The REAL Portlandia 

October 4-7, 2018  |  4 days / 3 nights |  $1,195

Share with Friends: 

“I grew up in Portland and have watched it grow, explode and come to life as a center of all-things outdoor, culture, food, beverage, sneakers — it’s really incredible to be part of a city on the move! After traveling the world and sharing my favorite cities with groups of women, I can’t wait to show off my home town! On this trip I’ll take you on a food crawl to visit some of my favorite restaurants, food carts, coffee roasters and breweries, we’ll spend a day in the Willamette Valley to try our famous pinot noir, explore Portland’s Forest Park and give you the locals-only tour of the City of Roses and all her magic.” Mary —- trip host for this adventure. To learn more about Mary, click here.

Trip Agenda

Day 1 – October 4
Make your way to Portland – the ‘City of Roses’ by 3PM to join the group at the hotel and kick off the long weekend of fun. We’ll start by making our way to Portland’s hip industrial east side for a spirit tasting and cocktail flight at a local distillery, meet the rest of the group and learn more about the weekend adventure ahead. Afterwards we’ll make our way to dinner at a local favorite hot spot. Arrival Airport: Portland International Airport in Portland, Oregon (airport code is PDX.) Dinner included.

Day 2 – October 5
Today we’ll discover one of Oregon’s most famous exports: pinot noir —- the light red wine that calls the Dundee Hills, Willamette Valley and McMinnville home. We’ll make our way around these famous wine growing regions to tour, sample and sip at a few wineries. We’ll enjoy lunch among the vines before heading back to Portland for dinner, an evening stroll around Northwest Portland, and a stop at Portland’s most famous (and creative!) ice cream shop. All meals included.

Day 3 – October 6
Start your day by stretching your legs on a hike through Portland’s Forest Park — the largest urban forest in the United States. After the hike up to Pittock Mansion, the day is your own to explore and discover why Portland is such an amazing city (and named one of the ‘52 places to go in 2017’ according to the New York Times!) You’ll have a map to guide you to famous Powell’s Bookstore, the Pearl District, Stumptown Coffee, food cart pods, local parks, bike rides along the waterfront, Washington Park Rose Garden, and more. After a full day of sight-seeing downtown, we’ll make our way to a new corner of the city for a food crawl to a few more local spots that you just can’t leave without trying! Breakfast and dinner included.

Day 4 – October 7
On this final day, everyone will either start the journey home or the next leg of their personal vacations. We’ll swap phone numbers, share photos and make plans for our next adventure and opportunity to ‘live big’ together. No meals included.

Trip itinerary is subject to change but will always maintain a spirit of adventure and diverse activities. Questions? Check out the FAQs (click here) for this trip.

Frequently Asked Questions

Who is going on the trip?

This trip is made up of 11 women: 10 guests and your Trip Host. A major tenet of Living Big is to make international travel more accessible to women who don’t want to go at it alone. To learn more about the philosophy, click here.

Can I join the trip solo? Or can I invite a few of my friends to join me on the trip?

Yes and yes to both questions! Some women join Living Big trips on their own; there to make friends and see the world, and others join Living Big trips because they want to share the experience with their friends, sisters, mothers or daughters and don’t want to do any of the planning!

You’ll find that the trips are structured in a way that you’ll have a good amount of group time, but also a fair amount of independent time to explore on your own, with new friends you met in the group, or with the friends joining you on the trip.

Who is the Trip Host? And what is her role?

On this trip your Trip Host is Mary. To learn more about Mary, click here.

The role of the Trip Host is to be there to make sure everything goes as smooth as possible, even when the inevitable travel bumps come our way – such as an unexpected rainy afternoon, traffic, missing luggage, etc. But more importantly, to be a resource that will give you the space you need to really enjoy the experience. So if throughout the trip there is something your Trip Host can do to support you in this regard – please let her know. For example, if you’re not feeling well, having trouble sleeping, not getting along with someone, not satisfied with something, etc. please please share these concerns. No one needs a ‘Mother’ on this trip – that’s not our intention, but if there are small adjustments that can be made to create more space for you to enjoy the experience —- the Trip Host will see what she can do!

How much does the trip cost? And what is included/excluded in this price?

The total price per person is $1,195. This includes the following:

  • Planning: all trip logistics, including pre-trip negotiations with all hotels and vendors, onsite coordination, useful information leading up to your trip such as advice on what to pack, how much to budget for spending money, etc.
  • Hotels: 3 nights accommodation based on a shared room.
  • Meals: see the daily itinerary for meals included each day. Dinners generally include a limited amount of hosted beer and wine.
  • Transport: ground transportation during the trip
  • Activities: all activities, unless specified in the itinerary, are included.
  • Gratuities for local guides and partners.

