Circle Oregon June 6th – June 14th, 2025

From

$3499.00

Duration

Tour Type

Overview

Embark on an Epic Oregon Adventure as we Circle Oregon!
Circle Oregon is a tour that will take you from the heart of Portland through some of the most iconic and beautiful areas of Oregon – and some of Washington! Starting with the Oregon Rose Festival celebration, you will be treated to incredible activities, gardens, lakes and experiences Oregon has to offer. Visit Crater Lake, watch an Oregon Shakespeare Festival production and travel up the incredibly beautiful coast all the way to Astoria. Check out the itinerary to get a more detailed version of the this tour!

Itinerary

Day 1 – Friday, June 6th: Arrival in Portland
Today, we will start the tour from Portland’s Heathman Hotel. We will grab a boxed lunch from the well-known Elephant’s Delicatessen before starting our Oregon journey by heading into Washington to visit Mt. St. Helens and learning about the incredible eruption that took place in May of 1980. After visiting with the rangers, enjoying the vistas and learning about the area and the impacts, we will head back into Portland and check out some cool sites and an excellent spot for incredible views of the Rose City. Tonight we will check into the Heathman Hotel and enjoy dinner in their on-site restaurant.
Day 2 – Saturday, June 7th: Rose Festival & Portland Spirit
Start your day off with a great breakfast at the hotel before we begin the day. You’ll view the Rose Festival’s amazing Grand Floral Parade from VIP seats before heading to Pioneer Square Mall to grab a bite to eat and check out the best place to do some shopping in Portland. Don’t forget to visit the Made In Oregon Store!. This afternoon, we will visit Pittock Mansion and Washington Park’s famous Rose Garden. You will also have a chance to visit one of the most beautiful Japanese Gardens in the country. This afternoon, we will return to the hotel to freshen up before heading out for a dinner cruise on the Willamette River on the Portland Spirit.
Day 3 –Sunday, June 8th: Portland to Bend
Grab breakfast at the hotel before we leave Portland and head toward Bend. Along the way, you will have the chance to stop and visit Multnomah Falls – a breathtaking waterfall just an hour outside of Portland. After the falls, we will visit Bonneville Dam and Locks – an incredible feat of engineering. Then we will be off to the Timberline Lodge for lunch. If you have never visited the Timberline Lodge on Mt. Hood, you are in for a rare treat. . it is truly a incredible place. After lunch, we will head on to the city of Bend in Central Oregon. Tonight, you will check into the Riverhouse Lodge on the banks of the Deschutes River. Relax, grab dinner on your own and enjoy the beauty of this spot.
Day 4 – Monday, June 9th: Crater Lake & Ashland
This morning, enjoy breakfast at the hotel before we make our way to one Oregon’s most incredible outdoor jewels – Crater Lake. Once we arrive, we will navigate around the lake on the Rim Road which offers incredibly beautiful photography opportunities. After taking in the views, we will head to the iconic lodge and you will have some time to grab lunch at the cafe while enjoying the natural beauty surrounding you. Following lunch, we will begin the drive to Ashland. Along the way, we will take a stop for a wine tasting. Tonight we will check into the hotel in Ashland, take some time to freshen up and then take a short walk to the Oregon Cabaret Theatre for a dinner show!
Day 5 – Tuesday, June 10th: Jacksonville & Julius Caesar
Enjoy breakfast at the hotel to start your day have a leisurely morning to explore. This morning, we will take a behind the scenes tour of a couple of the Oregon Shakespeare Festival theaters. After the tour, the group will head to Jacksonville, Oregon to explore this authentic western town. Enjoy the local shops, grab some lunch and have fun. This afternoon, we will head back to the hotel to freshen up before we have a nice group dinner before we see the OSF production of Julius Caesar.
Day 6 – Wednesday, June 11th: The Oregon Coast
Grab some breakfast fuel at the hotel and get ready to start the next part of this Oregon journey. We will head across the coastal pass and start our coast exploration in the great little town of Florence. Once in Florence, you will have time to enjoy lunch in one of the many great little restaurants before we head out for a giant dune buggy tour of the dunes – a vast state park that will blow you away. This afternoon you will take a short ride to Newport and check into the Elizabeth Inn & Suites. Tonight, we will have a group dinner at the excellent Clearwater Restaurant right on the Newport wharf.
Day 7 – Thursday, June 12th: The Oregon Coast
After breakfast at the hotel, we will make our way north up the coast to Depoe Bay – one of the most interesting spots on the coast. You will take a short cruise on the bay and learn about the local fishing and crabbing industry and the sea life that calls the area home. Soon, we will start up the coast on our way to Pacific City. We will make a stop at the Yaquina Head Lighthouse for some pictures and a short walk to incredible viewpoints! After the lighthouse, we will drive up to the beautiful beach town of Pacific City. Take some time to explore and have lunch at one of the local restaurants and check out the beautiful beach the town is known for. This afternoon, we will take one more short drive to Cannon Beach/Seaside, but not before we stop at the Tillamook Cheese Factory for some ice-cream – the best ice cream. This evening we will check into a great hotel and have a group dinner at a local restaurant.
Day 8 – Friday, June 13th: Astoria & Back to Portland
Enjoy breakfast this morning before we take a tour of Astoria – including a couple of spots where famous movies were filmed.  On the way, we will take a tour of the Lewis & Clark Expedition’s Fort Clatsop. We will make our way to Astoria after and visit the Astoria Column – which has a really cool representation of Oregon’s History and some of the most incredible views of the mouth of the mighty Columbia River. This afternoon, we will head back to Portland and check into the Radisson Hotel at the airport and have a final group dinner at the onsite restaurant (its a nice spot to eat).
Day 9 – Friday, June 14th: Heading Home
Today, after a final breakfast at the hotel, you will be on your way home with thoughts of Oregon and all the great exploration and fun you had on this tour! We can’t wait to see you come back again!!

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Booking Tour

Tour Information

Max Guests

32

Min Age

21+

Tour Location

Languages Support