10 islands to visit during the festive season

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The holidays are, of course, about hearth and home, spending the season with family and friends, but if you want to do something a little different have a look at these islands.

Whether you’re looking to escape winter weather, treat yourself to a cheap getaway, or trade seasonal traditions for travel, jetting off during the holidays can be a thrifty treat if you know where to go.

Islands are ideal destinations during the festival season. Depending on the destination, traveling to an island can bring substantial savings thanks to increased flight options and shoulder season discount. Bonus: some islands have fewer crowds in November and December. Travelers who can sneak away in between Thanksgiving and Christmas or the week after New Year’s Day can score even bigger savings as peak holiday travel is clustered around Thanksgiving week and the week between Christmas and New Year’s Day.

While it may be “high season” (with some of the more pricey air and hotel prices of the year) on many islands in the Caribbean, there are still plenty of islands that offer inexpensive vacation options. (And if you’ve got somewhere else in mind, we can help you snap up flights to anywhere else in the world too.) With hundreds of islands around the world, the choices are varied from bustling metropolises to remote and tranquil archipelagos. These are our favorite islands to visit during the holiday season:

Punta Cana, Dominican Republic

Dominican Republic
Escape the winter chill in Dominican Republic. (Image: Dominican Republic Ministry of Tourism)

Destinations that have many all-inclusive resorts are likely to have the best deals as they vie for travelers’ bookings. One of the most populous all-inclusive resorts destinations is Punta Cana, Dominican Republic. With so many options, there tends to be competitive pricing year-round, and savvy travelers can use this to their advantage to score upgrades and add-ons. But not all all-inclusive resorts are equal, so be sure to review our insider’s guide to all-inclusive resorts prior to booking your vacay.

Isla Mujeres, Mexico

Isla Mujeres
Idyllic Isla Mujeres is a relaxing retreat off the coast of Mexico. (Image: David Stanley, Cocos Beach via Flickr CC BY 2.0)

Mexico’s resort towns are perennially on sale thanks to an abundance of resorts, and many towns like Cancún were purposely built for tourism. Recognizing the importance of tourism on the economy, the Mexican government began transforming portions of its coastline into tourism destinations in 1967. Located approximately eight miles off Cancún’s coast, Isla Mujeres is a popular day-trip excursion, but travelers can stay on the island too.


Make memories in Martinique. (Image: Lauren Mack)

Even during Christmas and New Year’s, flights to Martinique and hotel rooms are a fraction of the price of other costly Caribbean islands that can be ultra-expensive during the holidays. The remote and rustic French island is a blend of French and West Indian influences, making it an amazing (island) alternative to France.

Prince Edward Island, Canada

Prince Edward Island
Take a winter getaway in PEI. (Image: Dennis Jarvis, PEI-00438 – Time to Leave via Flickr CC BY-SA 2.0)

Though the temperatures average just below freezing, Prince Edward Island transforms into a winter wonderland during festival season. The island is alive with winter carnivals and outdoor winter sports like downhill and cross-country skiing. Don’t miss the magnificent sunrise and sunsets, best viewed from PEI’s pristine beaches.

Canary Islands, Spain

Canary Islands
Kick back in the Canary Islands. (Image: cortto, qualsevol dia pot sortir el sol via Flickr CC BY 2.0)

Now that the exchange rate between U.S. dollar and Euro is nearly equal, it’s a good time to head to Europe, specifically the Canary Islands. The Spanish archipelago off northwestern Africa offers sun-filled days on black and white sand beaches and carefree nights lounge hopping in Tenerife, the largest and most populated of the seven islands.

Phuket, Thailand

10 islands to visit during the festive season 11
Enjoy sundowners in Phuket, Thailand. (Image: Jeff Gunn, Phuket, Thailand via Flickr CC BY 2.0)

Perennially popular Phuket, Thailand is a favorite for many reasons. Majestic mountains, lush rainforests and beautiful beaches beckon tourists from all over the world, and the plethora of accommodation options at all price points sweetens the deal. Phuket also offers a range of accommodations from inexpensive beach huts and cheap guesthouses that cost a few dollars per night to ultra luxe resorts, making it an island destination with all-around exceptional value.


Taiwan Lantern
Light the sky with lanterns in Taiwan. (Image: Taiwan Tourism Bureau)

It’s low season in Taiwan, so traveling to Taiwan during the festive season means visitors are treated to the lowest airfare prices of the year along with bargain hotel rates. The weeks before Chinese New Year and cooler temps may keep travelers seeking a beach vacation away, but there is plenty to see and do in Taiwan. From eating your way through the lively night markets, soaking in relaxing hot springs and exploring the National Place Museum in the capital Taipei to traveling around the island to coastal town Jiufen, the southern surf city of Kenting, or the lovely lantern-lit hamlet of Pingxi, there is plenty to see and do.

Montego Bay, Jamaica

Gail Frederick, Montego Bay, Jamaica (4) via Flickr CC BY 2.0
Gail Frederick, Montego Bay, Jamaica (4) via Flickr CC BY 2.0

December is one of the best times to visit Jamaica. Sandwiched between rainy season and the winter crowds, December is a sweet spot where weather and affordability collide. Montego Bay boasts one of the Caribbean’s largest airports, making flights easier to find and more affordable to book, especially when considering direct flight options. For even more savings, consider staying on the less touristy South Coast, about two hours by car from Montego Bay. With public beaches, cheap, local eats and a laid-back vibe, the stress of the holidays will melt away.

Virgin Islands

Have the beach to yourself in the Virgin Islands. (Image: Lauren Mack)
Have the beach to yourself in the Virgin Islands. (Image: Lauren Mack)

An abundance of islands and many flights keep prices lower in the British Virgin Islands and the US Virgin Islands than most other Caribbean locales. Whether you choose to travel to the eastern (British) side or the western (U.S.) side of the island group– or both – island hopping on the main islands of Anegada, Jost Van Dyke, Tortola and Virgin Gorda on the British side and Saint Croix, Saint John and Saint Thomas on the U.S. side is fun and inexpensive. Options include escaping the world on the remote and sparsely populated Virgin Gorda (accessible only by boat), sipping stress away oat the swim-up Soggy Dollar Bar off Jost Van Dyke, hiking on Saint John and perfecting your tan on one of Saint Thomas’ 40 beaches.


Silfra, Þingvellir National Park
Go snorkeling between the North American and Eurasian plates in Silfra, Þingvellir National Park in Iceland. (Image: Lauren Mack)

Numerous package deals and stopover programs via Icelandair afford travelers the flexibility to make your trip better with a stopover or make Iceland your travel destination. Icelandair provides the opportunity to stay for up to seven nights to explore the mesmerizing Blue Lagoon, chase the Northern Lights and be adventurous on glacier snorkeling excursions.

Which island is calling your name? Share with us in the comments and start your search at Cheapflights.

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Main image: iStockPhoto/RossHelen

10 islands to visit during the festive season was last modified: June 26th, 2019 by Lauren Mack
Author: Lauren Mack (163 posts)

Lauren Mack has traveled to 40 countries on five continents, including Cuba, New Zealand, Peru and Tanzania. For many years, she called China, and then Taiwan, home. Countries at the beginning of the alphabet, particularly Antarctica, Argentina and Australia are on her travel bucket list. Lauren is a multimedia travel and food journalist and explorer based in New York City.