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Writer's pictureLindsay Pfenning

Inspiration for your 2020 travel bucket list

Updated: Jan 5, 2020

What's on your travel bucket list? Looking for inspiration as you set those travel goals? Here’s what we checked off of ours in the last decade.


Favorite beach vacation


Of all the beaches in all of the world, we keep coming back to Hawaii. Its beauty is unmatched, and with new nonstop flights on lower cost carriers (thank you Southwest), it's more accessible than ever.


Where to go: There is not a bad island, but our favorites - Kauai and Maui hands down.

Kauai for the nature lovers, and those looking for true peace and quiet. The Na Pali Coast is one of the most stunning places we have ever seen. Pick up a permit and hike one day in, one day out on the Kalalau Trail to visit the hidden Kalalau Beach. If a 22 mile hike sounds like a bit much to you (it did to us, too!), book a helicopter tour through Safari Helicopters to see Na Pali's gorgeous beach, waterfalls and reefs from above. Snorkeling tours are another great option - swim with the turtles and gaze up at these cliffs from sea level. Before you leave the island - don't miss Waimea Canyon, Poipu Beach, Wailua Falls or eating pineapple from a roadside vendor.


Maui for the Road to Hana, the snorkeling, the beauty, the golf and the food - oh the food! People always ask if the Road to Hana is worth it. In a word - absolutely. Black and red sand beaches, waterfalls on top of waterfalls, banyan trees, a bamboo forest...but I had you at black and red sand beaches, right? The trip takes a full day and is not for the faint of heart. You will pass cars on one lane roads, take back to back to back hairpin turns, park on the side of a cliff for a photo op and probably swim under a waterfall. It will be the most memorable day of your vacation.


Must see: Hike the Pipiwai Trial from Oheo Gulch to Waimoku Falls before a refreshing swim in the Seven Sacred Pools (Pools of Oheo). This trail is worth it for so many reasons, not the least of which was the walk through an otherworldly bamboo forest. The sound of the wind blowing through the bamboo was absolute serenity. Our advice - take the Hana Highway early to avoid the crowds and finish your day (and the loop) by taking Piilani Highway to Upcountry. You will see diverse landscapes and a lot less people but beware - long stretches of the Piilani are unpaved, there are no gas stations and almost no food options. If our Mustang convertible could handle it, so can you! Added bonus if you are there in the Spring - Piilani takes you down roads lined with Maui's flowering Jacaranda Trees.


We swam with turtles off of Wailea Beach (we stayed at Grand Wailea so it was literally our backyard), snorkeled with the locals at La Perouse and ate and drank our way across the island. Have breakfast at Kihei Caffe (cash only) and divide your lunches and dinners between Lineage (the Poi Mochi was to die for), Lahaina Grill (Wagyu Beef Ravioli for the appetizer win) and The Mill House for a mountainside, farm to table dining experience. The setting was our favorite - even if you can't get a dinner reservation, visit early or late for drinks (hello Old Fashioned) and wander the plantation grounds. If you are a golfer, we recommend the Ritz Carlton at Kapalua - in addition to the incredible golf there, the drive past the resort on Highway 30 and 340 offers beautiful vistas, food trucks and local woodcarvers. Our round at Wailea Golf Club, where course views are second to none, was amazing as well.


Favorite 2nd city


Albuquerque has its charms, but its colorful neighbor to the north is our pick for a vacation a bit more #offthebeatenpath. Santa Fe's Pueblo-style architecture and vibrant arts scene make this a must-add to any travel bucket list.

Must see spots: Wander the Santa Fe Plaza and the surrounding streets to visit galleries and quaint shops, to listen to street musicians and to find unique pieces made by local artisans sold on the square itself. Loretto Chapel's staircase is a stunner and the Georgia O'Keefe Museum is definitely worth a stop.


Day trip: A visit to Taos is an absolute must! El Santuario de Chimayo is a beautiful stop along the way, whether you believe in the curative powers of its "healing dirt" or not. A visit to Taos Pueblo brings you to the heart of a living Native American community, and as one of the oldest continuously inhabited settlements in the United States, is a step back in time as well.


Favorite “new” destination of the last decade


We really couldn't decide, so this one ends up a tie between Croatia and Portugal.


