Bountiful Oregon including Crater Lake, Ashland Shakespeare Festival & Pacific Coast

July 28, 2021 thru August 4, 2021

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Discover the bounties of Oregon! From the beautiful gardens in Portland to the lush Columbia River Gorge, from the breathtaking views from Mt. Hood to the glorious Crater Lake National Park, from quaint Ashland to the expansive coast, this state is filled with spectacular things to see and do. The Ashland Shakespeare Festival is a treat for any visit. We’ll see two Shakespeare plays and get a behind-the-scenes tour at the festival. Enjoy gorgeous scenery and delight with fun things to see and do during an unforgettable week in the Pacific Northwest!



Roundtrip air included*




Columbia River Gorge cruise included


8 days, 7 nights

Activity Level 3


Appropriate for: Travelers who are somewhat physically fit and comfortable with longer days of touring (both walking tours and coach time).


13 meals (7 breakfasts, 3 lunches, 3 dinners) included




Roundtrip livery service from/to your home included

Tour Highlights

  • Portland City Tour
  • International Rose Garden & Japanese Gardens
  • Columbia River Gorge Cruise
  • Timberline Lodge / Mt. Hood
  • Crater Lake National Park
  • Ashland Shakespeare Festival
  • Coastal Lighthouses
  • Oregon Wine Country


  • Roundtrip air transportation to Portland*
  • All transfers and motorcoach transportation
  • Pick-up/livery service*
  • Gorge cruise
  • 7 nights lodging
  • 13 meals (7 breakfasts, 3 lunches, 3 dinners)
  • Admissions and tours as described
  • 2 plays at Ashland Shakespeare Festival TBD
  • Services of a tour director
  • Baggage handling
  • Bus refreshments
  • Driver tips


Tour Map

Day 1 - Home to Portland

Upon arrival in Portland we are picked up by our motorcoach and enjoy a city tour. We visit the waterfront, the Pearl and Cultural Districts, the International Test Rose Garden, where there are over 10,000 rose bushes of approximately 650 varieties, and the Japanese Garden, considered the most authentic Japanese Garden outside of Japan.  We check into our downtown hotel for a two-night stay and savor a Welcome Dinner to get to know your fellow travelers, hosted by your Tour Director, and get prepared for the next week of exploring Oregon. (D)

Day 2 - Portland

Today’s excursion takes us to the Columbia River Gorge, a canyon of the Columbia River. Up to 4,000 feet deep, the Gorge stretches for over 80 miles as the river winds westward through the Cascade Range, forming the boundary between the state of Washington to the north and Oregon to the south. We start with the beautiful scenic Columbia River Highway and a stop to see the vast landscapes from the Crown Point Vista House. We visit Oregon’s top stop, Multnomah Falls, a natural wonder that attracts 2.5 million visitors per year. We’ll also experience the natural wonders by water as we board a steamboat for a narrated cruising tour. Enjoy some free time this evening in Portland, with myriad restaurants and activities from which to choose. (B)

Day 3 – Mt. Hood & Bend

Get ready to feel “on top of the world!” We’ll travel from Portland to Mt. Hood for lunch at the Timberline Lodge, a historic landmark. Considered an architectural wonder, it’s still being used for its original intent—a magnificent ski lodge and mountain retreat for all to enjoy. We visit the Museum at Warm Springs, a striking piece of architecture housing a Native American heritage collections, and tour the New Basin Distillery, which brews small batch spirits with ingredients directly from its own farm, as we travel to charming Bend, on the eastern edge of the Cascades mountain range, under the volcanic peaks of the Three Sisters and Mount Bachelor, with the Deschutes river running through it, to check into our hotel. (B,L)

Day 4 – Crater Lake National Park

Today we travel south to Crater Lake. It is the main feature of Crater Lake National Park and is famous for its deep blue color and water clarity. The lake partly fills a nearly 2,148-foot-deep caldera that was formed around 7,700 years ago by the collapse of the volcano Mount Mazama. With a depth of 1,949 feet, the lake is the deepest in the United States. We then continue to Klamath Falls to stay the night in a delightful setting at the Running Y Resort. (B,L)

