“My Next Vacation” – Jamaica

In the next installment of “My Next Vacation,” I’m going to take a look at what it takes to get to Jamaica this winter! As you may recall, this series is intended to outline a step by step process to get you on your next vacation for pennies on the dollar. You’ve heard it from me and probably from others that it is possible to take a once-in-a-lifetime trip for a mere fraction of what it would cost otherwise. And you want in.

How do we do it? Well, banks want customers. They want you to use their credit cards. And they’d prefer that you not pay them off every month so that they can reap huge profits from you through their outrageous interest rates. In return for signing up for said credit card(s), they’re willing to give you a bonus of sometimes cash, other times credit card points or airline miles. That’s where we can leverage our wonderful credit scores and smarts to never succumb to carrying a balance and make out like bandits!

One thing to keep in mind is that in order for this to work, you need to plan ahead. You can’t decide that you’d like to take a trip in 3 months (or even 6 months) and expect to have the points/miles in hand immediately to do so. But once you get into the rhythm of garnering points or miles through credit cards, it is much easier to plan something closer to travel.

While I won’t delve too deeply into the foundation of pursuing this path, I’d be remiss if I did not mention that in pursuit of these miles and points, you MUST pay off your balance every month. You MUST have a great credit score. And you MUST not have a large purchase that you intend to finance in the next two years or so (think mortgage). If these apply to you, read on!

How do we do it?

A vacation to the islands of the Caribbean is on the minds of many these days. The weather is still amazing up here in the Northeast, but a fall crispness is here at night and colder weather is definitely on the horizon. So, it’s understandable that planning a winter getaway is a hot topic! These vacations can be expensive, but they don’t have to be. By signing up for 2 credit cards per adult, a family of four can take a winter break in the Caribbean at a highly discounted rate.

Wife starts by signing up for the Southwest Airlines Rapid Rewards Premier Business Credit Card from Chase. This gives her 52,000 Southwest Rapid Rewards once meeting the minimum spending required ($2,000 in 3 months). Wife also signs up for the IHG Rewards Club Select Credit Card which gives her 81,000 IHG points to spend at any IHG property in the world after spending $1,000 on the card within the first 3 months of card opening. IHG properties include hotel chains like the Intercontinental, Crowne Plaza, Holiday Inn, etc. Together, she will need to spend $3,000 on these two cards within 3 months. She should make sure she adds husband as an authorized user so he can help with the spending.

Once meeting the spending is on the horizon, husband signs up for the same two cards using the same process. Keep in mind that both of these cards are issued by Chase. Chase allows you to sign up for a business and personal credit card at the same time. If you have several cards issued by Chase, it may require you to call their reconsideration line should you be denied. This is one of my least favorite things to do. A close second to going to the doctor. But it may be the difference between getting a card or not.

So, now they have the miles and points they need for their vacation. Right now, Southwest charges as few as 7,840 points each way between Manchester, NH and Montego Bay in January, February, and March. Of course, school vacation weeks are more expensive, but that is ridiculously cheap. That’s less than 16,000 points per person, roundtrip to the Caribbean in the winter! For perspective, the traditional airlines charge around 35,000 miles! If you’re a family, you’d have enough Southwest points between the two of you for 6 roundtrip tickets with points left over! There will be taxes of about $122 per passenger that are unavoidable, but it’s still a great deal.

Now, onto the hotel. The Holiday Inn in Montego Bay is an all-inclusive. They charge 35,000 points per night or 30,000 points plus $40 per night or 25,000 plus $70 per night. So, using the 81,000 that each person has received through their credit card sign up, each person could redeem their points for 3 nights at 25,000 points per night plus $70 for a total cost for 6 nights of 150,000 IHG points and $420 out of pocket. And for families, up to two children under 12 are allowed in the room for no additional charge. Paid rates start around $300 a night before taxes for a standard room so this is a great deal. And to have all your food and drink included is pretty sweet.

I know what you’re thinking… A Holiday Inn? It certainly is no Park Hyatt or Waldorf Astoria property, but it gets decent reviews. We have never been to Jamaica but may give it some thought down the road when we’re looking for a quick getaway.

So, to summarize, a family of 4 would fly from the Manchester (or anywhere Southwest flies, Rapid Rewards required will vary) to Montego Bay and spend 6 nights at the all-inclusive Holiday Inn. The total miles required would be about 64,000 Southwest Rapid Rewards. The total IHG points required would be 150,000. The out of pocket cash component would be $908 (4 x $122 for the airfare taxes plus $420 for the hotel). Considering that this is inclusive of all meals and most entertainment, that’s a pretty great deal for a winter Caribbean getaway.

Keep in mind that you could do something similar to other Caribbean destinations. If you have something in mind and want to run it by me, I’m happy to help.

There you have it. Another great vacation highly subsidized by credit card companies! What are you waiting for?

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Our Frugal Life


  1. Wow, I’m not surprised I came to your blog through Club Thrifty’s comments – I feel like you and Holly should start a group travel-hacking blog! I went to Jamaica for my honeymoon and stayed at Sandals – Whitehouse. Beautiful place.

    • Ha! So true! Jamaica is such a great destination because of it’s beauty and ease in getting there!

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