Portland

We opened a Wine Spa this year, and it was just named one of the 100 Greatest Places in the World to Visit in 2025 by Time Magazine!

So let's celebrate! Join us for a magical long weekend in Portland, OR full of wine, fun, and girlboss energy. Wine, dine, and get inspired to chase your dreams with our CEO Kelly Lewis and your fellow dames on this adventure.

Spend a day wine-tasting through our favorite vineyards in the Willamette Valley, then fully relax and unwind in an afternoon of vinotherapy services at The Wine Spa. We're shutting down the spa exclusively for our Damesly gals - expect a day of relaxation, laughter, and fun!

For our local ladies, choose to either stay independently by selecting the "No Hotel Needed" option, or, choose a room type at checkout. For those who need the inspo as much as the relaxation, our CEO will offer 1-on-1 business coaching this weekend too!

Price from

$999.00

June 27-30, 2025

Per person based on double occupancy. Solo Rooms available.

Book Now
Questions?
Call Us 888-505-DAME

Picture Yourself

  • Wine tasting through beautiful vineyards in the Willamette Valley
  • Soaking in a bathtub full of wine, like a queen!
  • Toasting to entrepreneurship and making new friends
  • Poking around cute shops and cafés downtown
  • Exploring beautiful Portland, OR over a long weekend


Day by Day

Day 1 Day 2 Day 3 Day 4

Day 1: Welcome to Portland!

Welcome to beautiful Portland, OR!

Tonight at 7 p.m., we’re having dinner as a group with Damesly CEO Kelly Lewis.

We can’t wait to meet you!

Meals: D

Day 2: Wine Tasting in the Willamette Valley

It's wine tasting day! Today we’re off to explore the beautiful Willamette Valley, and taste some of the best wine in the region, including some of the wines we feature at The Wine Spa. We'll make stops at 3 of our favorite local wineries, where tastings are included. You can also opt to pre-order lunch or add charcuterie to any of our stops.

After a fun day, we will return to Portland, arriving about 5 p.m. Evening at your leisure.

Day 3: Wine Spa Day!

Today, we’re bringing you to our brand new wine spa — the first in the country! We’re closing down the entire spa for just our group today, with charcuterie, spa robes, and sparkling wines for the cutest spa party! Enjoy 20% off any of our spa treatments as we create a custom Damesly party just for us.

In between spa services, our CEO will offer 1-on-1s to help you get inspired to chase or build the business idea you've been dreaming of. It's going to be an inspiring and relaxing day - our favorite kind!

Later, we'll have our final dinner as a group.

Meals: D

Day 4: Departures

It’s departure day, and while we’re sad to see you go, we hope you’re leaving feeling properly wined and dined!

Meals: --

Hotel: --



  • Trip Length

    4 days / 3 nights

  • Activity Level

    Light

  • Perfect For

    Wine Lovers + Boss Betties

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Portland, OR: Wine Spa Weekend

Portland, OR: Wine Spa Weekend

Regular price $1,999.00 USD
Regular price Sale price $1,999.00 USD
Sale Sold out

Low stock: 4 left

Dates
Room Type
Payment Option
See our Reviews â–¶ View full details

Spaces on tours are sold per person. Deposits are non-refundable. Ensure your payment option is as desired before checkout. If paying deposit only, remaining payments can be made via client portal until 60 days before departure. See our cancellation policy for details.

Love this tour but can’t make the dates? Click here to make this tour private.

Includes

  • Hotel accommodation (shared and singles) if selected
  • Wine tasting in Willamette Valley
  • Dinner with our CEO
  • Transportation to listed activities
  • 20% off services at our Wine Spa
  • Gratuity for Damesly trip leader

Excludes

  • Flights
  • Travel Insurance
  • Meals + alcohol not included
  • Activities not listed
  • Gratuities at wineries + spa

Meet Your Trip Leader

Kelly Lewis

Kelly Lewis is a women's travel industry maven, author, speaker, business coach and the founder and CEO of Damesly. Raised in Hawaii, she's been to all 7 continents and over 85 countries. She is also the author of the best-selling title "Tell Her She Can't."

Read More

Additional Information

Flights: Fly into PDX. Plan to arrive before 6:00 pm on Day 1, and depart anytime on Day 4.

Want us to advise on flights? Email us at info@damesly.com

Weather: The weather in Portland in December is typically cool and grey. Expect temperatures in the 50s in the daytime and 40s at night.

Packing: Layers are the name of the game in the PNW! Pack jackets, scarves, sweaters, a beanie, and anything comfortable to walk in.

The Wine Spa is a brand new venture opened by our CEO Kelly Lewis. Find out more at the The Wine Spa website.

We require guests on this tour to be 21+ because of the included wine tastings.

At Damesly, our goal is to connect women through beautifully curated travel experiences. 

Our trips feature a high level of customer support and a focus on cultural interaction and experiences. We’re dames who work hard, and travel often. So when you use your coveted PTO days, we want you to have the best trip possible! To do this, we hand-select boutique hotels based on location and service. We look for unique properties that we think of as hidden gems, which may or may not be 5-stars. Our itineraries offer a mix of adventure and relaxation. We’re not afraid to get a little dirty to have the most fun experiences, but if there’s an infinity pool or a great spa afterwards — we’ll meet you there!

Traveling the world comes with rewards and challenges. Our traveler is someone who is easy-going and open minded to new experiences and cultures, ready to get out of their comfort zone and understands that travel leads to personal growth, even on its toughest days. Join us if you’re adventurous, kind, open-minded and ready for the trip of a lifetime. 

On this tour to Portland, you can expect big boss lady energy, drinking lovely wine, and explore a fun, quirky city. Activity level is minimal. We've chosen a hotel in the Northeast for its proximity to wine spa, cute shops and restaurants, and its distance from downtown.

Will you match me?
Of course! If you choose a space in a shared room but you're traveling solo, we will do our best to pair you with a roommate. Roommates are matched based on arrival time and perceived compatibility. Sharing a room is a great way to save costs, and make a new friend! However, we ask you to approach the situation with an open mind, some grace, and maybe a little humor.

While 99% our travelers are amazing, we can't guarantee that you'll hit it off with your roommate, or that your sleeping styles will be compatible.

Is sharing right for you?
If you are a light sleeper, get easily irritated or just know that you need your own space, sharing a room might not be for you. Likewise, if you know that you snore, sleep with a CPAP machine or have other health conditions, sharing a room might not be the best fit.

What if I don't get along with my roommate?
If you've tried but you absolutely can't get along with your roommate and need to separate, your trip leader will either swap things around, or, attempt to get you your own room. If the latter, additional charges will incur.

What if I book a double room, and you can't match me?
We book a certain amount of hotel rooms before any tour, and are bound by their rules. In the event that we cannot find a roommate for you before the tour, and your room converts to a single room, there may be additional charges.

Small group trips require at least 4 people to run. We will confirm as soon as possible when the trip has met its minimum; up to 60 days before departure. For this reason, we recommend waiting until after a trip has been confirmed to purchase airfare. Any tour can be converted to a private departure when a trip does not meet its minimum. Additional costs may incur. Alternatively, apply your credit to any small-group tour departing within 12 months. 

When you book a tour with us, our team will create a customer portal for you, where you can make payments towards this tour at your leisure. 

If you’d prefer, we can create a payment schedule for you, just let our accounting team know (accounting@damesly.com) Tours must be paid in full 60 days before departure. 

This tour to Portland must be paid in full by October 8, 2024. See our cancellation policy here.

Still have questions? See our FAQ or Contact Us.



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