How to Plan a Caribbean Family Vacation
(NOT to a big All-Inclusive)

June 8, 2024

How to plan a Caribbean vacation with kids

Table of Contents

Learn how to plan a Caribbean vacation with kids that's anything but cookie-cutter. Your time is too precious to do it the boring way.

Our primary goal at Mango Tree Travel has always been – and will always remain – to help parents plan easier and better family vacations. For us, that means travel experiences that please parents as well as children, and blend great travel experiences with much-needed R&R.

Since launching in 2022, we’ve learned a trick or two about how to plan a Caribbean vacation with kids. We’ve visited dozens of islands ourselves, and have planned hundreds of Caribbean family vacations for families who have returned home delighted and eager for the next adventure. 

As we start the exciting process of expanding our custom trip planning beyond the islands and around the globe, we want to share with you our approach to planning a Caribbean vacation that truly delights, away from cookie-cutter all-inclusive resorts. 

If that last sentence piqued your interest, you’ve found your people.  This article shares the Mango Tree approach to planning a Caribbean vacation with kids that will excite you but also put your mind at ease. Let’s dive in. 

How to plan a Caribbean vacation with kids

Reasons To Plan A Caribbean Vacation With Kids

We started our travel company with a Caribbean focus because the region calls to so many parents, especially on the East Coast.  The Caribbean offers manageable travel times; naturally kid-friendly activities like pools, beaches, and wildlife; and swoon-worthy hotels

As an avid scuba diver, and general beach lover, I learned to travel with our kids in the Caribbean. It’s such a great area for families with young children to plan their first vacations. And, as your kids grow, there are more exciting underwater and land-based adventures to experience together!   

When we were planning Caribbean vacations with our own kids, though, we noticed that many online travel resources push parents towards big all-inclusive resorts. 

While these certainly serve a purpose, they’re not the only way to plan a Caribbean vacation as a family – far from it.  And they’re definitely not how we travel with our own kids. 

Instead, we view the Caribbean as a fantastic place for families to learn how to have authentic travel experiences with kids that are still relaxing but don’t sacrifice cultural experiences for pool service and breakfast buffets.  That blend of experience and R&R is, in our book, the best reason to plan a Caribbean family vacation. 

Planning a Caribbean vacation

How to Start Planning a Caribbean Vacation

Step 1: Determine What Kind of Trip you want 

A great trip plan starts with an intentional vision.

The first step in planning your Caribbean vacation is to start with a blank page and envision what this trip will look like for your family.

Often, I find that people begin the trip plan process by asking, “Where do I want to go?” We start making lists in our minds of dream destinations like Italy, Greece, Costa Rica, or Barbados. While it’s great to keep these destinations in mind, I encourage you to think differently at the start.

Instead of brainstorming a list of destinations, start by envision the KIND of family trip you want. Think about what type of vacation will suite your family at this moment in your journey.

We’ve made mistakes before by planning extraordinarily adventurous trips with young children because we thought we wanted those experiences. However, at those moments in our lives, we really needed rest and relaxation and a hotel that reduced stress with a toddler, especially after not sleeping well for a year with a newborn. 

There are other times when planning ahead for an adventurous trip feels right, even if it means less downtime. What feels right depends on our kids’ ages, our current life stage, and our overall situation.

The bottom line: When thinking about how to plan a Caribbean vacation, take a beat to think about the big picture and flow of the day. By structuring your tropical trip with kids to balance activity and rest, you’ll ultimately have more fun and be more fulfilled than if you try to cram too much in. 

How to plan a Caribbean family vacation

So, take a few minutes and think about the type of trip you envision. And dream big – remember, we’re here to help you accomplish your dream trips with your kids. 

Do you need relaxation, adventure, or a mix of both? Underwater vibes or beachside cafes? Hiking and ziplining? Fine dining and childcare?  By starting with these questions, you’ll be on the right path to planning a Caribbean vacation that perfectly fits your family’s needs and desires.

There may be a surprising destination out there to match your vision that you haven’t even thought of yet!

Want a shortcut? Get our FREE Caribbean Family Travel Guide

Our comprehensive guide tells you what to prioritize at each stage of childood when traveling to the Caribbean, from newborn through teens, and includes 3 specific island and hotel recommendations for each age group.
Planning your Caribbean vacation has never been easier!
Planning a Caribbean vacation

Step 2:  Brainstorm Caribbean Destinations

I often get asked whether a particular Caribbean destination “is good for kids.”   It totally depends! In my view, just about every Caribbean island is great for some families, because family travel is not a one-size-fits-all sort of thing.  When planning a Caribbean vacation with kids, it’s really about finding the best match for your family.  

The Caribbean is not just a collection of interchangeable islands. While they all offer sand, sun, and beautiful beaches, each island has its own unique culture, travel logistics, hotel setups, and activities. 

Once you have a vision for your trip, the next step to planning a Caribbean vacation is to identify a few islands that might be the right fit.  

Start with our Guide to the Caribbean Islands (coming June 2024) – which sorts our favorite islands into categories to get you thinking about which islands will fit your travel goals. 

Once you’ve brainstormed, come back here, and move onto Step 3. 

Plan a Caribbean vacation

Step 3: Narrow Down Your Options Through Flight Research

When planning a Caribbean getaway, flight research can be a powerful tool to help narrow down your destination choices. By using Google Flights, you can explore and compare flights to  various destinations all at once, and see which ones offer convenient and affordable flight paths. 

This approach – starting your flight research without a fixed plan for where to plan your ultimate Caribbean trip – can open up possibilities you might not have considered, and make it easier to find a destination that aligns with your travel preferences and logistical needs.

