Away for the Holidays: The Ultimate Guide for a Tropical Family Vacation
We love travel and there’s no better way to celebrate the holiday season than a trip. Last year we enjoyed a couples trip and flew to Nashville over Christmas and embarked on an epic roadtrip that hit Memphis, landed us in New Orleans with friends for the New Year, and white sandy beaches of Alabama. This year we’re planning a tropical family vacation over Christmas—it’s one of the most magical ways to spend the holiday season. While much of the world is bundled up in scarves and boots, you and your family get to trade winter coats for swimsuits, snowflakes for palm trees, and holiday stress for warm ocean breezes. But as dreamy as it sounds, preparing for a Christmas getaway to a tropical destination requires thoughtful planning—especially when traveling as a family and when the holidays usually come with their own set of obligations, expectations, and traditions. With the right preparation, you can have a smooth, joy-filled holiday escape that blends festive spirit with island relaxation. This guide will walk you through everything you need to think about, from planning and packing to balancing holiday magic with beachside fun.
1. Start With Early Planning—Holiday Travel Is No Joke
Christmas is one of the busiest travel times of the year, and airfare, accommodations, and activities book out months in advance—especially in tropical destinations like Hawaii, the Caribbean, Mexico, Costa Rica, and Tahiti. If you’re dreaming of that palm-lined holiday, begin researching and booking as early as possible.
Start by determining your must-haves:
Do you want an all-inclusive resort or a beachfront villa with a kitchen?
Do you need kid-friendly amenities like a pool with slides, a kids’ club, or babysitting services?
How many bedrooms do you need for everyone to sleep comfortably?
Will you rent a car or rely on taxis and shuttle services?
Once you’ve identified your priorities, lock in flights and accommodations. Christmas flights are notoriously expensive, and the earlier you book, the more flexible you’ll be with departure times, seat assignments, and fares.
It’s also wise to check entry requirements for your destination—passports, visas, vaccinations, or digital immigration forms. Make sure all passports are valid for at least six months beyond your travel dates, as many tropical destinations require this for entry.
2. Make a Holiday Plan—Without Overplanning
When traveling over Christmas, many families worry about “missing” the holiday. The key is to bring your favorite traditions with you—but in a lightweight, portable way.
Think about what matters most to your family. Is it a special breakfast? Opening gifts? Watching a particular Christmas movie? Lighting a candle? Singing carols? Decide as a group which traditions you want to honor and which ones can be left at home.
A few ideas to keep the holiday spirit alive without taking up suitcase space:
Find custom stockings that match the vibe of your tropical destination. You can personlize stockings with names and it makes a great keepsake for everyone to have over the years. Stockings are easy to pack and can be presented Christmas morning at breakfast or gathering in your suite.
Wrap small gifts or put them in fabric gift bags you can fold and reuse.
Stream Christmas music while you get ready for the beach.
It’s also worth planning your Christmas Eve and Christmas Day itself. Do you want a special brunch? A beach picnic? A sunset sail? Many resorts host holiday dinners or festive buffets, but they book quickly—reserve early if you plan to join one.
Hosting an early holiday gathering before leaving for your tropical vacation is a beautiful way to savor the season and share festive moments with extended family and friends. It lets you enjoy your decorated tree, favorite dishes, and cherished traditions without feeling rushed before departure. Gathering loved ones early creates space for connection, gratitude, and celebration, ensuring no one feels left out while you’re away for Christmas. Whether it’s a cozy brunch, a cocktail night, s’mores and mulled wine by the fire, or a casual open house with cookies and cocoa, this tradition keeps the holiday spirit alive and allows you to fully embrace both your festive home and your upcoming getaway.
3. Packing Smart for a Christmas in the Tropics
Packing for a tropical vacation during the peak of winter can feel counterintuitive. While everyone around you is ordering peppermint lattes and bundling up, you’re pulling out bathing suits and sunscreen. Creating a well-thought-out packing plan helps prevent overpacking and ensures you have everything your family needs.
Clothing Essentials:
Lightweight, breathable clothing like linen, cotton, and moisture-wicking fabrics
Swimsuits (bring at least two per person)
Rash guards for kids and adults who burn easily or for enjoying surfing and water sports
A light sweater or wrap for breezy evenings
Comfortable flip-flops and breathable walking shoes
Sun hats and sunglasses for everyone
Toiletries & Health Items:
Reef-safe sunscreen (very important in many tropical locations)
Aftersun lotion or aloe
Bug spray
A basic family first-aid kit with bandages, Kids’ Tylenol, motion-sickness tablets, and antiseptic
Prescription medications
Saline spray and hand sanitizer, especially during winter travel
Beach Gear:
Many tropical destinations supply towels and even snorkeling equipment, so check before you pack. A few items worth bringing:
Collapsible sand toys
Reusable water bottles
Waterproof phone cases
A dry bag for boat days
A light beach blanket or sarong
Holiday Extras:
Small gifts
Foldable Santa hats
Downloaded holiday music and movies
A favorite treat or snack from home
4. Plan for Weather—It’s Not Always Perfect
The idea of a tropical Christmas conjures images of endless sunshine, but many warm destinations have unpredictable winter weather. Tropical Christmas often means dry season—but that can still include short bursts of rain, windy afternoons, or humid evenings.
To prepare:
Check typical weather patterns for your destination in December.
Pack a lightweight rain jacket or poncho for each family member.
