Is a Virgin Voyages Repositioning Cruise Right for Me?

A repositioning cruise is like a regular cruise, but turned up to an 11. With the extended length of these kinds of sailings, everything about the experience is multiplied and thereby a bit heightened — from the days spent at sea, to the number of meals you’re eating aboard, to the time spent with your fellow sailors. So, it’s important that you’re on a cruise line you really love. For me, that’s Virgin Voyages.

Why Virgin Voyages

A few of my top reasons why I think it’s the best cruise line out there:

• Adults only: Yup, zero kids on the ship, which is nice on its own, but it gives the whole cruise a fun adult playground vibe.

• Very queer: LGBTQ+ people have made up a significant portion of the sailings we’ve done, so while not a gay cruise per se, there are a ton of likeminded individuals to meet.

• No nickel-and-diming: Virgin stands out from comparable lines in how much is included in the fare: WiFi, all basic beverages, group fitness classes, all gratuities, all entertainment and all food, which means no "specialty" dining restaurants with up-charges.

Will I get cabin fever?

I think it’s true that a transatlantic or other repositioning cruise isn't for everyone. But, for me, they’re more worthwhile than I initially thought. Here are a few of the things I took away as selling points:

• Time to truly unwind: It takes me a bit of time to get into vacation mode, so a longer journey gave me that room to actually relax and settle into out-of-office vibes.

• Take work with you if need be: As a full-time travel advisor, I’m almost always in touch with clients and pressing ahead on itineraries and bookings. The WiFi on Virgin was fantastic, even in the middle of the North Atlantic Ocean. Not only could I take care of making travel arrangements, I did a Zoom consultation with a client with no issues.

• The port stops were fantastic: Almost all repositioning cruises make at least some port stops, and our time in Madeira, Málaga and Valencia was fantastic. While you have to be ready to spend a lot of time at sea, you can still get the opportunity to plant your feet on dry land and explore.

Lean into shipboard life

We had 8 days at sea from Miami to our first stop in Funchal, Madeira, so we made the most of the long stretch of time with nothing but long stretches of water.

• Never a dull moment: Virgin’s ships are just the right size — large, but not massive — so there’s always something to do. Cruising can also help with the decision fatigue I feel so often in life. At any point in the day, there are usually a handful of options from lazy — lounge in the hammock on my balcony — to medium — maybe an interactive game with the Happenings Cast — to active — say, pickleball or a dance party. I could choose to match my energy to the right activity but never felt overwhelmed with choice. We even took the opportunity to take a behind-the-scenes tour of the ship and see everything from food storage to the bridge. Oh, and I also spent a few hours in the chair at the Squid Ink tattoo parlor getting a very permanent souvenir.

• Build up some shipboard routines: I am admittedly a creature of habit, so I quite loved the time crossing the Atlantic to settle in and make the ship feel like home. Every morning I’d wake up and get my coffee in The Galley. Virgin doesn’t have a main dining hall like other cruise lines, but rather a 24-hour food court with lots of options. Then I would usually head to the daily Friends of Bill meetings; I’m sober and really appreciate the daily 12-step meetings you’ll find on board. Then I’d catch up on email and get a little work done. In the afternoon, I’d usually partake in some sort of activity or see a show, including acrobats, illusionists, comedians, oh my! Evenings were centered on dinner, usually followed by a bit of dancing and socializing at The Manor.

• If in doubt, just eat: Virgin has fantastic food, and nothing fills an empty day like treating yourself to something delicious. A few faves include: the chorizo burrito from The Galley or the apple cruffin at Razzle Dazzle for breakfast; the goat cheese polenta and the grilled shrimp with garlic yogurt from The Dock for lunch; and more Korean BBQ than you know what to do with for dinner at Gunbae. Special shout-outs to the strawberry-wasabi dessert from Test Kitchen, plus the chicken pesto pizza I may have indulged in during a few late nights at The Pizza Place.

You’re going to be limited for repositioning cruises to the dates when, well, ships are repositioning. They tend to be in shoulder seasons when transitioning from one region to another — in our case, Scarlet Lady’s move from winter in the Caribbean to summer in the Mediterranean. One thing to think about is the direction you want to travel. Going west to east as we did, you lose one hour every two nights. On a reverse trip from east to west, you’d gain an hour every two days, which I would have preferred, all else being equal.

Since you won’t be making as many stops as on other itineraries, think particularly about where the itinerary stops and what kinds of things you'd like to do on land. We did some fantastic hikes in Madeira and Málaga to get our bodies moving — and work off the nightly cheesecake habit I picked up.

I was also a big fan of the weather. Not only did we luck out with not a drop of daytime rain, the middle of the Atlantic was also delightfully temperate. It was never too hot, and we had some nice crisp evenings where you could walk the exterior deck with a light jacket — or just head straight for the hot tub.

Finally, there was a great sense of comradery on this sailing. It’s hard to tell if that’s normal or not, but taking the plunge on an epic voyage across the ocean brought us together in ways I hadn’t anticipated with our fellow sailors — many of whom I know we will keep in touch with for years and years to come. Not to mention next year, when we do the whole thing together again.

This trip report is part of our ongoing series on cruises. In need of further inspiration? Check out Michael Cole-Schwartz's guide, 4 Gays with 8 Days in Morocco.