Having led group wine tours through some of the world's most celebrated regions — the Rhine Valley, Champagne, the Wachau, Willamette Valley, and California's Central Coast — I return to Sonoma because nowhere else marries terroir, tradition, and genuine warmth in quite the same way. This five-day immersion is not a conventional winery hop. It is a considered journey through one of the world's most consequential wine regions, designed for guests who want to taste more deeply, understand more fully, and leave with a perspective they simply cannot acquire from a bottle alone.
From the sweeping mountain vineyards of the Alexander Valley to the fog-kissed reaches of the Russian River, Sonoma's microclimates produce wines of extraordinary range and precision. Over five days we will explore that range with intention — visiting estates that define the region's past and those quietly shaping its future, with exclusive access, private tastings, and the unhurried pace that genuine learning requires.
Every detail has been arranged: private chef dinners paired to the evening's wines, a carefully sequenced tasting education from the very first night, and a base of operations at one of the valley's finest private vineyard estates.
Our group has exclusive use of a premier vineyard estate nestled in the hills above Santa Rosa. Surrounded by working vines, the property offers sweeping views across the Sonoma Valley — the kind of setting that makes every glass taste better. Waking up inside a working vineyard recalibrates your palate before the day even begins, and it is a privilege I build every itinerary around when it is available.
Our table is in exceptional hands. Chef Michael Gomez — Food Network Bite Club winner alongside Tyler Florence, and a multiple-time top-ten finisher at the World Food Championships — prepares dinners each evening that are expressly designed to complement the wines we encountered that day. The pairing is not incidental; it is curated the same night with the same wines in mind. Food of this caliber, at this level of bespoke alignment with the wines, is rare anywhere in the world.
Before a single winery visit, we begin the journey at the table. On arrival evening I lead an introductory tasting and education class tailored to the specific estates and appellations on our itinerary. Having guided hundreds of guests through wine country on four continents, I know that orientation matters — guests who understand what they are looking for experience every subsequent tasting at a fundamentally different level.
The Kendall-Jackson Estate in Fulton is one of Sonoma's most thoughtfully managed properties — its culinary garden a living demonstration of how a winery's philosophy extends from vine to table. We have arranged a private guided tour, a seated estate tasting, and lunch on-property, as well as a special meeting with Culinary Gardener Tucker Taylor. Tucker's work illuminates the connection between soil, season, and flavor in ways that permanently deepen how you think about what is in your glass.
La Crema's home at the historic Saralee's Vineyard in Windsor is among the most important sites in Russian River Pinot Noir history. What makes this stop particularly compelling in 2027 is the estate's active commitment to regenerative farming — a practice I believe represents the most significant shift in quality wine production of the past decade. We receive a guided tour of those practices alongside a tasting that illustrates, glass by glass, what farming philosophy tastes like.
Stonestreet's mountain estate on the Mayacamas Ridge is one of the most dramatic vineyard settings I have visited anywhere in the world — a claim I do not make lightly. We ascend by off-road vehicle with a Stonestreet staff guide, tasting wines poured directly in the vineyard alongside boxed lunches, with the Alexander Valley spread below us. The elevation, the geology, and the wines all tell the same story: mountain fruit from extreme sites is in a category of its own.
Copain is the kind of winery that rarely appears on commercial tour circuits precisely because of its scale. Small-production, Rhône-and-Burgundy-inspired, and deeply focused — this is the sort of discovery that changes what a guest expects from California wine. The intimate tour and tasting here offers the kind of candid, unhurried conversation with winemaking philosophy that larger estates simply cannot replicate.
Set amid lavender fields in the Bennett Valley, Matanzas Creek is one of Sonoma's most serene properties. We take lunch on the grounds — with a friendly game of bocce ball — before an in-depth tasting and educator session led by one of Jackson Family Wines' specialists. This is not a standard pour-and-talk format; it is a structured educational experience designed to consolidate everything encountered across the trip into a coherent understanding of Sonoma's winemaking tapestry.
Hartford Court's Pinot Noirs and Chardonnays from the Sonoma Coast and Russian River Valley represent some of California's finest cool-climate expressions — a guided tour here is genuinely illuminating. On the return from day two, Siduri's Healdsburg tasting room offers a relaxed, unhurried stop for more Russian River exploration. And on the final afternoon, we make an unapologetic pilgrimage to Russian River Brewing Company in Santa Rosa — because after three days of immaculate wine, there is nothing quite like a pint of Pliny the Elder among friends.
Solo travelers are routinely penalized in group travel with a supplement charge that can add hundreds of dollars to a trip's cost. I have always found this arrangement unfair, and I do not practice it. Every guest on this journey pays the same rate and receives their own room. Traveling solo should be an uncomplicated pleasure — and here, it is exactly that.