The following are not included in the trip fee:

  • Round-trip airfare is not included, but gives you flexibility in using airline reward miles or extending your trip as you wish. Each guest is responsible for organizing their own airfare and transportation to the stated start and end cities.
  • A set amount of wine and beer will be purchased with each hosted dinner, but each guest will be responsible for alcoholic beverages beyond this amount.
  • Transportation to/from the airport.
  • While not required, each guest is encouraged to consult their existing insurance policy to determine what is covered while on the trip, and if needed, secure an individual insurance policy for the trip.
  • Any additional activities you want to book along the way: spa visits, private tours, souveniers, etc.
  • Spending money, additional tips for your Trip Host and excess luggage fees.

What are the health and physical fitness requirements to join on the trip?

Guests should take personal responsibility to ensure they are physically able and healthy to participate in all group trip activities, such as hiking on uneven surfaces for durations up to 4 hours, climbing up and down up to 500 steps, riding in trains and mini-vans for up to three hours at one time, walking on uneven surfaces, carrying luggage, and getting on/off various modes of public transportation. The trip is moderately strenuous and best enjoyed by anyone who is physically fit and enjoys active days. You should consult with a medical doctor to determine if you are healthy and physically able to participate.

Is there a minimum/maximum age to participate?

Women over the age of 21, that are physically able to participate in the trip itinerary, are welcome to join for this adventure. Please see the detailed itinerary and FAQ on minimum physical fitness requirements to learn more.

What should I do to secure my spot on the trip?

The first step is to request a spot, which you can do online (click here.) Once you request a spot, we’ll reach out to you to schedule a call to review the trip details, get to know you, give you a chance to ask questions about Living Big, etc. If after this conversation you’re on board to join for the adventure, you’ll receive a link to the registration page where you can formally register, submit your first payment and sign the trip waiver. Please note: registration is taken on a first-come, first-serve basis.

Is airfare included in the trip fee? What do I need to know before I book my flight?

Round-trip airfare is not included in the trip fee, but this gives you flexibility in using airline reward miles, to extend your trip any way you like, and to select the routes and airlines you prefer. Each guest is responsible for organizing their own airfare and transportation to the stated start and end cities.

You will be required to share flight details at least 4 weeks before the adventure commences. Inbound flights should arrive on October 4 by 3PM and depart anytime on October 7. Portland’s airport code is PDX.

Will I be sharing a hotel room? Can I choose my roommate?

Yes, everyone will be sharing a room with at least one other person, but you will have your own bed. You can request a roommate preference, and share sleeping preferences, on forms that you’ll be asked to fill out 10-12 weeks before your adventure begins.

There is not an opportunity for women to pay a single supplement in order to secure a private room. Here’s why: single supplements, while convenient for some willing to pay the fee, often prevent many single women from traveling because the cost is just too high, so the decision was made early on to not go down that path as a means to encourage more women to travel. And we find that sharing a room with another woman, and having an opportunity to connect with other women and learn about their lives in this way, contributes to what makes these trips very special.

Can you tell me about the type of accommodations we'll be staying at?

You betcha! We’ll be staying in Portland for the duration of this trip at a three-star property in the upper Northwest neighborhood. The hotel does have an elevator, but you may need to carry your luggage up about 3-5 steps to reach the elevator, and will need to carry your luggage to/from taxi’s.

What kind of ground transportation will we use?

We will be doing a good amount of exploration by foot, but also in local taxi’s, on local trains and in mini-vans. The mini-van rides will be about up to 90 minutes on some routes (but we’ll stop along the way to stretch and use the restroom!)

What should I pack?

About 10-12 weeks before the trip you’ll receive a detailed packing checklist and advised on what type of clothes and supplies you’ll need.

Do I need to carry my luggage?

Yes, plan on carrying your bags to/from the airport, on/off buses and vans and in/out of the hotel.

What will the weather be like?

Weather in Portland, during the early fall, is phenomenal! It’s crisp fall in all it’s glory! Temperatures averages between 60 degrees and 75 degrees fahrenheit. There might be occasional light rain and winds, and the temperature will vary depending on the area, elevation and time of day.

What if I don't need every hotel/activity/etc. on my trip?

