Why choose St. John for the holidays?
Because the island gives you everything a true holiday should: time together, simple pleasures, and the freedom to choose your own pace. November and December on St. John are a study? in bright mornings, warm water, and evenings that unfold on breezy terraces with the lights of Cruz Bay twinkling below. Whether you’re planning to cook a full holiday spread, hire a private chef, or enjoy a festive meal out, St. John gives you every reason to be thankful, and The Hills St. John turns that feeling into a finely tuned experience. From Turkey Day to tinsel time, think panoramic villas, concierge support, and that rare combination of privacy with easy access to beaches, hikes, and restaurants. Add in flexible stay options and you’ll see why coming here once often becomes a tradition.
How does The Hills turn Thanksgiving into “Feast, Relax, Repeat”?
It starts with the right canvas: high-elevation views, generous indoor–outdoor living, and kitchens designed for real cooking. At The Hills, “holiday-ready” isn’t a flourish, it’s a checklist. Spacious dining tables that actually seat your group. Islands and counters with room for prep. Refrigeration that holds the pies and the bubbly. And when you don’t want to lift a finger, the concierge lines up an in-villa private chef who handles the menu, the pacing, and the cleanup while you pour drinks and watch the sky change color. The result is simple and exactly right for the season: Feast. Relax. Repeat. The next day is for beaches, snorkel sets, and doing exactly as much as you want.
How to make a few days memorable.
Absolutely. If you don’t have a full week to unwind, The Hills now offers 4-night stays over Thanksgiving, the perfect way to enjoy a holiday escape even with a busy schedule. In practice, that means you can fly in midweek, ferry across, settle into your villa with provisions ready, and still have time for a chef-driven dinner, a north-shore beach day, a sunset sail, and a lazy brunch on the balcony before you head home. Four nights is enough to reset the clock, and it’s a far better memory than trying to make a single dinner at home and do all the heavy lifting.
Cooking, private chef, or dinner out—what’s your move?
Pick one, or better yet, mix and match. The beauty of The Hills is flexibility:
- Cook together: Treat the kitchen like a family project. Assign courses, put someone on cocktails, and turn the balcony into your carving station with a view.
- Pick up local fish and veggies for a family grill night. Season simply, and let the terrace do the mood-making.
- Bring in a chef: Keep the conversation flowing while an expert handles timing and technique. Picture appetizers arriving as the sun goes down, mains plated for the table, and dessert with coffee under the stars.
- Open the door to a professional who can provide sharable bites, a plated main dish, and a dessert that tastes like the holidays dressed for the tropics.
- Go out festive: Prefer a night on the town? Cruz Bay restaurants run lively holiday services in a walkable, waterfront setting. You get the bustle when you want it and peace when you don’t.
- For a night on the town, choose a dining room that matches your pace, white tablecloth or sandals-and-sundress, and enjoy walking through Cruz Bay.
Whichever path you pick, the outcome is the same: zero stress, full plates, and a day that actually feels like a holiday.
Which villas will help you enjoy the season?
Every party needs the right stage. Here are standouts at The Hills that match the moment:
- Bethel Vista: Built for gatherings with four spacious balconies so the whole family can spread out. Morning coffee on one terrace, golden-hour cocktails on another, and dinner under the open sky. Picture yourself sipping a cocktail as the sun sets over the Caribbean, while your private chef crafts an unforgettable holiday feast just steps away.
- Frangipani: A showpiece for celebratory weeks, featuring its own private pool for midafternoon dips and post-dinner stargazing. If your plan is long meals, long swims, and late mornings, Frangipani is your lane.
- Planning a more intimate Thanksgiving this year? Explore the cozy two-bedroom collection, perfect for couples, small families, or friends who want a quieter holiday.
- Mimosa: A two-bedroom with a private pool, rare at this size and ideal when you want all the amenities without the scale of a larger villa.
- View Come True A two-bedroom with wraparound balcony, two primary bedrooms, each with a king-size bed, luxury mattresses, and stunning ocean views.
If you’re undecided, share your headcount, dates, and how you like to spend your days. The team can match you with a villa that fits sleep style, kitchen needs, and balcony time.
How to make the most of the weeks between Thanksgiving and Christmas.
This is the island’s sweet spot: everything is humming, the water is warm, and the holiday rush hasn’t peaked yet. Use it. Book a long weekend or a full week to front-load your peace. The to-do list is gentle and generous:
- Beach-hop smarter: North shore for classic blue; south shore for quieter curves when swells pick up.
