Tips On Booking an Affordable Caribbean Vacation

Traveling isn’t cheap and traveling to a beautiful island for a week in the sun and sand can be downright budget breaking. Comments we see frequently on our Facebook page in response to gorgeous island location pictures include “maybe in our next life” or “if only I could afford it”.

We get it. We’ve been fortunate to have traveled to many tropical destinations over the years, but for many years we had to get very creative in putting together a package that we could afford. Here are a few of the tricks and tips we’ve learned that may just help you plan for an economical and well deserved beach vacation.

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1. Be flexible. If you’re determined to visit the one destination that you’ve always wanted to see at the time of year you want to see it, you may end up paying more. Make a list of several islands that you’d enjoy and explore the airfare and accommodations at each one.

2. Consider traveling during low season or the shoulder season. The Caribbean low season is generally considered to be June to mid-December. Unfortunately much of that time is also hurricane season. We generally avoid travel to the Caribbean during the peak hurricane months of mid-August to mid-October, but have enjoyed many wonderful vacations with great weather and cheaper prices in May, June, July, November and December. If you’re worried about the potential for bad weather, check into travel insurance to see if it can protect you from weather related delays and problems.

3. Look into different packages that combine airfare with accommodations and sometimes even transfers or car rental. We’ve booked packages through American Airlines Vacations and Apple Vacations and have also booked packages through some resorts and cruises that can quote airfare along with their accommodations. Costco and Sam’s Club also offer travel deals! The selection of resorts and destinations vary and can be limited in these type of packages, but it’s definitely worth researching.

4. Frequent Flyer miles. We used to get a lot of “mileage” out of these and although they are still available and widely used, we’ve found that they’ve become much trickier to use. That being said, there are still deals to be had for travel savvy individuals. Some companies offer lots of “free miles” for opening up a new credit card (we recently got 35,000 miles for opening up a new US Airways card – also good on American Airlines), and if you can be flexible in your travel dates or can plan way ahead, you may be able to score free or discounted flights.

5. Consider renting a villa, house, apartment or condo. This option can be extremely attractive if you are traveling with children or with a large group. We rented a villa on the beach with a pool in North Caicos with a total of 6 adults. We were able to cook many of our meals in the villa (which had a beautiful well appointed kitchen with granite countertops and plenty of dining space) and enjoyed lounging in the pool and walking the beach just steps from our villa. We split the cost of the villa per person and it was one of the most affordable accommodations we’ve come across. There are several good companies to check with, including VRBO and HomeAway and know that at least one offers insurance in case there are any problems with the rental. Be sure to check the cleaning rates and the deposit amount on your desired rental.

7. Consult a Travel Agent. Travel agents can know of special deals on airfare and resorts that we may not find on the internet, so it’s worth checking in with one to find out.

8. Call a resort directly. Resorts occasionally have specials, discounts or packages that aren’t widely publicized. If you have a particular resort in mind, call them directly to see if they have an upcoming deal – or if perhaps you could receive a free room upgrade!

9. Consider traveling on atypical days. If you have a little flexibility in your schedule, check the pricing on airfare and accommodations mid-week to mid-week instead of Saturday to Saturday.

10. Shorten your stay by one day. If you find a place you REALLY want to stay and it’s just a little over budget, check the pricing for 6 days instead of 7. This may put you right in the budget you’re looking for.

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11. Search RedWeek for timeshare rentals in your desired destination. Timeshare rentals are timeshares that owners rent to other individuals when they can’t use them themselves. is the largest online marketplace for timeshares. Owners post their timeshare units on the RedWeek site, and connect directly with travelers looking to rent – usually for a pretty good price!

Hopefully these tips will help you find a good deal on a Caribbean trip of your dreams to get your toes in the sand sooner rather than later.

Do you know of other deal-finding tips to share? If so, tell us about them!

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Are You a Vacation Reader?

Flying down to the tropics a couple of months ago, I sat next to a young woman anxious to get to her destination for the week to relax and unwind. I asked her what she liked to do to relax and unwind on vacation and she said she was most excited to find a quiet spot in the shade on the beach, curl up and read – non-stop she said, for the whole week.

She had chosen a book a day and started the first vacation read on the plane on the way down. She asked what books I had enjoyed lately and what books I brought down to read and I was a little embarrassed to say I just had a few trashy magazines that I’d purchased at the airport to thumb through. “Ahhh,” she said. “Not a reader, huh?”

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Ouch. Well, I actually am a reader. Really. It’s just that I’m not a huge vacation reader! Even though “reading material” is on my Tropical Vacation Packing List, I tend to leave the choosing and packing of it until all other essentials such as cameras, music, sunscreen, rum money, etc., are tucked safely in place.

To be honest with you, reading while on vacation is not my favorite thing to do. I love reading stories at home that help me escape to the tropics, like I’m Gonna Live My Life Like a Jimmy Buffett Song (Di Island Song Series, Volume 1) (actually the whole series by Anthony Bjorklund) and Leap of Faith: Quit Your Job and Live on a Boat by Ed Robinson and A Trip to the Beach: Living on Island Time in the Caribbean – written by Melinda and Robert Blanchard, owner’s of Blanchard’s Beach Shack in Anguilla, but when I’m on a tropical vacation, I find it a little hard to keep my face buried in a book. Although… I’ve got to admit that escaping into a great story while lounging in a hammock under a coconut tree and sipping on a pina colada can at times be, well, relaxing….

So, as I pack for an upcoming adventure, I have a goal. I’m going to try and read one book this trip. Probably one short book, but nonetheless one book.

If that goes well, I may even begin shopping for an electronic reader. My voraciously reading friend on the plane said that’s the way to go. That way I wouldn’t have to choose a book based on size and whether it would fit in my luggage, right? She recommended the following three.  Any feedback based on experience?

Kindle paperwhite1. Kindle Paperwhite, 6″ High Resolution Display with Next-Gen Built-in Light, Wi-Fi – Includes Special Offers

Nook Simple Touch Glowlight12.Barnes & Noble NOOK Simple Touch with GlowLight, Wi-Fi, 2GB, Includes Power Adapter

kobo glo3. Kobo Glow Digital Text Reader

Are you a vacation reader?
If so, perhaps you can give me some thoughts on a great, easy, light, fun, short book I can get for our next trip! :)


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Pictures and other content may not be re-used without written consent from Rum Therapy, LLC