Unfortunately, refunds aren’t possible for unused hotel rooms, meals or activities. The total trip price is a package deal; credits are not given for services not used. Please contact Living Big if you have questions or concerns about any trip activities due to a physical condition. If there is a reasonable alternative, we can explore it.

How do I communicate information like allergies, injuries, etc?

About 10-12 weeks before we begin our adventure, you’ll receive a pre-trip packet of information. This includes forms, questionnaires and waivers that you’ll need to submit no later than 8 weeks before the trip begins. These forms allow you to share these important details. Living Big will provide meals as outlined in the official trip itinerary and will work with you to try and accommodate special dietary requirements; however, Living Big is not required to provide such meals, supplements and/or any special requests beyond what is outlined in official trip itinerary.

Do I have to pay for the entire trip up front or can I make payments?

No, you do not need to pay for the entire trip up front. (Although you can, if you prefer.) Check out the Pricing, Payment and Reservation tab for payment details.

What is Living Big's policy on non-discrimination and violence?

Please take a moment to review the Living Big policy towards anti-discrimination and violence. Click here to review.

If you’re on board with this philosophy, and can join us in creating a safe, comfortable and judgment-free zone, then we’d love to have you join for an adventure!

What if I need to cancel the trip?

If you decide you need to cancel your trip the following refund schedule applies upon written notice of your cancellation:

  • Cancellations made on or before August 4, 2018:
    • Your trip deposit is nonrefundable. If you paid in full for the trip the deposit is $500.
    • You will be reimbursed 50% of what you have paid to date, less the nonrefundable deposit.
    • As an example, if you made a $500 deposit, then made two additional payments each for $250 (total paid = $1,000) then the amount you would receive back is $250.
  • Cancellations made on or after August 5, 2018:
    • All payments made to date are nonrefundable.

Travel insurance helps protect against last-minute cancellation, trip interruption, and to cover medical treatment or emergency medical evacuation during your trip. We strongly recommend you purchase travel insurance and flight cancellation insurance in advance of your trip. To learn about travel insurance, click here for a quick lesson!

What if the trip doesn't fill up or is cancelled?

The trip requires a minimum number of participants in order to take place at the stated price, since it takes into account group discounts, shared accommodations and other factors that create cost efficiencies. Once an adequate number of participants sign up for the trip, you will be notified. If a trip does not have enough participants, or if someone unexpectedly cancels, you will be refunded your deposit or you will be given the option to pay a trip supplement to continue the trip with fewer participants. Should additional participants sign-up after you have paid the trip supplement, this fee will be refunded. Your air travel itinerary is yours to decide, and we recommend you purchase flight cancellation insurance. Living Big is not responsible for additional expenses incurred by you in preparing for the trip including non-refundable air tickets, gear, medical equipment or travelers insurance.

What if I can't make payments according to the payment schedule?

If unusual circumstances arise and you can’t make payments on time please contact Living Big to discuss. Generally speaking, failure to make payments according to the schedule may result in losing your spot on the trip.

Trip Pricing

This trip is nearly all-inclusive of meals, all lodging, ground transportation, and all activities outlined in the itinerary, all the planning and booking (so you don’t have to do ANY work but show up!) and advice on what to pack, travel tips and a go-to resource who is here to answer any questions you have leading up to the trip, and on the trip, to help ensure that you have an amazing experience! Trip Fee: $1,195.

Payment Options

There are two options for payment:

  1. Pay the full amount by credit card or by check.
  2. Break your payments into equal monthly installments. Make a deposit of $500 to formally register for your spot, and then on the first of each month (following the month you made your deposit payment) your credit card will be automatically charged a set amount, so that the final payment is applied on July 1, 2018. If you decide to make monthly installment payments, you will receive a payment schedule based on when you register.

Requesting a Spot

If you’re interested in requesting a spot on this trip please make note of the following booking process and payment terms:

  • The first step is to request a spot, which you can do online. Once you request your spot, we’ll reach out to you to schedule a call to review the trip details, get to know you, give you a chance to ask questions about Living Big, etc. provided there are spots available on the trip.
  • If after this conversation you’re on board to join for the adventure, you’ll receive a link to the registration page where you can formally register, submit your first payment and sign the trip waiver.

Ready to join Living Big in Portland?

If you’d like to request a spot on this trip, or if you just want to learn more, fill out the form below and we'll be in touch very soon!
  • This field is for validation purposes and should be left unchanged.

Ready to request a spot on this adventure? Click here to get started!

If you're thinking
FOMO is real.
We get it.

Be the first to receive notifications of new adventures, travel tips and special offers right in your inbox.