- Hike at golden hour: Ram Head for drama, Lind Point for an easy town-to-beach connector.
- Snorkel for serendipity: Turtles grazing at Maho, patch reefs off Trunk and Hawksnest when conditions align.
- Shop and stroll: Pick up gifts in Cruz Bay, artisanal rum cakes, local crafts, reef-safe sun gear, then head back uphill for sunset.
- Sail into the season: Book a sunset charter; it’s the quickest way to feel like you’ve arrived.
What about the “tinsel time” build-up—how does December feel at The Hills?
December on St. John isn’t about crowded spectacle; it’s about light, music, and easy gatherings. The trade winds are steady, evenings are made for terraces, and the island leans festive without losing its calm. At The Hills, decorations nod to the season while letting the Caribbean take the lead—poinsettias on a table, a string of warm lights over a balcony rail. If you need to mix work and wander, Wi-Fi and quiet nooks make a half-day of emails painless so you can spend the rest of your time outside.
What should you book early, and what can you leave flexible?
Holiday logic applies: book the absolute must-haves, keep afternoons elastic.
- Now: Flights to STT, villa at The Hills, car rental, ferry timing to Cruz Bay, any chef night, sunset sail or boat day, special-occasion dinner reservations.
- Soon: Childcare, spa appointments.
- Flexible: Beach choices (decide with the day’s wind/swell), hikes, simple lunches, pool time.
With the essential elements scheduled, you’ll ride the island’s pace, not fight it.
How does a villa work with bigger families?
That’s where The Hills shines. Multi-generation trips need space and separation. With Bethel Vista’s four balconies, kids can spread out with puzzles while grandparents read in the breeze. If cousins want an afternoon splash without leaving the villa, Frangipani’s private pool handles it. For a tight-knit core, Mimosa keeps you together with the luxury of your own plunge; when an extra set of hands or guests join,View Come True’s elevated balcony can provide the peace of the holiday season. The goal is to gather by choice, not necessity—and to have quiet corners when you want them.
How do you handle the practical stuff?
- Arrivals: Fly into STT (St. Thomas), taxi to the ferry, cross to Cruz Bay, and head up to The Hills. The team can coordinate private transfers if you prefer a single, seamless handoff.
- Groceries: Stock essentials on day one. If you’re cooking a big meal, ask the concierge about pre-arrival provisioning so the heavy items are already shelved.
- Beach logistics: Taxis run reliable beach routes; if you rent a Jeep, go early for parking.
- Sun + sea: Reef-safe sunscreen, sun shirts, hats. Bring more water than you think you need.
- Rhythm: Early swims, shaded afternoons, and long sunsets. It’s the island’s recipe for a reason.
What if you want the holiday feeling without the holiday dates?
Traveling the first two weeks of December is the move: the same weather, a softer pace, and broader availability. You’ll still get festive lights, live music, and a celebratory mood, just with more space between beach chairs and more choice on dinner reservations. If your calendar can flex, your shoulders will thank you.
Can you make a tradition out of it?
Easily. The most common feedback we hear is that families arrive for one holiday week and decide to lock the next one before they leave. The formula is addictive: a villa that feels like your holiday home + a kitchen that delivers + a town you can walk without driving. Kids graduate from sandcastles to snorkels; grandparents trade cold mornings for warm breezes. People come back because the place meets them where they are each year, and the memories stack.
What’s the ultimate takeaway from Turkey Day through tinsel time?
That the holidays work best when logistics fade and the moments stay. On St. John, the elements line up, sun, sea, and easy community, so you can have a full plate without a full schedule. At The Hills St. John, that philosophy turns into a practical plan: a villa sized to your people, chef nights when you want them, flexible 4-night Thanksgiving stays when time is tight, and thoughtful touches that make the week glow. Whether you’re seated around Bethel Vista’s outdoor table, taking a midnight dip at Frangipani, or stealing a quiet morning at Mimosa or Starfruit, the season feels like it should: generous and unhurried.
Ready to make the season yours?
Swap the frantic holiday shuffle for sunsets, swims, and suppers that end in laughter. Book your next stay in the USVI through The Hills St. John and turn Turkey Day to tinsel time into a tradition worth keeping. Pick your dates, choose your villa, Bethel Vista, Frangipani, Mimosa, or Starfruit, and let the island and our team handle the rest. Your table is waiting, your view is better than you imagined, and your most relaxing holidays are one reservation away.
