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How I Saved $1542 of my $2651 Last Minute Caribbean Cruise Vacation

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Sometimes we have situations in our lives, when we do not plan our vacations. We may just, basically, need some get-away or change of scenery, especially if you can actually manage your time-off at your work. But last minute travel deals not necessary suppose to be and will be a “good offer”, as travel companies, agencies, airlines, hotels try to max out their income. Here come credit cards with their bonuses and rewards. And, if you know where to look, how to manage them — you can definitely save a lot on your trip.

Of course, to be frank, better to be strategic and just simply plan your accumulation of points and miles. As you may benefit from receiving better options. But, as we know, something less planned and unexpected trip turns out to be an amazing adventure. And having some “back-up plan” with rewards (points and miles) on loyalty programs balances makes it more flexible and affordable just to book vacation at any time we want.

So, that exactly the situation what happened to me and my wife last summer: we woke up one morning and decided – WE NEED TO GO ON VACATION ASAP. As we prefer more active vacation and less laying on the beach – we figured out that cruising is one of our best options we may have.

Why cruise or benefits traveling by sea?

1. All-inclusive food.

Through our vacations and trips we got to the point that spending time looking for restaurants and reviews is extremely time consuming. On a ship you can always find something to bite as everything (food wise) is included.

2. New day – new port.

You can’t beat this amazing benefit. On a cruise you don’t have to worry about transportation. While you sleep – your transported to a new port, island, country. More opportunities to see and experience something new.

3. Accomodation.

You cabin is your extended stay hotel room. Which is cleaned on a daily basis and it is so nice to go for a breakfast and find out that someone made your bed already.

Still, traveling on a cruise has some drawback: like bad weather – storm can somehow ruin your vacation. But, I have never heard a person who hated cruising (not counting people with “bad” motion sickness).

So, we decided to book a caribbean cruise. But with lots of stops.

We stopped on Royal Caribbean, as we cruised before with this company and their service was great. We stopped on a Caribbean 7 night cruise departing from Puerto Rico in June, which was departing basically less than in one month.

We agreed that we want to make exactly this cruise and visit these places (Caribbean islands) – and now we have the most interesting: plan everything, use right card, use best deal/offer, utilize proper miles/points, flights etc. Here we have to be strategic. And keep in mind lots of things.

Firstly, I have checked my balances on my loyalty rewards accounts. I’m using AwardWallet with its great mobile application. Strongly recommend!

I had over 100K on Chase Ultimate Rewards, me and my wife had a little bit more of 50K on AAdvantage account each, United Airlines – approximately 5K each, Delta – 11K, Hyatt – 2 free nights worldwide.

I keep in mind that I have Chase Sapphire Preferred account, with ability to transfer points to these travel partners:

  • British Airways Executive Club
  • Korean Air SKYPASS
  • Singapore Airlines KrisFlyer
  • Southwest Airlines Rapid Rewards®
  • United MileagePlus®
  • Virgin Atlantic Flying Club
  • Hyatt Gold Passport®
  • IHG® Rewards Club
  • Marriott Rewards®
  • The Ritz-Carlton Rewards®

The main task is to minimize expenses and maximize rewards. Also we have decided that spending another day in Puerto Rico would be nice as they have very interesting rain forest excursion and national forest.So we need to book accommodation for at least one night. 

Booking a cruise

Why do I start with a cruise? As it is the main travel part. And ship times are pretty strict.

Our itinerary looked like that:

Day Ports of Call Arrival Departure
1 San Juan, Puerto Rico 8:30 p.m.
2 Philipsburg, St. Maarten 9:00 a.m. 7:00 p.m.
3 Basseterre, St. Kitts 8:00 a.m. 7:00 p.m.
4 St. John’s, Antigua 7:00 a.m. 6:00 p.m.
5 Castries, St. Lucia 8:00 a.m. 5:00 p.m.
6 Bridgetown, Barbados 7:00 a.m. 5:00 p.m.
7 At Sea
8 San Juan, Puerto Rico 6:00 a.m.

