Cruising to a win #40Kfaraway


a cruise ship and a map

When the 40K to Far Away idea first came up (see: Challenge! 40K to Far Away), and when I learned that I would be assigned Chase Ultimate Rewards points, I had a great idea.  I remembered the Travel is Free post about how to find cheap repositioning cruises.  In that post, Drew mentioned having found a repositioning cruise from the Mediterranean to the US for only $149!  Since it’s possible to book cruises with Chase points at 1.5 cents per point value (if you have the Sapphire Reserve card), I decided to add a repositioning cruise to my itinerary!

Yes, I would most likely be stuck in an inner cabin without a view, but compared to Nick and Stephen who would be jockeying for space on cramped economy flights, I would be in extreme luxury.  My idea was to use miles to get to the start of the cruise in the most inexpensive way possible (OK, that part may be uncomfortable), and then cruise my way to a win.  Or, more likely, I wouldn’t win the distance challenge, but I’d be a happy camper nevertheless.

The image at the top of this post shows just one example positioning cruise that I found.  In this case, the dates don’t match up with what I need, but it’s really just an example.  The advertised rate for this cruise was just $759 per person.  If I could book that with Chase points, it would cost 40K points plus $159.  That’s a bit more than I could probably afford for this challenge (since I still need airfare too), but again this is just an example.  Most likely, I could find much cheaper repositioning cruises, especially if I wait until last minute to book.

a table with numbers and text

Problem #1: 13 Nights

The example cruise, above, is for 13 nights.  And that’s not unusual.  Most of the repositioning cruises that cross the ocean (that I found) take at least 11 days.  My wife can’t get away during the time of the challenge, so this would be my life, alone, for almost two weeks.  I don’t want to be away from her for that long.  And she doesn’t want to be stuck with all of the dog walking and feeding responsibilities that long.  And, frankly, I don’t really like cruises much, so it sounds unpleasant.  If it was three nights, sure.  But two weeks?  Ugh.  No.

And what about internet?  Part of the fun of this challenge will be posting pictures and videos along the way.  After paying for the cruise and positioning flights, I probably wouldn’t be able to afford on-cruise internet with my meager 40K + $400 budget.

Problem #2: Single pricing

Those great deals that cruises offer are per person, assuming 2 people per room.  I can’t book the above cruise for $759 when traveling alone.  I would have to pay the single rate.  For me, the above cruise would cost $1,328.  That’s way beyond my price range.


Cruising to a win was a nice fantasy, but I don’t think it will work.  It’s both too expensive and too time consuming.  Still, I think it will be really neat if I can incorporate multiple modes of transportation in my trip.  I’d like to include at least one train and one boat ride if possible.  For example, maybe I’ll take a ferry at some point to get from one airport to another.

a large white ship in the water


Want to learn more about miles and points? Subscribe to email updates or check out our podcast on your favorite podcast platform.
Notify of

This site uses Akismet to reduce spam. Learn how your comment data is processed.

oldest most voted
Inline Feedbacks
View all comments

[…] Cheap cruises can be expensive when booking for a single person […]


Cruises have their own little resort fees — the mostly mandatory gratuity. You get charged at the end. They are usually $12 to $15 per person per day. They are a cost of cruising but not identified in the advertised cheap price.


I haven’t read through all the comments on these parts. But I did read that winning parameters are not fully set. What do you guys think about allowing for reader vote to see who wins once all the trips have been completed? Readers decide which factors are important (distance, creativity, difficulty) and then the only thing left to argue is wether you guys she with the result or not.


Others might be bringing along loved ones, so why wouldn’t you be able to avoid paying the singles supplement and just bring someone along who is paying their way? Creative but fair way to win.


I’m guessing that gratuities, port fees, and taxes would also kill this idea. These extra fees can be almost as much as the listed price of a cheap cruise.


I *love* the cruise idea! While I understand the technicalities that make it impractical for the contest, I was totally with you. I’m a veteran cruiser and lover of cruises and have done a similar cruise – MIA-BCN for 11 days, $649/pax for a balcony. I think it was $400 for an inside cabin. Good thinking outside the box!