5 Luxury Destinations for Board Meetings & Executive Retreats in 2019

5 Luxury Destinations for Board Meetings & Executive Retreats in 2019

Successful leadership meetings and executive retreats inspire, motivate, recharge and challenge those most important to your business.

These high-end meetings are catered towards busy individuals who not only have a lot going on—they are able to go virtually anywhere they desire on their own. Choosing an irresistible meeting location is key.

Below, see 5 top destinations for meetings and retreats in 2019, plus "WOW" worthy properties being booked for events:

  1. Sea Island, Ga.  |  Sea Island Resort (The Cloister)
  2. Pebble Beach, Calif.  |  The Lodge at Pebble Beach
  3. Phoenix / Scottsdale, Ariz.  |  Four Seasons Resort Scottsdale
  4. San Diego, Calif.  |  Rancho Valencia Resort & Spa
  5. Miami, Fla.  |  Mandarin Oriental, Miami

Meeting & Retreat Destination Checklist

When hunting for the perfect executive and leadership retreat venue, most meeting planners look for the following:



“Most attendees are often well traveled and can go anywhere they want on their own. To maximize attendance, you need to make it unique to them,” advises Melissa Davie, Director of Events & Operations at Winspire. This requires choosing a location with built-in wow factor. “Hosting an event at Pebble Beach or Sea Island, makes it very hard for them to say no,” Davie says.


What’s the distance from the venue to the airport? Most planners tend to choose places that have direct access, with direct flights. Depending on your demographic, being 30 minutes or less from the airport can be important. That being said, the perfect 5-star resort for your meeting may be more 'tucked away'. That's fine, as long as the property is worth the drive.


Warm weather at anytime of the year is generally favorable, unless your group is seeking cold weather activities.


Travel trends vary each year on a number of factors: what’s in the news, what’s getting buzz on social media, where the best travel deals are. At Winspire, we keep our finger on the pulse of tourism trends to help you make an informed decision.

These 5 popular U.S. destinations certainly fit the bill.

1. Sea Island, Ga.

Home to two of the top 10 resorts in the continental U.S., Sea Island boasts comfort in every detail and genuine Southern charm. It's located between Jacksonville and Savannah international airports, with easy access from local regional and private airports.

Property Highlight: Sea Island Resort (The Cloister)

 ACCOLADES   Sea Island Resort has enjoyed 114 Forbes Five-star and AAA Five-Diamond honors; it is the only resort in the world to have received four Forbes Five-Star awards for 10 consecutive years.

 GROUP SIZE   Sea Island Resort offers several options for luxury accommodations. One we like: The Cloister, luxury rooms & suites that are detailed, spacious and feel like home.

 BEST TIME TO VISIT   The most popular times to visit are late spring or summer, but Georgia coast sees mild year-round temperatures (65 to 89 degrees F). In the winter, for example, the Cloister gets festive with floor-to-ceiling Christmas decorations and a gingerbread castle.

 ONSITE FEATURES   The Cloister features a cutting-edge Spa and Fitness Center, three swimming pools, Tennis Center, and Beach Club just steps away from five miles of private beach. Dine at the only Forbes Five-Star restaurant in Georgia, or enjoy a multi-course meal in the wine cellar.

2. Pebble Beach, Calif.

The spectacular coast of Central California, dramatic ocean views and championship golf offerings all provide a stunning backdrop for meetings and events. Plus, Pebble Beach is located just a short drive from three major airports.

Property Highlight: The Lodge at Pebble Beach

 ACCOLADES   Ranked #2 on Conde Nast 2018 Reader's Choice Top Resorts of Northern California.

 GROUP SIZE   Group Size: Good for large groups; accommodates up to 500.


 ONSITE FEATURES   The Lodge at Pebble Beach surrounds the 18th green of the Pebble Beach Golf Links. This 1919 cream-colored lodge includes 161 guest rooms, five elegant dining venues, and over 10,000 square feet of meeting space. Rooms offer wood-burning fireplaces and private decks overlooking the gardens, oceanside fairways, and Carmel Bay.