This journey goes well beyond the glass. It offers a deeper understanding of why Sonoma stands among the world's most important wine regions — one that will stay with you long after the last pour.
— Jan, Tour Sommelier and HostOur home for the week is a private estate perched above the Santa Rosa plain, surrounded by the vines that give Paradise Ridge its name. There is something quietly transformative about spending five nights inside a working vineyard — the rhythms of the estate become part of the experience itself.
An exclusive-use private property providing accommodation for the full group of 10 guests. Every guest has their own room — no single supplement, no room-sharing unless desired.
Located in the hills above Santa Rosa, the estate sits within Sonoma's premium wine-growing corridor, placing us minutes from the region's most celebrated appellations while offering the seclusion that makes true relaxation possible.
Chef Gomez brings a competition-grade pedigree to a deeply personal style of cooking. A Food Network Bite Club champion — winning alongside Tyler Florence — and a multiple-time top-ten finisher at the World Food Championships, he prepares dinners each evening that are crafted specifically around the wines tasted that day. His cuisine honors the produce of Sonoma's extraordinary agricultural landscape, creating pairings that feel inevitable rather than contrived.
There is no single supplement on this journey. Solo travelers pay exactly the same rate as everyone else and receive their own room. This is a deliberate policy — one I believe makes group travel what it should be: inclusive, uncomplicated, and equally welcoming of guests traveling alone or with a companion.
Please note: Itinerary is subject to change. All times are approximate.
Settle in, take in the views, and meet your fellow travelers at leisure.
An introductory tasting session led by Jan over dinner, calibrating the group's palates and setting the context for the days ahead. We cover the region's key appellations, varietals, and what to look for at each estate on our itinerary. This evening lays the intellectual foundation that elevates every subsequent experience.
A full breakfast on the estate before the first full day of tasting.
A private estate and garden tour, followed by a seated tasting and lunch on property. The highlight is a personal meet-and-greet with Culinary Gardener Tucker Taylor, whose work connecting Sonoma's soil to the estate's kitchen offers an irreplaceable perspective on wine and food as expressions of a single place.
A guided regenerative farming experience at the historic Saralee's Vineyard — one of the Russian River Valley's most storied sites — followed by a tasting that contextualizes La Crema's coastal Pinot Noir and Chardonnay program. Understanding the farming philosophy here changes what you taste in the glass.
Return to the estate for complimentary wine and snacks on the grounds, followed by Chef Gomez's first paired dinner of the trip.
A brief stop for exceptional coffee and freshly baked pastries before ascending into the mountains. The right start to a demanding day.
We ascend the Mayacamas Ridge by off-road vehicle with a Stonestreet guide, reaching elevations and vineyard blocks that are inaccessible by conventional transport. Wines are poured in the vineyard itself, alongside boxed lunches, against views of the Alexander Valley that are nothing short of extraordinary. Mountain-grown Cabernet Sauvignon from sites like this requires no further argument for the significance of altitude and volcanic soil.
One of the most intimate and intellectually rewarding stops on the itinerary. Copain's small-production, Old World-influenced approach to Sonoma fruit — Syrah, Pinot Noir, Chardonnay — is a compelling argument for restraint and precision in California winemaking. The tour and tasting here are unhurried and candid.
A relaxed, low-key tasting stop at Siduri's Healdsburg room on the way south. Siduri's single-vineyard Pinot Noirs from across the West Coast are consistently among California's most expressive — a perfect wind-down after the intensity of Stonestreet and Copain.
Hartford Court's Sonoma Coast and Russian River Valley Pinot Noirs and Chardonnays represent some of the finest cool-climate expressions in California. The guided tour and tasting here provide essential context for understanding how marine influence from the Pacific Ocean shapes the character of Sonoma's westernmost appellations — wines of tension, salinity, and remarkable length.
Lunch is served among Matanzas Creek's famous lavender gardens — one of Sonoma's most quietly spectacular settings — with a game of bocce ball before the afternoon's program. We then move into a structured tasting and educator session with one of the Jackson Family Wines specialists, offering a synthesizing perspective on the varietals and appellations encountered across the week. This session is designed to leave guests with a coherent and lasting framework for understanding Sonoma wine.
A deliberate and entirely necessary detour. Russian River Brewing is one of the most acclaimed craft breweries in the United States — home of the legendary Pliny the Elder and Pliny the Younger double and triple IPAs. After three days of meticulous wine tasting, a casual pint here is both a palate reset and a celebration. It is always one of the most talked-about stops of the week.
Wine, snacks, and a festive farewell dinner celebrating a spectacular week in Sonoma wine country. The table will have earned every glass.
A final morning meal together at the estate before guests depart. The vines will still be there. The memories — and the wines you carry home — will last considerably longer.
Space is limited to 10 guests.