Would you live on a cruise ship for over two months?
Jack Reynolds, who runs the digital marketing and social media agency SizzleHQ, is doing just that. Reynolds set sail on August 31, 2025, with plans to spend 78 days on cruise ships.
Earlier this year, he began receiving casino offers through Royal Caribbean's Club Royale website, many of them from September through November. Seizing the opportunity, he decided to try and get on as many cruises as he could, especially on ships he hadn't been on yet.
Altogether, his journey spans 88 days, including travel days from the United Kingdom and a post-cruise visit to Walt Disney World, and he plans to record his own content while onboard.
In an interview with Reynolds, which has been edited for length and clarity, we spoke about why he chose to take 18 back-to-back cruises and what he hopes to gain from the experience.
Why did you decide to book 18 back-to-back cruises?
(Credit: Jack Reynolds)
I chose 18 cruises because it was almost at the maximum limit of what I could achieve within my 86-day total period, while still having an element of variety and giving myself space in case of emergencies!
They aren't strictly back-to-back, as I will be travelling from Fort Lauderdale to Miami to change vessels, and I will spend one day traveling from Miami to Tampa by bus to get on the smaller cruise ships.
Other than that, I only have around 4 days on land! Most of those will be at the end of the journey when I go to Walt Disney World in Orlando!
Was there some sort of catalyst that helped you set your mind on it?
Recently, I sold my house, so there was nothing holding me back! It was the perfect time to travel on a trip like this.
I just turned 30, and it's been a stressful year! I am also using the weather, access to good food, and free access to a gym for 3 months as a catalyst to get healthy.
How long did it take you to plan and book all 18 cruises?
Not too long, maybe 3-4 weeks.
One of the most drawn-out parts was waiting to make sure that my visa wasn't going to run out in the middle of my travels. The ESTA visa waiver is 90 days, so 18 cruises for a total trip length of 86 days was pretty much the maximum I could do.
I also kept my eye on the casino website for more suitable offers.
What's the rough estimate for how much this experience is costing you?
This whole journey will cost me roughly £4,300, including my flights, tickets to Disney, food on land, etc. Thankfully, a lot of that is frontloaded before the cruises start. Some costs, like hotels and transfers, can be paid on the day of, helping to split the costs up nicely.
I also have no living costs, so I'm spending roughly £52 per day, which is less than it costs me to live in the UK! Plus, I noted down the collective cost for this. If they weren't casino comps on cruises alone, it would be £19,600 — I think I got a deal!
Read more: How much is a Royal Caribbean cruise?
What's been the biggest logistical challenge in planning 18 back-to-back cruises?
Really, it's giving myself enough time to get to each port and not overplanning. Also, figuring out what I actually need/want to do is another challenge; it's a total mental health reset for me, but I know Royal looks after me!
I've had nothing but great experiences on all classes of their ships!
Did you have a strategy to help you maximize your "free" days at sea?
Strategy? Not really. I have my own budgets.
I don't really spend that much in the casinos, but I try and spend a little bit on each cruise. I have some free play (a total of about $350) on these cruises, so this will contribute to extra excursions or internet!
In terms of casino strategy, I guess I do the $1.50 x 8, $3 x 4, then $6 x 2 trick to double the chances of getting money back. Of course, this also means that I've been known to rinse through money very quickly. I've gotten a few hand-pays in my time, though!
How many ships are you going on?
I'm going on 8 different ships, 6 of which I've never been on before: Oasis, Wonder, Jewel, Utopia, Adventure, Grandeur, Radiance, and Liberty.
Out of the 8, Wonder and Jewel of the Seas are the only ships I've sailed on before.
Read more: Royal Caribbean ships by age — Newest to Oldest
How often are you switching cabins, and what stateroom categories do you have booked?
(Credit: Jack Reynolds)
I'm having to switch cabins quite frequently.
Because this has been preplanned, I've let the cruise casino know beforehand, and my cabin steward takes my luggage to the next room free of charge, though I do tip when I can. Thankfully, my setup is very easy and portable.
There will be a couple of occasions where I stay in one cabin, though.
I've mostly selected interior cabins or whichever comps were on the certificates I received — a few of the certificates rewarded me with an ocean-view room!
On a recent cruise around Africa, I didn't use my balcony much. The main benefit I got from the more expensive cabin was the sunlight!
Will you be alone for the entire cruise?
Not in the strictest sense! I've found cruises are a fantastic way to meet new people in one of only a few ways that almost keep you within the vicinity of like-minded people in your adult life, along with school and work. In fact, I still have friends from cruises I took 2 years ago!
However, I am traveling solo, which has its benefits and perks! I'm also working each morning on the cruise, so I definitely will be able to be in touch and productive while onboard. Additionally, I phone my family regularly on WhatsApp.
Over the last 4 weeks and 6 cruises, I've made more friends than I have in the last 3 years. Cruises fix loneliness, genuinely!
Do you have any favorite spaces that double as great offices at sea?
(Credit: Jack Reynolds)
To be honest, I work best when it's quiet, so I can focus. I tend to stick my laptop in my room, because I can play games on it as well, then stay out of my room for the rest of the day!
I will be taking days where I go into ports and record content, or even just days off. Although I thought burnout was impossible on a cruise ship, I spent the first two weeks resting and taking it easy.
Read more: I work remotely from a cruise ship all the time, and a lot more people are doing the same thing
Did you book many pre-cruise add-ons (like drink packages, shore excursions, specialty restaurants, etc.)?
My first three cruises were aboard Oasis of the Seas. I prebooked internet and a soda package, as I'm a fiend for soda. After these cruises, though, I became a Diamond cruiser within the Crown & Anchor Society (I'll actually have hit 92 points after those 3, as I get double cruise points and sail for 14 nights total).
Because of my new status, I will take the free 4 drinks a day vouchers and buy a soda or two. If I become Prime in the casino, I can always get drinks for free there, too!
In terms of dining, I have experienced most of the specialty restaurants on Royal's ships, and I must say that I generally enjoy the Main Dining Room and included options. The value I get going into a specialty restaurant is limited. Maybe I'll go to a Chop's lunch or something, but I am not really planning on doing so yet!
How much is Wi-Fi costing you for 78 days on a cruise ship?
For the first 14 days, it cost $15 per day (so $210), but after that, as a Diamond cruiser and potentially Prime in the casino, I get 1 free day and 30% off per cruise, and some of the cruises are only 3 nights! This means that I'll book on board for those.
Later on in the trip, after the 12th cruise, I'll become Diamond Plus, so I will get 3 free days of Wi-Fi per cruise and 5 drinks per day! In total, I've calculated around $850 or £630 for nearly 3 months of internet at sea.
What are you looking forward to the most?
(Credit: Jack Reynolds)
I'm looking forward to the weather, rest, no responsibility (except where I'm eating), and the Royal Caribbean experience! I love Royal (although I'm not totally loyal), but above all, I love cruising! It's an amazing way to see the world and places that I have never been before!
I write music professionally and personally, so I also brought an electric guitar (with headphones, don't worry) to record and play music to keep me occupied in my relaxation time!
