Assembling a cheap award to paradise


a room with a bed and a desk and chair

The old $49 per year IHG credit card is no longer available to new applicants.  Worse, it no longer offers an uncapped free night each year.  Today, just like the IHG Premier card, it offers a free night at any property costing up to 40,000 points.  Across three different family accounts, though, I had 3 remaining uncapped free night certificates.  These legacy certificates can be used at any IHG hotel worldwide based upon availability. Our certificates were dangerously close to expiring, so I had little choice but to book the nicest IHG property I could find, and which I could get to relatively easily.

I decided to use our certificates at the Kimpton Seafire resort in Grand Cayman.  Pictured above is our King ocean view room on the 8th floor.  It’s glorious.  That’s all I’m going to say about the Kimpton for now.  I’ll write more in a future post.  This post is about how my wife and I got here.

Do you remember my post about how to book an impossible business class award trip to New Zealand?  This trip was like a mini version of that, but (mostly) in coach.  The New Zealand post showed how it’s possible to find awards to a mid-point in order to string together inexpensive award flights to make one complete trip.  I did the same for this trip.

Delta offers seasonal nonstop service from Detroit to Grand Cayman, but only on Saturdays.  And it wasn’t scheduled to begin until one of our certificates expired anyway.  So, the best we could do was to fly a one-stop route to Grand Cayman.

Via Google Flights, I found one-stop routes on Delta, United, AA, and even Air Canada.  Prices on any route that worked with our schedule were very high: over $700 per person if I recall correctly.  It’s possible that AA was a bit cheaper, but I only fly AA when I have no other choice.  Sorry AA, but my experiences flying you the last few years were rarely good.

Award availability was really bad too.  None of the 1-stop options were available at saver level award prices.  I think that Delta wanted something like 70,000 miles per person round trip, and prices on the other carriers weren’t much better.

So, rather than fork over big bucks or huge numbers of miles to book our flights, I looked for a cheap mid-way point.  Was there a place we could get to cheaply that would also offer cheap flights to Grand Cayman?

a map of the united states with blue dots

Via, I identified all of the non-stop routes that service Grand Cayman (GCM).  Fort Lauderdale (FLL) was one of the options.  I looked at this one first because I know from experience that cheap flights are often available between Detroit and Fort Lauderdale.  And indeed, that was the case.  Reasonable prices and awards were available for Delta’s nonstop flights.  If memory serves, we could have booked basic economy for 12,000 miles per person round-trip from Detroit to Fort Lauderdale, but we booked regular economy instead for 19,000 miles per person.  That’s a big premium, but I wanted to be able to use our Diamond elite status to qualify for upgrades, so I paid it.  For the record, we were upgraded only to Comfort+ on the way down, but to first class for the return.

Flights between Fort Lauderdale and Grand Cayman were super cheap.  Both JetBlue and Southwest fly the route nonstop.  For the outbound flight we booked JetBlue for only 3,100 points plus $5.60 per person!  I believe that the cash-only price was over $80, so this was an amazing use of JetBlue points.  Southwest had better timing for the return flight which we booked for only 3,120 Southwest points per person plus $84.58 in fees (extra fees are charged when departing GCM).

Let’s now put together all of our flight costs.  These are per-person (so I really paid twice as much altogether):

  • Delta round-trip from Detroit to Fort Lauderdale: 19,000 miles + $11.20
  • JetBlue from Fort Lauderdale to Grand Cayman: 3,100 points + $5.60
  • Southwest from Grand Cayman to Fort Lauderdale: 3,120 points + $84.58 in fees
  • Total round trip price per person: 25,220 miles + $101.38

Flying from Detroit to Grand Cayman for only 25K miles + $100 per person is an excellent deal.  By stringing together separate awards, we were able to get this pricing despite the fact that we had almost no flexibility at all in our travel schedule.  We had to visit Grand Cayman before our free night certificates expired and these were the only days we had available.

OK, enough blogging.  I’m going back to the beach.  See you later.

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

[…] The Kimpton Seafire Resort in Grand Cayman is an IHG property.  We stayed 3 nights using three separate uncapped IHG free night certificates (mine, my wife’s, and another family member’s).  Unfortunately, uncapped IHG free nights are no longer available through IHG credit cards. Instead, this resort is available for 70,000 IHG points per night.  Cash rates range from about $700 to well over $1,000 per night.  For details about how I booked our flights to Grand Cayman, see: Assembling a cheap award to paradise. […]


Greg, did you ever post the review for this Kimpton? Planning a 10 year anniversary trip this winter, trying to decide if this would be a good option.


