Your 2025 Holiday Guide

by Angela | Aug 28, 2025

You know that here at Sheldon James we love holidays, but we also love THE holidays. No matter what you celebrate, that period at the end of the year is a magical time of rest, reflection, togetherness, and fun. There’s no better way to honor the significance of the holidays than in a tropical destination with those you cherish most.

Our favorite destinations down south know how to create extra special moments with local events and also special activities created just for you either at the villa or in the local area. Here are a few destinations we recommend, along with suggestions on how to craft holiday memories to last a lifetime.

St. Martin

This dual-nation island offers double the traditions to choose from, wrapped in a beautiful bow made of green hills, golden sand, and turquoise water. St. Martin’s spacious villas are primed for in-villa activities, but it’s also one of our “busier” destinations (it’s all relative!) if you’re a traveler who likes to experience local culture and customs. These events take place over the holiday period and will thrill guests who choose St. Martin:

Christmas Village in Philipsburg: Step into the heart of the holiday season at this charming open-air market, where twinkling lights, local food stalls, handcrafted gifts and island-made gods, and Caribbean Christmas music create a warm and festive atmosphere.

Fireworks at Maho & Simpson Bay: Celebrate Christmas Eve and Christmas Day in style at some of the island’s most vibrant beach clubs. Expect live bands, DJs, festive cocktails, and spectacular fireworks lighting up the night sky—especially around Maho and Simpson Bay, where the party vibes run strong.

Creole Christmas Lunch: Indulge in a traditional island-style Christmas meal at beloved local spots like Yvette’s in Philipsburg or one of the iconic “lolos” in Grand Case. From stewed meats to plantains and Johnny cakes, it’s a flavorful way to enjoy the season with a Caribbean twist.

Carnival-Style Christmas Parade: Experience the energy of the island with this carnival-inspired parade that lights up the streets of Philipsburg and Marigot. Dancers in glittering costumes, pulsing steel drum bands, and glowing floats bring the season to life.

View our villas in St. Martin

Turks and Caicos

Our Turks and Caicos villas are among our most popular December destinations for good reason. While the islands themselves are a bit sleepy (wonderful, if that’s what you’re looking for), the villas are perfect for hosting on-site activities with our trusted providers whose dedication to five-star service only ramps up over the holidays. These in-villa experiences may just become new traditions for you and your family:

Kids’ Holiday Workshop: For families traveling with young children, we’ll transform a cozy corner of the villa into a magical holiday workshop just for them! Think cookie decorating with tropical-themed icing, seashell or driftwood ornament making, and hands-on DIY holiday crafts infused with island flair. To top it all off, there’s a surprise appearance by “Island Santa” who’ll stop by with small gifts or treats in hand.

Mystery Box Chef Challenge: Perfect for foodie families or groups of friends, this interactive culinary experience brings excitement right into the villa’s kitchen. Guests will handpick 3–5 mystery ingredients, and our talented private chef will whip up a surprise menu around them — right on the spot. The experience includes fun scorecards to rate each dish, MasterChef-style.

Cocktail Masterclass: Enjoy one of Grace Bay’s newest hidden gems — a boutique mixology cocktail bar that’s perfect for private group classes.

Pure Island Fun for the Young (and Young at Heart): From movie nights under twinkling teepees to bouncing off the water trampoline, our Kids Play program is filled with memory-making moments. Young guests can dive into a Mermaid Experience, enjoy arts and crafts, or simply run wild with island-inspired games and activities. It’s designed to keep little ones entertained — and parents perfectly relaxed.

View our villas in Turks and Caicos

Mexico - Los Cabos

Not an island, but an island unto itself in Mexico when it comes to elegance and exceptionally stunning ocean views. Mexicans are also adept at celebrating… well, just about anything… and the Christmas/New Year’s period is no exception. These activities are guaranteed to get you in the holiday spirit:

Villa “Winter Wonderland”: Who says you need snow to feel the holiday magic? We’ll turn your villa into a sun-kissed winter wonderland, adorned with twinkling fairy lights, lush garlands, poinsettias, and festive floral touches that bring seasonal charm.

Sunset Carolers: As the sun sets in a wash of gold and coral, enjoy the sounds of traditional villancicos (Spanish Christmas carols) performed by local singers. This magical moment unfolds just before a curated, candlelit festive dinner — served poolside or right on the beach.

Bonfire & Stargazing: Gather around a private bonfire set along the shoreline for a night of storytelling and stargazing. Sip on artisanal hot chocolate or ponche navideño (a spiced Mexican holiday punch), and let a local astronomer guide you through the constellations above — a blend of science, tradition, and holiday wonder.

Luxury Festive Whale Watching: Celebrate the season in true Baja style with a private, luxury whale watching excursion during peak migration season. Sip Champagne and nibble on holiday-inspired treats as you watch humpbacks breach and play in the waves.

View our villas in Cabo

We hope that these joyful ideas have piqued your interest and convinced you to spend your time down south this holiday season. Get in touch and tell us how we can make your holiday unforgettable at one of these, or our many other, fabulously festive destinations.

Discover our top villas

Your 2025 Holiday Guide

Experience Cabo at its best

Living the Ultimate Costa Rica Villa Experience

New adventures in Thailand and Sri Lanka