Almost-Free Caribbean Dream Vacation

Our recent trip to Ireland was epic to say the least. We discovered exactly why its called the Emerald isle – an abundance of green foliage assaulted our senses, and we enjoyed every moment of it. I’ll run you down the stories and share the pictures later because right now I want to talk about the only thing our Ireland vacation lacked… sun.

I’m not complaining. I wouldn’t have changed a thing. We did have a couple great days and the rain and clouds were tolerable and made for excellent pictures.  Yet, when I got home I had a message from a friend who, in seeing our Ireland pictures, finally grasped how freaking amazing it is – what we’re doing with credit card travel rewards. He loved the Ireland idea, but he and his wife have a different dream… a sunnier one.

They’d like to go to the Carribbean. They’d like to feel their toes in powdery white sand. They’d like to have some boat drinks. They want warm water and hot sun. I don’t blame them one bit.

His question was simple, “I have been trying to take my wife on her dream vacation and  you might be able to help. We have been dying to go to the US Virgin Islands, mainly st thomas or st john. Do you know of any cards or anything that we could sign up for that would give us a bunch of airplane miles or something that would help us negate the cost of just even getting us down there for a week?”

caribbeanHe asked the right guy. Another friend had posted this pic of white sand and crystal blue water and I was already Caribbean dreaming.  Here’s what I cooked up:

How to plan an almost-free Caribbean Dream Vacation

Walking to the Caribbean isn’t really an option. It’s really far from wherever you are and would also require you to walk on water. Not gonna happen. Driving may also be problematic because of that whole ocean thing.  You could take a boat but they’re slow and bumpy… unless you cruise, which is a great option but one that we’ve touched on in other posts.  In this case, you’re going to have to fly… and if you’re like me (and I hope you are), you’d much rather fly for very little money.

Each airline loyalty program has different award levels for different destinations. You can find all of them on our Using Airline Miles page, but I’ll just give you a shortcut and say this – one of the best value options is to use American Airlines (which has merged with US Airways) Mile SAAver off-peak award level to fly to the carribbean for 12,500 miles each way. That means you’d need 50k to take 2 people round-trip.

Now, don’t let “off-peak” scare you. I’m not going to send you to the Carribbean in the middle of a hurricane, but nor would I send you when it’s plagued by thousands of spring-breakers, families on vacation, or European nudists (unless you’re into that kind of thing). I’m going to urge you to travel in the “shoulder season.” That way you’ll possibly have a beach to yourself and It may require some flexibility and you may have to travel on a Tuesday instead of on a Sunday.

Looking at the calendar now, I start to find great availability about the time it starts to get cold around here. Hmm… how convenient? I think it would be better to go closer to November, but just for the sake of showing you, here’s an option for 25k miles and only $16 per person (that pesky little $16 is why we have to say “almost”-free).

St thomas


I don’t know how you can look at that and say that it’s anything but simple… now you just have to figure out how to get your hands on 50k AAdvantage points.

I know that you’ve trained your eyes to overlook advertisements – to ignore them and not click unless they have pictures of half-naked girls or shredded abs and offer to share one weird secret with you.  Yet, for just a moment, I want you to click this link and look at the offer with an open mind. Just give it a try. Once won’t hurt.

Before you get worried that I’m trying to sell you something, I have to tell you. We used to get paid commission on people who used our links to apply, but those days are over.  At this point, our blog is a hobby – a time-expensive hobby, but one that we love.

Anyways, you see that in order to meet the terms of the offer you have to spend $3000 in the first 3 months you have the card. Let me confront your worries. Just put every expense you have for the next three months on the card – your gas, groceries, utilities, entertainment, etc. Do you have $1000/mo in those charges? I’m sure you do. Pay the charges off immediately through your online login and don’t pay a penny in interest. Bam. 50k points.

You also see that the annual fee is waived the first year. Worried you’ll have to pay it indefinitely afterwards? Cancel it. We do it all the time.  If you need help, read Sheldon’s “Canceling a card is like breaking up with a girlfriend” post.

But if you’re thinking “but doesn’t it hurt my credit?” we have a page for that. You can check it out, but the short of is that it can – a little tiny bit – but that it can also have a positive effect on your credit and the benefits far outweigh the drawbacks.

Some of you are thinking, “Brad, we’re on board, bro, we don’t need more convincing about using our good credit to obtain frequent flyer miles and travel for free, we just need to know where and how we can stay for free.”

Where and How You Can Stay for Free

View from the cottage above Magen's Bay

View from the cottage above Magen’s Bay

I’m beginning to have a bit of a love affair with  On our recent trip to Ireland, our favorite places we stayed were the cute little cottages dripping with character and culture.  We had the added benefits of having space all to our own, the comforts of a home, and some brilliant hosts.

When I searched airbnb for places in St Thomas, the very first one to pop up was this sweet cottage with sweeping views of Magen’s bay – a beautiful place where I’ve thoroughly enjoyed snorkeling and laying in the sun.

If the views weren’t enough, the place is frequented by parrots, has an outdoor shower, and a gorgeous deck with all kinds of jungle canopy. The topper? It’s only $85/night! 6 nights here would be $571 including a small fee. Now, if only there were a way to get reimbursed for booking here.

Well I’ll be damned if there’s not a perfect way to do just that.  Check out the Capital One Venture Card and its “purchase eraser” feature. The spending requirement is the same as the other card and it gives you 40k points which are enough to erase $400 in purchases. Spending the $3k on the card will give you another 6000 points, so you’ll be up to $460 in reimbursement and you’ll be $110 into 6 nights in the cottage… not too shabby.

On top of that, if you’ll email me at, I’ll send you a $25 credit to airbnb!

There you have it… spend some money on food, entertainment, and shopping and you’re into your Caribbean dream vacation for less than it might cost you to stay home.

Do you want me to plan a trip for you, too? Where do you want to go? Comment below and we’ll put together an itinerary for you.

This entry was posted in American Airlines, Capital One, Caribbean, Cheap Honeymoons, Citi, Island Vacations and tagged , , , , , , , . Bookmark the permalink.

6 Responses to Almost-Free Caribbean Dream Vacation

  1. Rachel Holloway says:

    Very cool!! Those views are to die for!!

    I’d love some help choosing WHERE to go! We got the USAirways card you guys talked about a while back, and have some companion passes that expire at the end of 2015. We happen to have a sitter available to watch our kids July 29-Aug 4ish, but we don’t know where to go! We haven’t been on a trip just my husband and I for over 10 years–and we are READY! Spending the $250 minimum won’t be hard, but we want to get the best bang for our buck–and feel somewhat limited since it’s only the 48 states…
    We are thinking a coastal town or beachy area–somewhere relaxing, but with some fun things to see and do as well. Any great ideas on where we should go and how we can pull off this getaway without breaking the bank?

  2. Rachel Holloway says:

    P.S. We are in Texas…AMA is our airport.

  3. Deboni Park says:

    I tried to use your link for Airbnb but it did not work

  4. Annika Sommerville says:

    The link to sign up for Airbnb isn’t working. I’d be happy to sign up to get you $25 though!
    I have the other free venture card that gets me 1.25 points per $1. I might want to sign up for this one though to get that bonus!

Leave a Reply

Your email address will not be published. Required fields are marked *

* Copy This Password *

* Type Or Paste Password Here *