It’s the ‘Year of Whimsy,’ and Here’s Some Travel Inspiration that Feels Magical

Published on June 2, 2026

written by Brittany Anas, a Colorado-based travel writer and regular contributor to Forbes, Yahoo, Men’s Journal, House Beautiful, Delish and more.

Google Trends recently dubbed 2026 the “year of whimsy,” citing a rise in searches from people looking for ways to add more playfulness and wonder to their everyday lives.

An easy place to start? With your vacation plans, where you can give your wanderlust a dose of whimsy and craft itineraries that feel playful, nostalgic, and perhaps just a little bit magical.

Whether it’s sleeping in a luxury treehouse high above the forest floor, splashing around a dragon-guarded castle resort, or spotting an electric-blue iguana that looks like it wandered out of a fantasy novel, some destinations have a knack for inviting travelers to lean into wonder.

Ahead, find inspiration for your next trip. These light-hearted escapes all have something in common: They encourage vacationers to see the world through a more playful lens, where whimsical adventure, nostalgia and curiosity take center stage.

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Sleep Among the Treetops at Skamania Lodge in Stevenson, Washington

At Skamania Lodge, guests can book treehouse stays that serve as elevated hideaways tucked high among Douglas firs in the moody Columbia River Gorge. Suspended above the forest floor, these luxe retreats feel like nature’s version of a penthouse suite, complete with fireplaces, sweeping mountain views, and a healthy dose of nostalgia.

Treehouse guests can wrap up in plush robes, challenge each other to board games, or toast marshmallows with ready-to-go s’mores kits after a day spent exploring the Pacific Northwest wilderness.

Each treehouse comes with its own personality. The romantic Spruce Treehouses are made for couples, with views that stretch across old-growth forest toward the Columbia River. The Alder Treehouses are ideal for families, pairing a king bed with a tucked-away queen nook and an outdoor deck built for card games and late-night storytelling beside the indoor-outdoor fireplace.

For the ultimate perch, the Alpine and Noble Treehouses sit nearly 40 feet above the ground, delivering cinematic views of the Cascade Mountains.

When lofty lodgers get their heads out of the clouds and return to solid ground, the adventure continues. Guests can wander the Creek Loop Trail for an afternoon of forest bathing, tackle the Gorge Loop Fitness Trail with its forested workout stations, soar through the canopy on a zipline course, or channel their inner lumberjack with axe-throwing games.

Live (and Play) Like Royalty at Dellshire Resort in Wisconsin Dells, Wisconsin

You may know Wisconsin Dells as the “Waterpark Capital of the World,” but a new resort is expanding that reputation with a whimsical medieval realm all its own. At Dellshire Resort, the fantasy begins the moment you pull up and spot Golspar the Dragon, a 70-foot-long, 25-foot-tall fire-breathing sculpture crafted by Las Vegas metal artist Kevin Stone.

From there, the enchantment deepens. The four-story, castle-inspired resort captivates with cathedral-style windows, stone masonry facades, and torch-lit interiors that feel plucked from a storybook. At Serpent’s Bay, guests can drift between magical waters, from the oversized hot tub pavilion known as the Grotto to indoor and outdoor pools complete with a waterfall, swim-up bar, and children’s slide.

Families can also battle their way through Hero’s Hall, an entertainment center packed with games and attractions, or step into a mixed-reality experience that casts guests as heroes fighting to save Golspar from encroaching darkness.

At the end of the day, guests can retreat to their room and rest like royalty with walls decorated to look like a forest with illustrated trees and soft greenery in a watercolor style.

Spot Fantasy-Like Creatures Near The Sunshine Hotel & Suites in Grand Cayman, Cayman Islands

For a sunny getaway, check into The Sunshine Hotel & Suites where you can spend lazy days by the pool or head over to the sister property on Seven Mile Beach for beach yoga sessions and oceanside lounging.

But for a dose of whimsy beyond the sand, venture to Queen Elizabeth II Botanic Park where winding garden paths lead through lush tropical landscapes filled with butterflies endemic to the Cayman Islands. Keep your eyes peeled for the pygmy blue butterfly, one of the world’s tiniest butterflies at only about a quarter-inch wide. The park’s lake area is also a favorite spot for birdwatching.

The botanical park is also home to the Blue Iguana Conservation facility, dedicated to protecting the Grand Cayman blue iguana, which is known for its striking electric-blue scales. In the early 1990s, researchers estimated there were only 100 to 200 blue iguanas left in the wild. By 2002, that number had dropped to fewer than 25 individuals.

Thanks to intensive conservation efforts, including captive breeding and habitat protection, the species has made a remarkable comeback. More than 1,200 blue iguanas have now been released into protected areas across Grand Cayman.

Guided tours of the conservation facility can be arranged upon request, giving visitors a chance to learn more about one of the Caribbean’s greatest wildlife recovery stories and a chance to see a rare creature that looks like it's from a fantasyland. You might even get a chance to meet Forrest, a banana-loving iguana, and long-term resident of the park who is the unofficial ambassador for the species.

Explore more destinations across the Benchmark Resorts & Hotels portfolio, a collection of distinct, independent properties by Pyramid Global Hospitality. Located in diverse destinations across the globe, Benchmark’s resorts and hotels reimagine immersive travel, inspiring guests to create memories born from meaningful exploration, authentic moments, and innovative experiences – no matter the occasion. Benchmark guests can earn complimentary gift cards, on-property perks, and destination experiences through the collection’s signature Mosaic Rewards program.


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