the Sea” and “White Party” kept the energy high throughout the week. We LOVE a themed night. We dressed like shiny mermaids and sipped cocktails with pirates and sharks. Elvira Kurt’s comedy show had us doubled over laughing, and afterward, she was there to take photos and chat with guests like we were old friends. There was karaoke, dancing, shared meals, pajama parties, and constant opportunities to make new connections.

We were shocked, but delighted, that our elders were always the last ones on the dance floor. You couldn’t out-party a 60-something Olivian even if you tried.

Ports of Pride

Every port offered something new. In Grand Turk, we swam with stingrays and lounged on beaches with unreal, crystal-clear water. In Puerto Rico, we tasted piña coladas at Barrachina, the alleged birthplace of the drink, alongside delicious boricua bites. In Tortola, in the Virgin Islands, a sweet couple paid our cab fare when we didn’t have enough cash. “You gotta love lesbians,” we whispered to each other.

One of the most moving experiences was “Pride Parade at Sea.” Groups like “Olivians in Uniform” (veterans), “The Sisters” (Black Olivians), and “The Lilies” (late-in-life lesbians) paraded around the ship in full regalia. It was loud, colorful, sweaty, and joyful.  

“We were at the top of the rollercoaster, 

that slow, heart-pounding moment

right before the drop. 

Our first Olivia cruise felt just like that.”

After the parade, we slipped into the jacuzzi for a little downtime. Being wrapped up in each other right there on the pool deck felt completely free. The only thing anyone noticed was how good we looked in our suits. 

Toward the end of our trip, we were interviewed for Olivia Travel’s upcoming documentary where we sat on our veranda, soaking in the ocean breeze. From the stellar accommodations and destinations to the excellent dining and camaraderie, we marveled that this was our life for an entire week.

Safety and Belonging

As queer people, we’re used to having our guards up—watching for microaggressions, navigating subtle, or not-so-subtle, hostility. But on this ship? We let our guards down. We kissed without hesitation and danced without fear. We weren’t the only ones. Everyone we met commented on how freeing it was to just… exist.

The diversity on the cruise was refreshing. We had been on a traditional cruise before, and we could count the number of Black people on one hand. But on an Olivia cruise? BIPOC representation was visible and vital. There were many shades of brown, and it was beautiful to see. 

With every port, we felt ourselves expand. Braver, more free, more alive. Olivia doesn’t just take you to new places, it invites you to experience them through a different kind of lens, one focused on queer joy, connection, and community. We felt safe not just because the ports were welcoming, but because we were always surrounded by other Olivians. No one really felt like strangers because we all had one major thing in common. That quiet, collective comfort followed us wherever we went. 

A Family, Not by Blood, but by Choice

On our last day in the Bahamas at Half Moon Cay, we rode horses on the beach and shared one final dinner with a couple who invited us to visit their stable in Ventura. They told us we could come anytime to help care for the stalls and ride. As we packed our bags that night, we were already mourning the end of something magical.

We don’t throw the word “family” around lightly, especially for those of us who’ve had to create our own. But Olivia felt like family in the truest sense. Not the forced, blood-tied kind, but the kind you choose and build.

The final morning was full of tearful hugs. It turns out we had made a lot more friends than we realized. As we said our goodbyes, it became clear: Olivia isn’t just a travel company. It’s a living, breathing archive of queer history over 50 years in the making, a safe haven, a sisterhood, and a revolution at sea.

Ruby and Katrena are an influencer couple who invite their viewers to “live vicariously through us and look into our lives: the pretty, cringey, and the real.” Follow them @rubyandkatrena

Michelle Hair is a writer and editor whose work explores queer identity, travel, culture, and community. Her writing has appeared in GayCities, Queerty, Fandom, and other lifestyle and travel publications. She lives for good storytelling, open water, and the freedom of the road. More at michellehairwrites.com.