Budget-Friendly Caribbean Travel for Teachers

All-inclusive Hotel Riu Ocho Rios, Jamaica 2018.

How to Make Caribbean Vacations Affordable with Courage, Creativity, and a Teacher’s Salary

Simpson Bay Resort

Have you heard the quote, “Travel is never a matter of money, but of courage,” by Paulo Coelho? Taken at face value, we all know that’s a bit of bullshit. You absolutely need cold, hard cash to purchase plane tickets, lodging, food, and entertainment.

However, at the heart of the quote is a truth: travel is a mindset. Once you make it a priority, you can overcome the obstacles that keep your dream trips out of reach.

For starters, I’m sure you’ve heard people tell you to set up a vacation fund—because yes, it works. For our first few trips, I set up a separate savings account and had automatic deposits taken out of every paycheck. Done. Let it grow and forget about it for a while. When the money is taken out ahead of time, you naturally adjust your spending on non-essentials. You’ve taken the first step towards making travel a priority.

So where does courage—or mindset—come into play?

Actually, it’s one of the biggest obstacles we hear from people when we talk about our travels. You need the courage to be flexible—in your thinking and in the possibilities that exist. This is where you can truly save money and make an island trip fit into your budget.

If you have your heart set on one specific island, resort, or time of year, then yes—you can easily spend beaucoup bucks. I’ve heard people say, “Well, if I’m going to do it, I’m going to do it right,” meaning the best resort, the swim-out room, probably butler service, and so on. Then suddenly they’ve spent $10,000–$12,000 before even getting there. They either go once and never again because it cost a fortune, or the price tag scares them off completely—and they never go at all.

On the other hand, if you can be a little more flexible in your expectations, you’re already one step closer to making an island trip a reality. Lots of Mainers have traveled to Florida to escape the snow, but they never consider traveling to the islands because they believe it costs too much money. Not true! Traveling to the Caribbean can be much more affordable than traveling within the U.S.!

For our family of three, most of our vacations have ranged between $3,000 and $5,000 total, including flights and resorts—some even all-inclusive! We’re not luxury travelers, but we’re not roughing it in a hostel either. We love the convenience and comfort of beachfront resorts rather than the isolation of some cheaper Airbnbs.

So for the teachers out there, consider taking a Caribbean trip in June, right after school gets out. This is how we found both the time and the budget-friendly pricing for our first few trips. June is the off-season for the islands, which means lower prices, smaller crowds, and more opportunities for quiet, private tours.

And as for the weather—don’t worry! The Caribbean doesn’t get scorching hot like the southern U.S in the summer. Mid-80s during the day, 70s at night, with a tropical breeze off the water.

Meanwhile in Maine, June usually means bugs, cold water and 60-degree days. The “real summer” weather doesn’t hit until late July and lasts through September. So why not skip the cold start to summer and head for the islands instead?

I love traveling to the Caribbean right after school ends—no sub plans, no stress, just ocean air and a little tan to kick off my break. Over the years we have started our summer break with trips to Barbados, St. Croix, Panama, and the Dominican Republic.

Our favorite June vacation spot is Simpson Bay Villas on the Dutch side of St. Martin. Ocean view 1-bedroom suites with kitchens, swim-up bar, boat tours from the resort, and over 40 restaurants within walking distance! Direct flights from Boston also make this a convenient option for first time travelers. When we travel back to islands for a 2nd or 3rd time we usually like to try different resorts. However, Simpson Bay is one of only 2 resorts we have visited multiple times. It’s budget-friendly and so convenient. As a matter of fact, my husband just landed there today on a solo trip!

Let go of the mindset that Caribbean travel has to be an escape from snow. Have the courage to make this summer look a little different.

Traveling in June also opens up huge savings opportunities because you’re not tied to specific travel days. Before booking, I check the Hopper app for the cheapest travel dates across several Caribbean destinations. Then I plug those dates into Expedia and look for package deals. I always read reviews—first on Expedia, then double-check with Tripadvisor—until I find something that checks all the boxes.

It takes a bit of patience but having the courage to be flexible means I can usually find a great deal and a decent flight from Portland or Boston.

That’s courage in action—and it’s how we keep finding our next adventure.

Are you ready to make the shift to a travel mindset?

Because maybe Paulo Coelho wasn’t entirely wrong.
Travel does take money—but it also takes courage, creativity, and a willingness to say yes to what’s possible.