Looking for the best destination to host your next leadership retreat?
Whether you want to spark new ideas, strengthen bonds, or give your team a well deserved break, the right location can make all the difference, especially with tight budgets.
Global business travel spend is projected to hit $1.69 trillion in 2026, and meetings and events now account for over half of all corporate travel spend. That makes destination choice a bigger lever than ever. organizations with strong benefit and incentive programs cut turnover by 26% and boost retention by 14%, and well designed incentive travel programs can drive an 18% productivity lift and 112% ROI. A thoughtfully chosen destination isn't just a nice perk. It's a retention and performance tool your leadership team can measure.
Global business travel spend is projected to hit $1.69 trillion in 2026, with meetings and events now accounting for over half of that total. The destination you pick carries real weight, both for what you spend and for the ROI your attendees bring home.
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Strong benefit and incentive programs cut turnover by 26% and boost retention by 14%
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Well designed incentive travel programs can drive an 18% productivity lift and 112% ROI.
What are the best leadership retreat destinations?
Here are the top 10 leadership retreat destinations that will inspire growth and collaboration among your attendees:
| Location |
Flagship large-group property | Best-fit group size | Budget tier (per person/night) |
| Hawaii | Grand Wailea, A Waldorf Astoria Resort | 150 to 300+, fully scalable | Luxury, roughly $700 to $1,400+ |
| Florida Keys | The Ritz Carlton Key Biscayne | 150 to 300+ | Luxury, roughly $700 to $1,300+ |
| Cabo San Lucas | Grand Velas Los Cabos | 150 to 300+ | Luxury all inclusive, roughly $900 to $1,600+ |
| Sedona | Enchantment Resort | 20 to 75, stretching to about 150 | Luxury boutique, roughly $700 to $1,100 |
| Napa | The Meritage Resort and Spa | Flexible, small exec retreats through 300 person conferences | Mid tier, roughly $500 to $800 |
| The Southern U.S. | The Greenbrier | 150 to 300+, largest capacity on this list | Mid to luxury, roughly $500 to $1,000 |
| Lake Tahoe | The Ritz Carlton Lake Tahoe | 75 to 250 | Luxury, ski season pricing, roughly $800 to $1,400 |
| Jackson Hole | Four Season Resort and Residences Jackson Hole | 20 to 75, up to about 150 | Luxury, roughly $900 to $1,800+ |
| Whistler | Fairmont Chateau Whistler | 150 to 300+ | Mid tier, roughly $350 to $700 |
| Park City | Montage Deer Valley | 100 to 300, flexible down to small exec sessions | Luxury, roughly $900 to $1,800+ |
Not sure which of these fits your group size and budget? GoGather's site selection team narrows this list down to two or three real options based on your headcount, dates, and budget. Start a free site selection request.
What are the best beach locations for a leadership retreat?
1. Hawaii
Hawaii is one of our favorite destinations for a domestic leadership retreat, and it’s easy to see why.
Offering a wide range of tropical, beach, and shopping spots, it’s the perfect place for an executive getaway.
The island’s natural beauty (from stunning beaches to lush mountains) provides a calming, inspiring environment where your team can unplug and refocus on bigger goals.
What are the top resorts to stay at in Hawaii?
- Andaz Maui at Wailea Resort
- Grand Wailea Resort
- 1Hotel on Kauai
- Fairmont Orchid
- Four Seasons Resort Oahu at Ko Olina
For enterprise groups, Grand Wailea's 100,000 sq ft of meeting space (including a 26,700 sq ft ballroom) can comfortably scale from an intimate leadership team to a 300 plus person conference.
What are the top activities for event attendees in Hawaii?
- Group hike to a waterfall
- Snorkeling in places like Hanauma Bay (Oahu) or Kealakekua Bay (Big Island)
- Golfing at a Championship Course, especially at the Four Seasons Hualalai (Big Island) or the Kapalua Golf Club (Maui)
- Sunset dinner boat cruise
- Beachfront yoga and wellness sessions
Related: Looking for more? See our sample incentive travel program itinerary for Maui, Hawaii.
2. Florida Keys
Want to plan a corporate retreat that’s both memorable and productive?
