Winter retreats are more than just a getaway—they’re an opportunity to reconnect, recharge, and refocus your team. Whether you’re carving through fresh mountain powder, brainstorming with ocean views, or soaking in the energy of a buzzing city, the right destination can set the tone for a transformative experience.

From exclusive ski chalets to tropical beachfront villas, here’s our list of the top winter retreat destinations and exactly why your team will love them. Bonus: we’re sharing insider tips to make each experience unforgettable!

How to Plan a Winter Retreat Your Team Will Love

Set Clear Goals

Is the focus on team-building, strategic planning, or simply recharging? Knowing your objectives will help shape your destination and activities.

Choose the Right Destination

For adventure: Head to mountain resorts like Aspen or Whistler.
For relaxation: Opt for tropical escapes like Tulum or St. Barths.
For inspiration: Explore dynamic cities like NYC or Nashville.

Prepare for Winter Travel Challenges

Pro Tip: Always budget extra time for flights in case of weather-related delays.
Pack warm layers, gloves, and waterproof boots if heading to a snowy location—it’s better to overprepare than underdress.

Plan Winter-Specific Team Activities

Snowshoeing or skiing for adventure teams.
Cozy fireside brainstorming sessions for quieter teams.
Unique seasonal experiences like holiday market tours or private sleigh rides.

Incorporate Downtime

Retreats aren’t just about work; allow time for relaxation and connection to ensure your team leaves recharged.

Book Early

Winter is a popular season for retreats, so secure your venue, flights, and activities well in advance to avoid last-minute stress.

Mountain Retreats: Where Productivity Meets Slopes

1. Aspen, CO

Luxury and adventure collide in Aspen, where world-class skiing and private chalets create the perfect backdrop for both productivity and play.

What to Do: Snowshoeing adventures, VIP lift access, and après-ski at exclusive lounges.
Pro Tip: Hire a private chef for a cozy chalet dinner, complete with locally inspired dishes and Colorado craft cocktails.
Why It’s Perfect: Teams love the seamless blend of high-energy activities and cozy relaxation spaces for brainstorming.

2. Park City, UT

Just a short drive from Salt Lake City’s airport, Park City combines stunning mountain views with accessible luxury.

What to Do: Private sleigh rides, fireside brainstorming sessions, and group ski adventures.
Pro Tip: Plan your retreat around the Sundance Film Festival for an unforgettable cultural experience.
Why It’s Perfect: Its balance of adventure and relaxation makes it a versatile option for any team.

3. Whistler, BC

Canada’s Whistler Blackcomb offers unparalleled mountain experiences with powdery slopes, luxury lodges, and breathtaking scenery.

What to Do: Snowmobiling through serene backcountry trails, team snowshoe races, and relaxing spa retreats.
Pro Tip: End the day with a private dinner at the Bearfoot Bistro, where your team can try their hand at sabering champagne.
Why It’s Perfect: Whistler’s secluded charm helps teams disconnect from the daily grind and focus on big-picture goals.

4. Lake Tahoe, CA/NV

Lake Tahoe’s stunning alpine lake is surrounded by world-class ski resorts and serene hiking trails, offering a retreat destination that balances adventure and tranquility.

What to Do: Skiing at Heavenly Resort, snowshoeing along picturesque trails, and cozy fireside team sessions.
Pro Tip: Opt for a lakefront cabin with panoramic views to give your team a true winter wonderland experience.
Why It’s Perfect: Tahoe’s breathtaking scenery and versatile activities cater to every team’s vibe.

Beach Getaways: Sunshine and Strategy

5. Tulum, Mexico

Tulum’s laid-back vibe and natural beauty make it a retreat haven. Think beachfront villas, crystal-clear waters, and immersive cultural experiences.

What to Do: Paddleboarding sessions, private cooking classes with local chefs, and guided cenote tours.
Pro Tip: Start each day with a team yoga session overlooking the Caribbean Sea to boost focus and creativity.
Why It’s Perfect: The serene atmosphere creates the perfect space for both relaxation and meaningful team connections.

6. St. Barths

Sophistication is the name of the game in St. Barths. From luxury yachts to gourmet dining, this destination screams exclusivity.

What to Do: Charter a private yacht for a day of snorkeling and relaxation, followed by a sunset cocktail hour.
Pro Tip: Arrange for team wellness treatments—massages, facials, and more—at one of the island’s top spas.
Why It’s Perfect: St. Barths’ high-end experiences ensure your team feels valued and inspired.

7. Cabo San Lucas, Mexico

Conveniently accessible and effortlessly stunning, Cabo offers a winning mix of relaxation and adventure.

