Cruising with Comics on the Virgin Voyages Comedy Fest

I recently sailed with Virgin Voyages, an adult-only luxury cruise line, for its U.S. Comedy Fest.  The five-night sailing aboard the beautiful Valiant Lady from Brooklyn, New York to Bermuda departed on April 11, 2026. Virgin Voyages partnered with Don’t Tell Comedy, known for hosting pop-up comedy shows around the country at secret locations.

Here’s what went down…

Day 1 – Departure from Brooklyn, NY

Upon boarding, I squared away a few restaurant reservations for the nights I hadn’t pre-booked. On Virgin Voyages, there are no buffets or main dining rooms – only specialty restaurants, all of which are included in the fare. The food on Virgin Voyages is amazing. In fact, restaurants are inspired by Michelin Chefs and all the food is made fresh on board. It’s like eating in 5-star restaurants.

Insider Tip: Dining reservations become available either 45 or 60 days prior to sailing, depending on your type of cabin. Reservations open at midnight. Schedule a reminder on your calendar for shortly before midnight. Then, go into the app and book all your reservations at midnight to help ensure you get the days and times you want. Only a percentage of reservations are made available in advance. If you don’t get what you want, make the rest of your reservations as soon as you board the ship.

I then went straight to my cabin to drop off my bag, where I found a pack of Virgin Voyages Comedy Festival trading cards waiting for me. On Virgin Voyages, your cabin is ready as soon as you board. Most balconies have a red hammock – a signature feature of all Virgin Voyages ships. This is a personal favorite (and my wife’s too). It’s so comfortable lying in the hammock peacefully at sea. You can even purchase one on board, which is a nice way to spend Sailor Loot (on-board credit) if you have.

Insider Tip: Book a Sea Terrace cabin (balcony) and confirm in advance that the cabin has a hammock.

I then grabbed lunch at The Galley, a gourmet food hall with many options, from sushi to create-your-own salads to tacos to ramen. There’s even a home-made artisanal ice cream pop cart.  My personal favorite is the fries! Most of the food stalls in The Galley change for breakfast, offering a wide variety of made-to-order items from eggs benedict to fresh avocado toast.

After lunch, I checked out the activity schedule in the Virgin Voyages app; there were several comedy sets scheduled throughout the sailing each day. Some took place in the Red Room, the large theater, and some in The Manor, more of a nightclub setting..

Insider tip: In the app, favorite all activities and shows that you’re interested in and add the ones you’re planning to attend to your personalized schedule. Restaurant reservations and excursions (Shore Things) are automatically added to your personalized schedule.

In total, there were twelve comedians on board, all with impressive backgrounds, including network TV appearances and Netflix specials. The comedians on board were:

Shapel Lacey is a Los Angeles-based stand-up whose explosive stage presence is rooted in an unlikely origin story. A former award-winning competitive cheerleader turned diehard punk frontman.

Tacarra Williams, known in comedy circles as “The Beautiful Beast,” brings a fearless, commanding energy that turns every room electric. A former schoolteacher and life skills coach who now headlines iconic stages.

Emma Willmann –Emma is a Comedy Cellar regular whose presence and unflinching honesty make her a comedian to be reckoned with.

Eva Evans– Eva is a Brooklyn and Jamaica–raised comedian currently shooting Kevin Hart’s Funny AF for Netflix.

Usama Siddiquee – A Bengali-American stand-up comedian, Usama brings his high-energy, rapid-fire charisma to the stage.

Ian Levy– A New York–based comic with a silly, irreverent lens on life, love, and his many shortcomings.

Amy Miller – Named Comedy Central’s breakout comedian on Last Comic Standing, Amy delivers fearless, incisive material.

Shaunak Godkhindi – Based in New York, Shaunak is a writer and actor who brings his crowd-pleasing style to stages and college campuses across the country.

Laura Peek, A Los Angeles–based stand-up comedian and Nashville native, is celebrated for her dynamic storytelling.

Julio Diaz – Julio is a Brooklyn-born stand-up comedian commonly referred to as the Breakroom King, bringing raw, working-class honesty and unfiltered wit to the stage.

Mark Smalls –Mark is an LA-based comedian who brings an East Coast flavor to a West Coast vibe with his unique approach of attacking topics from both sides, bringing audiences of all ages and beliefs together.

Cole Garrett – Based in Los Angeles, Cole’s style includes energetic act-outs and performative storytelling.

When they aren’t organizing comedy festivals for Virgin, Don’t Tell Comedy transforms unique environments for comedy shows like barber shops, art galleries, or gyms by working with local businesses to create a house-party environment, which brings out amazing energy from the audience. They hold events in 250 cities worldwide and over 100 events each week. According to Kyle Kazanjian-Amory, CEO and Founder of Don’t Tell Comedy, “Virgin Voyages is totally flipping the narrative in how entertainment on cruise lines can be an incredible experience for everyone involved and shattering the stereotypes of comedy on cruises.” Kazanjian-Amory felt this cruise was the best version of a comedy festival with a festival vibe in a central location, allowing the comedians to interact with the passengers all around the ship.

