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5 Nights in California Wine Country - Napa & Sonoma

Every year a handful of our tribe celebrate the art of itinerary building by spending a week together, discovering or in this case, re-discovering a destination. We call this trip SmartFlyerONE. This year our team spent time in Napa and Sonoma celebrating the wine country way of life, including but not limited to: wining, dining, biking and plenty of spa-ing.


Smartflyer ONE 2017 via Elysium Productions

Trip Notes:

Where to Stay:

Trip Highlights:

  1. Bike riding from Sonoma Valley to Napa Valley with DuVine Cycling.
  2. Beautiful spa experience at Meadowood in Napa.
  3. Private visit to the Promontory winery.
  4. Wine Country fine dining at Farmhouse Inn‘s Michelin starred Restaurant.
  5. Dinner at Single Thread in Healdsburg.
  6. Cooking class at Cavallo Point in Sausalito.
  7. An early morning hot air balloon ride for sweeping views of Napa Valley.

5 night, 6 Day Itinerary:

Cavallo Point Lodge, Sausalito, California
Cavallo Point Lodge, Sausalito, CA

Day 1: Cavallo Point

Morning: Your trip starts the moment you step off the plane and land in San Francisco. You’ll spot a driver with your name and a Cavallo Point sign at meet and greet.

Afternoon: After you’ve checked in and have had time to settle into your accommodations, enjoy beautiful downtown Sausalito, or, simply enjoy the beautiful view of the Golden Gate Bridge from the hotel’s front porch.

Evening: If you’re feeling creative and hungry, join the Cavallo Point Cooking School and later, feast on your beautiful spread.

Farmhouse Inn, Sonoma, California

Day 2: Farmhouse Inn

Morning: You’ll be picked up from Cavallo Point Lodge and make your way to Healdsburg in Sonoma County.

Afternoon: Time for a pit-stop in Healdsburg! Lunch will be at SHED, a market cafe with an ethos in responsible farming, ingredient-driven cooking, and flavorful food (of course). Take your time exploring the market-side of SHED and the town of Healdsburg, your luggage will be delivered to Farmhouse Inn. Check-in to your room at Farmhouse Inn at your leisure.

Who says eating and shopping can’t wear you out? After you’ve checked-in, indulge in the Farmhouse Spa services. The first one to ever coin the term Farm-to-Spa, the beautiful Farmhouse Spa utilizes produce harvested on site, like fresh herbs, spring forest honey, and heirloom cider apples from the ranch.

Evening: Farmhouse Inn is synonymous with their Michelin Star restaurant, enjoy a beautiful dinner at the Restaurant this evening. The food served at the restaurant is sourced from Joe and Catherine’s Bortolomei Ranch or local artisan farmers, the wine program carefully curated and a beautiful mix of the best wines from Napa and Sonoma, and perfectly personal and warm service.

Single Thread, Healdsburg

Day 3: Farmhouse Inn, Single Thread & DuVine

Morning: Get out of bed before the sun and tour the Armstrong Redwoods State Reserve to start your morning right in a custom Mercedes Sprinter convertible van with a panoramic glass roof.

After your leisurely ride, meet your DuVine guides and get fitted for your bike for the week before breakfast. This morning, we’ll take you riding through the Russian River & Dry Creek Loop (34 mile – lollipop loop for full ride / 1400 feet climb.) Join DuVine and cycle through two of Sonoma’s most magical valleys. Follow your guides through the Pinot and Chardonnay vineyards of Westside Road. Quiet back roads open up to dreamy views of the Mayacamas Mountains and you’ll stop for a coffee among acres of vines. After a quick rest, you’ll pedal through the cycling haven of Healdsburg before continuing to one of the best vineyards to enjoy lunch at the beautiful Arista Winery.

