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8 Incredible Islands to Escape the Cold This Winter

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While there are still a few weeks to go before spring rolls around, you can beat the system by wintering in these summer locales, island hopping everywhere from Maui to the Maldives. TPG Contributor Lane Nieset takes us around the globe to eight beautiful spots worth spending some time in this season. The best part: They’re all bookable with points and miles.

1. Bora Bora 

Stay in one of the overwater bungalows at The St. Regis Bora Bora Resort overlooking the lagoon.
Stay in one of the overwater bungalows at The St. Regis Bora Bora Resort overlooking the lagoon. Image courtesy of The St. Regis Bora Bora Resort’s Facebook page.

French Polynesia is south of the equator, so while you’re braving snowstorms up north, Bora Bora is in full summer mode. Their summer (our winter) may technically be the rainy season with much higher temperatures, so crowds are fewer — you’ll also skip some of the crowds during their winter months (June through October) and be able to take full advantage of year-round beaches and lagoons glowing in hues of blue and green.

Where To Stay

The honeymoon locale is known for its overwater bungalows and the SPG Category 7 St. Regis Bora Bora Resort has some of the most luxurious, with thatched-roof villas perched over lagoons, sporting everything from al fresco whirlpools and showers to terrace pools suspended over water. Rates start at $1,105 per night in late February and March. Please note that the property has limited SPG participation when it comes to Starpoint redemption.

How To Get There

Air France and Air Tahiti Nui offer nonstop flights from Los Angeles (LAX) to Tahiti Fa’a’ā International Airport (PPT), which then connects you to Bora Bora Airport (BOB) with a 50-minute flight on Air Tahiti. For more tips on scoring lower flight fares, see TPG’s response to reader question, How Can I Redeem Miles for a Honeymoon Flight to Bora Bora?.

2. Amelia Island, Florida

Head off of Florida's Northeast coast for a luxurious stay at The Ritz-Carlton, Amelia Island.
Head off of Florida’s Northeast coast for a luxurious stay at The Ritz-Carlton, Amelia Island. Image courtesy of the hotel.

Island hopping doesn’t have to entail far-flung destinations. Look in your own backyard and you’ll find the US is teeming with tropical paradises set just off the coast, such as Florida’s Amelia Island, the only spot in the country to have been under the sovereignty of eight different flags since it was founded in 1562. Connected to Northeast Florida by two bridges, the island boasts 13 miles of beaches, plus 117 stunning holes of golf set along the Atlantic. Watersport lovers can do everything from scuba diving to deep sea fishing and dolphin watching, while landlubbers can tour the 50-block historic district of Fernandina Beach by foot or horse-drawn carriage.

Where To Stay

The beachfront Ritz-Carlton, Amelia Island features 446 rooms — all with coastal or ocean views — as well as an 18-hole championship golf course, four restaurants and the sea-inspired Ritz-Carlton Spa featuring custom-crafted salt scrubs and the Heaven in a Hammock massage, an al fresco treatment performed right in your hammock. Rates at the Tier 3 property start at $329 or 50,000 Ritz-Carlton Rewards points per night in late February.

How To Get There

Fly nonstop to Jacksonville International Airport (JAX), just a 35-minute drive from Amelia Island, from several US gateways including New York (JFK on JetBlue; LGA on American; EWR on United), Atlanta (ATL on Delta and Southwest) and Chicago–O’Hare (ORD on American and Southwest).

3. Maui, Hawaii

Picture yourself soaking up the Hawaiian sun at the Four Seasons Maui Resort.
Soak up that gorgeous Hawaiian sun on the beach at the Four Seasons Resort Maui at Wailea. Image courtesy of Shutterstock.

Winter here may be slightly cooler, but by cool we’re talking temperatures in the mid 70s and 80s, perfect for the Valley Isle’s numerous outdoor activities, which range from hiking into the 10,023-foot-high crater at Haleakalā National Park — or zip-lining down it — to diving and snorkeling in Molokini Crater.

Where To Stay

The winter months are also the perfect time for whale watching in these waters. At the 380-room Four Seasons Resort Maui at Wailea, many of the rooms and suites are designed at just the right angle to perfectly frame views of Wailea Beach and the Pacific. Guests can also swim up to the bar at the adult-only serenity pool, with its infinity edge overlooking the West Maui mountain range and the island of Lanai, or catch views of the water from the lanai at the resort’s Wolfgang Puck restaurant, Spago Maui. Rates start at $499 per night in March.

