Our “How To” series explains the best way to get to various destinations using credit card points, and tells you what card(s) you should sign up for in order to accrue the necessary points. This week’s destination: Caribbean (and an All-Inclusive!).
Welcome to Part 4 of the “How To” Series! As a reminder, if you haven’t seen the rest of our How To series, here are the other (and future) installments.
- Part 1: Fiji, Australia, and New Zealand (Thursday, 4/13)
- Part 2: Tahiti & Bora Bora (Thursday, 4/20)
- Part 3: Greek Islands / Europe (Thursday, 5/11)
- Part 4: Caribbean (and an All-Inclusive)
- Part 5: Bali / SE Asia (Thursday 5/25)
How To: Caribbean (and an All-Inclusive!)
If Michael Scott liked the Caribbean, you can like the Caribbean.
I am so excited about this post because Mexico, Costa Rica, Bahamas, Aruba, etc. are seriously some of the most incredible destinations to get to, and you can even do cruises to a lot of them with points! The Caribbean islands are so beautiful, but most importantly they are pretty cheap once you get there. So, things like food + excursions aren’t going to totally blow up your budget. Score! Let’s get started with free flights.
So, how can we get to everywhere we want in the Caribbean? I’m going to talk about Southwest mostly in this post, because I think they are by far the EASIEST and CHEAPEST airline for award travel, and because they allow you to use your Companion Pass on international destinations (so your flights can be half the cost!). Why are they the best for award travel? They don’t have a typical “award seats” program where they only release 4-6 seats per flight. Southwest releases everything to be available with points. Every single seat! SW points have a fixed value around 1.6 cents per point, so they just adjust the cost (in points) of a flight to match the cost (in dollars) of the ticket at that rate. So, a $160 flight would cost 10k points, etc. It’s a pretty sweet system!
So how much will a Caribbean trip really be in points then? Most of the other big carriers charge 30k points for a round trip ticket to the Caribbean, and it takes forever to find award seats on popular routes or dates. You might not even get the flight or times you want! And it’s NEVER going to be cheaper than their base price of 30k. Southwest, on the other hand, has this available from Vegas to Cancun for 3 months from now… for only 8.6k points ROUND TRIP.
Now, of course not EVERY Southwest flight is going to be that cheap – you should expect around 25k for a round trip. But if you book when flights come out (6 months in advance) you can easily get down to the 10-15k round trip range for Mexico, Costa Rica, etc. There’s more though…
But here’s why Southwest is the absolute best – if you follow our guide for the Southwest Companion Pass, you only have to pay for 1 OF YOUR TICKETS, because the other person flies free! Sweet mercy that’s good stuff right there. Remember you do still have to pay airport taxes for both people, but the actual ticket itself is free. Imagine getting 2 people round trip to Cancun, and only paying 8.6k points…that’s 51.4k points less than you would pay with any other U.S. airline program. That’s INCREDIBLE value.
So where does Southwest fly? Honestly, they fly to most of the big destinations in the Caribbean, such as Bahamas, Costa Rica, Aruba, México, etc. Plus they are constantly adding more (they just added Turks & Caicos starting in November!). Here is the full route map. Furthermore, you can always use Southwest to position yourself in Mexico City or San Juan, PR, to fly somewhere else like St. Thomas. Flights from Puerto Rico are ~$100 to St. Thomas and other nearby islands, so it can still be really affordable if you use the Companion Pass to get there. You can also go to Award Hacker and figure out which route would be cheapest on other non-Southwest routes, and then sign up for the card that can get you those points. Or just email us at email@example.com if you can’t figure it out! For this guide, I’m going to assume you will choose one of Southwest’s 17 Mexican/Caribbean destinations.
How can I get Southwest points?
