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Winter Fun: Ideas for Easy, Memorable Group Travel

Published December 31, 2025

When temperatures drop, it’s tempting to stay in, but with the right clothing and transportation, cold-weather activities are a great way to bring groups together. Whether it’s a company outing, a family weekend or a friends’ getaway, CharterUP makes it easy for groups to travel together, stay warm and skip the parking crunch.

Here are eight winter ideas to consider this winter season: 

Ski & Snowboard Weekends

Winter is prime time to head for the the mountains. A group trip means more time on the slopes and less time figuring out who’s driving or where to park.  

Whether you’re chartering a bus from Boston to reach resorts in Vermont or New Hampshire, or heading into the Rockies from Denver, CharterUP keeps the whole group together.

Ice Skating Outings

Outdoor rinks are a winter classic. Ice skating outings are simple to plan and work for all ages, whether it’s a school group or a casual weekend meetup.

Spend the day skating at Rockefeller Center in New York or head to the Maggie Daley Park Ice Skating Ribbon in Chicago

Snow Tubing & Sledding Parks

Winter tubing allows everyone to be part of the fun. No gear and no lessons, just grab a tube and enjoy the ride.

Visit the Snow Trails in Ohio or head to the tubing hills around Portland for a full day of fun and fresh air.

College Bowl Games & Winter Sports

Winter is packed with sports, from bowl games, NFL playoffs and hockey rivalries. A bus keeps your group together so you can enjoy the action.

Make it a full game-day experience at the Rose Bowl in Pasadena or cheer on your team at a college hockey matchup in Minneapolis.

Theater, Concerts & Holiday Performances

Holiday shows and winter concerts bring a welcome change of pace. A private ride makes the night smoother, especially when you’re headed downtown with a crowd.

Whether you’re heading to The Nutcracker in Philadelphia or attending a touring Broadway production in Seattle, having everyone arrive together makes the night run much smoother.

Brewery, Winery & Distillery Tours

Visit a winter tasting room and take a break from the cold. A chartered ride makes the day smooth and safe.

Groups love exploring the craft breweries around Grand Rapids or taking a winter wine tour through the Finger Lakes region.

Winter Festivals & Markets

Cold-weather cities know how to make the best of the season with outdoor music, fire pits, food vendors and cozy markets. Arriving as a group makes the experience even more memorable.

Plan a trip to the Winter Carnival in St. Paul or spend the afternoon exploring the Christkindlmarket in Milwaukee.

Indoor Climbing Gyms

Indoor climbing gyms are a great way to stay active when it’s cold outside. They’re perfect for groups looking for something fun and unique.  

Climbing Gyms are a great option for team outings, school groups or friends who want a physical challenge without facing the elements. 

 

Since winter’s already here, you might as well make the most of it. Choose your destination, grab your crew and let CharterUP take care of the ride.