Tailored Oregon escapes with expert local insight.
Custom Oregon travel planning for curious, discerning travelers
Oregon Bespoke Travel designs private, custom itineraries for couples, families, and larger groups, across Oregon’s coast, wine country, mountains, big cities and small towns. Every journey is shaped around your interests, pace, and sense of discovery, so you can experience this place with depth and ease.
The heart of bespoke travel
Rooted in the Pacific Northwest
Heather Rose is an Oregon destination specialist, travel planner, and founder of Oregon Bespoke Travel. Through expertly guided tours, private transportation, and custom itinerary design, she has helped thousands of visitors experience Oregon.
As the founder and Managing Partner of Peak Tours and Transit, Heather built strong relationships across Oregon’s tourism, hospitality, wine, arts, and small business communities. Her work has been guided by the belief that travel should connect visitors more meaningfully to place.
Heather’s deep regional knowledge is shaped by years of active engagement in Oregon’s tourism community, including annual attendance at the Governor’s Conference on Tourism and professional affiliations with Travel Portland, IATA/IATAN, the Oregon Outfitters and Guides Association, and the Portland Metro Chamber of Commerce. She also participates in industry programs and communities including Tourpreneur, Arival, and Travel Massive, and is a graduate of the Oregon Tourism Leadership Academy.
Through Oregon Bespoke Travel, Heather creates custom Oregon itineraries for discerning travelers who want insider expertise, providing journeys shaped around your interests, pace, travel style, and sense of discovery.
The Bespoke Difference
Bespoke travel is more than a list of bookings; it is a deeply personalized design process. We invest hours into research, relationships, and local coordination to ensure your journey is seamless, and entirely unique to you.
What We Plan
Oregon Bespoke Travel designs custom itineraries across the state of Oregon, from Portland and the Columbia River Gorge to Mt. Hood and Hood River Valley, from Willamette Valley wine country to Crater Lake and Oregon’s high desert.
Trips may include food, wine, gardens, makers, waterfalls, scenic drives, coastal towns, mountain lodges, family adventures, restorative nature-based travel, private guided tours, custom transportation, sporting events, theatre, live music, festivals, museums, wine weekends, and seasonal Oregon experiences.
Sample Pricing
Oregon Escape Plan
Signature Oregon Itinerary
Full-Service Bespoke Oregon Journey
Groups, Retreats & Special Occasions
Starting at $790
Starting at $1,490
Starting at $1,890
Starting at $2,190
Best for shorter trips, weekend getaways, Portland stays, Columbia River Gorge visits, wine country days, or Oregon Coast add-ons.
Best for 4-7 day trips, multi-region Oregon vacations, and families who want a polished trip plan.
Best for 7-10 day trips, luxury travelers, milestone celebrations, honeymoons, and family journeys requiring more hands-on support.
For family reunions, corporate retreats, wedding experiences, and complex custom itineraries.
A Note About Pricing
Oregon Bespoke Travel is first and foremost a custom itinerary planning service. Our planning fees compensate us for our expertise, research, route design, local knowledge, vendor recommendations, and itinerary creation. Planning fees do not include the cost of lodging, meals, transportation, admission fees, guide services, tastings, gratuities, or third-party experiences unless specifically stated in writing.
For full-service clients, we may assist with select local arrangements, private tours, guide services, transportation, restaurant reservations, or partner experiences when available.
Kind words from our travelers
"Our experience was very customized to our particular interests. This is definitely a service I recommend."
Marisela's family
Portland Vacation
"We quoted out several vendors and Heather was by far the most responsive, friendly, communicative and flexible. 100% recommend!"
Katie & t.
Willamette Valley Wedding
"So sweet and accommodating and amazing communication. Thank you for creating an unforgettable honeymoon!"
Alyanna
Southern Oregon Adventure
Begin Your Oregon Journey
Itinerary designed around you, with insider insight.
Tell us about your Oregon trip
We will respond within 72 hours. Because our planning is highly personalized, we accept a limited number of clients. If your trip is a good fit, we will reach out with a more in-depth questionnaire and next steps.