For each performance, two or three comedians performed fifteen to twenty-minute sets.  The comedians were rotated around and performed with different comedians for each show. But they switched up their material for each set, so every performance was different.  If you wanted to, you could attend three to four comedy shows per day, each lasting an average of 45-50 minutes.  All performances were included in the cruise fare.

In general, doors opened 30 minutes before showtime, and people started lining up earlier. If you have a coveted black bracelet*,  you can enter and secure seats before the doors open to everyone else. The bracelets replace the key cards you find on most cruise ships and act as your room key, charge card, and access when getting on and off the ship.

*Insider Tip: Book a Rock Star or Mega Rockstar suite to get a black bracelet.

Part of the fun about experiencing a comedy festival on a cruise ship is that, in addition to the scheduled shows, it’s easy to interact with the comedians as they roam the ship. And if you were in the right place at the right time, you could also be treated to special secret pop-up performances!

That evening, I ate dinner at Gunbae, the Korean Barbecue restaurant. At Gunbae, you are seated at a round table with strangers, and the chef cooks the food in the center.  When you walk in, you’ll immediately hear groups loudly chanting “Gunbae! Gunbae!” which I quickly learned was part of the resident drinking game involving strong counting skills and complimentary soju ( a Korean spirit made from rice). As this was my eighth Virgin Voyage, I’ve become an expert at this game and am considering entering competitive Gunbae tournaments 🙂 For some, eating with strangers could be uncomfortable, especially if some of the people are duds 😉 Luckily, this time, everyone was friendly and fun.

Insider tip – order the DakgangJeong crispy chicken appetizer. Also, I like to eat here on the first night of the cruise so I can meet people early on and make new friends.

After dinner, I attended some funny comedy sets and hit the casino. All Virgin Voyages casinos have a mix of slot machines and table games, including blackjack, Ultimate Texas Hold ’em, Craps, Three-card Poker, and Roulette. Another Virgin Voyages ship I was on recently also had Baccarat. The dealers are friendly, chatty, and helpful. In addition to the main casino, there is a high-limit room with some table games and slot machines, and a smoking room that has a few slot machines. You do get rated at the casino, so it is possible to earn free cruises based on your play or on losses. Who doesn’t love free???

Insider Tip: Scan your bracelet at the slot machine before you play so your play can be rated for comps. At table games, the dealers will automatically scan your bracelet.

Day 2 – Sea day

I started the day at Razzle Dazzle, enjoying my favorite breakfast item – sweet-and-spicy bacon – and also had an acai bowl and jalapeno-cheese croissant. So good! Breakfast is also served in The Galley food hall and The Wake restaurant. While The Wake and Razzle Dazzle have set menus, The Galley has a ton of options for a quick breakfast.

Insider Tip: Make reservations for brunch at Razzle Dazzle and The Wake.

There were many activities scheduled, including games, fitness classes, musical performances, and, of course, comedy sets. These aren’t your run-of-the-mill cruise ship activities. On Virgin Voyages, fitness classes include Boyband and Broadway dance classes. Musical performances included an a cappella group, The Magnets, as well as bands and singers performing in various lounges throughout the day.

One of the highlights of the trip was the Behind-the-Scenes ship tour, which can be purchased. During the two-and-a-half-hour tour, we visited areas of the ship that are normally off-limits to passengers – restaurant kitchens, food storage, the engineering room, laundry room, waste management/ environmental recycling room, backstage dressing rooms in the theater, provisioning, and the bridge. Each area was explained to us by a Virgin Voyages employee who works there. I learned so many things that I wouldn’t have otherwise known. Interesting fact – there are 25 pastry chefs on board!

Later that day, I played ‘Bingo with the Diva’ – the resident Drag Queen on board who’s a member of the 12 Happenings cast. The Happenings cast takes the place of a cruise director on other cruise lines. Bingo is more than a game; it’s a show with the Diva performing songs and dances in between bingo games.  What I like about Bingo on Virgin Voyages, compared to other cruise lines, is that the prize money is much higher. In the four games we played, the prize pools were $555, $1,110, $1,665, and $2,220. Unfortunately, I didn’t win… but watching the Diva perform was worth the price of the bingo cards.

From bingo, I went to the casino to play in the slot machine tournament. All entry fees are redistributed back as prizes (up to the first 50 participants, but we had fewer than 50). I didn’t win this either…but did win on a prior sailing.

Afterward, given that it was a Comedy Cruise, there was no shortage of entertainment, so I attended some more great comedy shows.

