Downtown Portland

Itinerary: Romancing the Wallet

• 1. SmartPark (3rd & Alder) portlandonline.com/smartparkPark

  3rd and Alder Directions

• 2. Red Star Tavern redstartavern.comDining

  503 SW Alder St. Directions

  In the timeless tradition of a true tavern, Red Star Tavern & Roast House greets travelers and regulars with a signature warmth and genuine hospitality. Shed the day’s concerns, settle in with the drink of your choice and lose yourself in Chef Thomas Dunklin’s exceptional regional American cuisine. Right in downtown Portland, Red Star sits at the corner of Fifth Avenue and Alder Street, adjacent to Hotel Monaco Portland. The historic building’s floor-to-ceiling windows grace the interior with natural light while the multitude of wood layers and the blaze of the wood-fired oven and rotisserie proffer their own golden tones. It’s a welcoming setting by any standard.

• 3. Via Tribunali www.viatribunali.comDining

  208 SW Ankeny St. Directions

  Via Tribunali has been called “more authentic than the pizzeria’s of Naples,” and even though that is a flattering exaggeration it is fair to say that our pizzeria’s have grown out of an almost unnatural passion for the food and wine of Southern Italy.

• 4. Rialto Poolroom rialtopoolroom.comDining

  529 SW 5th Ave. Directions

  The new Rialto boasts a wall of top-shelf liquor to wash down its fat Texas Burger ($8.50) and Cheez Whiz-ed Philly steak ($8) ginormous Cobb salad ($6) and such booze-worthy niblets as coconut shrimp ($7) oyster shooters (two for $2.50) and spicy Buffalo wings ($6).

• 5. El Gaucho elgaucho.comDining

  319 SW Broadway Ave Directions

  Doors will be whisked open by dapper doormen, your eyes will slowly adjust to the moody darkness inside and then the alluring essence of this ritzy steak house will surround you and make the outside world evaporate instantly. Don't expect breathtaking innovation here, just beefy goodness and straightforward special-occasion fare like hefty crab cakes, oysters Rockefeller and full-bodied French onion soup. The Angus dry-aged steaks come in all shapes and sizes, from the eponymous top sirloin served with so-what lobster slices and buttery barnaise to the brawny 24-ounce New York strip. Whatever the cut, every bite is tender enough to dispatch with a butter knife.

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