6 Warm Winter Holiday Escapes

Sydney, Australia

More than just beaches and surfing, Sydney has made its mark as a global culture hotspot year-round, with plenty to keep you entertained this winter.

Photo courtesy of Michael Evans / Alamy Stock Photo

What to Do

Overlooking Sydney Harbour, the sprawling Botanic Gardens of Sydney showcases Australia’s remarkable plant and animal life. Be sure to check out The Calyx  to admire the impressive, curved glass and living walls.

For a unique adventure in the heart of Sydney, visit the Archie Rose Bar & Cellar Door in Rosebery where you can try spirits blending, bartending, or mastering cocktails.

Of course, whatever the season, a trip to Sydney wouldn't be complete without visiting Bondi Beach. Big crowds are inevitable, so head there early in the morning or catch the last of the afternoon sun to avoid the rush.

Where to Stay

If you like to be in the thick of things, consider the Hilton Sydney (The Hotel Collection) with its stunning city center views. Be sure to visit the lobby to admire the bespoke sculpture ‘Vine’ by Australian sculptor Bronwyn Oliver. The piece is among the longest sculptural works in Australia.

To get the full Sydney experience, treat yourself to unparalleled views of the Harbour Bridge and Royal Opera House with a stay at Four Seasons Hotel Sydney (Fine Hotels + Resorts). Elevate your stay and enjoy artisan Epic and Signature cocktails at Grain Bar or sample modern Australian dining at Mode Kitchen & Bar. As a Platinum Card Member, you’ll receive a $100 credit which you can use towards dinner at Mode Kitchen & Bar.

Riviera Nayarit, Mexico

Crystal clear waters, sun-drenched 80 degree weather, beaches made for sunbathing and surfing, and breathtaking sunsets make Mexico a prime destination for a winter getaway. Consider Riviera Nayarit, which includes regions like Punta de Mita and Puerto Vallarta among its coveted destinations.

What to Do

Shoes and shirts are optional for many of the activities that draw travelers to the Riviera Nayarit region. From horseback riding at sunset along the white sand shoreline to surfing the clear blue waters, you’ll want to spend almost all your time outdoors.

Adventurous travelers can embark on an ATV or zip lining tour through the Sierra Madre Mountains, while those who prefer their recreation at a slower pace can wander through Vallarta Botanical Gardens or hit the local golf courses.

Families and couples can book a variety of nautical excursions, from whale watching and deep-sea fishing to snorkeling above colorful reefs teeming with vibrant sea life.

Where to Stay

An intimate oceanfront stay awaits at Susurros del Corazón, Auberge Collection, (Fine Hotels + Resorts), where accommodations feature handcrafted furnishings, local textiles, and floor-to-ceiling sliding doors. Be sure to inquire at reception about surf lessons tailored to any skill level.

For a bigger resort with family-friendly amenities, opt for Conrad Punta de Mita (Fine Hotels + Resorts), within an upscale gated community and adjacent to an 18-hole golf course. There are plenty of water sports on offer, along with a private beach and dedicated pools for kids and for adults only.

Down the coast from Punta de Mita, Marriott Puerto Vallarta Resort & Spa (The Hotel Collection), an all-inclusive, family-friendly resort steps from the beach with much to do for the whole crew, starting with the many swimming pools, including a relaxing infinity pool and Kids Club pool. Put your $100 credit toward a restorative treatment at the resort’s Ohtli Spa or a round of margaritas at the Ceviche & Tequila Bar.

Florida Keys, US

A string of islands south of Miami, between the Atlantic Ocean and Gulf of Mexico, the Florida Keys have a rich arts scene and quirky charm. You can also expect outdoor adventures, beachfront dive bars, and chic boutiques.

What to Do

Explore the lively bars and restaurants of Key West's Old Town, where you can indulge in fresh seafood and key lime pie, which originated here. Take in the local culture, from Islamorada's art galleries to Key West's Butterfly & Nature Conservatory and Ernest Hemingway's home and museum. Snorkel and scuba dive from reefs near Key Largo or relax on the sprawling beaches in Fort Zachary Taylor Historic State Park.

Where to Stay

Accessible only by seaplane or boat, Little Palm Island Resort & Spa (Fine Hotels + Resorts) is a true escape. Bungalow suites with thatched roofs capture the tropical vibe; each room has an expansive ocean view. (Prepare to unplug here: Rooms lack TVs and telephones.) Take a fishing trip, go scuba diving, or put your $100 credit toward a soothing spa treatment.

Isla Bella Beach Resort & Spa (Fine Hotels + Resorts) sits along a mile of waterfront that's ripe for exploration or relaxation. You can stroll 24 acres of landscaped tropical gardens, dip into five oceanfront pools, or kayak on the big blue itself. White-and-navy suites bring the outdoors in; all have stunning ocean views and private terraces.

On Stock Island, a short shuttle ride from the bustle of Key West, Oceans Edge Resort & Marina (The Hotel Collection) has six saltwater pools, a full-service marina, and ocean-view rooms with furnished balconies. Greet the morning on a paddleboard, sail the coastline at sunset, or relax on a daybed.

