Smooth Sailing: First-Time Repositioning Cruise Tips

Or, the journey of a thousand miles begins with one ship…

Levon and I love to travel - clearly, or we wouldn't be living such nomadic lives!  We’ve traveled by plane, train, car, bus, and ferry.  But until earlier this year, we had never cruised. Our notions about cruising were a mix of wild spring breaks and seasickness on repeat. And yet, we cruised for 12 days last spring, we’re slowly making our way to Fort Lauderdale, Florida as I write this for an 18 day cruise in November, and we’ve booked a 16 day cruise next April. What’s up with THAT? 

Well, we’ve discovered repositioning cruises.  

Selfie with the Celebrity Equinox

What is a repositioning cruise?

It is a one-way cruise that moves a ship from one region or port to another.  Most of the time, this means a cruise that moves a ship from one seasonal cruise market (such as the Caribbean) to another (such as the Mediterranean) during shoulder seasons (spring/fall). These cruises are usually significantly less expensive than typical cruising and are often comparable or less expensive than flying plus related travel expenses.  And for those concerned about the environmental impact of travel, cruising can be more environmentally friendly than flying on a per-passenger basis, especially for longer trips.

Why did we decide to take a 16 day cruise for our very first cruise?

Last year, we decided to chuck our typical slow travel (a month or more in one location) for three months of bouncing around Western Europe seeing friends, enjoying bucket list events like the Chelsea Flower show for me and taking classes for paragliding dune soaring for Levon, and generally checking out a few places we’ve considered as possible longer-term stays. I had a knee replacement in January and was in need of a regular physical therapy routine. And since Levon is 6’2”, folding him up like origami to fit into an economy seat is possible, but not terribly pleasant - and finding affordable business class tickets is so complex, the search deserves a separate blog post. Plus, now that we are retired(ish), we have time to take advantage of really slowing things down. So, we decided to throw caution to the wind and commit to a 16 day voyage across the sea for our very first cruise. 

What was it like?

We sailed on the Celebrity Equinox from Fort Lauderdale to Lisbon, stopping in Bermuda, the Azores, and Porto, Portugal. Since it was our first cruise, Levon’s 60th birthday, and our anniversary (we got married on Leap Day), we splurged on a balcony room with some added perks — complete with easy gym/pool/spa access, an additional dining room with healthy food options, and a few nice things in the room like yoga mats. Total cost? $4,548.50 for the two of us (including tips) in Aqua Class. That’s just under $380 a day, including meals, entertainment, and our stateroom. It did not include Wi-Fi, specialty dining, a drinks package, or excursions.  

Once we got over feeling like we were in a floating Marriott…Quelle surprise!  It was awesome!  It was just barely more expensive than if we had flown business class. And we arrived in Lisbon with no jet lag or deep vein thrombosis! 

We were worried about sailing across the Atlantic in shoulder season, but we had smooth seas and sunny skies the entire time.  The only thing that surprised us is that it was a bit chillier than we expected.

Our home for 12 days, room 1514

What We Loved:

1. Letting Go of the Wheel: Once aboard, we didn’t have to worry about anything. The toughest decision was what time to eat and what fun activities to try. This was never boring.

2. Exploring New Destinations: We enjoyed walks around King’s Wharf, Bermuda, and Ponta Delgada, São Miguel in the Azores. Our stops were short, but they whetted our appetite for future visits.

3. Gentle Rocking: No seasickness for us! In fact, that gentle sway put us right to sleep. 

4. Comfortable Stateroom: Our room was very comfortable and quiet, with a nice deck and enough space to feel at home.

5. Digital Detox: We took a break from the internet and enjoyed our days without scrolling through social media.

6. Delicious Food: We were pleasantly surprised by the food options—the variety and quality exceeded our expectations.

7. Not Crowded: Despite being sold out, it never felt cramped. Plenty of space in pools and restaurants meant no long waits.

8. Time Zone Shenanigans: Adjusting to time changes? No biggie! The ship shaved an hour off of the clock about every other night so that we arrived at our destination in the right time zone.

