For the days you'll retell.
Weddings, birthdays, slow afternoons in the vines — every booking is one party, one car, and a route shaped around your day.
The entrance. The exit. The photograph on the mantel.
There is a moment at every wedding when everyone turns to look. Make it the one where a red Cadillac rolls up the winery drive, chrome catching the light, and you step out onto the gravel in front of everyone you love.
How we choreograph your day
- Grand arrival — pickup from your hotel or getting-ready suite, timed to your coordinator's run sheet.
- Portrait window — the car parked where the light is best; your photographer gets 20–30 minutes with it, top down.
- Getaway exit — a slow lap of the drive while guests wave sparklers (ribbons and a “Just Married” plate on request).
- Coordinator-friendly — we liaise directly with your venue and planner on timing and access.
The last ride before the big day.
Forget the party bus. Roll up to the winery in a gleaming '69 convertible, sash and sunglasses on, with the whole crew in the frame for the photo everyone will post.
- Seats the crew — six including your chauffeur; up to five friends top down.
- Custom winery route — we plan the stops, confirm group policies and time the sunset photo stop.
- Everyone tastes — your chauffeur drives, so nobody draws the short straw.
- Decor on request — a sash-ready look, a sign or a playlist; ask your host when you book.
VIP treatment, 1969 style.
Turning 30, 50 or 80? Proposing on a hilltop? Welcoming a client team into wine country? Arrive like the occasion deserves.
Milestone birthdays
A surprise curbside pickup, their favorite songs from the year they were born, and a route past the places that matter to them.
Proposals & anniversaries
We'll know the quiet overlook, time the sunset and keep the ring a secret from the passenger seat.
Corporate & VIP
Executive arrivals, client wine-country afternoons and team-offsite showpieces.
Custom routes
Tell us the stops; we build the itinerary, book tasting rooms and plan photo pull-offs along the way.
An hour of sunset, or a whole day of vines.
Chauffeured time is $325 an hour with a three-hour minimum. Most couples book three hours; most groups of four book four to five hours for three tasting stops.
| Sunset Stroll | Vineyard Tour | Grand Tour | |
|---|---|---|---|
| Best for | Couples, proposals, a sunset photo cruise | Small groups, 2–3 winery tastings | A full wine-country day with lunch |
| Duration | 3 hours | 4–5 hours | 8 hours |
| Typical stops | 1 scenic overlook or a single tasting | 2–3 wineries on one trail | 3–4 wineries + lunch + Old Town |
| Route planning | Signature loop | Custom route on one wine trail | Fully bespoke itinerary |
| Est. at $325/hr | $975 | $1,300–$1,625 | $2,600 |
A day on the trail
Meet the car at 11. Coffee-fresh roads past rows of Syrah and Viognier. A first tasting on a terrace looking south over the valley; a long lunch under oaks; a second and third pour as the light turns gold. Back by 7, sun-kissed and very slightly sentimental.
Read the wine-tour guideA picture car with real presence.
Engagement sessions, fashion editorials, music videos, period film and brand campaigns — the '69 brings instant cinematic weight to any frame.
- Book as a DriveShare Event rental: $1,200/day, 3-hour minimum, non-driving
- The host delivers and positions the car on set
- Top up or down between setups; doors open for interior shots
- Owner liability and physical damage protection through DriveShare
Every occasion begins with a date.
Share yours and we'll confirm availability and a suggested itinerary the same day.