The Florida Keys offers a perfect backdrop where your team can relax, build stronger connections, and engage in strategic discussions.
With its stunning coastal views and relaxed vibe, your attendees can enjoy a variety of activities from kayaking through mangroves to unwinding at luxurious beachfront resorts.
Plus, the Keys are easy to reach and offer a tropical atmosphere that's usually more budget-friendly than similar destinations like the Caribbean or Hawaii.
What are the top resorts to stay at in the Florida Keys?
- Little Palm Island Resort, is the only private island resort in the U.S.
- The Ritz-Carlton Key Biscayne
- Ocean Key Resort & Spa
If your group is over 100 people, The Ritz Carlton Key Biscayne is the better fit. Little Palm Island and Ocean Key are boutique properties built for tighter executive groups of 20 to 75.
What are the top activities for attendees in the Florida Keys?
- Kayaking through the mangroves
- Snorkeling or scuba diving
- Team-building activities like beach volleyball or pickleball
- Wellness and spa sessions
- Fishing charter or boat day
Related: Want to see more? Take a look at our sample agenda for a company retreat in the Florida Keys.
3. Cabo San Lucas, Mexico
Cabo San Lucas is a top destination for incentive programs and leadership retreats, and it’s no surprise why. With stunning beaches, perfect weather, and a vibrant culture, it’s the ideal spot for teams to unwind, explore, and indulge.
Cabo San Lucas consistently ranks as one of our top picks for international programs, and here's why:
- Large selection of newer luxury resorts
- Spectacular beaches & warm weather
- Wide range of all-inclusive resorts
- Easy to get to and lots of fun activities
What are the top resorts to stay at in Cabo San Lucas?
- Chileno Bay Resort & Residences, Auberge Resorts Collection
- Grand Velas Los Cabos
- Esperanza Cabo San Lucas
- Montage Los Cabos
- The Cape, a Thompson Hotel, by Hyatt
- Waldorf Astoria Los Cabos Pedregal
Grand Velas Los Cabos' 16,370 sq ft convention center, including 20 breakout rooms, handles groups up to 300 plus without losing the all inclusive luxury feel.
What are the top activities for attendees in Cabo San Lucas?
- Beach day with your group
- ATV adventure through the desert
- Deep-sea fishing adventure
- Golfing with ocean views
- Snorkeling or scuba diving
In short -- Cabo is an easily accessible, sunny beach destination with a good variety of properties. There aren’t a lot of places in the US that offer this besides Hawaii or Florida, which can be far more expensive.
Related: Need more ideas for your Cabo retreat? Check out our sample incentive trip itinerary for Cabo San Lucas.
What are the best warm, non-beach locations for a leadership retreat?
4. Sedona, Arizona
Sedona is a fantastic choice for your next leadership retreat.
Often dubbed "Red Rock Country" because of its stunning red sandstone formations, this destination is a great place for your attendees to relax and spark new ideas.
Your leadership team can enjoy outdoor activities like hiking or jeep tours for team-building and then unwind with spas or dive into the local arts scene to help them recharge.
Keep in mind that Sedona can get quite hot in the summer, with daytime temperatures often climbing between 90°F and 100°F. If you’re planning a summer visit, be sure to choose a venue with a pool to stay cool!
What are the top resorts to stay at in Sedona?
Sedona's resorts are built for smaller leadership teams. Enchantment Resort's largest room seats about 320 banquet style, so this destination works best for groups of 20 to 150.
What are the top activities for attendees in Sedona?
- Red Rock Jeep tours
- Hiking and nature walks
- Hot air balloon rides
- Spa and relaxation sessions
- Sedona vortex tours
Related: Curious about the benefits of hosting an executive burnout retreat? Check out our article outlining the top 10 advantages of organizing one.
5. Napa Valley, California
Napa Valley is a fantastic choice for your next leadership retreat if you want to mix relaxation with inspiration.
With vineyard views and award-winning wineries, Napa offers the perfect backdrop for both strategic meetings and downtime. Its excellent dining and accommodations make it an ideal spot for team-building and relaxation.
If your attendees are flying in from out of state, keep in mind it’s usually about a 2-hour drive from San Francisco International Airport.
What are the top resorts to stay at in Napa?