What to Do: Host brainstorming sessions on ocean-view terraces, then unwind with a sunset catamaran cruise.
Pro Tip: Opt for beachfront meeting spaces that come with concierge services to keep everything running smoothly.
Why It’s Perfect: It’s the ideal spot for a warm, stress-free retreat that gets your team’s creative juices flowing.

City Escapes: Energy and Inspiration

8. New York City, NY

There’s no place like New York for teams craving culture, energy, and inspiration. From holiday magic to cutting-edge venues, NYC offers endless possibilities.

What to Do: Private tours of holiday markets, rooftop team dinners, and Broadway-inspired workshops.
Pro Tip: Schedule a rooftop cocktail hour at sunset to cap off the day with stunning skyline views.
Why It’s Perfect: NYC’s mix of fast-paced excitement and world-class amenities keeps your team engaged and inspired.

9. Nashville, TN

Music City combines vibrant culture with warm Southern hospitality, creating a retreat experience like no other.

What to Do: Songwriting workshops, live music outings, and private whiskey tastings at local distilleries.
Pro Tip: Plan a private team dinner at a historic mansion for a touch of charm and exclusivity.
Why It’s Perfect: Nashville’s unique team-building activities and lively atmosphere make it a crowd-pleaser.

10. Miami, FL

Who says winter has to be cold? Miami offers sunny skies, luxury resorts, and an electric energy that’s hard to beat.

What to Do: Ocean-view brainstorming sessions, private art tours in Wynwood, and team outings to Little Havana for authentic Cuban cuisine.
Pro Tip: Book a yacht for a half-day retreat activity—nothing sparks creativity like ocean breezes and panoramic views.
Why It’s Perfect: Miami’s blend of relaxation and high-energy activities keeps the team engaged and inspired.

How to Choose the Perfect Destination for Your Team

Adventure Seekers: Head to Aspen, Utah, or Whistler for adrenaline-filled activities and stunning snowy backdrops.
Relaxation Lovers: Tulum or St. Barths offer tranquil settings that inspire creativity and connection.
Culture Enthusiasts: NYC, Nashville, and Miami are perfect for teams craving energy, inspiration, and unique experiences.

At Offsite, we know that the perfect retreat is all about the details. From destination scouting to personalized itineraries, we handle it all so you can focus on your team’s growth.

FAQs About Planning a Winter Retreat

1. How far in advance should I start planning a winter retreat?

We recommend starting at least 3-6 months in advance. Popular destinations like Aspen, Tulum, and NYC fill up quickly during the winter season. Early planning ensures you get the best venues, flights, and activities without last-minute stress.

2. What’s the best way to budget for a winter retreat?

Start with a clear understanding of your total budget. A good rule of thumb:

40% for lodging and venues.
30% for travel (flights, transfers, etc.)—and remember to account for potential winter delays or changes.
20% for food and beverages.
10% for activities, AV equipment, and extras like swag.

Using tools like meetvamos.ai can help you monitor and optimize flight costs as you plan.

3. How can I keep my team engaged during a retreat?

A successful retreat balances work, play, and downtime.

Incorporate fun team-building activities like snowshoeing, yoga, or cooking classes.
Plan focused work sessions in inspiring settings (think beachside patios or cozy fireplaces).
Don’t underestimate the power of free time for organic connections and relaxation.

4. What if weather impacts our travel plans?

Winter travel can be unpredictable, so always have a backup plan.

Book refundable flights and accommodations when possible.
Allow extra time for arrivals to ensure the retreat starts smoothly.
Consider travel insurance to protect against delays or cancellations.

5. Does Offsite handle all the logistics?

Absolutely! From booking venues and activities to creating customized itineraries, we take care of all the details so you can focus on your team. We also provide contingency plans for unexpected hiccups, ensuring your retreat runs seamlessly from start to finish.

6. What destinations work best for winter retreats?

It depends on your team’s vibe:

For adventure and skiing: Aspen, Vail, Whistler, or Lake Tahoe.
For relaxation and warm weather: Tulum, St. Barths, or Cabo San Lucas.
For culture and energy: NYC, Nashville, or Miami.

7. Can retreats be tax-deductible?

In many cases, yes! Retreats focused on team-building, strategy, and planning are often considered a business expense. Be sure to consult your accountant for specific guidelines based on your location and business structure.

Got more questions? We’ve got answers! Reach out to Offsite, and we’ll help you plan a winter retreat your team will never forget. ❄️✨

Let’s Make It Happen: Book Your Retreat Today!

Winter retreats aren’t just about the destination—they’re about the experiences that spark creativity, connection, and growth. At Offsite, we specialize in handling all the details, from selecting the perfect location to curating unforgettable team-building activities.

Ready to plan a winter retreat your team will rave about? Contact Offsite today to get started!

Top 10 Winter Retreat Destinations for Teams Who Work Hard and Play Harder