Check the hotel’s website to see when the property offers value periods when rooms are on sale and you pay no resort fees — the next ones are March 5–13 and 18–23, and April 13–25. Cardholders of the Platinum Card from American Express and the Enhanced Business Platinum Card from American Express OPEN can save money and receive perks at the hotel by booking through the Amex FHR portal. For more hotel and activity options in Maui, check out our Hotel Review: A Week at the Sheraton Maui and A Trip to Maui and the Big Island on Points and Miles posts.

How To Get There

You can fly nonstop into Maui’s main airport, Kahului Airport (OGG), from several US gateway cities, including San Francisco (SFO on Hawaiian Airlines, Virgin America and United), Seattle/Tacoma (SEA on Alaska Airlines, Delta and Hawaiian Airlines) and Dallas/Fort Worth (DFW on American).

4. Saint Lucia

Hike the Gros Piton in Saint Lucia or admire the peaks from your hotel room at Sugar Beach, A Viceroy Resort. Image courtesy of author.
Hike the Gros Piton in Saint Lucia or admire the peaks from your hotel room at Sugar Beach, A Viceroy Resort. Image courtesy of author.

For a small Caribbean island that’s only 27 miles long and 14 miles wide, Saint Lucia is bursting with natural and cultural attractions — not to mention some of the most stunning open-room hotels showcasing the UNESCO World Heritage peaks of the Piton Mountains. Days can be spent here zip-lining through the rainforest, driving into a volcano and soaking up hot mud in the sulphur springs or just basking on the black- and white-sand beaches dotting the 98 miles of coastline.

Where To Stay

The 18th century colonial-style Sugar Beach, A Viceroy Resort is nestled in a 100-acre rainforest and once home to a sugar plantation, features 59 villas, eight beachfront bungalows and 11 Sugar Mill rooms, all with private plunge pools and views of the sugar mill ruins, lily pond and Gros Piton in the distance. Rates start at $855 per night in late February. Members of the Viceroy Discovery loyalty program receive perks such as complimentary internet access and bottled water, room upgrades, late checkout and local experiences like fishing excursions and rum tastings.

How To Get There

You can fly nonstop to Hewanorra International Airport (UVF), located about 33 miles south of capital Castries, from several US gateway cities like Miami (American), Atlanta (Delta) and New York (EWR on United; JFK on JetBlue).

5. Tenerife, Spain

Catch views over the Guía de Isora coast from a room at The Ritz-Carlton, Abama in Tenerife. a
Catch views over the Guía de Isora coast from a room at The Ritz-Carlton, Abama in Tenerife. Image courtesy of The Ritz Carlton, Abama’s Facebook page.

As one of the seven Canary Islands off Africa’s coast, Tenerife offers travelers a wealth of activities with eight year-round golf courses, the San Cristóbal de La Laguna UNESCO World Heritage site and up to 26 species of whales right off the southwest coast of the island. The archipelago’s largest island is also home to the third-tallest volcano in the world and the highest peak in Spain, Mount Teide, which stands more than 12,000 feet high. Winter travel is also perfect timing for taking part in one of the world’s most popular street parties, the Santa Cruz de Tenerife Carnival, which happened February 3–14 this year.

Where To Stay

Perched on a cliff along the Guía de Isora coast, the 469-room The Ritz-Carlton, Abama has two natural pools and an exclusive beach (accessed by riding a funicular), as well as a Dave Thomas-designed golf course, 10 dining options including two Michelin-starred spots (M.B. and Kabuki) and a luxurious spa with a hydrotherapy pool. For the best views in the house, book the Imperial Suite, which sits on top of the citadel with floor-to-ceiling windows showing off panoramic views that continue as you step out onto a private terrace with a heated pool. Rates at this Tier 3 property start at 310 euros (~$350) or 50,000 Ritz-Carlton Rewards points per night in late February. For more info about the Canary Islands, see TPG contributor Lori Zaino’s post, 10 Amazing European Islands That You May Not Know About.

How To Get There

Unfortunately, there are no nonstop flights from the US to Tenerife, but you can fly into Tenerife-South Airport (TFS) from major European hubs like London–Gatwick (LGW on British Airways, Iberia, Norwegian and EasyJet), Munich (MUC on Norwegian, TUIfly and Lufthansa) and Vienna (VIE on Air Berlin, Niki — Air Berlin’s budget-friendly option — and Austrian Airlines).

6. Jamaica 

Stay in Rockhouse's Afrian-inspired village carved into volcanic rock along Pristine Cove in Negril.
Stay in Rockhouse’s African-inspired village carved into volcanic rock along Pristine Cove in Negril. Image courtesy of Design Hotels.

Jamaica is the quintessential Caribbean island and a winter favorite, from the nightlife in Negril to the white-sand shores of Montego Bay and Dunn’s River Falls near Ocho Rios.

