Skip to content



  • Enjoying a welcome dinner on a Portland Spirit Dinner Cruise

  • Visiting Sea Lion Caves

  • Savouring a unique dining experience - Native Salmon Bake

  • Experiencing a guided boat excursion along the Oregon coast

  • Learning "pioneer spirit" history at the End of the Oregon Trail Interpretive Center

  • Viewing spectacular natural beauty at Young River Falls, Crater Lake, Devil's Punchbowl State Natural Area & more!

  • Delight in a tasting and lunch at an Oregon winery





Arrive on Own near O'Hare

Airport with Gathering

Night & Group Air

June 22 - July 1

Chicago Area

Departures with

Group Air

June 23 - July 1

Indiana Departures

with Gathering Night

& Group Air

June 22 - July 1

Iowa & Minnesota

Departures with Gathering

Night & Group Air

June 22 - July 1

Double Occupancy





Single Occupancy





Triple/Quad Occupancy









  • Lodging as listed on itinerary

  • Luggage handling for one (1) suitcase per person, if available

  • Tickets/admissions to listed attractions (Unless listed as "Optional" or "On your own")

  • Gratuities for local guides

  • Meals as listed on itinerary

  • Guidance of a professional tour manager


Activity Level - 4

Good mobility is needed. There will be prolonged standing, stairs, energetic activities and walking distances up to two miles over varied landscapes.

June 22

* Travelers departing from IOWA, MINNESOTA and INDIANA take advantage of a transfer to our 'gathering overnight' hotel in the Chicago area

June 23

* Your adventure begins! Relax on your ride to Chicago's O'Hare Airport for your flight to Portland, OR
* Arriving in Portland, the Portland Japanese Garden awaits!
* This evening, we'll enjoy a locally sourced meal aboard a Portland Spirit Cruise featuring live piano music and the captain's historical narration of Portland waterways.
* After our cruise, we'll check in to the AC Hotel by Marriott Downtown or similar - Portland, OR

B, D

June 24

* We start our morning with a self-guided tour ath the End of the Oregon Trail Interpretive Center before exploring Oregon's natural beauty at Young River Falls.
* Enjoy free time to explore and dine on your own in Astoria.
* Our overnight will be at the Best Western Columbia River or similar - Astoria, OR


June 25

* Witness stunning vistas as we drive along Oregon's coast.
* Enjoy exploring and lunch on your own in Tillamook, known for being the gateway to the Three Cape Scenic Loop.
* A picturesque stop awaits us at Cape Meares Lighthouse.
* Prior to our overnight at Comfort Inn & Suites or similar - Lincoln City, enjoy time to explore and dine on your own.


June 26

* Visit a stunning Oregon winery for a tasting and lunch!
* Explore Grants Pass, then enjoy dinner on your own.
* Turn in for the first of two nights at the Holiday Inn Express & Suites - Central Point or similar - Medford, OR.

B, L

June 27

* Enjoy a full day of fun at Crater Lake National Park.
* Explore the national park with a guided trolley tour of Crater Lake - keep your cameras handy!
* Together we will visit the tiny town of Rim Village inside the park, where you will enjoy lunch on your own.
* After a day filled with adventure, return to the hotel to rejuvenate and enjoy dinner at your leisure.


June 28

* Enjoy lunch on your own in the town of Florence.
* A truly unique visit awaits us at Sea Lion Caves, a privately owned wildlife preserve and bird sanctuary. If we are lucky, we may catch a glimpse of sea lions in the caves or along the rocky shores.
* Tonight, a special dining experience - a traditional Native Baked Salmon dinner.
* Our overnight will be at The Mill Hotel Casino or similar in the Coos Bay area, a historic bayside community.

B, D

June 29

* Explore Newport, a town that is rich in marine life and beautiful beaches, before enjoying dinner on your own.
* Our overnight will be at the Holiday Inn Express Newport or similar - Newport, OR


June 30

* This morning, we'll have a guided boat excursion. While being surrounded by natural beauty, we'll also be on the lookout for whales, porpoise, seals, sea lions, pelicans, bald eagles, and an abundance of marine birds.
* Another picturesque stop awaits us at Devil's Punchbowl State Natural Area, a renowned whale watching site.
* Our dinner together will be the perfect time to share your personal Oregon highlights.
* Our overnight will be at the Country Inn and Suites by Radisson Portland Airport or similar - Portland, OR

B, D

July 1

* We bid a fond farewell to the beautiful state of Oregon as we start our journey home.
* Upon disembarking from the plane, you will be greeted by your transfer driver for your return trip to your chosen tour departure location.
* You return home with wonderful memories and tales of your adventure to share with family and friends.


B=Breakfast, L=Lunch, D=Dinner

Below is a list of pick-up points available on this tour.

Below is a list of pick-up points available on this tour.

Name Address Contact Details
IA-Coralville (Pre) McDonald's Restaurant - 2794 Comerce Dr
with 'Gathering' Night
IA-Decorah (Pre) Legacy Tour & Travel office - 703 Dudley St
with 'Gathering' Night
IA-Newton (Pre) Hawkeye Stages - 300 E 17th St S
with 'Gathering' Night
IA-Waterloo (Pre) Hawkeye Stages - 3315 Titan Trail
with 'Gathering' Night
IL-Alsip DoubleTree Hotel - 5000 W 127th St
IL-Chicago Area At Home PickUp - for those that qualify
IL-Rockford WalMart Super Center - 7219 Walton St
IN-Metro Chicago (Pre) Home PickUp - Lake,Porter,LaPorte counties
with 'Gathering' Night
IN-Mishawaka (Pre) Legacy T&T office - 620 W Edison Rd
with 'Gathering' Night
MN-Byron (Pre) City Hall (next to LT&T) - 680 Byron Main Ct NE
with 'Gathering' Night

Please select the number of passengers that will be travelling

From Price Book Now Call Back Telephone Favorites

It is not possible to display any suggested tours because JavaScript is disabled in your web browser.