The Best (and Worst) Destinations for a Retreat

A good retreat is one that accomplishes its goals, showcases the host company in a favorable light, and meets the reasonable expectations of the attendees. If you’ve been tasked with the responsibility of choosing a destination for your firm or company retreat, we have done a lot of the research for you, including identifying a recommended resort that can accommodate both small and large groups. 

The factors considered in choosing the best destination for a domestic or global retreat include: 

  • your goals for the retreat, 
  • the convenience of the location, 
  • budget and value, 
  • the existence of facilities having sleeping quarters and meeting facilities that can accommodate your group size, 
  • climate and weather issues, and 
  • passport and visa requirements. 

While no location is perfect, there are some that increase the likelihood of a great retreat experience and others that make a successful retreat unlikely. What are your goals for your retreat? Traditional goals for a retreat include education, strategy development, rapport-building, and rejuvenation for your team. If that’s your situation, choose a location that will facilitate learning, privacy, togetherness, and relaxation. You’ll want to avoid locations that are popular for partiers or families, as those influences would be distracting.

What’s your budget? Can you afford to consider destinations in the Caribbean, Hawaii, Canada, and Mexico or should you focus solely on the mainland USA? The more senior or sophisticated your team is, the more you should budget. You’re asking folks to take time away from their families, give up a weekend, and “skin and grin” when they’d rather be home with their feet up zoning out in front of the television. So, choose someplace luxurious to make them look forward to the task. Oops, I meant to say “trip” not “task.”

When it comes to weather, that isn’t as important a consideration as many make it. The destination needn’t necessarily involve a beach or warm temperatures. What’s important is that there are many opportunities available for your team to engage both in small and large groups. You want opportunities to learn new things, pursue favorite pastimes, and be as true-to-self as is appropriate in a work setting so that genuine rapport is built. 

With those aims in mind, what follows are our Top 5 and Bottom 5 destinations in North America & the Caribbean for a traditional retreat together with the reasons we arrived at our conclusions. 

What if you’re not planning a traditional retreat? What if, by contrast, your retreat is a reward for high performers rather than a strategy gathering? Then, my Bottom 5 may be tops for you! 

Top 5

  1. Sonoma, CA: Wine country was built for the firm retreat. First, the scenery is beautiful with rolling hills planted with vineyards and colorful flora creating a feeling of wellness. There is a focus on gathering around food and wine, which promotes team building. The climate is perfect—warm by day and cool at night. Additionally, there are numerous daily flights into San Francisco International from just about anywhere, and Sonoma is on the mainland, so there are fewer covid travel restrictions to fret about. Sonoma is priced right, compared to Napa Valley. For accommodations, I recommend The Lodge at Sonoma Resort which has terrific indoor and outdoor spaces for seminars and group activities. There are fire pits to warm outdoor gatherings. Most guest rooms open to the outdoors providing fresh air. Plus, your team will be thrilled to collect Marriott reward points during their stay. The downsides are possible smoke from wildfires(!) during the summer season from June through September, coordinating ground transportation from SFO to Sonoma, and the fact that most hotels in the area that are large enough to host a sizable retreat have monotonous corporate décor. The Lodge is, I’m afraid, no exception.
  1. Kauai, HI: This one is my personal favorite. Hawaii is a great location for a retreat, especially if your Asia-Pacific counterparts will be joining you in this common stayover choice for them. The weather is perfect all year long, not too warm or too cool. My favorite Hawaiian island for a retreat is Kauai because it’s so sustainable. Plus, it’s insusceptible to wildfires or other natural disasters. Among the developed parts, it is easy to find pure luxury. I recommend The Lodge at Kukui’ula which has 1-to-3-bedroom cottages and bungalows set along ocean frontage and a championship-level golf course. The décor is island-themed, designed to fit the location rather than the Hyatt’s corporate brand. These individual residences have private bedrooms and bathrooms (including some with secluded outdoor showers) together with common areas where team members can convene. The property includes an organic farm open to guests who want to make use of their full kitchens (perhaps for a group cooking lesson?). Other group activity options include hiking, sailing, fishing, kayaking, tennis, and golf.  The downsides of this idyllic location are price (though the Hyatt reward points may make the expense more palatable) and the travel distance for any European colleagues. There’s also the short flight from Honolulu to Kauai that must be timed to avoid a stayover in Honolulu, though this should be doable since there are more than 15 flights per day between these two islands. There is no ferry service between the islands.
  1. Montego Bay, Jamaica: If no one is traveling from Asia, this destination is attractive. Airfare is reasonable from the States. The weather is hot year-round like southern Florida. Jamaica’s natural beauty is impressive with a combination of ocean frontage and foliage-covered mountains. I recommend the Half Moon resort. This is a beautifully landscaped 400-acre resort that caters to groups. They have significant spacious open-air and indoor group facilities. They offer a choice of hotel rooms or villas. Rates, while pricey, can come with meal plans. Among roughly a half dozen on-site dining options is a Beach BBQ. Group activities include sailing, water-skiing, tennis, and horseback riding, all onsite, plus excursions to hike in the Blue Mountains or to an organic farm for a wholesome private dinner. Even a covid quarantine should not be a problem at Half Moon because the resort has a medical center located right in Half Moon Village. Travel to Jamaica from most countries requires only a passport and no visa. The downsides are the unpredictable hurricane season from July through early November, and if you have any team members from Asia-Pacific, the travel time is some 17 hours. Maybe plan for them to work from a US office the week before the retreat. 
  1. Charleston, SC: This may be the best choice for national or regional firms because it’s easy to reach from the East Coast, and compared to the other locations on this list, it is inexpensive. There are some cool walking tours (including haunted graveyard tours) that make for a wicked group activity, and the southern hospitality is hard to beat. I recommend The Beach Club at Charleston Harbor and Marina, which looks as if it were torn from the pages of Coastal Living magazine, with white wooden furnishings, shades of blue décor, and individual balconies. Its location directly on the Atlantic provides ready access to boating activities and is a short water taxi ride to downtown Charleston for ground excursions. The downsides are the resort is kid-friendly and many of its comparatively limited group meeting spaces are outdoors–open to East Coast elements such as rain, humidity, and extreme heat. Also, there’s hurricane season from June to October.
  1. Banff, Canada: Banff’s remote location in the mountains coupled with ample luxury resort facilities make for an ideal location for a retreat. You can ski in winter or navigate the trails via hiking boots or horseback in summer. I recommend the Fairmont Banff Springs. Located in one of the 7 UNESCO World Heritage Canadian Rocky Mountain Parks, this haven has a golf course, spa, and the Fairmont taste and service that make the brand a favorite among corporate travelers. (In my opinion, the Fairmont brand is among the least “cookie-cutter” of the chain hotels.) Plus, there’s an onsite bowling center that you can reserve for a super fun team building evening. The downsides are travel restrictions that can recur unexpectedly as covid ebbs and flows and the distance, roughly 90 miles, between the Calgary, Alberta International airport and Banff. Also, please note that Canada requires citizens of most Asian countries to have a visa. So, be sure to announce the location far enough in advance for attendees to secure the necessary travel documents. (Note: Banff beat out Jackson Hole, Wyoming because the substantial increase in cost for Jackson Hole does not appear to be compensated by extra benefits not available in Banff.)

