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  • 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

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Jun 23 2025 $4,580.00 Loading

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