It’s the most wonderful time of the year … or is it? Winter holidays often mean some sort of staff-wide celebration—be it a luncheon, gift-giving session or cocktail hour. And while these events are intended to boost morale and spread holiday cheer, they can quickly wind up a disaster if not carefully thought out and budgeted.

With Southwest Florida operating at full-steam in winter season, you may find yourself fighting for space at a popular venue or restaurant. And if you wait too long (read: procrastinate) it can leave your company party-less and you seeming like the Grinch who stole the office bash.

Anxiety kicking in already? No need. Gulfshore Business has put together a guide to help make the party planning process easier. We’ve highlighted a few venue types and asked experts some plaguing questions— Should you serve alcohol? What’s an appropriate gathering time? Should employees invite a guest?

During the legwork, we also found that most places have sufficient spots to incorporate groups ranging from small to large and weekend parties are on the rise.

Read on to see what else we’ve discovered, then take a deep breath and relax. Because when it’s time to celebrate this year, you can already have a plan in place.

Dinner Is Served

Holding a corporate holiday gathering in a restaurant is a low-stress way to get everyone together. “Everything you need to make your party a success is already provided— food, alcohol, privacy and entertainment,” says JoNese Bird, sales manager at Seasons 52 in Naples.

Each restaurant is different in its offerings (private rooms at Seasons include audio/visual projector, where companies can choose to display banners or stream videos, and guests are treated to complimentary valet parking) and can often honor requests within reason.

“I assist my guests with all the details of planning their event from start to finish,” Bird says. That can mean dressing tables with a certain color tablecloth or putting out party favors that are supplied in advance.

Restaurants may also include preset menus featuring three-to-five courses, making ordering easier on the guests and spending easier on the host’s wallet. Alcohol may not be included in some fixed menus, so Bird suggests employers plan ahead. “I always recommend that the host pre-selects the wine—one red and one white— to be served,” she says. “This helps control cost.”

Fine dining restaurants may have multiple rooms ranging in capacity and privacy levels. It’s best to inquire online or with a sales manager for which venue is most fitting for the event.

WHEN TO BOOK A RESTAURANT: At least 30 days in advance
BEST TIME OF DAY FOR THE PARTY: Before 6 p.m. or after 8 p.m.
BEST DAY OF THE WEEK: Monday through Wednesday for increased availability; Thursday through Sunday for popularity
RESERVATION PRICE: Most of the time none, but spending minimums may apply
BEST FOR: Small to mid-size companies
APPROPRIATE TO SERVE ALCOHOL: Yes
COMMON TO INVITE A GUEST: No
PRIVACY LEVEL: Moderate to complete
BONUS TIP: For large corporations of 80 or more, ask the restaurant of choice if it can be completely rented out. “Most restaurants have a buyout price. If a company wanted to bring their entire business to a location, a restaurant most always has a price that you could do so,” Bird says. Make those calls at least 90 days in advance.

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Have a Ball(room)

Consider holding more formal gatherings within a hotel. Similar to a restaurant, in-house dining services are available and rooms vary in size and style, including outdoor options. And many resorts have an entire event team. “Our onsite professional event team—which includes world-class ‘culinarians’ as well as experts in décor, floral design, event technology and event planning— makes it possible for us to plan with as little as 24-hour’s notice,” says Claudia Valdes, catering sales manager at The Ritz Carlton Resorts of Naples. But venues fill up fast, so Valdes says the sooner you book the better. Guests at the Ritz and similar resorts can choose from grand ballrooms with bright natural light or outdoor locations overlooking golf courses or waterways. Each room is unique in its appeal.

Décor can range from traditional to contemporary or elegant to playful. Incorporating a specific theme for a holiday party is doable, but Valdes says it’s a seasonal menu and overall welcoming atmosphere that’s emphasized in such places.

A perk to celebrating with staff at a resort is the possibility of discounts and deals. Valdes says The Ritz-Carlton Resorts of Naples waive venue fees for all corporate holiday parties.

WHEN TO BOOK A BALLROOM: 4-6 months in advance
BEST TIME OF DAY FOR THE PARTY: Noon for luncheons, after 6 p.m. for dinner
BEST DAY OF THE WEEK: Friday or Saturday
RESERVATION PRICE: Varies. Deals and discounts may apply.
BEST FOR: Small to large companies
APPROPRIATE TO SERVE ALCOHOL: Yes
COMMON TO INVITE A GUEST: Yes
PRIVACY LEVEL: Moderate to complete
BONUS TIP: The varied sizes of venues are fitting for most any size company. The Ritz-Carlton Resorts of Naples, for instance, can hold 20 to 200 guests.

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Breaking Tradition

For a place where employees can really let loose, try thinking outside of the box-shaped dining table and select a venue with an activity or distinctive visual appeal.

