The Best of Oregon (Private Tour)


Southern & Central Oregon


July 5th - 13th, 2021


From $2900 PP

Spend 8 days with us on an Oregon pickleball adventure, exploring some of the best sights and pickleball this beautiful state has to offer. Each day will be jam-packed with instruction, recreational play with local players, off-court activities, and lots of food!

*Please note this is a private tour. If you are not part of the group, but are interested in joining a similar tour, please contact us at


Purchase your trip:


Trip Details

What’s Included

  • 8 nights at 3-star accommodations with complimentary breakfasts
  • Transportation to/from Eureka (exact location TBA)
  • All meals excluding breakfast on Day 4 and dinner on Day 7
  • All activities including tours, wine tastings, pickleball clinics, local transportation, etc.

What’s Not Included

  • Additional alcoholic beverages outside of organized tastings
  • Travel insurance, medical coverage, etc. 

Group Size  15

Activity Level  7/10


Various (See Below)


Trip instructors


Print Itinerary
Day 1
  • Afternoon private van pickup in Eureka (3:00 PM)
  • Short scenic stroll at Jedediah Smith Redwoods State Park
  • Dinner in Crescent City, CA and brief tour introduction
  • Drive to Grants Pass (2:00 hrs) and check into Weasku Inn
Day 2
  • Homemade breakfast at Weasku Inn
  • Applegate Valley scenic drive (0:30 hrs) to Wooldridge Creek vineyard for tour (pending reopening) with wine and charcuterie lunch
  • Afternoon recreational play with Grants Pass/Ashland/Medford area clubs
  • Dinner at nearby restaurant with local players
Day 3
  • Homemade breakfast at Weasku Inn
  • Morning clinic beginning at 8 AM with Pickleball Trips instructors (2:30 hrs)
  • Check out from accommodation 
  • Lunch at local Grants Pass restaurant
  • Drive to Bend (3:30 hrs) with stop for scenic walk at Diamond Lake
  • Check into Riverhouse on the Deschutes
  • Dinner on the river in downtown Bend
Day 4
  • Breakfast at McKay Cottage
  • Morning visit to Smith Rock State Park
  • Deschutes Brewery tour & tasting
  • Lunch at local restaurant
  • Afternoon recreational play with Bend club members
  • Dinner at Bend brewery with local players
Day 5
  • Breakfast on your own at Riverhouse on the Deschutes
  • Morning clinic beginning at 8 AM with Pickleball Trips instructors (~2:30 hrs)
  • Check out from accommodation 
  • Lunch at local Sisters restaurant
  • Drive to Corvallis (2:15 hrs) with scenic stops along the way
  • Check into Courtyard Corvallis followed by dinner downtown
Day 6
  • Breakfast at Courtyard Corvallis
  • Free morning for relaxing, outdoor activities, or preparing for afternoon event
  • Catered lunch at pickleball courts
  • Half day, friendly round robin with Corvallis/Albany area clubs
  • Dinner at nearby brewery with local players
Day 7
  • Breakfast at Courtyard Corvallis 
  • Check out from accommodation 
  • Drive to Roseburg (2:00 hrs) with scenic stops and lunch along the way
  • Check into Hampton Inn & Suites
  • Afternoon clinic with Pickleball Trips instructors (~3:00 hrs)
  • Dinner on your own in historic downtown Roseburg
Day 8
  • Breakfast at Hampton Inn & Suites 
  • Short morning hike to waterfall and olive farm visit with lunch
  • Afternoon recreational play with Roseburg club members
  • Final dinner with Pickleball Trips group at local winery
Day 9
  • Breakfast at Hampton Inn & Suites
  • Drive to Eureka (4:30 hrs) with a stop for lunch
  • Arrive home around 4:00 PM

Cancellation Policy

60 – 31 Days Prior to Arrival: 20% of the Total Costs
30 – 4 Days Prior to Arrival: 50% of the Total Costs
72 Hours or Less Prior to Arrival: 100% of the Total Costs

Travel Insurance

We strongly encourage all travelers to invest in travel insurance to both minimize your financial risks of traveling and provide you with peace of mind to fully enjoy the your trip. Travel insurance can provide many helpful resources including refunds or assistance for any of the following situations that may arise before or during a trip:

  • You need to cancel your participation on the tour
  • You need to cancel or change a flight
  • Lost baggage during the trip
  • Stolen items during the trip
  • Medical costs during the trip

We suggest you talk to your insurance provider to ask about the travel insurance plans available to you. You can also compare policies online. Here are two well-known travel insurance providers to consider:

Travelex Travel Insurance
Travel Guard
You can also use to compare multiple companies’ plans.