We credit Croatia's rise in popularity to its beauty, both natural and architectural - coastal structures have a heavy Italian influence but become more Austrian and Slavic as you head inland (visit Zagreb for an amazing array of culinary treats). With many islands, few cruise ships, and its own currency, it's a much more affordable option than Greece. Head to the Istria Peninsula for rolling hills, olive oil and wine tastings. The coastal waters are crystal clear and perfect for snorkeling and scuba diving, but pack water shoes as beaches here are more rocky than sandy.

While Portugal has become a travel darling, and is a part of many European itineraries, there are still so many areas as yet undiscovered by the hordes of tourists.

Its people are welcoming, the coastline stunning and the meals - olive trays, fresh seafood and port for every one! The southern Algarve coast (we stayed at the

gorgeous Pine Cliffs Ocean Suites in Albufeira) boasts beautiful beaches and jaw-dropping rock formations, while the western coast is known as a surfer's paradise with its towering waves and laid-back feel. From Lisbon to Sintra (visit the Castle of the Moors and the cobblestone streets of Centro Historico), we continued north to Peniche (a beautiful coastal town) and toured the historic castle at Obidos (dine at Restaurante a Nova Casa de Ramiro).


Favorite outdoor adventure destination


Adventure seekers and outdoor lovers can’t go wrong with a visit to any of the National Parks in the Rocky Mountains, US or Canadian. Whether you choose Rocky Mountain itself, Grand Teton, Yellowstone, Banff or any in between, adventure awaits!


On the water: Raft in Glenwood Springs, Colorado in the White River National Forest. Take the half day trip with Whitewater Rafting LLC (the guide had us swim in the hot springs while giving us a history lesson on the canyon itself after tackling some class III-IV rapids) and then grab dinner at Slope & Hatch (delicious fast-casual tacos and cocktails) after your day on the river.

On land: So many parks, so little time. We spent a total of 5 days exploring Yellowstone and Grand Teton, and felt like we could have filled another week. Yellowstone’s Old Faithful is as awe-inspiring as you imagine it to be, but some of the hikes (Lost Lake Trail, Mount Washburn) and wildlife viewing points (Lamar and Hayden Valleys) brought us to our favorite spots in the park. Take time to explore beyond the crowded tourist stops for a truly unique experience, and don't miss staying in a gateway town for a night (Livingston, MT was our choice) before heading into the park's crowded lodging system. A lesson we learned the hard way - stay at different hotels in Yellowstone throughout your visit or you will spend a huge chunk of your time driving - it is a massive park! Grand Teton is much smaller in size, but its views are larger than life. The hikes to Hidden Falls and Inspiration Point get crowded fast (start out early to avoid the masses) but are so worth it. If heights aren’t your thing, stop after the views of Hidden Falls. The path up to the point is relatively easy, but there are a few vertigo-inspiring areas with no barrier between the granite-carved trail and a drop of about 6000 feet. On the way back to your car, stick your toes in crystal clear Jenny Lake to soothe even the most road-weary feet.


Out of country: Visit our neighbor to the north and stay in the affordable Canmore east of Banff for a diverse restaurant scene and amazing fishing along the river through town. Don't miss Lake Morraine and Lake Louise, but also don't let their inviting blue waters fool you - way too cold to swim! There are canoes for rent, but don't be surprised to find snow in the summer months (like June when we were there). Snow and all, we hiked up the mountain but paid close attention to the signs warning against wandering off with less than 3 people and bear spray, and were on the lookout for protective mother elk. The wildlife, lakes and vistas unlike any other part of the Rockies make this majestic area one that everyone should visit.


Favorite culture trip


Our final destination of the decade and our favorite culture trip was (what else?) a mother/daughter road trip through England. We stuck to the back roads between castles and manor homes to discover hidden villages and lesser known points of interest (like Avebury - similar to Stonehenge but free and open so we got to walk right up to the stones and their adorable furry companions).

Favorite stops: We loved York and felt transported to the Moor House from Jane Eyre while wandering the town. Chatsworth House, complete with garden maze, was the filming location for Pride & Prejudice. Althorp (Princess Diana's family estate), Blenheim Palace (family estate of the Duke of Marlborough) and Jane Austen's home in Hampshire were beautiful stops.

Day trip: We took the ferry through New Forest National Park (along with all of the English families on camping holiday) to the Isle of Wight to see Osborne House (the summer home of Queen Victoria), the Needles and the Cowes Week sailing competition.


The time together was unforgettable.

Consistently named as favorites by clients and friends, and our top trips of the last 10 years, these spots must be on your travel bucket list for the 2020's!


We will always tell you to take the trip.


Explore | Dream | Discover | The Road

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