Bring a foldable umbrella—helpful for shade as well.
Build flexibility into your itinerary for weather shifts.
Indoor backup activities—like cooking classes, aquariums, or escape rooms—can save the day if an unexpected rain cloud rolls through.
5. Plan Activities That Everyone Enjoys
Every family has different travel styles. Some people want to lie on the beach all day; others thrive on adventure. Balancing the group’s preferences makes the vacation more harmonious.
A few family-friendly tropical activities to consider booking ahead:
Snorkeling or glass-bottom boat tours
Whale watching (December is prime season in many destinations)
Paddleboarding or kayaking
Zip-lining
A rainforest or waterfall hike
Local cooking classes
Catamaran sunset cruises
Cultural experiences such as dance performances or craft workshops
Make sure to leave enough downtime. Tropical vacations are best enjoyed at a slower pace, especially over Christmas when the goal is relaxation and connection.
6. Keep Everyone Happy
Traveling with children or multiple adults adds a layer of complexity—but also extra joy. To keep everyone comfortable and content, consider the following:
For younger kids:
Bring a few familiar comfort items like a favorite stuffed animal or bedtime book.
Pack plenty of airplane snacks—airport food can be hit or miss.
Use a small backpack for each child with entertainment items for travel days.
Choose accommodations with a kitchenette if your child is a picky eater.
For teens and adults:
Give everyone some autonomy—encourage space to rise early or sleep late as each family member prefers and let everyone coordinate their free time to minimize stress and maximize relaxation
Vote or rotate who gets to choose an outing or restaurant
Encourage a mix of unplugged time and digital downtime.
Pack an extra power bank; teens go through battery life fast on flights and long travel days.
For everyone:
Build buffer days. Between jet lag, adjusting to new climates, and holiday excitement, keeping the first day light helps prevent meltdowns for kids—and adults.
7. Food Planning: Enjoying Local Flavors While Staying Comfortable
Food is often one of the best parts of a tropical vacation. Fresh seafood, tropical fruits, coconut everything, and vibrant spices make every meal memorable. But when traveling with family, especially around Christmas, it helps to have a flexible food plan.
Consider:
Checking in advance whether your resort offers kid-friendly menus.
Researching vegan or vegetarian options if your family has dietary preferences (many tropical destinations excel here).
Booking at least one special Christmas dinner or holiday brunch.
Packing familiar snacks from home to avoid holiday-week price hikes.
Bringing electrolyte packets—they’re helpful in hot climates.
If you’re staying in a rental home or villa, stocking a few basics on arrival—fruit, yogurt, bread, coffee, snacks—keeps mornings easy and reduces hangry moments.
8. Travel Days: Reduce Stress During One of the Busiest Times of Year
Airports during Christmas are famously chaotic. A few steps can make your travel days much smoother:
Arrive earlier than you think you need to.
Use airline apps for mobile boarding passes, delay alerts, and seat changes.
If traveling with kids, dress them in layers—they can go from cold airports to warm planes quickly.
Bring an empty reusable water bottle to fill after security.
Keep all travel documents in one folder or digital app for easy access.
Pro-tip for Hamptonites traveling: The TWA Hotel at JFK is a great overnight option for early flights out or late night returns. If you fly JetBlue like we do, it’s an extra bonus because the hotel connects to the JetBlue terminal. You can also book blocks of time at the hotel during daytime hours to make sure you arrive comfortably early for your flight and have a comfortable room to hangout it in before takeoff (we also love to make use of the year round heated rooftop pool)
If you’re traveling with gifts, remember that wrapped presents may be opened at security. Stick to unwrapped items, gift bags, or digital gifts to reduce the risk of delays.
9. Staying Safe and Comfortable in a Tropical Destination
Safety is part of any good family travel plan. A few essentials:
Hydrate more than you think you need to—tropical sun is strong.
Apply sunscreen every two hours, especially for kids.
Take breaks from the sun between 11 a.m. and 3 p.m.
Only swim where lifeguards or posted signs permit.
Watch for rip currents on beaches known for waves.
Keep passports and valuables in a hotel safe.
Teach kids a “meeting point” in case they get separated in crowds.
10. Handling Holiday Emotions While Traveling
Traveling over Christmas can sometimes stir unexpected emotions. You might miss family gatherings, snowy mornings, or the familiar rituals of home. Kids may feel this too.
Make space for conversation and flexibility.
Acknowledge the differences: “This year Christmas will look different, but we’re creating a new memory together.”
Create mini-moments that feel comforting: a hot chocolate night, a favorite movie under the AC, or even calling loved ones back home.
The beauty of a tropical Christmas is that it doesn’t replace your traditions—it adds to them.
11. Enjoying the Magic of a Holiday Away From Home
A tropical family vacation over Christmas is a gift in itself. The warm sun, turquoise water, and swaying palms create a backdrop that turns simple moments—reading by the pool, watching the kids splash in the waves, taking a family walk at sunset—into sparkling memories.
Let go of perfection. Embrace slow mornings, spontaneous adventures, and the bliss of doing nothing at all.
In the end, the most meaningful part of the holiday is being together. Whether you’re building sandcastles instead of snowmen, exchanging gifts on a balcony overlooking the ocean, or simply holding hands on a warm December evening, you’re giving your family something priceless: time, connection, and a story you’ll remember for the rest of your lives.