Learn our best Google Flights hacks for planning your Caribbean vacations

Plan a Caribbean vacation
Photo courtesy of Baoase Luxury Resort in Curacao, a Mango Tree favorite.

Step 4: Research Hotels In Your Preferred Destinations 

Once you have a few ideas for islands that fit your desired vibe, which have reasonable flights too, it’s time to consider your hotel options!  Before you press the purchase button on your flights, make sure there’s a family-friendly hotel that excites you – and that has availability! 

Our “Find a Hotel” feature lets you search a database of family-friendly options using various filters and criteria, from location to childcare options, room categories, price points, and luxury level. 

We can help you find the most fabulous luxury family resorts in the Caribbean and the tiny boutique hotels with character. What you won’t find in our database, however, are mediocre budget all-inclusive resorts. While those can sometimes be the right choice, they’re not hard to find, and they aren’t the focus of our approach to how to plan a Caribbean vacation you’ll remember for years to come. 

We’re here to help you discover hotels with a bit more charm.

Plan a Caribbean vacation

Step 5: Sketch Out Your Itinerary Using Google Maps To Explore With Kids 

You’re booked! Now what? While it might feel easier to stay at an all-inclusive resort, the Caribbean has much to offer beyond these properties!  As your trip approaches, get excited by planning some activities with a kid-focus – and others with parents in mind too. 

Consider renting a car or using taxis to explore beaches, towns, and adventures both underwater and on land. Our Caribbean destination pages provide detailed information on island vibes, getting around, and the best off-resort experiences.

When planning a trip, using Google Maps can be a game-changer for organizing your itinerary.  The minute you’re leaning towards a destination, create a map in My Maps called “Destination – Trip Research.”  Add everything you learn to the map as you go! Mark restaurants, activities, and points of interest, adding notes and details

This approach does two things: It keeps everything in one place, and helps you to visualize your trip. 

You’ll see where your potential accommodations are in relation to activities and restaurants that interest you.  By the time your research is complete, the map will be a colorful, layered visual guide of your trip, with each day’s potential itinerary sketched out. You’ll see which activities naturally group well together, so you don’t waste time criss-crossing an island, and your days will make more sense. 

By taking notes directly on the map, you can keep all crucial information in one place. This methodical approach saves time and reduces stress, making travel planning with kids much more manageable. 

How to plan a Caribbean family vacation

Get a Done-For-You Caribbean Itinerary

Each our hand-crafted Caribbean Travel Guides includes a comprehensive Google Map pinning our best hotel, activity, and dining recommendations.

Tips For Planning a Caribbean Vacation To Make It Run Smoothly

A big part of figuring out how to plan a Caribbean family vacation is deciding how to approach your days – both your travel days, and your vacation days in destination. 

Learning little tricks and tips to deploy along the way can make your life as a traveling parent so much easier. And that’s true, of course, whether you’re in the Caribbean or any other part of the world. 

Here are a few things we incorporate into our trip plans, both in our travel guides and custom itineraries for Mango Tree clients:

Look into Airport Fast Track Services

Consider whether there’s a fast-track immigration service available at your destination airport, which many of the busiest Caribbean airports offer, including in: 

– Jamaica

Turks and Caicos

Saint Martin


This service has proven invaluable in our own travels, and for lots of Mango Tree clients, allowing for a bypass of long immigration lines and faster arrival at the hotel – and the beach! 

Connect with the Hotel Concierge

I find hotel concierge teams at luxury resorts often are underutilized. But a hotel concierge team is a fantastic resource to help you arrange excursions and dining reservations! 

While you can certainly get recommendations from Facebook groups and friends, hotel concierges often have more up-to-date information and can suggest new places you might not have heard about. 

Connect with your hotel concierge about three months before your trip and ask for recommendations on excursions and dining reservations, especially ones that require advanced booking.

Set a Calendar Reminder to Purchase Gear

Here’s one way that I urge you NOT to be like me.  I’m a last minute shopper.  Do as I say and not as I do, and try not to wait until the last minute to buy travel gear. 

Kids can outgrow clothes quickly, so it’s essential to check their sizes and ensure everything fits. I can’t even tell you how many times I’ve gone to pack sandals for spring break, only to realize none of last summer’s shoes still fit. 

Packing light is possible, but some key items like a snorkeling vest or toddler toys can make a big difference.  

Something new I’m trying: Set a reminder for two to three weeks before your trip to think about what you need. 

If part of your goal for planning your Caribbean vacation with kids is to get your kids snorkeling, don’t miss our guide to teaching kids to snorkel!

Plan for Meal Times

Restaurants in the Caribbean often don’t open until noon for lunch and 6 PM for dinner. This can be challenging if your kids wake up early. Plan ahead by checking restaurant opening hours and bringing extra snacks. Booking a room with a kitchen can also help you manage meals and avoid any emergency situations.

Don’t Overschedule Yourself

Finally, always remember: Kids (and parents, let’s be honest) get tired quickly in the sun. Balance big adventures with low-key afternoons. Plan for one or two full-day excursions and make sure to include downtime to relax and enjoy the beach or pool.

By following these steps and tips, you can ensure a smooth and enjoyable trip to the Caribbean with your kids. 

Let Mango Tree Help You Plan Your Caribbean Family Vacation 

If you like our tips, why not let a professional implement them for you, and customize the perfect trip for your family? 

The Mango Tree team of family travel advisors can help you plan and take one more thing off your to-do list. We love planning trips to the Caribbean for our clients, and can’t wait to bring your dream vacation to life.