Arrive in San Francisco, California, pick-up your rental car and take the short drive to Napa Valley, which includes a trip across the famous Golden Gate Bridge. Stop for a photo in front of the iconic bridge at Battery East Vista above Fort Point National Historic Site. Once across the bridge, take the opportunity for a second look at Golden Gate Bridge Vista Point in Sausalito before entering the quaint Mediterranean-inspired town. Stop for lunch and enjoy more spectacular views of San Francisco Bay before continuing onto the town of Napa. In the heart of the wine region, downtown Napa offers a wealth of dining and nightlife options, as well as local arts and craft stores to explore. You can stay here or just outside of town in one of the many fabulous Napa Valley resorts.

Begin your exploration of Napa Valley's fabulous vineyards in Yountville. Throughout this winery-hopping trip, drive if you have a designated driver; alternatively, hire a car and driver, or use ride-hailing apps like Uber or Lyft. Start your day at Domaine Chandon, one of the most beautiful locations for sipping wine in the valley. The lawn and terrace offer natural landscaping, strewn with native oak trees, an ideal environment for relaxing in the sun while enjoying the selection of sparkling wines. Depart Yountville for the short journey to St. Helena, passing such famous wine brands as Cakebread Cellars and Rutherford Estates along the way to V. Sattui Winery. As well as having three tasting rooms, V. Sattui features an artisan deli, offering a charcuterie selection from their own salumeria and more than 200 cheeses. Combine these local delicacies with V. Sattui's wine selection and more than two acres of outdoor space, and you're ready to experience the ultimate Napa Valley picnic. Before you depart, take the opportunity for a self-guided tour, and explore the estate gardens, underground wine cellars and museum caves. After lunch, head back toward Napa for another must-visit for wine connoisseurs, the Opus One Winery in Oakville. Sitting amid lush vineyards and a grassy lawn, the Opus One building rises gradually from the landscape, immersing visitors in the gorgeous setting. Appointments are required to visit Opus One. Options include the Estate Tour & Tasting, Library Tour & Tasting, or a tasting, which includes a 4-ounce pour of the current vintage in the stately partner's room or on the valley-view terrace. Dining options are plentiful in the Napa Valley, but don't miss The Restaurant at Auberge du Soleil, which is renowned as the first fine-dining establishment in Napa Valley and boasts 13 consecutive Michelin Star awards. Local ingredients, spectacular views and an unmatched wine selection combine for a dinner you'll be talking about for years to come.

Begin your second day in Napa Valley at one of wine country's true landmarks, the famous chateau at Domaine Carneros, inspired by the classic 18th century Chateau de la Marquetterie in Champagne, France (home of the legendary Champagne Taittinger). Enjoy a brunch of sparkling wine, caviar and smoked salmon from your private table on the terrace overlooking gardens, a lake and the vineyards. Next, follow the lesser-trafficked Silverado Trail for a tasting at Luna Vineyards. Once again, reservations are required due to the personalized nature of this experience, whether you choose to sit on the wrap-around porch or indoors. Luna Vineyards also has a beautiful tasting room in the Village at Vista Collina. End your Napa Valley experience in vintage-luxury style with dinner aboard the Napa Valley Wine Train. Ride in 100-year-old railcars along a 150-year-old rail corridor on a 36-mile route Napa Valley Wine Train, California from downtown Napa to St. Helena and back, stopping at celebrated Napa Valley wineries along the way. To pair your elegant meal with panoramic views, choose the elevated Vista Dome car featuring special windows that get you closer to the landscape.

Depart Napa along the Silverado Trail, which winds its way northwest to Calistoga, home to famous mineral hot springs and historic mud baths. Visit the Old Faithful Geyser of California or the awe-inspiring Castello di Amorosa, a Tuscan-inspired castle and winery. For a more energetic side trip, get an early start and visit the Robert Louis Stevenson State Park just outside Calistoga. Take the 10-mile, round-trip hike to the summit of Mount St. Helena (a 1,800-foot elevation gain), which offers breathtaking views of Napa Valley, the San Francisco Bay region and even Mount Shasta and Lassen Peak on clear days. This is a strenuous hike, which will take 2.5 hours to summit and another 1.5 hours to descend. Break up the rest of your journey to Redding with a stop at New Clairvaux Vineyard, located in the small town of Vina. The historic vineyard is a unique wine destination: It's home to Trappist-Cistercian monks, an order with a wine-making history that dates back nearly a thousand years. A visit to the tasting room is a must, but the peaceful grounds also include a church, bookstore and chapel. Other areas of the monastery are reserved for overnight stays or available to see on tours only. Once you have checked into your hotel in Redding, fill up on a hearty steak dinner at Cattlemens Steakhouse, a locally owned restaurant serving fresh, hand-cut beef.

