Downtown Portland is a fabulous weekend getaway, and is full of luxe hotels, trendy restaurants, and hip shops. Portland is the epitomy of cool style and design, and has a thriving foodie scene, giving New York a good run for its money.
I love the huge selection of hotels in downtown Portland, each with its own distinct vibe.
Some of my favorite boutique hotels are the trendy Duniway and Porter hotels, and both have stunning, indoor swimming pools! There's also the hipster Clyde Hotel in central downtown, and Hollywood inspired Hotel DeLuxe. The chic Nines Hotel has an amazing rooftop restaurant and a striking atrium.
After I've checked in to my hotel there's no need to drive, because everything is so walkable in downtown Portland!
I always start out at Pioneer Courthouse Square to do some people watching. If I'm lucky I can also catch an outdoor concert in summer.
From here I can visit the Pioneer Place Mall on the next block, and shop at big brands like Nordstrom, Apple, Louis Vuitton and Sephora. There's also some independent boutiques from local Portland designers, like Wildfang and Odessa. Shopping in downtown Portland is also pretty awesome, because there's no sales tax!
I've discovered that all the best restaurants in downtown Portland are along 12th Avenue in the West End, and my top picks are Bamboo Sushi and Dolly Olive for italian.
There's also plenty of theaters and museums in downtown Portland along a beautiful section of parkland known as the South Park Blocks. These twelve blocks have open lawn areas shaded by a canopy of mature elms, and loads of public art and picnic areas. There's even a year-round Saturday market with over a hundred vendors.
I can catch live performances at the Arlene Schnitzer Concert Hall and Antoinette Hatfield Hall at the South Park Blocks.
There's also two museums well worth visiting at the South Park Blocks. I can stop by the Portland Art Museum to see Monet's Waterlillies (1914) and Vincent Van Gogh's Ox-Cart (1884), or check out the excellent exhibit on the Oregon Trail at the Oregon Historical Society Museum.
10 best things to do in downtown Portland
1. Enjoy restaurants along 12th Avenue.
I highly recommend the cluster of restaurants along 12th Avenue in downtown Portland's West End. Some of my favorites are Bamboo Sushi, Grassa (italian), and Dolly Olive (mediterranean). This is a city that attracts world class chefs and is at the forefront of food trends.
2. Visit Pioneer Courthouse Square.
The natural starting point for a visit to downtown Portland is the bustling Pioneer Courthouse Square. This is a huge 40,000 square foot block, fondly referred to as the "Living Room" of Portland.
I usually stop for a Starbucks at the square, then soak up the fun atmosphere by sitting on the steps and observing everything.There's plenty of music and concerts here, and the Christmas Tree Lighting Ceremony attracts big crowds each year.
3. Find popular brands at Pioneer Place Mall.
I always set aside some time to visit the Pioneer Place Mall, conveniently located one block from Pioneer Courthouse Square. This upscale mall has Gucci, Nike, Louis Vuitton, Tiffanys and Apple.
4. Hang out at Director Park.
If it's a beautiful, sunny day and I'm in search of the perfect lunch spot, I head to Director Park in downtown Portland. It's easy to find, and is just one block from Pioneer Courthouse Square. This whole park was constructed on top of a parking garage!
I pick up a gourmet sandwich at Flying Elephants at Fox Tower, then find a table on the terrace overlooking the 1,600 square foot fountain. The European-style Bosque is another unique feature of this park, with a giant chess board.

- Odessa: 410 SW 13th Ave
- Wildfang: 404 SW 10th Ave
- Frances May: 1136 SW Alder Street
- Adorn: 1016 SW Washington St
- Mercantile Mutual: 729 SW Alder Street (more classic designs).
Men's boutiques:

Odessa has the most stylish store interior!

Don't forget to check out the shoes at Odessa (410 SW 13th).

Stop by Tender Loving Empire (412 SW 10th) for gifts, with clothes, shoes, artisan made jewelry, and home accessories. They also support a successful record label with the proceeds from their five shops!
I can always find the latest street fashions at the highly successful Wildfang boutique (404 SW 10th).
6. Caffeinate in downtown Portland.
My favorite coffee shop in downtown Portland is Case Study Coffee Roasters, offering the quintessential Portland coffee experience with homegrown, craft-roasted brands.
7. See Monet and Van Gogh at the Portland Art Museum.
The Portland Art Museum is on the South Park Blocks in downtown, and attracts 350,000 visitors a year. Highlights of the collection include Monet's Waterlilies (1914) and Vincent Van Gogh's Ox-Cart (1884).
8. Visit the Oregon Historical Society Museum.
I spent a few hours at the Oregon Historical Society Museum in downtown Portland, and was really impressed!
They have an award winning "Experience Oregon" exhibit about the difficult journey that thousands of settlers made along the Oregon Trail. It's very evocative and really captures the hardships and bravery of these pioneers.
9. See live musical performances at concert halls in Downtown Portland.
It's so convenient that I can walk from my downtown Portland hotel to a choice of concert halls for live music, dance and performance:
- Arlene Schnitzer Concert Hall is at the South Park Blocks in a stunning 1928 Italian Rococo Revival building (events).
- Antoinette Hatfield Hall is at the South Park Blocks, and home to 3 theaters; the Winningstad Theater (events), Newmark Theater (events), and Brunish Theater (events).
- Keller Auditorium is closer to the waterfront, and hosts operas, ballets and musical theater (events).

10. Stay at a luxe hotel in Downtown Portland.
I'm always inspired by the gorgeous interiors of hotels in downtown Portland. It's clear that this is a city that embraces beautiful design. Each hotel offers a uniquely different experience, ranging from hipster, to European-style or Hollywood-themed. It's anything but cookie cutter, and a huge departure from the usual bland chain hotels.
I've put together a list of some of my favorite hotels:
- Hotel DeLuxe embraces a vintage Hollywood esthetic, with a 1950s cocktail bar.
- Clyde Hotel has a hipster, industrial feel, and is tailored for the cool crowd.
- Nines Hotel will take your breath away with it's striking atrium dining area, and rooftop restaurant. It's in the old Meier and Frank department store.
- Porter Hotel is a downtown boutique hotel with an indoor swimming pool, and rooftop bar with cosy firepits.
- Duniway is another stylish downtown hotel with an indoor swimming pool, and brasserie with coffee and craft cocktails.
- Hotel Lucia is full of eye-catching artworks, and even has its own video game arcade and free bicycle rentals!

The Hollywood style lobby in Hotel DeLuxe.
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