Ultimate Guide to Planning Your Company Retreat to California’s Wine Country

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As VP of Corporate & Group Sales for WineCountry Media – which owns and runs NapaValley.com, Sonoma.com, and WineCountry.com – I’ve helped companies from around the world plan their corporate and group meetings, retreats, and events in California’s Wine Country. And every time, there are important items these companies haven’t thought of before contacting me about their upcoming meeting or retreat.

So I want to share my top 14 considerations a CEO, executive assistant, or event planner should keep in mind when planning a corporate retreat to California’s Wine Country. My private, battle-seasoned checklist for creating a successful Wine Country retreat to earn kudos from your colleagues and make you look like a pro meeting organizer.

Right then: Let’s dig in. Below is the actual questionnaire I use for every new corporate client, one I’ve honed from working with a wide variety of companies and the services they, and their employees, need once they arrive. By the last question, you’ll have a solid grasp of the when, where, what, and how needed to plan your next successful Wine Country team event.


The Questionnaire


#1. What is the purpose of your event?

Of the 10 most common types of company events, it helps to know exactly what category your event falls in, so that the group salespeople at the Wine Country hotels and resorts know how to respond to the RFP (Request For Proposal) accordingly. An executive meeting or employee team training seminar, for example, will most likely be held indoors, often in a window-free meeting room to avoid distractions, whereas a team incentive trip dinner might be held outdoors in a vineyard or in a wine cave. Providing the correct label on your event at the start could prevent multiple problems later.

#2. How large is your group?

Be aware that most Wine Country hotels and resorts consider 10 persons to be the minimum size of a “group.” Any size smaller than this will most likely not get you the benefits of a group booking. If you don’t know the exact size of your party, that’s okay – hotels expect this and will give customers some leeway on unbooked rooms.

Once we know the estimated number in your group, we then match it with the most appropriate Wine Country hotel or resort. Smaller groups tend to match better with small-to-medium-sized properties, and the unique service they provide is often more personal, whereas the large resort properties can save you thousands in transportation costs by having everything your groups wants or needs on-property: restaurants, spas, wine tasting, and even a bowling alley at the Meritage Resort and Spa.

#3. Has your group been to the Wine Country before? If so, where did you stay?

It’s not uncommon for group event coordinators to say they want to stay in Napa Valley, then end up staying in Sonoma County, even when they had no idea that hosting a retreat in Sonoma County was even an option (usually it’s the average Napa Valley hotel room rate that helps convince them). If the client has been to the Wine Country before, then they usually have a clear idea of where they want to host their event. And knowing where they stayed and dined lets us know not to send RFPs to the same venues, unless they specifically request it.

#4. Do you want to stay in Napa Valley or Sonoma County?

About 90% of corporate event clients say they want to host their retreat in Napa Valley, but when Sonoma County is recommended as well, they are usually open to that as an option. What usually determines their final destination is cost: A hotel room in Sonoma County is typically about 30% less than Napa Valley, and most people gasp when they hear the average cost of a summer weekend room rate in Napa Valley.

#5. How many rooms will you need for your group?

This question often elicits laughs. The thought of company executives sharing a hotel room is pretty amusing to executive assistants. But you’d be surprised how often this stumps the person tasked with planning the corporate event. Does the company want to save money by having the team share rooms? Will some of the staff want to bring their partners (or can they)? Next to budget, having a clear idea of how many rooms you’ll need is one of the most important factors of booking a company retreat.

#6. What is your arrival and departure date?

The industry standard answer to this question is to give the arrival date and departure date, in this format: We will be arriving on Wednesday, March 3 and departing on Sunday, March 7. Just saying it’s a 3-day retreat is unclear, and when it comes to booking a $40,000 event, clarity is key. If you don’t know the exact dates your group will be staying, a hotel sales person can only give you an estimate on costs and probably won’t hold a block of rooms for you. It’s not a deal-breaker but having a clear arrival and departure date will make everyone’s job easier.

And FYI, many Wine Country hotels and resorts have 2-night minimums on weekends, so if your corporate retreat ends on a Saturday, you may be charged for Saturday night as well. And because Wine Country is such a popular destination for tourists on weekends, booking your event Sunday through Thursday could save you thousands of dollars.

#7. Is your arrival and departure date flexible?

While it’s helpful to have travel dates set in stone, it’s not crucial. Hotels and resorts often ask if your group event dates are flexible, as they’re sometimes sold out on those specific dates or even just the first or last day. Saying you’re okay with Monday-Tuesday or Tuesday-Wednesday gives the hotel salesperson much more leeway.

#8. What is your estimated budget?

You’d be surprised how often a new group event client doesn’t have an answer to this question, either because they weren’t given a budget, or the corporation is contacting us to determine what their budget should be. Having an estimated budget isn’t crucial but very useful for determining the caliber, timing, and location of a hotel or corporate retreat venue. For an average group event (hotel, meeting space + F&B + A/V, transportation, meals), a minimum of $500 per person per night is a good place to start.