- Auberge du Soleil
- Carneros Resort and Spa
- Bardessono Hotel and Spa
- Solage, Auberge Resorts Collection
- The Meritage Resort and Spa
The Meritage Resort and Spa is the most flexible property on this list, with 50,000 plus sq ft of indoor space that scales from a small executive offsite to a 300 person leadership conference.
What are the top activities for attendees in Napa?
- Wine tastings and vineyard tours
- Spa and wellness activities
- Hot air balloon rides
- Cooking classes and culinary tours
- Hiking, biking, and nature strolls
Looking to plan a work retreat that improves team morale and productivity?
Related: Check out our article for tips on organizing a retreat that meets your goals, fits your budget, and creates lasting memories for your team.
6. Southern United States
The Southern United States is a fantastic option for your next leadership retreat, especially if most of your team is based on the East Coast.
From the historic charm of South Carolina’s Lowcountry to Tennessee’s lively music scene, there’s plenty to inspire and engage your team here.
Plus, the region’s incredible hospitality will make your team feel welcomed and taken care of throughout their stay.
What are the top resorts to stay at in the Southern U.S.?
- The Sanctuary at Kiawah Island Golf Resort (South Carolina)
- Blackberry Farm (Tennessee)
- The Greenbrier (West Virginia)
- The Cloister at Sea Island (Georgia)
- Omni Hilton Head Oceanfront Resort (South Carolina)
- The Inn at Little Washington (Virginia)
The Greenbrier in West Virginia is the single largest capacity property in this roundup, with over 200,000 sq ft of meeting space and 40 plus breakout rooms, making it the strongest pick here for large scale leadership events.
What are the top activities for attendees in the Southern U.S.?
- Wine and whiskey tastings
- Hiking, biking, kayaking outdoor adventures
- Historical tours
- Golfing
Related: Who’s making incentive travel feel less like work and more like wow? Find out in this year’s top 10.
What are the best mountain locations for a leadership retreat?
7. Lake Tahoe, California / Nevada
Lake Tahoe is a fantastic spot for your next leadership retreat. The refreshing alpine scenery and variety of outdoor activities offer a nice break from the usual business routine.
Just note that attendees flying in from Reno-Tahoe International Airport will need to drive about an hour to reach the lake. However, the breathtaking views and activities make the trip well worth it.
What are the top resorts to stay at in Lake Tahoe?
- The Ritz-Carlton, Lake Tahoe
- Edgewood Tahoe
- Everline Resort & Spa Lake Tahoe - Destination by Hyatt
The Ritz Carlton Lake Tahoe fits mid size groups well (roughly 75 to 250) but isn't the right choice if you're planning for 300 plus attendees.
What are the top activities for attendees in Lake Tahoe?
In the winter:
- Skiing and snowboarding
- Spa and wellness sessions
- Indoor hot yoga classes
In the summer:
- Hiking and nature walks
- Boating or water sports
- Golfing
- Mountain biking
Related: Is wellness a top priority for your team? Check out our guide on planning executive wellness retreats for all the insights you need.
8. Jackson Hole, Wyoming
Jackson Hole is a fantastic choice for your next leadership retreat, blending rustic elegance and rugged adventure.
With its breathtaking mountain views and plenty of outdoor activities like hiking and skiing, there’s something for everyone to enjoy. Plus, the charming downtown has great dining, shopping, and accommodations.
What are the top resorts to stay at in Jackson Hole?
Jackson Hole skews toward higher end executive retreats. Four Seasons Jackson Hole tops out around 275 to 280 for a single event.
What are the top activities for attendees in Jackson Hole?
- Skiing and snowboarding
- Wildlife safaris in Grand Teton National Park (spot bison, elk, and other animals)
- Hiking and scenic trails
- Local dining and brewery tours
- Hot air balloon rides
Related: Looking for an incentive trip location your team will rave about? These places check all the boxes.
9. Whistler, British Columbia, Canada
Whistler is a great choice for a leadership retreat if you're looking to inspire your team while enjoying some downtime. With breathtaking mountain views and plenty of outdoor activities, it’s ideal for adventurous groups.
Whether you’re hitting the slopes in winter or exploring hiking trails in summer, there’s plenty to keep everyone engaged.
