The REAL Portlandia

July 19-23, 2017  |  5 days / 4 nights |  $1,495

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“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 to my favorite wineries (including an EPIC outdoor feast) up to Mt. Hood for an afternoon of hiking and SUP’ing, to Hood River to walk, shop and explore, on a food crawl to visit some of my favorite restaurants, food carts, coffee roasters and breweries and give you the locals-only tour of the City of Roses and all her magic.” Mary —- Living Big trip host for this adventure. To learn more about Mary, click here.

Trip Agenda

Day 1 – July 19
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 – July 20
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 – July 21
Make sure you wake up rested, because today we’re heading to Mt. Hood to go stand-up paddle boarding on a beautiful alpine lake. After a picnic lunch and hike around the lake, we’ll make our way to the charming town of Hood River for an evening of small-town shopping, sipping local craft beer and noshing on some of the best pizza around. All meals included.  

Day 4 – July 22
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 5 – July 23
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. Breakfast 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 people 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 $1,495. 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, travel tips, local advice and more.
  • Hotels: 4 nights accommodation based on two people sharing a room.
  • Meals: see the daily itinerary for meals included each day. On some days, you’ll be on your own for a meal. Some alcohol, water and snacks are also included.
  • Transport: all ground transportation during the trip is included.
  • Activities: all activities, unless specified in the itinerary, are included.
  • Gratuities for all local guides.

The following expenses are not included in the total trip price:

  • Round-trip airfare is not included, but gives you flexibility in using airline reward miles or to extend your trip as you wish. Each guest is responsible for organizing their own airfare and transportation to Portland and the host hotel.
  • 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.
  • 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 or outside of the coordinated group trip: spa visits, private tours, etc.
  • Spending money, additional tips for the 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 activities outlined on 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?

Click on the ‘Register Now’ tab by clicking here to get started! Please note: registration is taken on a first-come, first-serve basis.

Is airfare included in the trip fee?

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.

What do I need to know before I book my flight?

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 July 19 by 3PM and depart anytime on July 23. 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, and you will have your own bed. You can request a roommate preference on forms that will be included in your Trip Packet, which you will receive approximately 12 weeks before the adventure begins.

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 60 minutes on one route, and about 90 minutes on a second route (but we’ll stop along the way to stretch and use the restroom!)

What should I pack?

Prior to the trip, you’ll be given a 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 July is relatively warm, with temperatures averaging between 65-85 degrees fahrenheit. There might be occasional light rain and winds.

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 (click here) 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 12 weeks before we begin our adventure, you’ll receive your Trip Packet. It includes forms, questionnaires and waivers that you’ll need to submit no later than 8 weeks before the trip begins. The forms in the Trip Packet 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 Trip Pricing tab (click here) for payment details.

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 May 24, 2017:
    • 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 May 25, 2017:
    • 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 (click here) to discuss. Generally speaking, failure to make payments according to the schedule may result in losing your spot on the trip.

Oh no! The trip is sold out -- but I really want to go on this trip!

Because all Living Big adventure are kept to small groups, it’s highly likely that the trips will sell out. If we had our way everyone would be able to join (but we can’t grow that fast!)

It’s highly likely that there will be a second Living Big trip to Portland offered in 2018 — so be sure to contact Living Big (click here) to request early notification list for that trip. Alternatively, you can work with Living Big to plan your own trip to Portland that mirrors the Living Big trip, or make any modifications you like! To learn more about custom travel design, click here.

Trip Pricing + Payment Options

See below for key details and next steps to save your spot!

This trip is nearly all-inclusive of all meals, all hotels, ground transportation, and all activities outlined in the trip details tab (click here), 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!

Please note that spots are limited, and registration is taken on a first come, first serve basis.

There are two options for payment:

  1. Pay the full amount by credit card or by check.
  2. Break your payments into three installment payments:
    • Payment 1: make a deposit of $500 to formally register for the trip
    • Payment 2: 50% of the remaining balance ($497.50) will automatically be charged to your credit card on April 1
    • Payment 3: the remaining balance ($497.50) will automatically be charged to your credit card on June 1
    • Note: if you decide to make installment payments, payments are only accepted by credit card. 

Have Questions?

Thank you for your interest in this Living Big Adventure! If you have any questions, or would like to discuss details of the trip before you register, please fill out the form below. A member of the Living Big team will reach out to you within the next 48 hours, unless we’re out hosting an adventure.