Where To Stay

While there are plenty of places to stay and the main attraction is soaking up the sun — as well as a bounty of alcoholic beverages — on the beach, some of them, like Design Hotels‘ Rockhouse Hotel in Negril, are a destination all their own. The thatched roof village of 34 villas is built into the jagged volcanic coastline in Pristine Cove with stone staircases and ladders leading right down to water that’s perfect for snorkeling. The Pushcart Restaurant and Rum Bar helps round out the Jamaican experience with live reggae music and a menu filled with home-style cuisine and produce picked straight from the onsite organic garden. Rates start at about $180 per night in early April. Design Hotels is part of the SPG brand, so members may receive some perks at select hotels — this hotel, however, does not offer the option to book with Starpoints.

How To Get There

Fly nonstop to Montego Bay’s Sangster International Airport (MBJ) from several major US hubs including Chicago (ORD on American and United; MDW on Southwest), New York (JFK on JetBlue, Delta and Caribbean Airlines) and Fort Lauderdale (FLL on JetBlue, Caribbean Airlines and Spirit Airlines).

7. Phuket, Thailand

Spread out in a Sea View Pool Villa at The Naka Island off Phuket.
Spread out in a Sea View Pool Villa at The Naka Island, a Luxury Collection Resort & Spa off Phuket. Image courtesy of The Luxury Collection.

Similar in size to Singapore, Phuket is Thailand’s largest island and one of the most popular when it comes to beaches and parties — November to April is considered the “hot season,” and travelers often crowd the beaches on Phuket’s southern coast. Fans of Leonardo DiCaprio’s film The Beach may recognize the setting if they island hop over to the nearby Phi Phi archipelago.

Where To Stay

Another spot travelers can island hop to is Naka Yai, home to The Naka Island, a Luxury Collection Resort & Spa off the eastern coast of Phuket. The SPG Category 6 hotel is engulfed in mangroves and gardens with 67 Thai-style villas scattered throughout featuring luxury amenities like outdoor soaking tubs overlooking Phang Nga Bay and beachfront private pools. Rates start at about $436 per night in mid-March with breakfast when you book 30 days in advance; while the hotel is a member of SPG, it has limited participation in the Starwood Preferred Guest Program. For more Thailand travel tips, see our Destination Of The Week: Phuket, Thailand and How to Navigate Thailand’s Boundless Beach Scene posts.

How To Get There

Unfortunately, there are no nonstop flights, but you can fly into Phuket International Airport (HKT) from major international hubs like Dubai (DXB on Emirates), Abu Dhabi (AUH on Etihad Airways) and Seoul–Incheon (ICN on Asiana, Korean Air).

8. Maldives

Turn this dream destination into a reality cashing in points for a winter stay at Park Hyatt Maldives Hadahaa.
Turn this dream destination into a reality by cashing in points for a winter stay at Park Hyatt Maldives Hadahaa. Image courtesy of the hotel.

This bucket list destination and dreamy honeymoon spot definitely skews on the pricier (read: expensive) side of the travel spectrum, but with the number of points hotels scattered around the Maldives, the islands are more accessible than ever.

Where To Stay

Set in one of the world’s deepest atolls, North Huvadhoo Atoll, the 50-villa Park Hyatt Maldives Hadahaa is a private island paradise. The leading green resort in the Maldives, the hotel is also home to a five-star PADI dive center, two restaurants and The Vidhun Spa, featuring five private villas and an 80-foot tranquility pool and jacuzzi. Rates start at about $825 or 25,000 Hyatt Gold Passport points per night in late February. Get the ins and outs of booking a points stay here in our post, Park Hyatt Maldives Hadahaa Returns to Category 6, and check out, Top 13 Ways To Get To The Maldives Using Miles and Points.

How To Get There

While there are no nonstop flights from the US to the Maldives, you can fly to Male International Airport (MLE), the main international airport in the Maldives on Hulhule Island, from major international hubs like Colombo (CMB on Emirates, China Eastern and Sri Lankan), Dubai (DXB on Emirates) and Istanbul (IST on Turkish Airlines). To get to the Park Hyatt Maldives Hadahaa, Maldivian offers domestic flights to Kooddoo Airport (GKK), which range from an hour to an hour and 45 minutes while a speed boat takes travelers on the last leg of the trip.

Bottom Line

Now is the time to escape the cold weather and head out on a gorgeous (and warm!) tropical vacation. And if you do your homework and use points and miles to fly and stay there, you can save a lot in the process. Don’t miss our post, Escape to These 5 Small Caribbean Islands with Points Hotels, for even more island getaway ideas.

Share some of your favorite winter island destinations with us in the comments below.

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