- Southwest cards (go for the Companion Pass to max your value)
- Chase UR cards (see Best Credit Card list for options – since you’re going to have to pay for airport taxes anyway, I would say get the Sapphire Reserve since the $300 yearly travel credit, or $600 total in credits in the first year of card membership, will cover your $450 annual fee)
- Marriott Nights and Flights package (this gets you 7 nights somewhere and 120k points at different airlines, including Southwest. It is probably the highest dollar value per card sign up, but doesn’t get you the Companion Pass unfortunately)
Since we are literally talking about 30 different destinations in the Caribbean, I can’t list every single one – but I will give a guide as to how I would plan any destination. To give a super-quick summary here, you have four options for free lodging in the Caribbean:
- Find chain hotels (Marriott, Starwood, Hilton, IHG, etc.) and pay for those with their points from their credit cards or from a Nights and Flights package. Use Award Mapper to search your preferred destination and see what chain hotels are there – then email us if you still are confused!
- Book any hotel with Chase UR points in the Chase Travel Portal (as a reminder, this is just a normal Orbitz-like travel portal where instead of paying with cash for something, you can use your points). 95% of all hotels on Trip Advisor are on the Chase portal, so search there to see which ones sound interesting.
- Book a cruise with Chase UR points. Look for cruises on the cruise company websites, then call Chase to book.
- Book any hotel or AirBnb with cash and then use checking account bonuses or “redeemable points” from the Arrival+ card to offset the cost. I won’t go into much detail on this because I think this is the least exciting option, but you can certainly do it if that’s what you want!
Just so you can see MY process for picking a hotel and getting it for free, I’ll give three examples below: Cancun, Costa Rica, and a 6-island cruise.
Cancun: An Adventurous and Luxurious Stay for 7 nights
A quick search on Award Mapper for Cancun shows that there are literally tons of chain hotels in the area, so your possibilities are almost endless. Here are two options I’ve come up with for people who want adventure-filled Cancun or people who want relaxing Cancun:
For the thrill-seeker: Stay 5 nights at the Aloft Cancun and 2 nights at the Hyatt Zilara (adults only) or Hyatt Ziva (kids allowed). The Aloft is an awesome Starwood hotel right near the beach that costs 3k SPG points a night (normally is about $150/night, so it really is ridiculously cheap with points – 5 cents of value per point is incredible!). Since SPG gives you the 5th night free, you will only pay for four nights (so 12k SPG total). The reason I suggest this is because you can use this hotel as your home base for excursions for the first 3-4 days – Tulum, Chichen Itza, Cozumel, etc. You don’t need to feel guilty about leaving your all-inclusive resort, and can enjoy all the fun adventures Cancun has to offer! Then, when you’re ready to just chill and enjoy your last 3 days, you check in as early as possible to the 5-star, all-inclusive, adults-only Hyatt Zilara, which normally costs about $800-$1000 a night, but is only 25k Hyatt points per night. Eat ’til you explode, enjoy the swim-up suite, frequent the beach, and don’t pay a dime for anything. Perfect mix of adventure and relaxation. This is what we are personally going to do next summer or fall!
To earn SPG points, you can sign up for the Marriott or SPG card – read our description of both on the Best Credit Cards page. To earn Hyatt points, you can either do the Hyatt credit card for 2 free nights or any Chase UR card and transfer the points to Hyatt from there. See the Best Credit Cards page for a more complete description of those options.
For the chill-seeker: Stay 7 nights at the JW Marriott Cancun or the CasaMagna Cancun, both incredible Marriott resorts (but not all-inclusive). To do this, go for the Marriott Nights and Flights package, since that will be the best value for your points. You also could do 2 of the Hyatt credit cards mentioned above to do 4 nights at the Hyatt Zilara – plenty of chill time and luxurious relaxation there!
Costa Rica: Monkeys, Rainforests, and a little Down Time
San Jose and Liberia are both Southwest destinations, so either one is a good starting point. I’ve never been to either one, so maybe some readers can comment below with tips for either place. From what I’ve heard, San Jose is a good launching point for excursions, river rafting, jungle, etc. It is also the closest to the east coast (where the Caribbean Sea water will be warmer than Pacific Ocean water), whereas Liberia is more relaxing. I could be totally wrong though, so someone please fact-check me on this.
