Delta Air + Resort + SCUBA + Car + Chase UR points = 25th Anniversary to Remember!

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I am stoked. It takes a lot to get me excited about travel, but I am really stoked! I have booked our 25th Anniversary trip and I could not be more pleased. We are spending two weeks on Grand Cayman Island. I will break it down but we are flying free, staying free, diving free, car free, food free…. well I think you get the idea. This trip would have cost $5000+ but will cost us almost nothing thanks to points and the bulk of it from Chase and Ultimate rewards.

First the AIR part. Delta has nonstop flights from ATL to GCM. So, I hop from SBN-ATL-GCM! I can get coach Economy comfort seats for just 35,000 points each low level. Seriously, 35k +tax to be in the Cayman Islands? Who knew? I think I have found a new favorite place on the planet and will be island hopping for years to come!

I will hold off telling where we are staying for now, but it looks great (see photo above for the view). The reviews are positive. This is just the kind of place we want to go. It will be private & has a nice beach and swimming and is non-touristy! We get two weeks to decompress and enjoy some warmth just when our “bones” are getting cold.

So how did we get this. Air, simple, DELTA AMEX card each. The DELTA AMEX GOLD card is enough on it’s own almost to get you there. Next, we EACH have over the past about 1.5 years applied for:

  • a Chase Freedom card

Right now our grand total is 350,000 UR points, but with the INK PLUS cards we will end up with almost 500,000 all-in! Our resort and SCUBA package, booking via Ultimate rewards reps, gave us 1.25 points value and will cost 243,000 points. Another way of looking at UR points with simple math is find the best price and you get 20% off that price of the hotel, resort, air or car. Now I want this to be as free as I can. So, I will do some spending for food, entertainment etc. on the Sapphire card as well and just do a statement credit for $1000-ish at just 1 cent each so all my other costs are also FREE!

I will tell you one note of caution with Ultimate rewards and booking everything. Obviously I booked my air via Delta on Skymiles. I also looked at booking my car with UR points. But, for two weeks, the best price and ONLY vendor they could use was AVIS. The price was $571.32 and if you turn that into UR points you are looking at 45,706 points (at a penny a point $457.06). Now the other option I have is just to book anyplace and give myself a statement credit for 1 cent per point. I found, so far, a Thrifty car for $430 all-in. Just a little cheaper, but still cheaper. Plus, I will EARN UR points for paying for it with my Chase Sapphire UR card, no foreign transaction fees and I will earn AA miles from the Thrifty Rental. You can see why NOT paying “THROUGH” UR points for this car rental is clearly better.

So there you go. I am stupidly stoked to be able to spend two weeks with my best friend, Lisa, on Grand Cayman Island this winter. Do we all see the value of points? I do! – René


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  1. have fun. I am planning to do a similar trip for my family next year. maybe not 2 weeks though.

  2. I am stoked for you as well….coming back to reality will be challenging I am sure.

  3. Have a great time and I liked your ideas. One thing I didn’t understand which is kind of personal, is that a 25th anniversary or a trip with Lisa? Or both 🙂

  4. Rene, congrats on 25 years, you need to try a good cheap eats place off 7 mile beach called “Chicken Chicken”, its nothing fancy, but the food is very cheap and really good.

  5. Two weeks, tough life.

    Great place, been several times and snorkel/scuba hasn’t been topped elsewhere yet, nor has water color. Turtles just swim up on beaches, not overdeveloped yet. Not touristy when cruise ships aren’t there. You’ll love it!

  6. Wow, what a great trip. Be sure to visit us at Camana Bay and treat each other to fresh, local food, shopping and entertainment!

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