The price approximate for a 7 night cruise on Royal Caribbean line with this itinerary showed $1430 for inside cabin as what was left and, which is pretty much ok with us, as we will only be sleeping there. Of course, oceanview is preferable, but that is unexpected trip.

Where and how to book a cruise? 

Here I had several variants in my situation:

  • book a cruise with Chase Ultimate Rewards points by calling representative
  • maximize miles and points with booking via airlines special dedicated websites
  • utilize online travel agencies (most common way)

I keep in mind that I have United Airlines miles, which are going to expire in 8 month. So that was my first option. As we know, that any activity on the balance prevents points from expiration and extends the period. When I check on a special dedicated United Cruises website – it shows me that I will receive 2 United MileAge miles per $1 spend. Which is not bad. And that is pretty much all bonuses. I have also checked AAdvantage Cruise portal – but I could get only 1 bonus mile per $1 spend. Which is not that great and I have pretty enough AAdvantage miles(50K) to fly just in case of my needs.

So, I decide to check Priceline, keeping in mind that if I pay with my Chase Sapphire Preferred card I will get same 2 points per $1 spend as it is travel expense and part of Chase Ultimate Rewards benefits.

And Priceline is running pretty interesting promotion :

priceline cruise promotion
We were eligible to get $100 credit per cruise cabin for drinks, spa or food

That was a better deal compared to $1430×2=2860 United MileAge Plus bonus miles. As I wanted to minimize our expenses, and as I know drinks on board of any cruise ship are pretty expensive.

So I payed with my Chase Sapphire Preferred card and get $1430×2=2860 Chase Ultimate Rewards points, which can be a statement credit of at least $20. Part of benefits of Chase Ultimate Rewards program or transferred to one of the Chase Ultimate Rewards travel parters when Chase Sapphire Preferred credit card.

Always check for bonus offers on different online travel agencies – they may differ! The prices will be pretty much the same, but you may benefit from other additional perks. Also consider calling representative.

Why I did not book cruise with Chase Ultimate rewards points?

While I was searching for best option to book a cruise I was thinking about flight. As cruise ship was departing from San Juan, which is pretty far from USA mainland…. Lets discuss the flight.

Booking a flight to San Juan, Puerto Rico in less a month during high season with Chase Ultimate rewards

If cruise was pretty easy – choosing a flight was more challenging!

Objectives: where to book, which card to use, shall I use points and miles?

First of all, dates. As we decided to visit Puerto Rico rain forest, we would need to come one day earlier or one day later.

Where can I book any flight?

Firstly check with (I have a strong feeling that google is developing this more than ITA MATRIX).

The picture is not very promising as one round trip flight start as low as $450 per person.

Atlanta to San Juan round trip flight during high season price starts as low as $400 pp

I also have AAdvantage miles (50K on each account). Checking award seats in less a month was not lucky at all : 95K AAdvantage miles per round trip Atlanta – San Juan is extremely expensive and not smart. As we know that regular USA (mainland) to Caribbean according to American Airlines award chart is 17500 miles one way or 35000 miles roundtrip.

American Airlines price of roundtrip ATL-SJU in AAdvantage miles during high season in less than month
American Airlines price of roundtrip ATL-SJU in AAdvantage miles during high season in less than a month

Since I have Chase Sapphire Preferred card with Chase Ultimate rewards, I can transfer points to these airlines:

Note: that I’m checking domestic USA airlines.

United Airlines 

Travel partner of Chase Ultimate rewards. And here was no luck as well.

Southwest Airlines

Wanna Get Away from Southwest definitely a program to check! There are lots of options : times and dates.

southwest wanna get away
ATL-SJU price in points for airfare in less a month booking

Very affordable, I should say. But I’ve noticed the flight has a layover, which is pretty short — 50 minutes.