 OFFSITE FEATURES   Soak in stunning views of Monterey County with a tranquil trail ride through the towering Del Monte Forest, on the world-famous 17-Mile Drive, or at charming seaside towns like Carmel-by-the-Sea.

3. Phoenix/Scottsdale, Ariz.

Host your next meeting in the Sonoran Desert and enjoy near-perpetual sunshine, jaw-dropping sunsets that paint the desert sky, and a walkable downtown with independent restaurants, craft brew-pubs and live-music venues.

Property Highlight: Four Seasons Resort Scottsdale at Troon North

 ACCOLADES   Has maintained a AAA Five Diamond rating for more than 15 years.

 GROUP SIZE   Four Seasons Scottsdale has 25 adobe casitas with 199 generously sized guest rooms and 22 luxury suites. Their largest venue can fit 430 guests.

 BEST TIME TO VISIT   November through April offer blue skies with highs in the upper 60s to low 80s. The most popular time to visit is late winter and spring, particularly during baseball spring training.

 ONSITE FEATURES   The Four Seasons features locally inspired spa treatments, a bi-level pool with private cabanas, Southwest cuisine, tennis courts and tournaments, cultural demonstrations and more.

 OFFSITE FEATURES   Try observing dramatic valleys, saguaro cacti and the slopes of Pinnacle Peak with an aerial tour of Sedona, a cycling trip through the vineyards, horseback rides and more. Four Seasons guests enjoy special privileges at Pinnacle and Monument golf courses, plus complimentary shuttles to and from the Resort. Other popular activities include hot air ballooning, art gallery tours, shopping and day trips to Sedona or Oak Creek Canyon.

4. San Diego, Calif.

With easy transportation to and from the San Diego International Airport, San Diego boasts a near-perfect climate, miles of beaches, world-class visitor attractions, charming eateries and craft breweries.

Property Highlight: Rancho Valencia in Rancho Santa Fe, CA

 ACCOLADES   A hidden gem, the resort is described by Conde Nast as "peak California." Orange groves, bright pink bougainvillea, and Spanish Colonial architecture give the resort its unique feel. Rancho Valencia was just ranked #3 on Conde Nast 2018 Top Resorts in Southern California. It's a AAA Five Diamond Hotel and #2 Best Hotel in California according to U.S. News & World Report.

 GROUP SIZE   Good for smaller groups, as there is a limited amount of hacienda-style suites (49).


 ONSITE FEATURES   Suites range from 900 to 1,300 sq. feet and offer amenities like heated toilet seats and soaking tubs. The luxury villas offer a full kitchen, a living room, outdoor hot tub and fireplaces. The state-of-the-art Serenity Yoga Pavilion offers classes on a wooden deck overlooking a pond and garden. Rent bicycles, schedule a tequila tasting, saber champagne bottles(!) and more.

5. Miami, Fla.

"There's a plethora of 5-star properties in Miami, it’s easy to get to, and you have the beach," Davie says. Its world-famous dining, shopping, sports teams and cultural offerings are putting 'The Magic City' at the top of many meeting planners' destination lists - especially for events taking place in the cooler months.

Property Highlight: Mandarin Oriental, Miami

 ACCOLADES   #18 on Conde Nast 2018 Reader's Choice Awards for Top Hotels in Miami

 GROUP SIZE   With over 350 rooms, this hotel well for very large groups.


 ONSITE FEATURES   The hotel is ideally situated near Miami and Fort Lauderdale International Airports. After meetings, unwind in the private infinity edge pool or at the three-story waterfront spa offering a range of globally-inspired wellness treatments. A 1.3 mile jogging path provides a scenic route to recharge.

 OFFSITE FEATURES   The Mandarin is a quick walk or drive away from Miami’s most bustling nightlife and neighborhoods, including South Beach. Conde Nast raves of the hotel, "It’s kind of a miracle that one could feel so secluded so close to downtown Miami" - perfect for attendees who want to see more than just the beach.


We hope this list gave you plenty of inspiration to take your next meeting to the next level. Click below or leave a comment to start brainstorming dozens more ideas that fit your goals, target demographic and budget with Winspire.

Contact Winspire Experience Agency