Bottom 5

  1. New York City: The Big Apple is congested, expensive, and the climate is almost never ideal (too cold in winter; too hot in summer). Plus, some team members may live there or have friends there and want to stay home, finish work in the office, or connect with their friends or alumni rather than joining the group. Unless part of your programming is to teach networking out in the field, NYC is probably a poor choice.
  1. Orlando: Disney may be “the happiest place on earth” but hold your retreat in this children’s paradise at your own risk. What parent can tell their five-year-old “I went to Disney and all you get is this T-shirt”? What’s more likely to occur is that they’ll bring their children with them and spend an inordinate amount of time assuring that their children have fun rather than spending that time engaging with colleagues or otherwise achieving the retreat’s objectives.
  1. Cabo San Lucas: This town is hardly authentic Mexico. It’s an artificial town developed expressly for the global party set with partying and shopping that rival Miami’s but with more expensive airfare. Its inconvenient location in Baja Mexico gives it a slight advantage over Miami, though, because the “riff-raff” cannot easily (or affordably) get there, making it far less congested than South Beach.
  1. Miami: I have made Miami my home for the past 20 years. I love living in a gated resort community. However, in my opinion, Miami is the second worst location to hold a retreat. South Beach is warm and beautiful, but too much excitement beckons. And, if you try to hold the event in another neighborhood away from SoBe, your team will spend every waking moment plotting their escape. Let your team look for eye candy on their own dime. If you are committed to being in Florida, consider Sarasota instead.
  1. Las Vegas: While I love a weekend in Vegas with my friends, I consider Las Vegas the single worst place to hold a firm or corporate retreat. The Strip is simply too much of a distraction. Everything your team wants to do is conveniently located on a single street that they can’t wait to get to. The gaming, the shows (hardly an interactive team-building excursion), the people-watching, the pool parties (which are clothing optional), the guys peddling “Molly” in the lobby. Need I say more?

Now that you have the location in place, here are a few topics to consider

Shavon Jones, Esq. is a sales trainer, deal lawyer, the author of two business books (52 Sales Tips & How to Use Them and Sales for Lawyers) and the publisher of For Lawyers Only magazine. For more information, visit https://sales4lawyers.com

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