Day 5 – Ashland

After a leisurely morning, we travel by way of the Volcanic Legacy Scenic Byway and arrive in Ashland to explore the town and grab some lunch. We check into the Plaza Inn & Suites at Ashland Creek for our two-night stay. Tonight, we’ll see Shakespearean play TBD. (B,L)

Day 6 - Ashland

This morning, for a special treat, we take a backstage tour to see how the Shakespeare Festival makes these amazing performances happen. Then we continue to a nearby winery for a tour and tasting. And tonight, we’ll have a group dinner before we return to the festival to see a Shakespearean play TBD. (B,L)

Day 7 – Oregon Coast & Newport

We’re off to the Pacific coast today, starting with a visit to a historic Oregon lighthouse.  We’ll continue along the coast and onto Newport, along the most incredible part of the Oregon Coast, with a stop at the Sea Lion Caves private nature preserve. Tonight, we have a Farewell Dinner and check into the Best Western Plus Agate Beach for our final night. (B,D)

Day 8 – Portland to Home

As we make our way back to Portland to catch a flight home, we’ll make a stop at the Astoria Column, overlooking the mouth of the Columbia River on Coxcomb Hill in Astoria to get some final memorable views of the scenic state of Oregon. (B)

***Please contact us for special pricing if you are joining the tour from outside of Tucson.

Package Pricing

$3,753 per person

Double occupancy

Deposit: $200

$4,662 per person

Single occupancy

Deposit: $200

Price Includes

Roundtrip air transportation to Portland*
All transfers and motorcoach transportation
Pick-up/livery service*
River Cruise as described
7 nights lodging
13 meals (7 breakfasts, 3 lunches, 3 dinners)
Admissions and tours as described
2 plays at Ashland Shakespeare Festival TBD
Services of a tour director
Baggage handling
Bus refreshments
Driver tips

Booking Policy

We pride ourselves on great service and an enjoyable experience for all and will go over our booking policies after you make your request for booking. If you’d like to learn more about our booking policies before your trip, give us a call at (520) 325-8839, or visit our Booking Policies page. Click here for more information on our booking policies.

Travel Insurance

We recommend that all travelers purchase a travel protection plan to help protect themselves and their trip investment. Travel protection plans can provide coverage for trip cancellation, trip interruption, emergency medical expenses and emergency evacuation/repatriation, trip delay, baggage delay, and more. For your convenience, we offer the following plan for this tour:


360° Adult Group Choice Flyer– Provides an overview of benefits and coverage limits

360° Adult Group Choice Policy – Provides the full coverage term details, including exclusions and limitations

$248 covers trip costs $3,001-$4,000. $313 covers trip costs $4,001-$5,000. Cost may be more or less depending on your total trip cost. If you do not wish to purchase now, the plan can be purchased any time prior to final payment.

Contact us to purchase. If you have questions about coverage, please review the policy or contact Travelex Insurance Services at 888.574.7026 or email Travelex Insurance Services, Inc. CA Agency License #0D10209. Travel Insurance is underwritten by Berkshire Hathaway Special


The Activity Level 3: Moderate.

Expectations: Expect a moderate amount of walking. There will be time to rest on the coach and between attractions. To enjoy this tour, you should be prepared to walk slightly longer distances, climb stairs and tolerate periods of standing, for example on city walks, sightseeing stops or ship excursions. The daily pace and timing can fluctuate significantly between longer and shorter travel days, with additional activities possibly occurring in the early morning or evening. There may be some changes in altitude or temperatures.

Appropriate for: Most travelers beginning with those who are moderately fit, lead semi-active lives, are comfortable participating in long days of activities and expect some physical exertion.


For your reference, we send to you a detailed itinerary approximately 3-4 weeks prior to the scheduled tour departure. This has day-by-day times and events, hotel information where you can be reached in case of an emergency, and airline information.