So I decided to move to my last option – checking and maybe booking flight through Chase Ultimate rewards.

Why? I know that according to Chase Ultimate rewards terms and rules, if you book a ticket thought Chase Ultimate Rewards portal – I have a 20% discount on travel or in numbers $500 airfare will be 40000 Chase UR points.

And to my surprise Chase Ultimate Rewards portal shows me direct/non-stop flights for a price of 36928 points per ticket with Delta airlines. Cannot say extremely happy with Delta..But, as you remember, my goal is to minimize expenses on a unexpected trip. So that definitely works with me. So I book though Chase Ultimate rewards portal using my Chase UR points.

Chase Ultimate rewards ticket to San Juan, Puerto Rico
Price of ATL-SJU flight on Delta airlines through Chase UR travel portal

So, paying “0” dollars out of pocket. I decided to check same flight on

ATL-SJU price of Airfare on
ATL-SJU price of Airfare on

$521 per person.

Booking a hotel in San Juan, Puerto Rico

So, what is left in terms of miles and points: AAdvantage untouched, United untouched, Chase – approximately 32K left, Delta – 11K untouched.

My plan is not only to minimize my expenses, but also to be strategic about future trips. So I decided not to touch AAdvantage miles and to get rid of Delta Skymiles. As I plan to close the Delta card and they devaluated their loyalty program pretty strong.

I open, and search for my options.

And we chose pretty much nice hotel. The Condado Plaza Hilton.

And the actual price:


We can actually take regular king room, but price difference was only $10. showed $179.

So another $100 saved and staying in Hilton Junior Suite should be nice. We are excited!

A have also checked Chase Ultimate rewards – but lowest was more than $1K a night. Which is not a deal.

Another option was Hyatt. As I has 2 free nights with Hyatt. The Hyatt hotel on San Juan close to the port and city is Category 2, which for me was not smart to use as I can can max out these 2 night with any HYATT worldwide up to category 7.

Another option was transferring points from Chase Ultimate rewards to Hyatt and book this Hyatt hotel for 8000 points, which is pretty good option as well as for our date the price value in dollars was $146. But since I wanted to get rid of Delta Skymiles that was a better option for me.

I did not check Marriott, Ritz-Carlton and IHG group hotels as I have reached my goal. But these are other options, since they are travel partners of Chase Ultimate rewards program.


Since we want to visit Puerto Rico rain forest, we can save some money on that with points and miles as well.

Chase Ultimate Rewards program allows us to book activities with 20% discount.

Just have a look.

Puerto Rico Rain Forest with Chase Ultimate rewards
Puerto Rico Rain Forest can be booked with Chase UR points with 20% discount

But we have not decided yet, we may use these 30K Chase UR points towards a statement and slash our cruise price by another $300.

Bottom line

So, as you can see booking a last minute vacation can be very and very affordable.

So far we have spent:

$1430 – cruise

$72  – junior suite Hilton hotel room


$1042 for 2 roundtrip non-stop flights with Chase Ultimate rewards

$100 for 11500 Skymiles spent on Hilton hotel

What we will or already earned:

$1430×2=2860 Chase Ultimate Rewards points (as 2 points per 1$ spend on travel expenses)

$72×2=$144 Chase Ultimate Rewards points (as 2 points per 1$ spend on travel expenses)

2300 Skymiles each of us for ATL-SJU-ATL flight, ironically but Atlanta is Delta hub and it was best flight option:)

$100 Statement credit on spa, food or drinks.

And we can potentially slash cruise price with $300 as we still have approximately 30K Chase UR points.

And you can actually have cruise for free if you have enough Chase UR points.

Hope you will enjoyed this 2369 words post and find it useful for your future trips and vacations!

And you can see the great benefits of Chase Sapphire Preferred card with Chase Ultimate rewards. I can strongly recommend everyone open one for you and for your spouse/partner as use Chase Ultimate reward program to save on your vacations. Even if it is unplanned and a last minute decision.

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