Regarding budgets, a word you’ll want to have in your lexicon is “concessions,” which is hotel lingo for freebies. While we don’t negotiate group rates for you, a hotel or meeting venue will often offer extra concessions for our clients because we work with them so often. In short, booking your corporate event through us will save you money and asking for addition concessions – such as waving the resort fee or Wi-Fi fee – will save you even more money.

#9. What is the ballpark spend on room rates?

If a corporate event client doesn’t have a budget in mind, they almost always have a ballpark idea of how much they want to spend on a room per night. Room rates for groups are typically less than “leisure travel” rates, and Sunday through Thursday rates are almost always far less expensive than weekend rates, as Wine Country is a popular weekend getaway destination.

Knowing how much you’re willing to spend on a hotel room is very helpful in determining which hotels are the best fit for your group. At the low end for summer, expect to pay about $250 per room night in Sonoma County. For a luxury property in Napa Valley during high season, expect to pay about $500 to $600 per room night at a minimum.

#10. Will you need transportation as well?

Again, you’d be surprised at how many people tasked with putting together the company’s group retreat don’t factor in transportation costs, both from the airport and off-sites from the hotel. Very few hotels in the Wine Country have direct shuttle service from the San Francisco and Oakland airports (the Doubletree Sonoma Wine Country is a rare exception), so if you need a ride from the airport or to a winery from your hotel, you’ll need to book a transportation company well in advance. At WineCountry, we’ve partnered with several local transportation companies and will be happy to recommend the best fit for your group.

#11. Will you need meeting space? If yes, what days will you need to reserve meeting space and for how many persons? Will you need audio/video and F&B? Does your group have any other needs?

Almost every corporate or group event needs some sort of meeting space or boardroom, either within a hotel or at a winery. Questions you’ll want to have answers to in advance include: For how many persons? For what period during the day? Will you need food & beverage service? Do you want alcohol served (such as at a winery)? Will you need audio/video equipment? How do you want the tables and chairs arranged? Will you have any breakout sessions?

The typical cost of renting a meeting space varies greatly in Wine Country. We have some hotel partners that often wave their meeting space rental fee (usually if the client agrees to a minimum F&B charge), while others charge four-figure minimums. If you’re going to ask for concessions, the meeting space fee is a good place to start.

#12. Will you need help arranging lunch or dinner?

For most corporate and group events taking place in Napa Valley and Sonoma County, lunch is included in the meeting space F&B charge, either as a box lunch or buffet-style setup either inside the meeting room or in the hallway. If you and your co-workers want to have lunch or dinner away from the hotel , we’re happy to offer recommendations for you (we’re all food snobs here, so we won’t steer you wrong). One popular option is to have a group dinner at a winery, either outside among the vines or in a wine cave, such as the fantastic cave dining experience at the Pine Ridge Vineyards in Napa Valley.

Keep in mind that if the restaurant or winery isn’t within walking distance – one great reason to book a downtown hotel – you’ll probably need to hire a transportation company if you want to travel as a group, which can get pricey. Alternatively, Uber and Lyft are available throughout Wine Country.

#13. Will you need help arranging activities, such as wine tasting?

When in Rome, right? Almost every corporate and group event that we help plan includes a visit to one or more wineries for a tasting experience and recommending wineries is our specialty. As with dining at an off-site restaurant, keep in mind that if the winery you want to visit isn’t within walking distance, you’ll probably need to hire a transportation company or ride sharing service. And although you may just be tasting wine via little sips, you’d be surprised how quickly your blood-alcohol level can build up beyond .08%.

#14. Are you interested in doing other activities besides wine tasting, such as team building cooking competitions?

Along with wine tasting, there are dozens of other activities available in Wine Country that we can help arrange for your group event, everything from Sip-n-Cycle bicycle tours to gourmet food and wine tours, team building events (cooking competitions are really popular), wine blending lessons, and vineyard walking tours. To view a wide range of fun Wine Country activities for your group, check out WineCountry Experiences.


If you’ve made it to the end of this article, congratulations! You now have all the answers to host a fun and fruitful corporate or group event in California’s Wine Country. The next step is to give me a call at (415)518-1402,or email me at matt@winecountry.com. I’ll not only help you find the ideal venues for your next corporate event or team event, I’ll put you in touch with the right person you need to talk to – and probably help save you money as well.

Lastly, did I mention that our Recommendation & Referral Service is free? We earn a small commission from our hotel partners on the room fee, but it’s the hotel that covers that cost, not you. So there’s really no reason not to use our Recommendation & Referral Service for corporate and group events to Napa Valley and Sonoma County.


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Author

Matthew Poole

Before joining the team at WineCountry Media as VP of Group Sales, Matthew Poole was a bestselling travel journalist, writing and contributing to more than two dozen travel guides for California, Hawaii, and abroad. He also served as Executive Editor at WineShopper.com and Editor in Chief at BBQ.COM and founded the online travel company LocalGetaways.com. You can reach Matthew at matt@winecountry.com.

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