Wine Country by Private Chauffeur from Thousand Oaks

One of the quiet perks of living in Thousand Oaks, Westlake Village or Simi Valley is that two genuinely great wine regions are a day trip away. Go north on the 101 and you reach the Santa Ynez Valley — Los Olivos, Solvang, Ballard Canyon and the Sta. Rita Hills — in a little over two hours. Stay closer and there's the Ventura County wine trail: Ojai, Camarillo and the Oxnard plain, an hour or less from home. The only problem with either is the obvious one: someone has to drive. This guide is about solving that properly.

Why a chauffeur instead of a designated driver

A designated driver means one person in your group tastes nothing and spends the day watching the clock. A rideshare between tasting rooms means waiting in a parking lot in Los Olivos hoping a driver is nearby — they usually aren't. An hourly chauffeur is the version where everyone tastes, nobody navigates, and the SUV is waiting outside each stop with cold water in the cabin and room for the cases you'll inevitably buy. See how hourly chauffeur service is priced: you reserve a block of hours and the vehicle and driver are yours for the day.

Itinerary A: the Santa Ynez Valley classic (10–11 hours)

8:30 a.m. — pickup in Thousand Oaks or Simi Valley. North on the 101 through Ventura and Santa Barbara; the coastal stretch past Carpinteria is the prettiest freeway in the state.
10:45 a.m. — first tasting in Los Olivos, where a dozen tasting rooms sit within a two-block walk. Your chauffeur parks once; you stroll.
12:30 p.m. — lunch in Los Olivos or a short drive to Solvang for its Danish bakeries and a wine-and-charcuterie stop.
2:00 p.m. — an estate winery in Ballard Canyon or along Foxen Canyon Road, where the vineyard views are the point.
3:30 p.m. — a last stop in the Sta. Rita Hills for Pinot Noir and Chardonnay, or a Santa Ynez tasting room on the way back.
5:00 p.m. — depart. Home to the Conejo Valley by 7:15 p.m., cases in the back, nobody counting drinks.

Itinerary B: the Ventura County wine trail (6–7 hours)

10:00 a.m. — pickup. Up the 33 to Ojai for a tasting room in the arcade and a walk down Ojai Avenue.
12:30 p.m. — lunch in Ojai, then down through Ventura to the coast.
2:00 p.m. — Camarillo's wineries and tasting rooms near the Old Town district, followed by a stop on the Oxnard plain.
4:30 p.m. — a sunset stop at Channel Islands Harbor or the Ventura waterfront before the drive home on the 101.

The best wine days are the ones where the drive is part of the pleasure — a quiet cabin, the coast out the window, and nothing to do but decide where to taste next.

Practical details that make the day work

Group size — a luxury black SUV seats up to five comfortably; for six to ten we run two vehicles with the same itinerary.
Reservations — many Santa Ynez estates require tasting reservations, especially on weekends. Book them before you book the car, and share the schedule with us so timing is exact.
Purchases — the cargo area handles several cases; wineries will also ship, and your chauffeur can coordinate pickup times.
Timing — weekday tastings are calmer and cheaper; harvest season (September–October) is the most beautiful and the busiest.
The drive north — Thousand Oaks to Los Olivos is about 2 h 10 min; Simi Valley about 2 h 30 min. Camarillo to Ojai is about 45 min.

Weekend version: stay in Santa Barbara

Many Conejo Valley couples turn the day into a weekend: a chauffeured tasting day on Saturday, a night in Santa Barbara or Montecito, and a return on Sunday. We can structure this as an hourly booking on Saturday and a fixed transfer home on Sunday. Visitors flying into LAX for the same trip can start with our LAX ⇄ Santa Barbara transfer at a fixed $360.75.

Reserve an hourly chauffeur

Occasions we book most often

Birthdays and anniversaries for couples and small groups
Bachelorette and bachelor days in Solvang and Los Olivos
Client entertainment and team outings for Conejo Valley companies — see corporate transportation
Visiting family who want to see the Central Coast without renting a car
Pre- and post-wedding tasting days for guests staying in Santa Barbara — see our wedding transportation guide

How to book a wine-country day

Reserve hourly service through the site with your pickup address, start time and an estimate of hours; add your tasting reservations and we'll confirm the chauffeur, the vehicle and the timeline. Questions about a custom route? Call (805) 660-6439 or email [email protected].

Plan your chauffeured wine day

Good to know

Frequently asked.

How much does a private driver for a Santa Barbara wine tour cost from Thousand Oaks?

Wine-country days are booked as hourly chauffeur service in a luxury black SUV, so the cost depends on the length of your day — a Santa Ynez Valley trip from the Conejo Valley typically runs 9 to 11 hours. Enter your pickup address and start time in the booking search for an instant quote, or call (805) 660-6439 for a custom itinerary.

How far is the Santa Ynez Valley from Thousand Oaks?

Los Olivos and Solvang are roughly 120 miles and about 2 hours 10 minutes from Thousand Oaks via the 101, and about 2 hours 30 minutes from Simi Valley. The Ventura County wine trail — Ojai and Camarillo — is 45 to 60 minutes from the Conejo Valley.

How many people fit in the SUV for a wine tour?

Up to five passengers with room for wine purchases in the cargo area. For groups of six to ten we coordinate two vehicles on the same itinerary.

Do you help plan the winery stops?

We're happy to suggest routes and timing based on the itineraries above, but tasting reservations should be booked directly with the wineries — many Santa Ynez estates require them on weekends. Share your confirmed times with us and your chauffeur will keep the day on schedule.

Book this trip