We just went last week to use our last two uncapped nights also! I cannot day enough nice things about this place. Everything was gorgeous and the sand and water were perfect. Certainly the resort was not cheap food wise but since we were only there three nights it wasn’t as terrible. This was one of my favorite hotel redemptions ever – I think I will have to start collecting more IHG points or look to use sapphire 1.5 to go back!


We just went there in October and used IHG Premier card for 4th night free instead of my 2 free uncapped nights. My first time to Grand Cayman but that was my best hotel experience outside of St. Regis Florence.


Such a timely post Greg as I’m going next week. Using final three free uncapped nights and points for a 5 night stay, taking our 20 month old for her first plane trip and going with my parents. Can’t wait. Look forward to seeing your further report. How’s the weather and water temp? Thoughts on restaurants on site? Any other suggestions for offsite activities with a toddler?


We just burned 3 as well at the Fiji Intercontinental. Suite upgrade. Awesome stay! 3rd time we have stayed there over the years using those free night certs between my wife and I and the two IHG cards.


I’m less and less inclined to value these ‘free’ night certificates at all – don’t like the pressure to use them – seemed you felt compelled to take this trip.


Living in Miami has its perks. I often fly to Haiti for 5k jetblue miles roundtrip from FLL. Meanwhile, those flights often cost $500 out of pocket on AA.


Yes same thing from the West coast to Hawaii that’s why IT’s Full of Them CHEAP ….


Very cool, but would be interested to see you address the issue of irregular operations when booking tickets on multiple carriers, especially for what sounds like a pretty short trip. Seems like some snow in Michigan could cause the whole thing to fall apart. This could be addressed by sufficient buffers between flights, but that’s hard to do when the entire trip is intended to be pretty short.


So make sure u add in the Hotel,Shuttle and Food to the cost to keep it honest Sir .


We LOVED the Seafire resort even more than the Ritz. The beach is nicer and the resort is nicer, in my opinion.

Greg, here’s a tip: print your confirmation page. When we went last February to use our free night certificate, we showed them that nowhere on the page did it mention the resort fee. The receptionist promptly waived the fee with no fuss. We also got upgraded to an amazing top-level suite!

Well worth it for the free night if you can’t get to Bora Bora.


Good for u for being Nice (Fr.) ..I guess I screwed up I upgraded my card to the Top IHG one . BUT they didn’t tell me it changed the reup date when I did that from June to Dec. which I can’t use that year. So I canceled it !!! BUT 2 nites @ that hotel or Bora Bora (Pora Pora they say) as in OOP’s .


How did you generate that map of all the non-stop destinations from Grand Cayman? Thanks.


“Via, I identified all of the non-stop routes that service Grand Cayman (GCM).”


Did “stay human” social code get you any upgrade? I’m on the same boat with the cert and booked two nights in mid Jan! Cant wait! How do you like the property?


Any concerns that since you had two separate tickets for two different airlines that if any problems would arise, such as flight cancellation or change in schedule, that you wouldn’t be protected and could be stuck in Ft Lauderdale.


How much buffer did you leave in FLL?


Great hotel. stayed there last year. while resort fee is high, it does include free parking along with the free use of buided sailboat/Cat which typically would clost 120-150+ per use at any other resort.
Def the best resort on the island. We might bo back during spring break.

Quick question. The IHG 40k Cert expiration states to book and stay prior to expiration. I noticed I can still book with the cert for a stay past expiration. Can I do that? Can the cert be extended? say similar to Marriott certs by calling in? Any suggestions?


That worked for me a few years ago in Hawaii got old and new 2 nites. $1100 per nite Free boat should be free carS for that cost in Feb,


I just did the same trip (albeit from DEN) last month to use up our 3 IHG certs. Also did separate tix to FLL and used Southwest one way and JetBlue the other way to fly FLL-GCM! One of my three certs did let me book beyond the expiration. But I booked the rooms in March and that certificate was an older one that expired back before the May ‘19 policy change date.


I went there a few years ago on SW like $25k and $90 fees I guess I paid . The high cost of hotels and 1 stop wasn’t really worth it but my last trip there was 25 years ago . I don’t know if I would waste my non SW points for GCM but who knows if non-stop and out of hurricane season. For the time and money Hawaii is a much better deal as in non-stop lots to do and it’s the USA .