The times listed on the itinerary are all approximate. We cannot be held responsible for schedule changes due to unforeseen circumstances with the weather, transportation agents, highway conditions, hotels or contracting agents.


You will be issued your boarding pass the morning of our departure, after your arrival at the Tucson International Airport. If you have an American Airlines frequent flyer number, or a TSA number, please call our office at least 3 days prior to the tour to ensure we can note these in your reservation.

If you are joining the tour from locations other than Tucson, we make other arrangements for you to join the tour. Please call our office for more details.


Do not forget to bring your government issued picture ID to show at the airport. A Driver’s License or Passport is preferred. If you do not have the proper ID, the airline will turn you away.


We have arranged for handling for one piece of luggage per person regarding the skycaps (where available) and hotels. If you check through luggage note that the maximum weight for the checked piece of luggage is 50 pounds and maximum size is 62 inches (length + width + height). If your bag weighs over 50 pounds the airlines will levy an extra fee that you will be responsible to pay. If you feel the need to lock your checked through luggage and your bag is searched, your lock could be damaged in the process. You can purchase a TSA (Transportation Security Administration) accepted and recognized lock at any luggage store. Make sure you ask for a TSA approved lock. These locks are the kind that TSA screeners can open by using a special tool without breaking. Passengers can carry-on 1 bag (dimensions are limited to 10x16x24 inches), plus a personal type bag, like a purse. We advise that you pack your carry-on lightly. There are restrictions regarding your carryon baggage and contents due to enhanced security
measures. Attached find a list regarding commonly asked about items as well as an update. If you have further concerns, please visit the TSA's Web-site at There is room inside the motorcoach for your hand carried bag.


On American Airlines our airline for this tour, passengers are assessed a $25 fee per checked in bag, by the Airlines, upon checking in for the flight.


It is always a good idea to carry on your person a list of medications that you are taking and an emergency contact phone number while you are traveling. And we suggest making a copy of the itinerary and provide it to a friend or family member.


The traditional end-of-tour gratuity to your tour director is not included. If you feel your Tour Director helped you enjoy your tour, we suggest you enclose a gratuity in an envelope and present it individually at the end of the tour. Simply as a guideline, one may consider a per person, per day gratuity of $8.00 per tour guide as an average to be modified by one’s own personal experience. All hotel porterage and airport skycap (when available) fees are included. We also include the gratuities for the coach/livery drivers. Maid tips are not included.


For your convenience, we have a (round-tour) door-to-door pickup service with each multi-day tour. (This service is not available to all clients depending on your location.) Approximately 2 to 3 days prior to the departure date you will receive a call from our office and we will tell you your assigned pickup time. (These times can vary up to 15 minutes depending on traffic.)


If you would like to request special accommodations at the hotel(s) where we are lodging, please call us as soon as possible and we will forward these requests for you. The phone numbers of the hotel(s) where we are staying are listed on the itinerary.

Many hotels around the country have instituted a "reconditioning fee" of $300 or more that is levied upon a guest that smokes in a non-smoking room. If this occurs during our tour you will be responsible for paying this fee to the hotel prior to check-out.


We pay close attention to your requests but please realize that these are merely requests and cannot be guaranteed.


Pleasurebent Tours acts solely as an agent in arranging hotels, transportation, sightseeing, baggage-handling, and other services and does not assume any liability for injury, damage, loss or delay due to any act or default of any company or person. We, along with our subcontractors, reserve the right to make changes to an itinerary if it is necessary for the proper handling of a tour.


The average daytime high temperatures during our tour in Oregon is typically in the mid 70’s to lower 80's and the average night-time temperature is usually in the mid 50's. Please be sure to bring a sweater and/or rain jacket, along with good walking shoes and a hat. There are no dress codes for the areas we take you on this tour. Most patrons at the Shakespeare Festival dress comfortably so they can walk around town or the park before or after the play. Some patrons coming from a nice dinner may be more dressed up, but formal attire is not the norm. There will be opportunities to use swimming pools so you may wish to bring a swimsuit.

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