Winter Vacation Ideas at a Glance
Best for: Golfers, surfers and Francophiles, plus anyone who refuses to let the weather cancel their favorite trip
What’s inside: Four warm-weather destinations matched to three summer passions, with twelve hand-picked hotels
Standout picks: Aurora Anguilla Resort & Golf Club, Rancho Santana, Tropical Hotel St Barth
Book with a travel advisor: Exclusive perks like hotel credits, upgrades and daily breakfast, where available
Just because it’s chilly out where you live doesn’t mean you have to forgo your favorite summer vacation. These winter vacation ideas start with the trip you already love.
I’m a huge advocate of booking winter vacations that capture the same essence as your favorite warm-weather getaway. Chasing waves and teeing off don’t have to be saved for sunny mornings, and exploring historic, cobblestone streets doesn’t have to be limited to short spring breaks.
So this winter, tell me what you miss the most about your summer vacations. I’ll use it to plan a winter getaway that will make you forget about the weather back home.
If you love golfing, head to Anguilla
If your perfect summer day starts with early tee times followed by long afternoons lounging by the water, then you’ll love Anguilla. The Caribbean island offers year-round warmth, pristine beaches and world-renowned golf courses.
Aurora Anguilla Resort & Golf Club is always my first suggestion for golfing fanatics. The large resort is anchored by an 18-hole Greg Norman-designed course with sweeping views of the Caribbean Sea and the neighboring island of St. Martin. The Caribbean Travel Awards named it Caribbean Golf Resort of the Year in 2025. Why stay: You want the course right outside your door and a big resort with everything on site.
But here’s a hack: you don’t have to stay at Aurora to use its golf course. If you’d rather slumber at a boutique hotel, let me book you at Quintessence Hotel Anguilla, only a 10-minute drive from the golf club. The beach resort marries a secluded oceanfront residential feel with the perks of a five-star hotel (as in, a quiet beach and a glittering infinity pool). Why stay: You want boutique quiet after your round, with the course a short drive away.
Or go for Zemi Beach House, located right on Shoal Bay, widely regarded as one of the most beautiful stretches of oceanfront on the island. It’s a great place to unwind after an early afternoon at the course. Why stay: Shoal Bay is your reward after the back nine.
Anguilla is also the go-to Caribbean destination for global foodies. Tell me your culinary preferences, and I’ll tailor your dining plans to a T(ee).
If you love arts and culture, head to Uruguay
If your favorite summer trips revolve around museums, galleries and long walks through historic neighborhoods, let’s head south to Uruguay. Bonus: our winter is their summer, so you trade the cold for long, warm days on the coast.
Some of my clients did exactly this last year. They started with a few nights in Buenos Aires, then crossed the Río de la Plata and made their way along the Uruguay coast, town by town. Here’s how I’d build that route for you.
Start in Buenos Aires at the Park Hyatt, set in the Palacio Duhau in Recoleta. Even if you stay elsewhere, at least have lunch there. Why stay: Classic grandeur in one of the city’s most elegant neighborhoods.
For a bolder, more design-forward stay, book the Faena in Puerto Madero. Why stay: You want a hotel with as much personality as the city around it.
Then cross to Colonia del Sacramento, whose historic quarter is a UNESCO World Heritage Site. Posada Plaza Mayor sits right in it, in a building that began as an 18th-century Portuguese ranch and later became an 1860s mansion. There are just 17 rooms, and the central courtyard, with its climbing vines and three-tier fountain, is where you’ll want to spend your afternoons. Why stay: History lovers who want to walk out the door and into the old town.
In Montevideo, Hotel Montevideo is a gem. It’s in Pocitos, a short walk from the beach, and its rooms pair antique-inspired pieces with modernist design classics. Every room has at least one balcony, and the hotel holds a Michelin Key. Why stay: Design lovers who want a polished city base near the water.
Finish in José Ignacio at Posada Ayana, which one client told me was one of the most original hotels he has ever stayed in. It’s easy to see why. Each of its 17 rooms is different, the owners display a collection of work by female Uruguayan artists, and the grounds are home to a James Turrell Skyspace, the first freestanding one in South America. Why stay: Art lovers who want a beach hotel with a real point of view.
Don’t let the cold weather put a damper on your hobbies. When it comes to travel, I’m a firm believer that there’s a destination for every hobbyist, no matter the time of year.
If you love surfing, head to Nicaragua
Chasing waves and beach naps don’t have to end with the setting summer sun. If you love surfing, let’s follow the Pacific coast south to Nicaragua. Its quiet beaches, friendly locals and consistent waves make it one of the world’s most underrated surfing destinations.
