Settle into the heart of Oregon wine country with a two-night stay in a chic downtown Carlton home. With three suites, modern living spaces, and a location just steps from tasting rooms and cafes, it’s the perfect retreat for couples or friends. From there, your wine adventure begins! A private luxury tour for six with NW Wine Shuttle will take you through the rolling vineyards of the Willamette Valley, complete with tastings at Utopia, L’Angolo, and Stoller. Relax, sip, and let your wine concierge handle every detail while you soak up the beauty of one of the world’s most celebrated Pinot Noir regions.

VRBO: Date to be mutually agreed upon. Restrictions apply. Valid December through April. No Holidays and no three-day weekends. Valid for two nights. Six people maximum. L'Angolo: Expires 09/202/2026. Stoller Estate: Does not include gratuity. NW Wine Shuttle: Gratuity is not included. Lunch is not included. Valid 11/01/2025 - 04/30/2026. Booking subject to availability. 6–8 hours of tour time (typically 3–4 winery stops). Pick-up/drop-off in the Portland metro or surrounding area. 

Prepare for an extraordinary night where world-class music, exquisite wine, and culinary artistry blend into one unforgettable experience. //Renowned pianist Michael Allen Harrison will captivate you with an intimate live performance, while acclaimed winemaker Steve O%u2019Neill hosts a once-in-a-lifetime evening unlike any other: // Winemaker as Chef: Indulge in a gourmet meal crafted personally by Steve O%u2019Neill. // Private Vineyard & Barrel Room Tour: Step behind the scenes and discover where the magic begins. // Wine Conversation with Steve: Hear insider stories from the only Oregon winemaker to have three wines on the Top 100 list at once. // Live Music Performance: Michael Allen Harrison sets the perfect soundtrack to the evening. // Take Home a Treasure: A 90+ point bottle of wine, signed by both Steve O%u2019Neill and Michael Allen Harrison. ///This isn%u2019t just dinner...it%u2019s a rare, one-of-a-kind celebration of wine, music, and artistry you%u2019ll remember forever.

To be sold for $250 per person. Location: Kason Winery

Escape to Sunriver for a three-night stay at Bennington Properties’ 9 Sumac Lane, the perfect base for relaxation and adventure. Kick back in style, then head out to explore with a Wanderlust Tour for two and a Family Fun Pass from Alpine Entertainment—guaranteed to keep everyone smiling. Savor the flavors of the region with a $300 dining credit at Rancher Butcher Chef, plus enjoy a Classic Tasting Experience for four at the Stoller Wine Bar in Bend. Whether it’s outdoor exploration, family fun, or simply unwinding with great food and wine, this Sunriver getaway has it all!

Bennington Properties: Excludes: Martin Luther King Weekend, President’s Weekend, Memorial Day Weekend, Oregon Spring Break, June 21 to Labor Day Weekend, Wed-Sat of Thanksgiving Week, and Dec 20 to Jan 7. Expires 11/30/2026. Reservation required. Home includes air conditioning, Pack-N-Play and highchair for your little ones and more. Alpine Entertainment: Some Holiday blackout dates do apply (December 24th -January 1st, and July 4th). Full certificates must be used at one time regardless of the size of the party. Expires: 09/01/2027. Summer attractions are seasonal and only valid when local schools are out in June through Labor Day. Certificate is good for all day wristbands for one day. Ice Skating is seasonal and only valid December 1st through April 1st. Certificate is good for one full skate session. Wanderlust: Tour is for two people. Choose from any Wanderlust Tour half-day adventure, including canoeing, kayaking, volcano tours, cave tours, or snowshoeing in Central Oregon's beautiful natural areas. Expires: 08/13/2026. Not valid for special events. Stoller Estate: Does not include gratuity. 

Start your own private cellar—or elevate the one you already have—with this 30-bottle wine cooler, fully stocked with 36 bottles of premium wine from Oregon and Washington. From bold Willamette Valley Pinots to rich Columbia Valley reds, this collection celebrates the best of the Pacific Northwest. Free delivery and setup are included within 30 miles of Portland—making it as effortless as it is indulgent.