A short distance from Redding, you will find Indian Peaks Vineyards in the historic town of Manton. Visit the tasting room to sample the winery's full selection of wines, finishing with a dark chocolate truffle and signature "Donna's Dessert" wine. Lunch is also available most weekends. Time your summertime visit with a Friday or Saturday evening for live music and s'mores. Head back into Redding for a visit to Moseley Family Cellars, where you can both taste and learn about the wines. They'll tailor the tasting experience to your level of wine Redding, California knowledge. Make reservations for dinner at Moonstone Bistro, a hidden gem that's focused on using fresh, seasonable, organic, local and sustainable ingredients.

Next, your wine tour route takes you to the beautiful Rogue Valley in the state of Oregon. Your first stop in Oregon will be Ashland, sitting at the base of the Cascade and Siskiyou mountain ranges and home to a vibrant arts scene, which includes the Oregon Shakespeare Festival. Just a short distance from town, visit the Irvine & Roberts Vineyards, open for wine tastings Wednesday through Sunday. Take in the spectacular views of the surrounding valley and mountains from the outdoor terrace, while enjoying pinot noir and chardonnay. Continue north to Paschal Winery, with its hilltop tasting room overlooking pear orchards and the local mountain ranges. Take time to relax over lunch and enjoy a custom tasting of wines, paired with a cheese and charcuterie selection.

Continue to explore the beautiful Rogue Valley with a visit to Del Rio Vineyard Estate, located just outside small-town Gold Hill on the Rogue River. Its tasting room is situated in a historic hotel and includes an outdoor picnic area with vineyard views. Take a quirky side trip before heading back to Grants Pass to visit the House of Mystery at the Oregon Vortex. The house is situated on what is rumored to be a sort of "whirlpool of force." It will have you questioning everything you see, maybe even your own height. Back in Grants Pass, enjoy a tasting and lunch at Schmidt Family Vineyards in the warm, elegant tasting rooms. The food is prepared fresh and incorporates seasonal ingredients from the winery's gardens. Take time to savor a wine pairing from a selection of red, white, rose and dessert wines. After lunch, visit the fully-organic Wooldridge Creek Vineyard, Winery, Creamery & Charcuterie overlooking the Applegate River Valley. Sip hand-crafted wines while snacking on cheeses and cured meats, all produced on site. There's seating for every season too, whether in the gardens and patio, under the shade of trees or close to the fire. The farm is also home to dwarf goats, chickens, a mini donkey and a mini horse, among other pets. A great dinner choice is River's Edge Restaurant, located on the banks of the Rogue River and offering a menu of locally sourced ingredients. Arrive just before sunset and watch the sun go down over the river and surrounding hills.

Take a detour from wine tastings to visit Crater Lake National Park. Formed by a volcanic eruption and eventual collapse of the volcano more than 7,000 years ago, Crater Lake is the deepest lake in the USA and one of the deepest in the world. The strikingly blue, pristine mountain lake is well worth the detour. Rejoin your wine trail in the Umpqua Valley, and stop at Abacela Winery in Roseburg, which offers unique wines that include tempranillo, albarino and blanco dulce varietals, as well as delicious small plates served in a spectacular tasting room with gorgeous views. If the weather permits, do not miss touring the vineyards. Continue your journey north to Eugene, located at the south end of the Willamette Valley on the banks of the Willamette River. This picturesque, lively city offers a mix of arts, culture, outdoors and dining. For an exceptional culinary experience, have dinner at Grit, located in the historic Shamrock House with a menu inspired by local produce.