Plus, Whistler Village is full of lively restaurants, shops, and bars, making it a great spot to relax and unwind after a busy day of activities.
What are the top resorts to stay at in Whistler?
- Four Seasons Resort Whistler
- Fairmont Chateau Whistler
- The Westin Resort & Spa, Whistler
- Pan Pacific Whistler Mountainside
Fairmont Chateau Whistler's 32,000 plus sq ft across 12 function rooms supports groups from 10 up to 1,500, making it one of the more scalable options for larger leadership conferences.
What are the top activities for attendees in Whistler?
- Skiing and snowboarding
- Mountain biking
- Hiking and scenic trails
- Zip-lining
- Shopping in Whistler Village
- Golfing
Related: Looking for more international executive retreat location ideas? Explore our article for some suggestions.
10. Park City, Utah
Park City, Utah, is a great choice for your next leadership retreat, thanks to its beautiful scenery and range of outdoor activities.
With over 7,300 acres of skiable terrain in the winter and miles of hiking and mountain biking trails in the summer, Park City has something for everyone. The charming downtown area also offers a variety of shopping, dining, and street events for attendees to enjoy.
Plus, Park City has over 300 days of sunshine a year, making it a reliable choice for pleasant weather during your retreat.
What are the top resorts to stay at in Park City?
- Montage Deer Valley
- Stein Eriksen Lodge
- Waldorf Astoria Park City
- The St. Regis Deer Valley
- Hotel Park City, Autograph Collection
Montage Deer Valley's 60,000 plus sq ft of indoor and outdoor space (max single event around 400) gives Park City strong flexibility across group sizes.
What are the top activities for attendees in Park City?
- Mountain biking
- Golfing
- Skiing and snowboarding
- Shopping on Main Street
- Scenic gondola rides
- Hiking and nature walks
Related: For more inspiration, check out our list of company retreat ideas designed to boost morale and productivity.
Frequently asked questions. (FAQs)
1. What is a leadership retreat, and how is it different from a typical team outing?
A leadership retreat is a focused, multi-day gathering designed to pull executives and senior leaders out of day-to-day operations so they can align on strategy, build trust, and recharge together. a retreat is different from a holiday party or a happy hour, because the format typically blends structured strategic sessions with unstructured time for relationship building. Because of this the demand for retreats keeps growing: the corporate retreat industry is projected to reach $73.7 billion by 2034, growing at a 9.1% annual rate, according to Allied Market Research.
How long should a leadership retreat last?
Most leadership retreats run three to four days. That gives enough time for real strategic work and downtime without pulling senior leaders away from their teams for too long. Shorter, more frequent off-sites have also become more common as companies look to keep the benefits going year round instead of relying on one big annual event.
Do leadership retreats actually make a measurable difference?
20% of employees worldwide report being engaged at work, according to Gallup's most recent State of the Global Workplace data, and a face-to-face request is 34 times more likely to succeed than the same ask made over email, according to Harvard Business Review research. Bringing leadership together in person, rather than relying on remote check-ins, addresses both problems directly.
How much does a leadership retreat typically cost?
Budgets vary widely by group size, destination, and length of stay, but data from retreat booking platforms shows companies with 21 to 50 employees spending an average of roughly $3,700 per person, including flights and lodging, on a retreat lasting about four days.
For a deeper breakdown of what drives retreat costs up or down, check out our step-by-step guide to planning a successful company retreat
When is the best time of the year to plan a leadership retreat?
Fall (September and October) and late spring (May) tend to be the most popular windows for corporate retreats, balancing good weather at most destinations with fewer scheduling conflicts around major holidays.
Ready to plan your next leadership retreat?
Leadership retreats are a powerful tool in today’s business world. They give leaders the space to recharge, refocus, and strengthen team alignment.
No matter your industry, whether you’re leading a trucking & transportation logistics team, a fast-growing technology or SaaS company, a home services organization, or a franchise network, a well-planned retreat can spark fresh ideas and lasting connection.
GoGather handles site selection, budgeting, and full logistics for leadership retreats ranging from 20 person executive offsites to 300 plus person conferences. Tell us about your group and we'll help you shortlist the right destination.