St. Barths

St. Barths has long been known as an upscale Caribbean retreat for those seeking a luxury beach vacation with a distinctly European feel. A small island marked by pristine beaches, lush foliage, and a dynamic social scene, St. Barths is a great getaway for couples or friends seeking an escape from the everyday.

What to Do

St. Barths makes it easy to bask in the good life; couples and friends can sun on the beach, shop, and stay out late at fine-dining restaurants and cocktail bars.

The island has a family-friendly side, too, and activities for any adventure seekers. You might charter a private boat, spend a day hiking the picturesque hiking area Colombier area, or commandeer the resort’s paddleboards and kayaks to explore the scenic waters at your leisure.

Where to Stay

A secluded resort set upon 18 acres of beautifully manicured property that overlooks two beaches, Rosewood Le Guanahani St. Barth (Fine Hotels + Resorts) comprises 66 colorful yet tasteful suites, some with private pools – if there’s availability, you’ll be treated to a complimentary room upgrade upon arrival.

In the heart of St. Jean’s Bay, one of St. Barth’s most popular beachside towns, Tropical St Barth (The Hotel Collection) is a boutique hotel perfect for those who like to be at the center of the area’s shopping, dining, and nightlife scene – and just steps from the beach. Suites feature private terraces and sweeping ocean views, and you can enjoy it all the longer with late check-out, when available.

Cheval Blanc St-Barth (Fine Hotels + Resorts), puts you directly on Flamands Beach, the longest of all the area’s stunning white sand beaches. Nestled among gardens, the resort’s suites feature white décor and soft wood accents that both echo and complement the beauty of its location. After soaking up the Caribbean sunshine, put your $100 credit towards a spa treatment like the Sun Prelude Ritual, which hydrates the skin.

Singapore

A fascinating blend of cultures, cuisines, and sights, Singapore offers a change of pace like no other. And while our winter does align with theirs, expect a tropical climate; temperatures tend to be around 75- 85° F.

What to Do

Singapore certainly knows how to make a good first impression. Home to not only the world’s tallest indoor waterfall, but also a butterfly garden, Singapore Changi Airport will excite you the minute you touch down.

But don’t get too comfortable – there’s plenty to enjoy in this bright and welcoming city-state. Tuck into local favorites like chili crab or laksa (a spicy coconut curry noodle soup) at the bustling hawker centers, hit the beaches and Gardens by the Bay, or wander neighborhoods like Little India, full of Hindu temples and street art.

Explore our 4-day Singapore itinerary for more insider recommendations.

Where to Stay

The reimagined Mandarin Oriental, Singapore (Fine Hotels + Resorts) is a luxurious sanctuary in Marina Bay. Perfect for exploring the city’s culture, arts, and high-end shopping, it also offers serene indulgence. Unwind at the spa or by the outdoor pool with skyline views from poolside cabanas.

The Conrad Singapore Marina Bay (Fine Hotels + Resorts) rises high above Marina Bay with panoramic views of the Singapore skyline. Enjoy spacious rooms and luxury suites, elegant restaurants, an outdoor pool, and an intimate spa. The hotel is near landmarks such as Esplanade, Merlion Park, Suntec Convention Center, and the Singapore Flyer, as well as art museums and galleries.

Alternatively, experience life at the W Singapore Sentosa Cove (The Hotel Collection) , an urban oasis lifestyle hotel with a relaxed approach to luxury and stunning Marina views. Relax in one of 240 vibrant guest rooms and suites, explore flavorsome dining outlets or while away an afternoon at AWAY Spa and WET Deck, one of Singapore’s largest 24-hour outdoor pools. Plus, this property goes beyond the standard benefits of The Hotel Collection to provide complimentary daily breakfast for each day of your stay.

Belize

On the Caribbean coast just south of Mexico, Belize is a tropical getaway where you can get your adrenaline pumping or slow down with wellness experiences. Beaches, jungles, and ancient Mayan cultural sites offer plenty to explore, while amenity-rich resorts deliver next-level luxury.

What to Do

Investigate ancient Mayan ruins and archeological digs. See towering waterfalls and splendid wildlife on a hike through the jungle. Go cave-tubing, snorkel from the Belize Barrier Reef (part of a UNESCO World Heritage site), or spend an afternoon on white sand beaches and in adjoining bars.

Where to Stay

Set on the Caribbean coast of Ambergris Caye, Alaia Belize, Autograph Collection (The Hotel Collection) is an ideal base if you’re here to sail or snorkel (the nearby Belize Barrier Reef Reserve is home to plentiful marine life). Rooms and villas have a crisp contemporary design; amenities include six restaurants and bars and a fully equipped wellness center. A concierge can take you to Secret Beach or on a rainforest tour.

Tucked into the lush heart of Belize’s Cayo District by the Guatemalan border, Ka’ana Resort (The Hotel Collection) is a boutique retreat surrounded by rainforest and Mayan-era antiquity. Suites and private villas are thoughtfully designed with natural textures and open terraces. Relax at the pool or at the yoga deck and spa, which uses botanical ingredients in treatments. Another day, you might go zip-lining or tour ancient ruins on horseback before circling back for artisanal cocktails and organic cuisine.