Oregon Wine Country Tour

On Cloud Wine is Travelex International’s newest collection of luxury wine and culinary journeys, thoughtfully designed for travelers who savor exceptional wines, remarkable cuisine, and unforgettable destinations.

From the rolling vineyards of Oregon’s Willamette Valley to the legendary wine regions of Europe and beyond, each journey blends luxury accommodations, curated tastings, authentic local experiences, and the beauty of wine country.

Whether you’re a seasoned wine enthusiast or simply enjoy discovering new destinations through food and wine, On Cloud Wine invites you to travel beautifully—one extraordinary vintage at a time.

Discover the beauty, flavors, and elegance of Oregon’s celebrated Willamette Valley.

Our inaugural On Cloud Wine journey invites you to experience one of the country’s premier wine regions, where award-winning vineyards, exceptional cuisine, and luxury accommodations come together for an unforgettable escape.

March 19–23, 2027
5 Days • Luxury Wine Journey

Designed for travelers who appreciate thoughtfully curated experiences, outstanding wines, and the perfect blend of relaxation and discovery.

🏨 Stay at the award-winning The Allison Inn & Spa

🍷 Explore Oregon’s renowned Willamette Valley wine country

🍽️ Savor exceptional regional cuisine and thoughtfully curated culinary experiences

🌿 Relax among breathtaking vineyard landscapes

🥂 Enjoy an intimate group experience with fellow wine enthusiasts

✨ Create unforgettable memories in one of the world’s most beautiful wine destinations

👤 Escorted by one Travelex International Staff Member

• Roundtrip Economy Airfare from Chicago O’Hare to Portland, OR ** if you wish to upgrade, please let us know **
• Roundtrip Airport Transfers from Portland Airport to The Allison Inn & Spa
• Welcome Dinner
• 4 Nights at a 5-star hotel w/breakfast
• 3 Visits to local vineyards with tastings
• 1 Visit to an Olive Oil Vineyard with a tasting
• 1 Private Cooking Class with wine
• 7 Meals:  4 Breakfasts, 1 Dinner with an optional 2^nd Dinner, 2 Lunches
• All taxes & gratuities

Day 1: March 19, 2027 (Friday)

9:45am – Leave Chicago O’Hare

12:22pm – Arrive in Portland, OR

Project Expedition will transfer all to The Allison Inn & Spa in Newberg, OR

Check into the Hotel

7pm – Welcome Dinner at the Dining Room (in the hotel)

Day 2: March 20, 2027 (Saturday)

7am to 9am – Breakfast in the Jory Restaurant

10am – Pick-up to go to the Eola Amity Hills

The Eola Amity Hills is a small region just south of the Northern Willamette Valley and is up against an independent volcanic chain that runs down the middle of the Willamette valley. An absolutely beautiful region.

Dukes Family Vineyards
The vineyard tasting room and winery are located at the vineyard and private residence of Pat and Jackie Dukes just like at Varnum however this property is STUNNING! The tasting room sits at the bank of a man-made reservoir which originally was Pat’s “Man Cave”. The wines are very thought out and stellar. Their production consists of  Sparkling Bruit, Chardonnay, Rose’ and Pinot Noir, all grown right there at the estate. Pat will be making pizzas that day for lunch too. Actually, they are opening that day specifically for us.

Redridge farms at Durant Vineyards
This property has the only olive mill in the Pacific Northwest. There is a nursery and has great gourmet foods and gift shop too. We will get to tour the olive mill followed by a seated “Blue Glass” olive oil tasting class. Blue Glass is because the oils are sipped from Cobalt Blue glasses. A very fun and interesting session. Then we hit the gift shop and walk the nursery

Dinner on your own

Day 3: March 21, 2027 (Sunday)

8:30am – Breakfast in McMinnville

McMinnville is such a cool little town to visit. 3rd St. which is their “Main St.” is about 10 blocks of tree lined streets with great shopping opportunities and options, wine tasting rooms, restaurants, bars and café’s, an ice cream parlor and benches to just sit and watch the world go by. You can easily spend the better part of the day there.

3pm – Private Cooking Class & Wine Pairing at Folly Of Man Vineyard

Hosted by Heather Ciprani. Heather is an amazing chef and instructor that also knows how to keep the experience fun and memorable

Evening on your own

Day 4: March 22, 2027 (Monday)

7am to 9am – Breakfast in the Jory Restuarant

Visit the Northern Willamette Valley

Elevee’ Vineyards
Owned, operated and hosted by owners France and Tom Fitspatrick. We met Tom when he was head of winemaking at a nearby winery named Alloro Vineyards. When he and his wife France had a couple vintages of their own wine they opened a tasting room in their garden atop the vineyard. Just recently they had the opportunity to purchase an existing vineyard not far at all from theirs. Now they have an official tasting room to host our guests.

Moffett Vineyards
Trent is probably one of our favorite people in the Willamette Valley. He grew up in the Napa Valley planting vineyards with his Dad when he was 9 years old. He now lives in Oregon and produces very expressive Burgundian Varietal wines. He pours wines he thinks are showing best at the time and he is doing a blending class with you.

Optional Farewell Dinner at a Local Restaurant – to be determined

Day 5: March 23, 2027 (Tuesday)

7am to 9am – Breakfast at the Jory Restaurant

10am – Transfer to Portland Airport

Flight to Chicago O’Hare Airport at 1:12pm

Arrive in Chicago at 7:35pm

Travelex International Code of Safety
The physical level for our tours is considered moderate: Participants must be able to stand and walk unassisted for 45 minutes on average, often over uneven pavement. Participants must be able to climb stairs, get on and off a motor coach unassisted, and carry your own luggage if needed.

Guests must advise Travelex International at time of booking of any physical, medical, or other special needs that require an accommodation or special assistance, for which we may be able to make a modification. Please call us if you have concerns regarding participation.

NOTE: The American with Disabilities Act is inapplicable outside of the United States. Facilities outside the United States for disabilities may be limited. 

Travelex International reserves the right to dismiss any traveler (at his/her own expense) who does not meet the physical standards outlined or engages in any unsatisfactory behavior that may considered abusive, offensive, or dangerous toward themselves or to any other participant on the tour.