That evening, I attended A Ship Show, a dinner show featuring circus acts, singing, and dancing. This was a nice change of pace from a normal dinner seating.

And then…more comedy.

While talking with other passengers, it seemed most booked this particular sailing specifically because it was a comedy cruise. Many traveled across the country to attend. According to Virgin Voyages, there were 2,600 passengers, mostly from the US, the UK, and Canada. The average age of the sailors was 50, which is slightly older than the norm. Keep in mind, there are no kids allowed on Virgin Voyages. There were 249 solo sailors. There is plenty to do if you are traveling alone, including scheduled activities for solo sailors.

Day 3 – Partial day at sea, followed by a partial day and an overnight in Bermuda

I played music trivia, one of my favorite Virgin Voyages activities! That evening, I ate dinner at Razzle Dazzle, which is creative American comfort food with some great vegan options. However, after the ship’s upcoming dry dock, it will be converted to Indian cuisine. I attended a few more comedy shows after dinner and squeezed in some work using the ship’s Wi-Fi, which is included in the fare.

Day 4 –  Half-day in Bermuda and then back at sea

I played Loteria Gigantica, aka Mexican Bingo, which is pretty much a funny tequila drink fest with a bit of Bingo thrown in. They serve much more than I could drink. By the end of the game, the crowd was stumbling to the next comedy set…

That evening, I ate at The Wake, which is the steakhouse on board. I’ve eaten here on every sailing, and the steak is phenomenal, as are the steak sauce and twice-baked potatoes. After dinner, it was time for Scarlet Night, Virgin Voyages’ signature ship-wide party where the ship is transformed into a red wonderland. Rather than having a formal night, everybody is encouraged to dress in red, and it’s such a cool sight to see a sea of red all around the ship.

Scattered around the ship are various activities, from a photo booth to pop-up shows and karaoke. It culminates at the pool for a dance party, out of and in the pool! When I say in the pool, I mean people dancing in the pool while still wearing their clothes. By the end of the night, you can’t get the “This is your Scarlet Night’ song out of your head!

Day 5 – Another sea day

I played some more bingo and another slot tournament. Didn’t win again 🙁

In the afternoon, I attended an espresso-themed game show hosted by the Diva. This was a mix of trivia and Rupaul’s Drag Race. Definitely unique to Virgin Voyages.

That evening, I ate at Extra Virgin, the Italian restaurant, where all the pasta is homemade, and they serve fresh focaccia. I started with the braised mini meatballs and the charcuterie board, followed by the Pappardelle al Ragu, my go-to Italian meal on all my Virgin Voyages sailings.

Insider Tip: Get the affogato for dessert!

The two specialty restaurants I did not go to this sailing were The Test Kitchen, an experimental menu and presentation restaurant, and Pink Agave, the Mexican-themed restaurant. There’s also a pizza place where you can get individually made-to-order, artisan pizzas, as well as a few other casual counter-service outlets, such as “Lick Me Till Ice Cream!” where they serve scooped ice cream (no drippy soft-serve here!)

On Virgin Voyages, unlimited soda and water are included. There are two coffee bars serving specialty coffees for an extra charge.

Insider tip: Repeat sailors get Blue Extras or Deep Blue Extras, which provide free coffees, laundry service, a cocktail party, early boarding, and a bar tab.

The final comedy show I attended was located in the Red Room for the headliners. These sets were 20 and 40 minutes, definitely longer than the rest. Emma Willmann opened, and Shapel Lacey headlined. In addition to his prepared material, Lacey did a lot of unscripted crowd-work, which was hilarious! I thought this was the best show of the week.

Day 6 – Back in Brooklyn

I squeezed in another breakfast at Razzle Dazzle so I could get one last serving of my favorite bacon.

So many activities, not enough time. And on regular, non-theme Virgin sailings, there’s even more to do: close-up magic shows by the Happenings Cast member called the Charmer, as well as full theater productions including circus acts, dancers, and singers. Although no sailors seemed to care, as they came on board to see comedy shows, and lots of comedy shows were what they got!

Virgin Voyages successfully pulled off an amazing Comedy Festival at sea. Logistically, this can be very challenging, but it seemed to go off without a hitch. The quality of everything was fantastic, and as usual, service and food were top-notch; there were a ton of creative activities, and having the opportunity to see hilarious comedy around the clock was the icing on the cake.

Sadly, the cruise ended, and we had to get off the ship.

However…

Virgin Voyages is holding another Comedy Festival on August 20, 2026, for a seven-night sailing out of Portsmouth, UK, with stops in Bruges, Amsterdam, and Hamburg. If you are interested in getting more information or booking, please let me know.

About Miles Man

Miles Man provides a unique service: helping travelers book trips with miles and points through its Award Booking Service, as well as paid trips, as a certified IATAN Travel Agency.