When temperatures drop, incentive groups start looking for warm, sunny destinations that offer relaxation, adventure, and a sense of escape. Winter remains one of the highest-demand booking seasons for corporate travel, and selecting the right destination can dramatically impact participation, satisfaction, and ROI.
Below are the top warm-weather destinations for corporate incentive travel this winter, combining accessibility, high-end resorts, group-friendly activities, and unforgettable experiences.
1. Los Cabos, Mexico: Ultra-Luxury Meets Breathtaking Coastlines
Los Cabos continues to dominate the incentive market because it offers premium all-inclusive resort options, world-class dining, and the perfect blend of relaxation and adventure. We have personally hosted several events here and always receive tremendous feedback from attendees and it remains one of our top recommendations.
Why it’s ideal for winter incentives:
- Fast, easy flights from major U.S. airports
- High concentration of incentive-ready luxury resorts
- Whale-watching season (Dec–Feb)
- Endless group activities: catamaran sails, desert ATV rides, private beach dinners
Perfect for: high-achieving sales teams, VIP rewards, executive groups
2. Scottsdale, Arizona: Warm Days, Elevated Experiences
For domestic programs, Scottsdale remains a winter favorite offering lots of sun and resort excellence.
Highlights:
- Five-star resorts and desert wellness retreats
- World-class golf courses
- Outdoor adventures: hot-air ballooning, desert tours, horseback riding
- Culinary scene ideal for private group experiences
Perfect for: budget-flexible programs, shorter trips, wellness-focused teams
3. St. Lucia: A Caribbean Paradise With High-Impact
If you want views that stop people in their tracks, St. Lucia delivers. Keep in mind airlift into St. Lucia still has a way to go but with that said more challenging airlift is what keeps St. Lucia off the beaten path. This destination is perfect for NYC companies with direct flights or companies looking for 4 night incentive programs.
Why it’s trending for 2026:
- Luxurious adults-only and boutique group resorts
- Iconic Piton mountain views
- Exceptional private group sailing and snorkeling
- Fine dining and rum-inspired culinary experiences
Perfect for: intimate groups, luxury-forward incentives, island lovers
4. Hawaii (Maui & Oahu): Resilient, Culture-Rich, Unforgettable
Despite evolving travel landscapes, Hawaii continues to be a top contender for incentive planners. We are heading there in 2026 for four different events that we’re sure will amaze!
Benefits:
- No passports required for U.S. attendees
- Deep cultural programming options
- High-end resorts with strong group infrastructure
- Exceptional landscapes for adventure
Perfect for: large corporate groups, cultural immersion programs
5. Costa Rica: Nature, Adventure, and Pure Wellness
Costa Rica remains a top performer for groups seeking sustainability, adventure, and meaningful connection. New hotels are continuing to pop up in Costa Rica which is much needed as inventory constraints have been one of the main challenges when trying to book peak season incentives.
What makes it a standout:
- Eco-conscious resorts with strong CSR elements
- Adventure options (ziplining, hiking, rafting)
- Volcanic hot springs & wellness-rich experiences
- Picturesque Pacific coastlines
Perfect for: purpose-driven programs, outdoor-forward groups
6. Bahamas: Classic Caribbean Appeal and All-in-One Convenience
The Bahamas remain a tried-and-true destination, offering warm weather, beautiful beaches, world-class resorts, and a wide range of group programming options all within easy reach. The Bahamas’ tropical climate delivers year-round sun and warm temperatures, making it ideal for winter incentive trips.
Why planners love it:
- Easy U.S. access and many direct flights from major hubs
- Resort-driven group experiences and water-based activities
- Diverse offerings from private islands to large flagship resorts
- Rich cultural heritage and culinary experiences
Perfect for: large teams, broad-appeal incentives, classic tropical experiences
7. Anguilla: Elevated Luxury & New Direct Connectivity
Anguilla is gaining major traction with planners due to its serene, upscale atmosphere and an exceptionally high concentration of luxury hotels in close proximity to one another, among the Caribbean’s best for quality over quantity. With direct seasonal flights from Boston and Baltimore on AnguillAir (operated by BermudAir) launching December 19th, access has become significantly easier for Northeast U.S. groups. Additionally, Anguilla’s new airport terminal opened December 2025, enhancing the arrival experience and supporting future growth.
Highlights:
- Direct U.S. flights from Boston (BOS) & Baltimore (BWI) starting December 2025
- Newly updated Clayton J. Lloyd International Airport terminal for improved flow and service
- Small-island luxury with a high density of 5-star hotels and boutique resorts close to each other
- Pristine beaches, world-renowned restaurants, and calm island charm
Perfect for: luxury incentive groups, premium experiential programs, boutique group experiences
Winter incentive travel is all about sunshine, accessibility, and destination appeal. In 2025–2026, groups are prioritizing luxury, wellness, adventure, and smooth logistics, which is exactly what these destinations deliver.
Selecting the right warm-weather location sets the tone for the entire program, and helps companies reward teams with an unforgettable escape when they need it most.
If you are looking for more travel inspiration and expertise, reach out to Executive Group Travel for more information, we’re here to help!
