48 hours in Portland

Where to stay

In the heart of downtown Portland, Woodlark Hotel is comprised of two renovated historic buildings joined to create a single hotel of 150 guestrooms. The accommodations are elegantly decorated with plants, brass accents, and emerald headboards. In addition to the hotel’s stellar food and drink spaces, guests can order pints of local favorite ice cream Salt & Straw delivered to their rooms.

For an Eastside stay, book a room across the river at Jupiter NEXT, the newly-opened wing of the Jupiter Hotel. The boutique property boasts an art gallery and music venue onsite in addition to retro-accented decor and sweeping views of the West Hills, Tilikum Crossing Bridge, and the historic Central Eastside.

Day 1

Begin the day at Canard, a celebrated French cafe by day and wine bar by night. Order the omelette with goat cheese and herbs and the market green salad with crunchy quinoa.

Choose your adventure:

Slide 1 of 2
  • Option 1: Fitness

    With about 70 miles of hiking trails, Forest Park is a wild oasis within city limits. Start at the Lower Macleay Park trailhead and trek for about one-and-a-half miles among tall trees and past the 1930s Stone House, an abandoned structure rumored to be haunted. Continue onto a one-mile stretch of the 30-mile Wildwood Trail up to Pittock Mansion, a historic house whose manicured property offers vistas of the city and Mount Hood.

  • Option 2: Culture

    With Vibe Luxury Tours, you can design a personalized day of tastings in the Willamette Valley that includes transportation to and from your hotel in Portland (wine country is about an hour southeast of the city). Be sure to stop at Anne Amie Vineyards, one of the area’s first wineries, for the sweeping views and a taste of their pinot noir.

Make your way to Kachka for lunch, a beloved Russian restaurant on the east side of the city. It’s known for its pickled vegetables, smoked fish, and Eastern European dumplings. The Perlovka salad with barley, sorrel, mushrooms, pickled pear, and hazelnuts is a nice addition to the table.

Reserve in advance at Han Oak, a renowned Korean-American eatery in the Kerns neighborhood. Don’t leave without sampling the kimchi plate, the chilled buckwheat noodles, and the grilled mackerel ssam with lettuces, pickled daikon, and scallion salad. Pair it with a glass of natural wine from their curated list.

Day 2

Breakfast is a great opportunity to enjoy Coquine, a cozy spot near Mt. Tabor Park specializing in sustainable, seasonal ingredients. Try the yeasted barley waffle or the smoked green farro with asparagus, spring greens, and herbed yogurt.

Choose your adventure:

Slide 1 of 2
  • Option 1: Fitness

    Biketown, Portland’s bike share system, is run by Nike and has hubs all over the city. Grab a set of wheels and cycle the two-mile-long Waterfront Loop, where you’ll ride along both sides of the river and across two bridges.

  • Option 2: Culture

    Powell's City of Books is the largest independent bookstore in the world, complete with nine color-coded rooms and over 3,500 different sections. Peruse their selection, then walk west for about 20 minutes down W Burnside St. You’ll arrive at the charming NW 23rd Ave, where you can pick up unique handmade products like leather goods and jewelry.

Grab a midday meal of Vietnamese comfort food at Lela’s Bistro. Don’t miss the lemongrass chicken salad, portobello banh mì, or the vegetarian pho with tofu, broccoli, cauliflower, and carrots.

Next, explore Portland’s extensive selection of breweries. In the Mississippi Avenue neighborhood, try the Starburst IPA at Ecliptic Brewing before visiting Stormbreaker Brewing for the Right as Rain Pale Ale and Widmer Brothers Brewing for a Hefeweizen.

For dinner, enjoy a full Mediterranean spread at Tusk. Choose from offerings on their ever-changing menu like hummus with kale and walnuts, shelling beans with asparagus and za’atar, and Chinook salmon with morels.

Conclude the trip with a drink at Scotch Lodge, a cocktail bar for whiskey lovers. Sip on the No Sleep Till, a libation of mezcal, single malt Scotch, amer, and coriander-infused vermouth.

48 hours in Milan

There are over 100 miles of cycling paths inside the city.