San Jose: I would maybe spend 2-3 days in the big city at the Sheraton San Jose (3k SPG a night) to use as home base for big excursion days, and then head on down to Los Suenos Marriott Ocean & Golf Resort for some relaxation (90 min drive) on the beautiful beaches of Costa Rica. Los Suenos is usually around 40k Marriott a night, so try to stay for 5 nights to leverage the benefit of the 5th night free! Apply for the Marriott or SPG cards listed on our Best Credit Cards page to get enough Marriott/SPG points for these two hotels.
Liberia: I think Liberia is more of a relaxation part of Costa Rica – at least the better hotels there make it seem that way. Here I would recommend the following: 7 nights at the JW Marriott Guanacaste using the Marriott Nights and Flights Package, or 5-6 nights at the Hyatt Andaz Papagayo, which is just 15k Hyatt points a night. The JW Marriott is a seriously incredible property, and I have had quite a few friends go there in the past year or so. They all recommended it highly! The Hyatt Andaz Papagayo is a great deal because is usually $350-$400 a night, so at 15k points you are getting at least 2.0-2.5 cents each out of your Chase UR points, which is awesome! I wouldn’t use my Hyatt 2 Free Night Certificates here (the bonus from the Hyatt Credit Card) since those are best used at higher-tier Hyatt properties, but I would definitely transfer Chase points to Hyatt for this. Additionally, if you have had the Hyatt CC for longer than a year, you get a free anniversary night at a Category 1-4 Hyatt – the Andaz Papagayo is the perfect location to use it at! Maybe sign up for the Hyatt cards now, use them at a fun place like Cancun the first year, and then head to Costa Rica your second year to stay here. To stay using Hyatt points transferred from a Chase UR card or learn about the Hyatt anniversary free night, read more and apply at our Best Credit Cards page.
Southern Caribbean Cruise: 6 Islands in one trip!
Okay so Mary and I are HUGE fans of cruises. We thought we would hate it when we first went, but we seriously had so much fun and really liked waking up on a new island every morning. Since a lot of the good Caribbean cruises leave out of Puerto Rico, we are going to use Southwest to get there for free, and then Chase points to cruise for free. We went on a Carnival cruise (which I know is probably on the lower-end in terms of luxury) but absolutely loved it – you can book any cruise company you want though. If you go in the summer or late summer, you can get some amazing deals! The picture below is for a Southern Caribbean cruise (which is the same one that we did back in 2015!), leaving from San Juan:
Getting to see St. Thomas, Barbados, St. Lucia, St. Kitts, St. Maarten AND Puerto Rico is honestly incredible, and considering it comes with unlimited food and transportation between each place? It’s really, really hard to beat. Cruises can’t be booked online in the Chase portal, so you have to call them at their Travel Portal Number, 1-855-234-2542, in order to book it. Tell them what cruise it is, and the prices should be the exact same as what you see online!
Remember that if you have the Chase Sapphire Reserve, your points are worth 1.5 cents each, meaning a $669 cruise would cost you 44.6k points. If you only have the Chase Sapphire Preferred or Chase Ink Preferred, the same cruise will cost you 53.5k points – which is still a good deal, just not quite as good. For that reason, I would highly recommend getting the Chase Sapphire Reserve as ONE of your Chase UR cards since you can pool all Chase points together between spouses/family members (to get that better 1.5 cents per point rate!). Make sure you check out our Best Credit Cards page to see a full review of all Chase UR cards and the application links. We always appreciate if you use our referral links!
Overall, spending $0 on a trip to the Caribbean, with flights paid for by Southwest and everything else paid for with Chase points on a cruise – that’s pretty appealing. I just might have to book this again…
There are tons of options all across the Caribbean. If you don’t mind getting a few cards between you and a spouse, go for the Marriott Nights and Flights package to experience extreme relaxation for a week (and end up with tons of airline miles left over for another trip). If you want a full all-inclusive experience, go for the Hyatt credit cards and stay at 5-star luxury adults-only places and eat all you want. If you want more adventure, go for cheaper hotels so that you don’t feel guilty leaving all day. And if you want it all paid for, including food and every activity, go for a cruise with Chase points. No matter what method you choose, your Caribbean vacation is looking waaaay more appealing than Michael Scott with his Jamaican braid from Sandals.
Best of luck, and as always, comment below or email us at firstname.lastname@example.org with any questions!