Guests can surround themselves around sleek motorcycles at Six Bends Harley-Davidson in Fort Myers. “There’s a certain ‘cool factor’ with any event held on the same site as a brand new Harley-Davidson store,” says Jeff Hickcox, director of event programming at Six Bends. “It’s definitely a unique setting.”

The location includes multiple other venues, including the Top Rocker Lounge, which doubles as the prevent room for celebrity performers who play concerts onsite. Its lounge has a built-in bar and access to a full catering kitchen.

Another option is to ditch the ties and heels and blow off steam at an arcade, amusement park or golfing range, such as Alico Family Golf in Fort Myers, which comprises mini golf courses, a sports café and large patio area.

WHEN TO BOOK AN ENTERTAINMENT VENUE: 30 days in advance for private parties, 4-6 months in advance for larger events.
BEST TIME OF DAY FOR THE PARTY: Afternoon or evening
BEST DAY OF THE WEEK: Friday or Saturday
RESERVATION PRICE: Varies. Six Bends, for example, ranges from $500 to $4,500.
BEST FOR: Small to large companies
APPROPRIATE TO SERVE ALCOHOL: Yes
COMMON TO INVITE A GUEST: Sometimes
PRIVACY LEVEL: Semi to complete
BONUS TIP: Unexpected venues like those at Six Bends can serve as conversation starters for staff members who don’t usually connect. Games at activity-based venues can help with team building and provide “a physical activity that promotes a health state of enjoyment, competition and personal satisfaction,” says Alico Family Golf instructor Kraig Feighery.

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On the Job

To some, the definition of fuss-free is keeping things as casual as possible. By holding a party in-office, attendees needn’t fret about dressing up or driving, and you can skip the headache of researching and reserving space. Best of all, it’s easy to control cost.

Keep fees to a minimum by holding a potluck, as the law firm of Henderson, Franklin, Starnes & Holt, P.A. commonly does. “The firm will provide the meat, turkey or ham, and attorneys will bring in side dishes,” says Suzanne Boy, attorney at the firm and president of the Society of Human Resource Management, Southwest Florida chapter. But be mindful of staff-wide dietary needs.

Office celebrations don’t need to be restricted to a certain time, Boy says. Depending on the length of festivities, you can plan any meal of the day in-house. But only include alcohol for parties late in the day.

If convenience is a concern over cost, hiring a caterer eliminates the need for buying or baking. Evelyn Cannata, general manager at Windsor Office Suites, suggests securing a chef no later than the second week of November.

Keep in mind that a large amount of eats in the office can get messy (and be daunting to clean up). To eliminate the aftermath but keep with the in-office feeling, consider reserving a similar space. Windsor provides rentable office suites for a range of company sizes.

WHEN TO BOOK: Give employees about two weeks lead-time.
BEST TIME OF DAY FOR THE PARTY: During office hours; 5-7 p.m. for cocktails, 5:30-8:30 p.m. for heavier meals.
BEST DAY OF THE WEEK: Thursday or Friday
RESERVATION PRICE: Varies. Four hours with a caterer at Windsor costs an average of $200.
BEST FOR: Small to mid-size companies
APPROPRIATE TO SERVE ALCOHOL: Only in the evening
COMMON TO INVITE A GUEST: No
PRIVACY LEVEL: Complete
BONUS TIP: If supplying alcohol, stick to beer and wine. Boy suggests handing out drink tickets to control consumption and ensure safety.

Options Aplenty

If a party just isn’t in the budget this year, there are more ways of spreading holiday cheer. Gift giving is a fun way to show endearment, but Boy says to keep presents even. “The important thing is to be fair and give as equally as possible across the board,” she says. “It would create more harm than good if certain employees were given bigger and better gifts. It’s the thought that counts.”

Gifting staff with customized letters of appreciation is another pleasant gesture.

“Handwritten holiday cards often go a long way with employees,” Boy says.

WHEN TO BOOK: Set aside time for presents if coworkers are gifting one another as well. Otherwise, distribute during an unobtrusive hour.
BEST TIME OF DAY: During normal office hours
BEST DAY OF THE WEEK: Friday
BEST FOR: Companies of any size
APPROPRIATE TO SERVE ALCOHOL: No
PRIVACY LEVEL: Complete
BONUS TIP: Not holding an event means no unforeseen issues, but “by in large the benefits of having [a party] and the morale boost it gives outweighs the small chance of a liability,” Boy says. 

Things to Keep in Mind

When celebrating a winter holiday, the prevailing trend is to hold a generic-themed gathering on a neutral date to cover all beliefs and traditions, says Suzanne Boy, president of the Society of Human Resource Management, Southwest Florida chapter.

Celebrations should always be voluntary so employees are not compelled to rebook vacations or neglect outside obligations. “I think just letting everyone know that they are invited and you hope they come and can choose not to come would make them feel less pressured,” she adds.

If parties are mandatory or held during office hours, Boy says employees are still on the clock and should be compensated for their time. After-hours gatherings do not need to be. GB