Eugene has a diverse collection of wineries, and your day should begin with a visit to Silvan Ridge Winery, popular for its exquisite Willamette Valley pinot noir and pinot gris, as well as other micro-production varietals from the Rogue Valley. The property includes a photo-worthy clock tower and amphitheater, with tastings on the patio or around the indoor fireplace. A short trip from Silvan Ridge is Sarver Winery, which produces small lot runs of regional wines including pinot noir, pinot gris and chardonnay. Enjoy a tasting with gourmet cheeses, spreads, salamis and fresh baked breads, while taking in the spectacular surrounding valley. Head back to Eugene and explore the 5th Street Public Market and its locally owned stores and eateries. For a culture break, visit the Museum of Natural and Cultural History or the Jordan Schnitzer Museum of Art before taking the 30-minute trip to King Estate Winery for dinner. One of the largest organic vineyards in the world, this beautiful estate also has 30 acres of organic gardens and orchards, including a full acre of lavender. Arrive early to enjoy a tour and tasting before dinner. The stately on-site restaurant is focused on pairing local wines with local ingredients. The gourmet menu features vegetables, fruits, herbs and flowers grown on property. It's a truly memorable dining experience overlooking equally remarkable scenery.

Just north of Eugene in Junction City, you will find Pfeiffer Winery, a boutique winery and tasting room, specializing in small lots of high-end pinot noir and pinot gris that are only sold at the winery. If you are lucky, you might be able to listen as the winemaker discusses the varietals in his informal "Pinot Clinic." The winery offers tasting experiences in its cozy Italian grotto-inspired tasting room, as well as in its water garden and tiki bar. A short distance away is Walnut Ridge Vineyard, housed in a unique French Colonial-style tasting room that features reclaimed timbers, gas lamps and a wood-burning fireplace. Enjoy wine and small plates on indoor or outdoor seating areas in the heart of the vineyard amid breath-taking vistas of the Cascade and Oregon Coast mountains. Continue into the heart of the Willamette Valley to Newberg for dinner at The Painted Lady, a charming farm-to-table fine dining restaurant that's tucked away in a Victorian house in a quiet neighborhood just steps from downtown. After a day of traveling, you'll appreciate the prix fixe menu focused on fresh and local meats, seafood, organic vegetables and award-winning wines, all served in the polished yet homey dining room.

Your Willamette Valley tour continues in Dundee at Erath Winery, one of the pioneers of the Willamette Valley wine scene and a leading producer of pinot noir for more than 40 years. A tasting at Erath brings classic Oregon pinots together with views of the surrounding Jory Hills. For a tasty and laid-back lunch break, visit Red Hills Market, also in Dundee. Here, you might meet local farmers, chefs and winemakers as you browse goods from local farms and vineyards. The market is also a restaurant offering a locally sourced, hand-crafted menu; eat in or take out for a picnic at your next winery (just make sure the winery accepts outside food). Across the street from Red Hills Market is the Argyle Tasting House, where you can enjoy intimate indoor or outdoor tastings of sparkling wine, riesling, chardonnay or pinot noir selections. Another nearby winery is The Four Graces, named after the original founders' daughters whose names encircle the capsules on some of the wines they offer. Their son Nicholas is known as the "Keeper of the Four Graces," and his name appears on the Dundee Hills Reserve pinot noir. The quaint tasting room is a historical farmhouse on the Foley Family Estate. Visitors can stroll through the demonstration vineyard and bring a picnic to enjoy with Four Graces wines. In the evening, take a short drive to Dayton to dine at Joel Palmer House, named for its location in the historic home built by Joel Palmer, who co-founded the town of Dayton in 1848. The menu is focused around wild mushrooms and truffles, which are gathered by restaurant staff and incorporated into family recipes with other locally raised ingredients. Naturally, the cuisine is complemented by local Oregon wines.

The last leg of your Willamette Valley tour starts at Sokol Blosser Winery just northeast of Dayton. Another of Oregon's pioneering wineries, its founders first planted pinot noir vines on a 5-acre plot in 1971. Today, visitors can enjoy seated tasting experiences in a variety of distinct spaces - luxury or casual, indoor or outdoor - all surrounded by vineyard views. For your final winery experience, visit the Clubhouse at Domaine Serene to enjoy exquisite pinot noir and chardonnay, surrounded by the picturesque vineyards of the Winery Hill Estate. Drop in for a tasting, or schedule an intimate tour in advance. Combine your tasting with a culinary offering, whether a refined pairing experience or a more casual charcuterie board. After lunch, depart the Willamette Valley for big-city Portland, and arrive in time to explore the rich culinary scene, which is renowned for its originality. Housed in a restored industrial building, Olympia Provisions Southeast started as the city's first salumeria but has expanded into a restaurant with an innovative take on rustic Spanish and Mediterranean cooking. Come hungry enough to start your meal with a charcuterie board and end with a plate, such as the fantastic choucroute garnie (dressed cabbage with house-made sausages).

Return your rental car prior to your departure flight.