Get ready for the ultimate year of romance and adventure! From soaring high on a hot air balloon ride to savoring dinners, wine experiences, theater nights, Blazer games, and live music—this dazzling collection of date nights, curated by the Play It Forward Board Members, is your ticket to unforgettable memories all year long!

Hot Air Balloon Ride: Flight season runs April through October, Friday through Monday, in addition to Thursdays in August, weather permitting. Reservation required. Expires: 10/01/2026. Reser: Can only be redeemed for selected Reser Presents performances in 2025-2026 Season, opens Sept. 2025. Based on availability. Blackout dates may apply. Tickets must be reserved in advance. MAH Christmas Performance: Dates: Choose from any date from December 13th - December 24th Location: The Old Church - 1422 SW 11th Ave, Portland, OR 97201. Amaterra Winery: Expires 03/13/2026. Portland Spirit: Based on availability. Expires 08/15/2026. Advance reservations required. Not valid for Holidays, Christmas Ship Dinners or Specialty Cruises. Stoller Estate: Does not include gratuity. Portland Center Stage: Seating is subject to availability. Community Giving ticket vouchers may not be redeemed for special engagement performances. They expire at the end of the season on May 17, 2026. Please note we are not able to extend the expiration date of these vouchers. Blazers: Valid for the 2025-2026 Season only. Game to be mutually agreed upon. 

Lakeside Dinner at Mike & Karie Richardon’s - La Casita Grande. An unforgettable evening awaits! Gather with 20 couples for an exclusive lakeside dinner at a stunning private donor home, where elegance meets entertainment in a breathtaking setting. The evening features a tequila collection and guided tasting, offering guests the chance to savor unique and premium selections. To make the night even more magical, renowned pianist and composer Michael Allen Harrison will provide a live performance, adding his signature artistry to this once-in-a-lifetime event. This extraordinary package combines fine dining, exquisite spirits, live music, and a spectacular setting—a truly memorable night of community and celebration.

Cornell Cottage is Cannon Beach magic! This beautifully restored 1915 gem is just a block from the beach and two from downtown. With vintage charm, cozy nooks, a gas fireplace, clawfoot tub, checkerboard floors, and a dreamy outdoor shower, there’s space for everyone—including your four-legged friends. Sleeps up to 10, pet-friendly, with a firepit and separate guest space in the renovated garage for ultimate comfort.

Date to be mutually agreed upon. Blackout dates may apply. 

Grab a buddy and head out with legendary guide Will Kessi for a Spring Chinook Salmon fishing adventure you’ll never forget! From the deck of a 26-foot Willie Nemesis Class boat, you’ll troll the Willamette with herring and spinners in search of the elusive Spring Chinook—at a top-secret spot just a few miles from Scappoose Marina (blindfolds optional). Whether you’re reeling in a trophy fish or just laughing at the “tru-ish” fishing stories, it’s a day full of action and fun.

Licenses and tag not included. Date to be mutually agreed upon. Blackout dates may apply. Expires 09/20/2026.   

Take to the skies with Master Greg Default! Three lucky adventurers will soar above Central Oregon in a Cessna 182/G, experiencing breathtaking aerial views and the thrill of flight. Your 3.5-hour journey departs from Aurora State Airport and includes a celebratory lunch at Pine Street Tavern to toast your adventure. Perfect for friends, family, or anyone craving a unique perspective on Oregon!”

Date to be mutually agreed upon. Weight restrictions may apply.

Pack your bags for five nights in paradise! Emmert Casa #3, a beautifully restored historic beachfront estate, offers sweeping Pacific views, marble floors, and even a private elevator. Wake up in the master suite with floor-to-ceiling ocean views, then savor fresh breakfasts and delicious dinners prepared daily by your longtime private concierge.

Mazatlán House: Date to be mutually agreed upon. Expires: 09/20/2026. Not valid for the weeks of Thanksgiving, Christmas or New Years Day.