First-Timer’s Guide: What to Expect on Your First Olivia Cruise or Resort Vacation

There’s something magical about your first Olivia vacation. You arrive somewhere beautiful, look around, and realize: this whole experience was created for you.

You’re surrounded by LGBTQ+ women from all over the world. The entertainment reflects our community. The pool deck, dance floor, restaurants, and gathering spaces are filled with people who came for many of the same reasons you did: to explore somewhere new, have an incredible vacation and experience it the company of people who accept and celebrate you for exactly who you are.

Here’s what you can expect, from getting ready and packing for your trip to your last night dancing at Club O.

Olivia isn’t simply booking space at an LGBTQ+-friendly hotel or reserving a group of cabins on a ship. On our cruises and resort vacations, we take over the place and the experience and make it Olivia.

That means a ship or resort filled with lesbians and LGBTQ+ women, plus entertainment from our community, and activities and community programming created specifically for our guests. You can dance with your wife, girlfriend, or someone you just met. You can head to a comedy show where you’re part of the story and not the punchline. You can grab a chair by the pool, strike up a conversation, and discover that the person next to you lives three blocks from your best friend.

Those little moments are part of the Olivia magic.

For more than 35 years, Olivia has created vacations around the world for our community: over 400 trips, more than 360,000 guests. You can travel with us just about any way you like: cruises, riverboats, land adventures, and luxury cruises. Many people book a large cruise or a resort for their first trip. The programming is similar on both, so the choice really comes down to destination and whether you'd rather wake up somewhere new every day or enjoy a destination you can explore more thoroughly.

Cruises give you the fun of waking up somewhere new, with multiple ports to explore and a ship full of entertainment, dining, activities and Olivia programming.

Resorts give you a beautiful home base for the week, with days built around the beach, pool, activities, entertainment, local excursions to explore, or plenty of time to do absolutely nothing if that’s your idea of a perfect vacation.

Every Olivia vacation has its own personality, but they all share something important: the freedom to experience an extraordinary place and feel the incredible relaxation that comes from traveling with your community.

Arriving on your first Olivia trip knowing absolutely no one? Don’t worry, you won’t be the only one.

From New Olivian gatherings to our Solos program, and every activity in-between, there are plenty of easy ways to meet new friends from Day 1.

On select trips, you’ll receive a pink New Olivian bracelet, a little signal that this is your first trip. Don’t be surprised if it leads to a few extra hellos, a helpful hint or two, invitations to join a table, or someone telling you, “You’re going to love this.”

Here’s the good news: there isn’t much you have to do when you book. A few things are worth handling early, though, and none of them take long. Take care of these and the rest of the wait is just anticipation.

Explore your payment options. Olivia offers payment plans that can make it easier to plan ahead and spread the cost of your vacation over time. Ask an Olivia Travel Consultant which options are available for your trip.

Consider travel protection. Travel can be unpredictable, so we strongly encourage insuring your vacation. Olivia offers options that can help to cover cancellations, delays, medical needs, lost luggage and other unexpected situations.

Tell us about your specific needs. If you have dietary, mobility or other specific needs, complete Olivia’s questionnaire before you travel. Our team works with guests and our travel partners to help you prepare for your vacation and understand what accommodation may be available.

Join the trip's private Facebook group. This is where fellow travelers (and often your future friends) start introducing themselves before you ever meet in person.

We know one of the biggest questions first-time guests have isn’t about the ship, the resort or even the destination. It’s: “Will I fit in?”

Olivia brings together a wonderfully varied community of LGBTQ+ women. Some guests arrive with a partner or a big group of friends. Some come by themselves. Some have been “out” for decades, some are still not able to be out in their daily lives, while others have only recently come to their LGBTQ+ identity.  Some want to dance until our nightly Club O closes. Others would rather have dinner with new friends and be happily in bed watching a movie by 10pm.

There’s no one way to be an Olivian.

Our New Olivian programming helps you get your bearings and meet other first-timers. On select trips, dedicated New Olivian Coordinators host gatherings where you can ask questions, learn how things work and start seeing familiar faces around the ship or resort.

Traveling solo? Our Solos program makes it easy to meet other guests traveling on their own, with dedicated coordinators, meals, meetups, and activities throughout the week. You can arrive solo without having to experience the vacation alone.

Olivia also creates opportunities for guests to connect around shared identities, life experiences and interests through gatherings and community programming. Depending on the trip, these may include Olivians of Color and Friends, Olivians in Uniform, OWLs (Older, Wiser Lesbians), LILLys (Later in Life Lesbians), Trans & Nonbinary Olivians, Gen-O, and sober-support gatherings through Turning It Over.

Outside of these specific programs, every meal, every activity, every moment by the pool, and every night of entertainment, karaoke, and dancing on an Olivia trip give you opportunities to spark new friendships.

One of the best things about an Olivia vacation is that your day can be as full or as gloriously empty as you want it to be.

You might start your morning with yoga or breakfast with new friends. A few hours later, you could be taking a dance class, joining a pool game, listening to a fascinating speaker or heading off to explore a destination you’ve always wanted to see.

Or you might claim the perfect lounge chair and not move for three hours. We support that plan too.

Afternoons can bring pool parties, workshops, community gatherings and spontaneous adventures. On a cruise, you may be exploring a new port. At a resort, you might spend the afternoon in the ocean before wandering back for happy hour.

Then the energy changes.

Evenings bring live music, comedy and performances featuring incredible LGBTQ+ talent and allies. After the show, there may be more live entertainment, a party or Club O, Olivia’s signature dance club.

Many vacations also include theme nights, giving you an excuse to break out the sequins, pajamas, neon, costumes or whatever else the theme inspires. Dressing up is part of the fun for many Olivians, but it’s never a requirement.

Whatever your vacation mode is – it’s valid! Opt in or opt out of whatever interests you most.

We believe travel can create connection far beyond our own community. That sense of connection is also why so many first Olivia vacations lead to second, fifth and twentieth Olivia vacations.  By the end of the week, you’ll understand why we say, Beautiful Together.

The places we visit matter to us.

We all know travel has an environmental impact. Olivia works to make a positive difference through sustainability initiatives and partnerships that support communities and environmental projects around the world. For every trip we plant a tree for each guest, team member, and artist in a women-led Nepal forest project. We also carbon reduce/offset the team and artist’s air travel for every vacation. In addition we find local nonprofit partnership at many of our destinations, and have created partnership helping with ocean and coastal conservation, dog adoption, school supply funding, and many other organizations that support women in the communities we visit.