Quiet swim up bar at Belizean Shore Resort, Ambergris Caye, Belize

I’ve never been very good at following the script.

As a kid in New York, I wanted the opposite of what everyone around me seemed to want. While my classmates dreamed of thriving in busy social scenes, I was daydreaming about rural Maine — a place where I could wander the woods, breathe deeply, and feel connected to the natural world.

After college, I walked away from a predictable economics career and chose a classroom of little ones in one of the poorest districts in the state. It wasn’t glamorous, but it was meaningful.

Our home is an ordinary ranch-style house… if you ignore the alpacas peeking into the living room window. I make teas and tinctures from the plants in my yard and take classes on herbal medicine for fun. My life has never been about doing what’s expected — it’s about doing what feels true.

So it’s probably no surprise that when it comes to travel, our family habits look a little different too.

We’ve skipped the big mainstream childhood milestones — no Disney parades or character breakfasts — but our son has:

Swum with stingrays, sea turtles, and sharks
Played in remote waterfalls in Maine and the Caribbean
Jumped off pirate ships in Barbados

We care less about trends and more about experiences that shift our perspective and leave us with stories to tell. Less about checking boxes, more about being where we feel alive.

That approach shapes the way we travel: memorable, intentional, and a little against the grain.

Here’s to keeping it real — real advice for normal families who want to keep it simple and make the most of their island getaway. You do not need to feel intimidated by keeping up with the popular crowd. Our go-to Caribbean travel habits might surprise you… and they might just make your next vacation easier, calmer, and a whole lot more enjoyable.

1. It’s Okay to Choose the Resort Over an Airbnb

It’s easy to see why so many people love stand-alone Airbnbs — extra space, privacy, affordability for groups, and all the conveniences of home.

But that’s just it: they can be too much like home.

Buying groceries, taking out the trash, doing laundry, cleaning the kitchen… those ordinary tasks don’t belong on vacation.

We tried an Airbnb once in St. Croix. It was a small building with only three other apartments. Our son had his own room, it was right on the beach, and we had a gorgeous porch overlooking the water. At first, it sounded like an introverted traveler’s dream — quiet, peaceful, serene.

But besides the million-dollar view, everything else felt a little too familiar — too much of our everyday routine in a place that was supposed to feel like an escape.

Resorts, on the other hand, offer amenities you simply can’t replicate: live entertainment, music, water sports, lazy rivers, massive pools, swim-up bars, water parks, beach BBQs and multiple restaurants. Even smaller boutique hotels often have coffee shops, themed dining, or fitness classes.

I may be an introvert, but I love listening to live music, people watching, or joining a quiet yoga class. Being an introverted traveler doesn’t mean wanting to be isolated. We seek deeper experiences — and can feel fulfilled by observing life around us.

There’s a certain joy and camaraderie amongst other travelers — that light, happy vacation energy — and it’s easy to miss when you’re tucked away in your own private rental.

That said, I’m not completely anti-Airbnb. Many condo-style Airbnbs are located within resorts and include access to pools, restaurants, beaches, and activities.

And if space is your main concern because you’re traveling with teens or a larger family, resort accommodations are still absolutely possible with a little digging. Booking a flight-and-resort package through Expedia often saves money and makes family travel more budget-friendly.

A few examples we’ve loved:

The Villas at Simpson Bay (St. Maarten): Kitchens, two trundle beds, two balconies, and a separate bedroom for parents (mentioned in a previous blog).
Belizean Shores (Ambergris Caye, Belize): A kitchen, living area, and a giant loft our teenage son claimed immediately.

Both offered pools, waterfront activities, and quiet swim-up bars — and not the spring-break kind. Enjoy your rum punch or fresh fruit mocktail while floating under the tropical sun and know you’ve found your island escape.

Swim-up bar at Belizean Shores Resort, Ambergris Caye, Belize

2. You Do Not Need to Rent a Car

This one is tough for people from Maine. We are used to traveling everywhere by car, and it’s fiercely tied to our independence. But our family has never rented a car on vacation — not because we’re against it, but because we’ve simply never needed one.

Uber is mostly nonexistent in the Caribbean, but taxis are easy to find at the small island airports. It’s nothing like the long taxi lines at major airports in the U.S.! As soon as you reach the exit doors, there are handlers everywhere asking if you need a ride.

You can do a quick Google search or join Facebook groups beforehand to find the standard taxi rate to your resort, so you don’t need to haggle.

Because so many islands are dependent on tourism, there are also plenty of tour companies offering private or shared airport transfers if you prefer to book ahead. For peace of mind, we’ve used these services in larger places like Jamaica or Costa Rica when the ride to our resort was longer.

We always book excursions to explore new places as well. Catamaran trips are our go-to, and if it’s our first time on an island, we book a guided tour to learn about the local culture, history, and landscape. Resorts make this easy: most excursions include hotel pickup.

We don’t have to navigate unfamiliar roads, learn to drive on the left, or stress about parking. And honestly? The local drivers usually share the best stories and insights.

We also dedicate days to simply enjoying resort amenities — so again, no car needed.

Vacationing car-free removes so much stress and maximizes your downtime. If we’re not staying at an all-inclusive, I make sure we can walk to restaurants by checking Google Earth before booking. I like keeping things simple:

No time wasted picking up or returning a rental
No navigating tight island roads and traffic
No “Did we park in the right place?” panic

Pro Tip: Always pack some motion sickness wristbands 🔗 for island vacations, especially the driving! They are a great chemical free way to prevent nausea in cars, planes and boats.

For us, car-free = relaxation.

**3. You Can Check a Bag**

Our most “against the grain” habit?

We do not travel with carry-ons.

I know — the internet has convinced everyone that carry-on-only is the only smart way to travel. But for us, the convenience and ease of checking a bag far outweigh any downsides.

We each pack a checked bag and weigh it at home to stay under the airline limit of 50 pounds. (Stay tuned for my next blog where I’ll share the Caribbean essentials most people forget!)

We also bring small under-the-seat travel backpacks stocked with:

Two days of clothes
Toothbrushes and small toiletries
Downloaded movies and playlists
Snacks

My husband and son use simple Adidas backpacks from Amazon 🔗— nothing fancy. I recently ordered a Bagsmart travel backpack and will let you know in a future post whether travel-designed bags make much of a difference.

We’ve only lost a bag once, and our backpacks kept us perfectly comfortable until the airline delivered it.

Here’s what we gain by checking bags:

No scrambling for overhead bin space
Savings from bringing full-sized sunscreen, soap, and toiletries (which are pricey in the islands)
More clothes (because nothing dries in tropical humidity)
Zero pressure to pack neatly on the last day — toss it all in and go
Room for large items like snorkel gear

And honestly? Contrary to popular belief, checked bags are often faster. You drop your luggage off immediately at the airport and walk around hands-free — no dragging a carry-on through food courts, bathrooms, or sprinting to make a connecting flight.

By the time you clear customs, your bag is usually already on the carousel.

For a low-stress, simplified airport experience, checking a bag just makes sense.

Make the Vacation Fit You

Real travel doesn’t have to fit perfectly packed into a designer carry-on. And it doesn’t have to match what Pinterest, YouTube, or the loudest voices online tell you is “right.”

There are absolutely ways to save money without compromising the full island resort experience. But more importantly, your vacation should reflect you — your energy, your priorities, your idea of joy.

You don’t need to follow the same path as everyone else.

Make the choices that lower your stress and maximize your time to explore, relax, and embrace the moments that make you feel alive.

That’s what it means to travel a little against the grain.