10 Cool-Weather Islands for Autumn and Winter Travel

by  Karen Gardiner | Updated on Feb 7, 2024
Reykjavik, Iceland
Reykjavik, Iceland / patpongs/iStock

Winter predictably sees travelers heading to tropical islands for their vacations, but what about the cooler weather islands? There are a few advantages to heading someplace where you'll be packing a sweater rather than a swimsuit: fewer crowds, better deals, and plenty of interesting things to do.

Here are a few of our favorite cold-weather island getaways.

1. Shetland Islands, Scotland

You'll have to wrap up warm if you're planning to visit Shetland in winter, but you may be rewarded with a sight of the Northern Lights; its far-north location makes it the best place in the British Isles to see them. Besides the aurora borealis, winter brings unique festivals, such as Up Helly Aa, a Viking fire festival held in Lerwick on the last weekend of January.

2. Iceland

You'll have an even better chance of seeing the Northern Lights in Iceland -- and, as a bonus, the flights there at this time of year are pretty affordable compared to peak season (summertime). If you get chilly, head to the Blue Lagoon to warm up and soak in the postcard-worthy surroundings. 

3. Bornholm, Denmark

While Denmark is certainly afflicted by cold winter weather, it is usually less severe than in the other Scandinavian countries. (November and December temperatures usually range from 39 to 44 degrees Fahrenheit.) Although Bornholm is generally thought of as a summertime island, there's tons to see and do in winter.  You can skate on the ice rink in Rønne’s main square (Store Torv), go cross-country skiing, or hit the slopes between Østerlars and Gudhjem.

4. Vancouver Island, Canada

Vancouver Island is another great place if you're looking for a ski or snowboarding vacation. You'll get plenty of snow at Mount Washington Alpine Resort. If snow sports aren't for you, you can enjoy the many art galleries and cafés in town as you take in the stunning, rugged scenery.

5. Kihnu, Estonia

The brave souls who venture to chilly Estonia in the winter shouldn't miss Kihnu, which is located off the coast of Pärnu. The island retains rich cultural traditions (the Kihnu cultural space is regarded as a Masterpiece of the Oral and Intangible Heritage of Humanity by UNESCO). The islanders are known for their handicrafts and brightly colored, decorative traditional clothing. On St. Catherine's Day (Nov. 25th), you'll likely see traditional ceremonies and rituals, but if the water is frozen, you'll have to get there by plane rather than the usual ferry.

6. Prince Edward Island, Canada

It can be brutally cold and difficult to get around in winter, but, for adventurous spirits, Prince Edward Island offers over 600 miles of trails for snowmobiling, snowshoeing, and cross-country skiing.

7. San Juan Islands, Washington

One of the best things about visiting the San Juan Islands in winter is that you'll miss the crowds typical of summer. You can still usually enjoy hiking and the outdoors, but if you are forced inside by poor weather, make sure you have a comfortable place to stay. The MacKaye Harbor Inn on Lopez Island occupies a former sea captain's house that was built in 1904.

8. Chiloé, Chile

Chiloé has a year-round rainy, temperate climate, with an average temperature of 50 degrees Fahrenheit, so while it never gets very hot, it rarely snows, either. Brightly painted palafitos (homes held up on stilts) line the waterfront, and multi-tiered, candy-colored churches resemble fairy-tale castles. Fittingly, the island is known for its rich folklore, filled with stories of sorcerers, sirens, and ghost ships.

9. Naoshima, Japan

 Art lovers will appreciate this Japanese island for its permanent art installations, such as the giant sea-facing pumpkin by Yayoi Kusama, and the top-notch museums, which include the Tadao Ando-designed Chichu Art Museum, where you can find works from James Turrell, Monet, Walter de Maria, and more. 

10. Nantucket, Massachusetts

The summer crowds will be gone and you'll get to stroll along the empty, windswept beaches in peace. Activities on offer out of season include seal-spotting tours with Shearwater Excursions and stargazing at the Maria Mitchell Liones Observatory. (Nantucket is thought to be one of the best star-gazing spots on the East Coast.) 

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