Portland pulls on its finest dress for the holidays, and this three-day celebration places you right in the heart of it all. From a candlelit Holiday Tea in one of the city’s most storied libraries to an evening gliding along the Willamette aboard the Portland Spirit, from the soaring grace of The Nutcracker at Keller Auditorium to the joyful chaos of a holiday artisan market — every moment of this tour has been thoughtfully curated to capture the warmth and wonder of the season. We will stay in the heart of downtown Portland at the elegant Heathman Hotel, a landmark property that sets the tone for the entire experience. All that remains is to settle in and let the city’s holiday spirit wash over you.

Our journey begins this morning with coach pick-ups along the I-5 corridor, and the anticipation builds with every mile as we make our way toward Portland.

Step into the festive warmth of the Heathman Hotel for our first experience of the tour: a Holiday Tea in the beautiful Heathman Library. Surrounded by floor-to-ceiling bookshelves and the quiet elegance of this beloved gathering place, we will settle in over tea and seasonal bites before checking into our rooms for the weekend.

Enjoy a Holiday Tea in the beautiful Heathman Library, surrounded by floor-to-ceiling bookshelves and the quiet elegance of this beloved gathering place.

The afternoon is free to freshen up before we set out together for Pittock Mansion, the grand hilltop estate that overlooks all of Portland. Decorated beautifully for the season, the mansion offers a guided tour that brings the history and splendor of the home to life.

Board the Portland Spirit for a holiday dinner cruise along the Willamette River, dining in style as the city’s lights shimmer on the water and the Holiday Ship Parade drifts past.

After a leisurely breakfast at the Heathman, the day begins at a relaxed pace — time to stroll the shops along SW Broadway, find a gift or two, or simply enjoy coffee in the lobby before the afternoon comes to life.

We will make our way to Keller Auditorium to take our seats for Oregon Ballet Theatre’s beloved production of The Nutcracker — two hours of stunning choreography, Tchaikovsky’s timeless score, and the wide-eyed wonder that this ballet never fails to inspire.

As evening draws near, we head to the Oregon Rail Heritage Center for a festive steam train ride, a wholly unique Portland experience.

Stay at the elegant Heathman Hotel, a landmark property in the heart of downtown Portland.

Our final morning together begins with breakfast at the Heathman before we check out and set off for one last Portland adventure.

Spend the late morning at Crafty Wonderland, one of the Pacific Northwest’s most beloved holiday markets, where independent artists and makers fill the Oregon Convention Center with handcrafted gifts, ornaments, and one-of-a-kind finds.

We return to the Heathman for a group lunch before the grand finale.

A performance of the Oregon Symphony’s Holiday Pops at the Arlene Schnitzer Concert Hall. Few experiences capture the full spirit of the season quite like this one — a magnificent hall filled with the sound of the symphony and the songs that have defined Christmas for generations.

When the final note fades, we will board the coach and begin our journey home, carrying with us a weekend’s worth of warmth, wonder, and memories made together.