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Destination Guide: Portland, Oregon

Portland, Oregon
Allianz - Portland, Oregon

First-time visitors to Portland often expect to find a twee, self-conscious city, as portrayed in the long-running IFC show “Portlandia.” While Portland has plenty of quirk, it’s also defined by its urban grit, lush natural beauty, charming Craftsman neighborhoods and world-class food. You probably won’t find an artisanal knot store or a chicken named Colin (although then again, you might).

In this five-minute travel guide, we’ll suggest some of the very best things to do, see and eat in Portland. Make sure you pack a raincoat — and your travel insurance!

3 Reasons to Buy Travel Insurance for Your Portland Trip

Many people think you only need travel insurance for big, expensive international trips — but that’s not the case! Fortunately, insurance can protect you from the most common mishaps on domestic trips.

  1. Insurance takes the sting out of travel delays. Late departures are really common, unfortunately; in 2018, nearly 19 percent of domestic flights were delayed.1 If your flight to Portland is one of them, travel delay benefits may reimburse you for meals, accommodation and transportation expenses during that covered delay. Or, with the OneTrip Prime and OneTrip Premier plans, you can choose a fixed inconvenience payment of $100 for covered travel and baggage delays. No receipts required — just proof of delay!
  2. Travel insurance can safeguard your vacation expenses. What if you fall seriously ill right before your planned trip? Or what if a family member is hospitalized? Or what if your house floods? Travel insurance with trip cancellation benefits can reimburse you for your prepaid, non-refundable trip costs if you must cancel the trip for a covered reason.
  3. Travel insurance can protect your baggage, too. If you land in Portland, Oregon, and discover that your suitcase went to Portland, Maine, don’t panic! The baggage delay benefit can reimburse you for the reasonable additional purchase of essential items during your trip during a covered baggage delay, up to your plan’s limits.

What’s the best domestic travel insurance plan? That depends on what you need. The OneTrip Basic Plan is an affordable option for domestic travel, with up to $10,000 in trip cancellation benefits. If you travel frequently, whether in the U.S. or overseas, an AllTrips annual travel insurance plan might be your best bet. To find the right plan, get a quote!

3 of the Best Things to Do in Portland

  1. Hike Mount Tabor. An ancient cinder cone — the remnant of an extinct volcano — forms the base of Mount Tabor Park in southeast Portland. Steep trails take you through lush fir forests and past historic reservoirs. From the top, you’ll enjoy sweeping views of the city and Mount Hood.
  2. Shop the Saturday Market. Portland’s home to a huge outdoor arts-and-crafts market, held every weekend from March to Christmas Eve on the banks of the Willamette River on Old Town. You’ll find live music, food trucks, and cool creations from local artists, from housewares to fine jewelry to T-shirts.
  3. Lose yourself in roses. You have to visit the gorgeous International Rose Test Garden in Washington Park, where more than 10,000 roses bloom their heads off from May through October. New rose varieties are tested here before going to market. The rose garden is widely considered one of the best things to do in Portland, which means it can get crowded on nice weekends.

3 Boutique Hotels in Portland

In a city as unique as Portland, why stay in a generic hotel? Check into the McMenamins Kennedy School, a historic elementary school that’s now an inviting hotel. Some of the guestrooms still have the original chalkboards, and there’s also a restaurant, several bars, a movie theater, a pool and a brewery. It’s pet-friendly, too.

Originally built in 1909, Sentinel is a Portland landmark named for the blocky robot gargoyles that adorn the roofline. This luxury hotel offers large and comfortable rooms, a beloved restaurant (Jake’s Grill) and a moody bar. A nice touch is the Room At The End Of The Hall on the sixth floor, a cozy lounge in which guests can find coffee, soft drinks, snacks and news­papers around the clock.

If your style leans modern, consider The Jupiter, a Portland boutique hotel with a split personality. One side offers smaller, more affordable rooms; the Jupiter NEXT rooms add more space and luxury, with memorable city views. Don’t miss late-night music at the Doug Fir Lounge.

3 of the Best Places to Eat in Portland

Portland is rightly famous as a foodie city, especially for vegans, vegetarians and fans of global cuisine. Here are just a few suggestions, although the options are nearly endless.

Start your day with a hearty breakfast at The Hazel Room, a quintessentially Portland place: It’s cute, everything’s locally sourced and there are tons of vegetarian options. Try the made-from-scratch biscuits, the tofu stack or the rosemary grapefruit brulee.

At the other end of the price spectrum is Holdfast, an unusual fine-dining experience that’s centered on foraged and local ingredients. Guests sit around a large counter and watch the chefs at work as they create a 10-course tasting menu of  beautiful, simple and creative dishes. Reservations are required; open Thursday through Sunday.

And for dessert… you thought we were going to say Voodoo Doughnut, didn’t you? While it’s worth visiting the iconic, kitschy bakery, we’re going to recommend Pix Patisserie instead. You’ll find precious French pastries, luscious chocolates and the world’s best Champagne and sparkling wine list.

Wherever your next adventure takes you, be sure to protect yourself with travel insurance. There’s a plan for every budget and every destination. See your options here.


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May 06, 2019