Glass Beach, Bermuda; Ponta Delgada Botanical Gardens, Sao Miguel, Azores (remember, Levon - the tiny person in the photo - is 6’2”!); Ponta Delgada town center, Sao Miguel, Azores

What We Didn’t Love:

1. Entertainment Choices: Lots of magicians, comedians, and crooners, but we found our taste in entertainment didn’t align with the onboard offerings.

2. Finding Our Tribe: We met some great people in our last 2 days on board, but otherwise, we had nice chats with lots of people who we somehow never ran into again, as big as the ship was.

3. Dress Code: Formal nights are really not our thing and with our minimalist packing, dinner jackets and ball gowns were out of the question.

4. Questionable Activities: Some activities, like art auctions, left us scratching our heads. Seriously, who 1) buys this stuff and 2) has enough room in their suitcases?

In the eye of the beholder?

What to consider if you want to try a repositioning cruise

Our experience convinced us we’d do it again, and a travel agent is a must! They work with cruise lines to find you the best deals and perks— at no extra cost to you. A good travel agent can help you decide which cruise line and ship is right for you plus get you all kinds of additional perks, like shipboard credit and the best rooms.

Repositioning cruises are long, so they’re best for those with more time to spare. However, many cruisers we met treated the cruise as their entire vacation—flying home after arriving in Lisbon. ¯\_(ツ)_/¯

Do your research! Each cruise line caters to a specific market, and not all ships are created equal. Older ships will often be significantly less expensive than the newest ships, but with significantly fewer activities, glitz, and glam.  

Bring your own entertainment— Having a Kindle was great and we downloaded movies/TV shows before we got on board. The ship had a library, but it was pretty lame. And our stateroom had a decent TV, but it mainly played ‘90s romcoms starring Meg Ryan (no complaints, I loved watching Sleepless in Seattle and French Kiss again) and a handful of recent movies on demand.  But having our own stuff on hand was key.

Lastly, the cheaper the fare, the more sea days (aka - days with no port stops) you’re likely to encounter. We had four sea days on our first cruise. We were intimidated by this at first, and then we blinked and they were over.  Our cruise next April will have 7 sea days (EGAD) —stay tuned!

What’s Next?

We’re gearing up for an 18-day one-way cruise from Fort Lauderdale to Buenos Aires on the Sapphire Princess. We’ll have port days in St. Kitts; Fortaleza and Rio, Brazil; Montevideo, Uruguay; and end in Buenos Aires. Our total comes to just over $282 per day for the two of us (trip and tips). Plus, our amazing travel agent friend got us $525 in credits we can apply to any costs on the ship (including crew tips).  

And in April, we’ve snagged a great deal on a 16 day repositioning cruise from Tampa to Rome on the Celebrity Constellation for $3559 (trip and tips) thanks to our savvy travel agent, a few coupons, a credit card rebate, and catching a sale for 75% off the second person a few weeks ago.  

If this sounds enticing and you want to explore options that might work for you, here are a few resources you may find helpful:

• We used YouTube to research repositioning cruises extensively in the beginning. Channels like Ben and David’s and Gary’s are excellent.

• We use RepositioningCruises.com to find most repositioning cruises, like our cruises to Portugal and Rome. We read specific ship reviews at Cruise Critic. And we then track prices using Cruise Watch. All of these companies are travel agents so you can use them to book your cruises, but you don’t have to. (Our cruise to Argentina took more sleuthing.  If knowing more about how we found that cruise would be interesting, let me know in the comments.)

• The Points Guy is always a wealth of great travel advice and research.  They have a good guide that explains a lot more about repositioning cruises and a list of interesting routes in 2024/2025.

• Ten Degrees Warmer on YouTube shares a great free spreadsheet that we use to price out repositioning cruises, compare them to flying, and determine which offers the best deal overall.

• If you are worried about getting seasick, check out this great article. 

Do you see a repositioning cruise in your future?