Rancho Santana is one of my favorite picks for surfers headed south. The property spans 2,700 acres of Nicaragua’s Emerald Coast, which boasts offshore winds about 330 days a year. There, I can book you a surfing boat trip and an at-sea photo shoot. If you consider yourself a novice, the property also offers lessons and private coaching led by its in-house surf instructors. Why stay: Surfers of every level, with plenty to do on and off the water. Also, the very best churros I’ve ever eaten in my life.
For a more intimate stay, consider Mukul Resort. It’s set within a 1,670-acre private beach community on the Emerald Coast, just in front of Manzanillo Point, known for a powerful left-point wave that experienced surfers love. Like Rancho Santana, Mukul has a full-time surf team that can create coaching plans and point you to the best secluded surf spots. Why stay: Experienced surfers who want a smaller, more private base near a serious wave.
No matter the property, I can arrange post-surf adventures, like beachside horseback riding and mountain biking, to explore the rest of Nicaragua’s lush landscape.
If you love the South of France, head to St. Barths
If you love spending summer afternoons exploring the cobblestone streets of the South of France, lingering over late lunches and window-shopping the boutiques, then let’s plan a trip to St. Barths.
The island is known for its year-round warmth, world-class shopping and crystal-clear waters. But close your eyes and you’ll forget you’re in the Caribbean. French is the official language of the island, which is an overseas collectivity of France.
For a secluded stay, I suggest Hotel Christopher St. Barth, located on a quiet northeastern slice of the island. The intimate hotel has only 46 accommodations, and the spa and infinity pool both offer panoramic views of the coast, striking the perfect balance between coastal Caribbean and chic French living. For an ultra-private getaway, I’ll book you a villa with a private pool. Why stay: Couples who want quiet, views and a smaller hotel.
If you’d rather stay closer to the action, let me book you a suite at the Tropical Hotel. The Michelin Key-awarded property is surrounded by vibrant gardens and a pristine coastline. In my opinion, it’s the perfect blend of the French Riviera and the Caribbean, with 24 chic accommodations and a swimming pool with sweeping views of the bay. For an exciting afternoon, I can also arrange a helicopter tour of the island. Why stay: You want to be near the action, with a pool overlooking the bay.
Don’t let the cold weather put a damper on your hobbies. When it comes to travel, I’m a firm believer that there’s a destination for every hobbyist, no matter the time of year.
Frequently Asked Questions
What are the best winter vacation ideas if I miss summer?
Start with what you love most about summer and find the winter destination that matches it. Golfers love Anguilla, surfers head to Nicaragua’s Emerald Coast, and anyone who misses the South of France will feel at home in St. Barths. Tell me your favorite summer trip and I’ll find its winter twin.
Can you play golf at Aurora Anguilla without staying there?
Yes. You don’t have to stay at Aurora to use its Greg Norman-designed course. You can pair the course with a boutique stay like Quintessence Hotel Anguilla, about a 10-minute drive away, or Zemi Beach House on Shoal Bay.
Is Nicaragua good for beginner surfers?
It can be. Rancho Santana offers lessons and private coaching with its in-house surf instructors, so first-timers are in good hands. Experienced surfers may prefer Mukul, which sits in front of Manzanillo Point and its powerful left-point wave.
Do they speak French in St. Barths?
Yes. French is the official language, and the island is an overseas collectivity of France. Between the boutiques, the long lunches and the language, it’s the closest the Caribbean gets to the South of France.
When should I book a winter getaway?
As early as you can, especially for holiday weeks. Small hotels like the 24-room Tropical Hotel have limited inventory, and the best rooms go first. If you want to travel this winter, reach out now and I’ll tell you honestly what’s still realistic.
Why book a winter vacation with a travel advisor?
You get a trip matched to how you actually like to travel, plus exclusive advisor perks like hotel credits, upgrades and daily breakfast, where available. I also handle the details, from surf coaching to a helicopter tour of St. Barths.
READY TO PLAN YOUR WINTER ESCAPE?
Every hotel in this guide is one I can book for you with exclusive advisor perks where available, from hotel credits to upgrades to daily breakfast. Tell me what you miss most about summer, and I’ll build the winter trip around it. Get in touch.
Marilyn Olson is a luxury travel advisor and the founder of Studio M Travel, a member of Fora (X) and the Virtuoso network. She personally vets and hand-selects every property she recommends. She books winter escapes for her clients with exclusive advisor benefits, including hotel credits, daily breakfast, room upgrades and more.
Reach out at studiomtravel.com or marilyn.olson@fora.travel and let’s start planning.