Lunch at Arista Winery. Arista’s 36-acre estate is located in the Middle Reach of the Russian River Valley on famed Westside Road just outside the idyllic wine country town of Healdsburg, California. They are ideally suited to grow Pinot Noir and Chardonnay because of the unique and complex soils that blanket the estate and their close proximity to the cooling fog and maritime influence of the Pacific Ocean.

Evening: Dinner at Single Thread Farms. Single Thread Farms is located on five acres between the Russian River and the historic San Lorenzo Ranch in Healdsburg, California. Farmed by Head Farmers Katina Connaughton and brother Vince Rothermund, along with the Single Thread Farm team, the property consists of a greenhouse, shade structures, loamy fields, chicken coops, an heirloom fruit orchard, olive trees, bee hives, and a cattle paddock all surrounded by Cabernet Sauvignon, Zinfandel, and Chardonnay vines. The farm supplies vegetables, fruit, herbs, flowers, honey, eggs, and olive oil to the restaurant kitchen.

Sonoma County, California, DuVine Cycling
Processed with VSCO with c2 preset

Day 4: Meadowood & DuVine

Morning: Breakfast at leisure at Farmhouse Inn followed by another beautiful day hitting the road with DuVine Cycling from Sonoma to Napa. Get ready for this 43 miles bike ride with 1900 feet of climbing. You’ll feel like you’re pedaling back in time as wine country turns to bucolic fields of cattle accompanied by gorgeous views of Mount Saint Helena. Once in Napa, you’ll make your way past world-renowned wineries along the historic Silverado Trail before reaching Meadowood, your final destination.

Note: at anytime guests may choose to take the DuVine transportation rather than bike if they are not able to complete the trip.

Afternoon: Lunch at Davis Estates, Calistoga.  In 2011, the Davis family purchased the century-old estate winery and began their ambitious restoration project to create a distinguished winery. Mike Davis has a long and fond association with the Napa Valley. Growing up in San Mateo County just south of San Francisco, his family spent summer vacations at the Napa Valley Ranch Club. Davis Estates is the culmination of a life long dream. Here the vision is carved from this historic site as an estate winery focused on wines of the highest pedigree.

Evening: Spend the evening at relaxing at your luxurious accommodation at Meadowood or head to Meadowood’s world-class spa to work away those knots from a full morning of biking through the valleys.

Hot Air Balooning in Napa Valley

Day 5: Meadowood

Morning: This morning, your day begins with a hot-air balloon ride over Napa Valley.  After, head back to Meadowood for a leisurely breakfast, don’t forget the delicious english muffins from Model Bakery.

Afternoon: Food Truck Lunch at Clif Family Winery. Their story begins with Gary and Kit’s cycling adventures through Italy where long days of cycling would end in leisurely evenings of good wine, food and hospitality. As great lovers of food, wine and adventure, Gary and Kit sought to bring these memorable experiences to their Napa Valley home with their Clif Family tasting room and Bruschetteria food truck. The organic farm and vineyards located high atop Howell Mountain provide a bounty of grapes, olives, fruit and vegetables to fuel your journey.

After lunch, we head over to the enjoy one of Napa’s most exclusive winery at PromontoryThe legacy of Bill Harlan’s Napa Valley cult-Cabernet continues with his newest release, Promontory. A visionary, Bill Harlan set out to create a legacy within the Napa Valley and within that, produce the region’s version of a first-growth Bordeaux, one that would be come as prestigious and rare as those that wear the name Lafitte or Margaux on their label. And in the 1990s with Harlan Estate, and later BOND, he succeeded. Now, as he passes the torch to the next generation, his son Will is at the helm of Promontory Estate.

Evening: For your last night’s dinner, and to celebrate a beautiful week in Napa and Sonoma, we are spending the evening at The Restaurant at Meadowood.  A modern American restaurant with the mission the cause positive impact in Napa Valley by working exclusively with the area’s artisans, growers, and foragers.

Day 6: Departure

11:00 AM: Time to check-out and head home!

Meadowood Spa, Napa Valley

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