California Wine Country Luxury

Today you’ll enjoy the rustic simplicity of tranquil byways over Chalk Hill and through the Alexander Valley. You’ll head south, circumnavigating Healdsburg, beneath a horizon of endless vineyards. Along this stretch of road you'll see the grapes, smell the fermentation, and almost taste the wine. You’ll pass many unique and distinctive wineries that will tempt you for a visit on our way to the suggested lunch stop of Jimtown Store, a Sonoma County Landmark with some of the best sandwiches west of the Mississippi! If you’re feeling up for a challenge after lunch, Pine Flat Road is just around the corner. This 11-mile climb entertains local cyclists and pros alike with a challenging climb that's rewarded with views of the surrounding valleys. If it's not for you, take a shorter option to town and enjoy our charming accommodations. Or, wandering the town plaza of Healdsburg is a must, with its small-town charm and historic appeal. Or simply enjoy an afternoon glass of wine at the hotel. Tonight you'll gather with your fellow travelers for an incredible Californian farm-to-table feast at our local favorite restaurant, Chalkboard. It is here that the farm culture of Sonoma comes to life and is embodied in fresh, local savory foods that make this area second-to-none.

Featured meal:

Dine at Chalkboard

Chalkboard’s Chef Shane McAnelly creates refined family-style dishes with whimsical touches for a comforting and charming dining experience. Drawing from local producers such as Snake River Farms and the restaurant’s own Chalk Hill Winery gardens, dishes change daily and provide the freshest ingredients one can find, oftentimes picked that very morning. Start with mouthwatering bites of maple-glazed pork belly biscuits; or, if you’re in the mood for something lighter, the yellowfin crudo offers a zesty, citrusy alternative. Gluten-lovers shouldn’t miss out on the freshly homemade pasta, from classic linguine to short rib radiatore, and vegetarians will enjoy the abundance of garden veggies creatively accessorized with puffed rice, Calabrian chile, sorrel, green garlic, or Asian pears. With a little something for everyone, enjoy your first round of drinks on Trek Travel and savor the unmistakable terroir of Healdsburg’s own wine country.

This morning offers a great opportunity for a walk over to our guide favorite, Flying Goat Coffee. Sit and enjoy a macchiato and watch the square come alive before strolling back to the hotel for our ride start. Today we ride through the Russian River Valley, known for its tantalizing Pinot Noir on our way to Armstrong State Natural Reserve. Avid riders can push their legs by tackling the toughest climb of the week, Sweetwater Springs, with grades reaching 20%. There is also a gentler ride to Armstrong Woods Park via Westside Road. Once you’ve arrived stop and admire the majestic towering redwoods and enjoy a hike to visit the oldest (1,400 years old), or the tallest (310 feet high) trees in the park. Lunch is on your own today in the town of Guerneville, or stop off at Korbel's on-site gourmet deli. You may even choose to cleanse the palate with a little bubbly! Then, choose a shuttle back to our hotel, or venture into Healdsburg for some shopping and a tasting at one of the many winery rooms on the square. If you decide to ride back you’ll have the opportunity to sample at a variety of wineries like Gary Farrell, Porter Creek, or Armida Tonight you are on your own for dinner at one of the many famed restaurants in bustling Healdsburg. Whether it's Italian, French or basic pub fare, Healdsburg has you covered.

Today, you'll make your way out of Healdsburg to Yountville, a charming town well known by foodies for Thomas Keller’s French Laundry, along with a host of incredible high-end foodie establishments. Begin your day with a ride through the beautiful Alexander and Knights' Valleys, home to some of the finest Sauvignon Blanc, Cabernet Sauvignon, Malbec, and Merlot due to the high heat of summer and grapes ripening to their fullest potency. You'll soon crest the hill marking the transition into Napa Valley, before descending into the spa town of Calistoga where you can enjoy lunch on your own with the help of your guides. Choose to hop in the van for a quick ride to our brand-new hotel for 2018, the North Block Hotel, where you can sit under a cabana by the pool or book a massage at the renowned North Block Spa (please pre-book in advance by calling 707 944 8080) or complete your ride down the famed Silverado Trail, home to some of the finest wineries in Napa Valley. Rejoin your newfound friends tonight for dinner at James Beard Award nominee chef Richard Reddington’s Italian-inspired restaurant Redd Wood.

Today’s options are many as you ride out of the Napa and Sonoma Valleys and into less discovered but equally inviting cycling territory—the Pope and Chiles Valleys with its switchbacks, high canyon walls and scrub-brushed hillsides. Enjoy a gourmet Trek Travel picnic lunch with our good friends at Summit Lake Vineyards, a small family-owned winery perched atop Howell Mountain. We've been joining them for lunch and wine for over a decade, and each time we visit, it's a true delight. Heather, the daughter of the bunch, is the vineyard guru serving you some of the most incredible Petite Sirah, Cabernet, and Zinfandel you've ever tasted. Afterward, you can choose to ride or shuttle back to the hotel for a relaxing spa treatment, or to relax by their pool. This evening, you'll dine as a group at one of Thomas Keller's prized restaurants, Ad Hoc. Originally created for showcasing the American comfort food of his childhood, Ad Hoc has become a staple in the "culinary capital" of Napa Valley. Featured as one of Food and Wine magazine’s “25 Places to Try" you'll experience four, family-style courses, changing nightly. It's sure to be a meal you'll never forget.

Take an optional short morning spin along the Ride the Vine Trail to loosen up your legs. If you are not up for a ride, enjoy a peaceful morning at the hotel, strolling over to the famous Bouchon Bakery for a morning snack. Be sure to get there early before the line makes its way out onto the sidewalk! You will say farewell to your guides at 11:00 AM at the North Block Hotel and depart via private shuttle back to San Francisco.