What counts as adventurous, of course, depends entirely on comfort level. For some, a challenging hike with sweeping views is enough to spark a surge of adrenaline. For others, the real thrill lies beneath the ocean’s surface: Perhaps during a nocturnal scuba dive, descending into inky water illuminated only by a dive light?

Los Angeles-based psychotherapist and avid traveler Camille Tenerife says there’s something about travel itself that makes bold choices feel more accessible.

“When we are outside of our regular routine, we become more motivated and even energized to try new things,” she explains. “Our brains are more open to adventure because that is the mindset we have put ourselves in. The mentality of time being limited in this location also adds to the courage that we may have.”

Distance from everyday pressures plays a role, too. We may feel safe enough to explore because we're not stressed about the usual responsibilities like work emails or dishes, or any of our other day-to-day responsibilities.

“This allows us to feel more confident in approaching adventures,” Tenerife says.

In other words, travel creates a psychological permission slip—a temporary window where risk feels manageable and new experiences feel urgent.

Ahead, five darecations to consider, from whitewater rafting in Bend, Oregon to snorkeling above shipwrecks in Bermuda.

Grand Cayman: Swim With Stingrays and Go Scuba Diving

Guests at The Sunshine Hotel & Suites on Grand Cayman can tailor their beach days at Seven Mile Beach to suit any pace, from leisurely swims 150 to 200 feet offshore to snorkel over coral reefs teeming with tropical fish and the occasional sea turtle, to gliding across the calm, crystalline water on a paddleboard.

For travelers looking to add a dose of adventure, the hotel can arrange excursions through Red Sail Sports. Highlights include a visit to Stingray City, where guests can wade among these famously gentle marine creatures, whose flat, diamond-shaped bodies can span up to five feet across and were originally drawn to the area by discarded scraps from local fishermen.

Divers can also explore the waters just off Seven Mile Beach, descending below the surface to discover vibrant reefs up close. The most daring option, however, may be the Grand Cayman Night Dive, an otherworldly experience that reveals a hidden nocturnal ecosystem of marine life and plant species that only become active after dark.

Vail, Colorado: Ride a Mountain Coaster

After the snow melts, Vail transforms into a summertime adventure hot spot. Beyond hiking with llamas, you can load your mountain bike onto the gondola at Vail Mountain and cruise back down on a thrilling descent. Mountain vacationers can also spend the day soaking up the on-mountain excitement at Epic Discovery, easily reachable from Tivoli Mountain Lodge.

It’s a fantastic vacation option for families, and one of the biggest highlights is the sled-style alpine coaster, The Forest Flyer. Each sled is equipped with hand brakes, making you the captain of your own ride. Take it slow and savor the crisp mountain air as you wind through the forest—or let it rip and race downhill at speeds of up to 25 miles per hour.

Vail’s mountaintop adventure center sits at the top of the Eagle Bahn Gondola in Lionshead and also features a rock climbing wall and a bungee trampoline for even more high-altitude fun.

After a day of thrills, head back to the Tivoli Mountain Lodge and cozy up around the firepits or enjoy a dip in the hot tub.

Bend, Oregon: Raft the Deschutes River

With the snow-capped Cascade Mountains as a backdrop and the Deschutes River winding through downtown, Bend, Oregon, is a haven for nature lovers. Perched along the river’s edge, Riverhouse Lodge serves as an ideal basecamp for adventure.

In summer, travelers can head out on the Deschutes for a day of rafting with guides from Sun Country Tours. Options include the Big Eddy Thriller, which moves from gentle stretches into splashy Class III rapids. Flowing through basalt canyons and high-desert landscapes, the Deschutes is a bucket-list whitewater destination for thrill-seekers.

For those craving more, Bend delivers at every turn.

Darecation-goers can craft full itineraries of outdoor adventure, from paddling excursions with Bend Kayak School and Rentals to zip-lining at Mt. Bachelor Ski Resort on a tour that drops nearly 1,400 vertical feet down the volcano’s slopes.

After a full day outside, unwind back at the lodge in a Riverview Room with a fire pit and enjoy some s’mores and stargazing.

Bermuda: Snorkeling Above Shipwreck Sites

Did you know Bermuda is known as the “shipwreck capital of the Atlantic”? The island’s reefs have played a role, sending vessels to the ocean floor. In all, nearly 300 wrecks lie beneath the ocean surface, some ships dating back to the 1600s. Today, divers descend into the depths to explore these haunting relics, while snorkelers glide across crystal-clear waters, spotting the outlines of wreckage below.

Guests staying in the cottages at Cambridge Beaches Resort & Spa can rent snorkeling gear from H2O Sports and head straight into those turquoise waters to discover coral reefs and the island’s remarkable collection of shipwreck sites.

One of the most popular dive sites lies just a mile offshore from Horseshoe Bay. Built in 1943, the Hermes was en route to the Cape Verde Islands when engine trouble forced the crew to abandon the 165-foot vessel. The deserted ship was later sold for just $1 to the Bermuda Dive Association and now thrives as an artificial reef. Remarkably intact, it has become a favorite among divers.

The outfitter also offers motorboat and kayak rentals, making it easy to explore Bermuda’s waters. Back on land at the resort, guests can play an old-fashioned game of croquet, hit the pickleball courts, or lounge at the infinity pool overlooking Mangrove Bay.

Hanover, New Hampshire: Hike a Section of the Appalachian Trail

Every year, 3 million people visit the Appalachian Trail, and more than 3,000 attempt the ultimate challenge: A full “thru-hike” from Springer Mountain, Georgia to Mount Katahdin in Maine. The legendary footpath that stretches for more than 2,000 miles passes directly through Hanover, New Hampshire—routed through town in part because of Dartmouth College’s longstanding traditions of outdoorsmanship.

For guests of the Hanover Inn, the trail is quite literally right outside the front door. That means hikers can lace up their boots and explore a scenic, forested section of the moderately challenging trail just steps from the inn. After a day on the path, return to the inn and unwind at Pine Restaurant, which overlooks the historic Dartmouth College Green and proudly claims to serve the “best martini on the entire trail.”

To celebrate its unique connection to the Appalachian Trail, the hotel also offers a seasonal Appalachian Pit Stop Package designed especially for those on the long-haul trek who are pausing for a night. The package invites hikers to rest and recharge in comfort, and includes a room with a soaking tub and luxurious bath amenities and a $50 dining credit for room service.

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.