Family Vacations Teenagers Actually Want to Go On

Planning a vacation that the whole family will enjoy can be challenging. Especially if you have teenagers in the mix. Convincing them to put down their phone or to take a break from video games and engage with the family is easier when they are excited by the activities planned.

Ontario’s Southwest is full of fun, opportunities to learn, and ways to spend genuine quality time together. To help you with the planning, we’ve created an itinerary that's packed full of suggestions to build a perfect family vacation.

For the most part, these suggestions work best for trips in warmer weather; however, there are many options that you can pick if you’d like to visit in the colder months. If you see "❄" beside a suggestion, that means that it's open in the winter as well as the summer. "✿" indicates that you can only do those activities in the spring. 

A Charming Trip to Chatham-Kent

Chatham-Kent offers a mix of educational, recreational, and cultural experiences. With a deep-rooted history in the underground railroad, beautiful lakefront views, and prosperous agriculture, there is something for everyone. 

Where to Stay in Chatham-Kent

Willow Barrel Retreat ❄ and The Retro Suite Hotel ❄ are two unique accommodations that will stand out in your teenager's memories. Each offers a unique blend of comfort, style, and adventure, ensuring your family's stay is anything but ordinary.

Willow Barrel Retreat is perfect for the adventurous family. Located in Erieau, Willow Barrel Retreat offers a variety of cottages and suites on the shores of Lake Erie. This is the ideal location if you have a teen who is eager to explore the outdoors. With kayak, paddleboard, bicycle, and canoe rentals available, the opportunities for adventure are endless.

The Retro Suite Hotel, on the other hand, is a celebration of creativity and nostalgia. From motorcycles to sports, each room has a unique theme and whimsical design that will have your teen asking to return to try out a new room. 

What to do in Chatham-Kent

Your family may want to extend your vacation to make time for all of these exciting activities:

• Learn about the Underground Railway at the following museums and historic sites:
  • Black Mecca Museum ❄ As of September 29, 2025, CKBHS & Black Mecca Museum is currently open for virtual tours only until further notice. Take a virtual tour here.
  • Josiah Henson Museum of African-Canadian History
  • Buxton National Historic Site & Museum 

• For those who enjoy playing games together, you can visit one of the following arcades, entertainment centres, or board game cafes:
  • Level Up Arcade & Bowling ❄
  • Flying Squirrel Trampoline Park Chatham ❄
  • Turns & Tales ❄
• Pick your own peonies at Fleur de Roy ✿ (from May 31st until June 10th, 2025)
• Spend the day with wildlife at the Greenview Park & Zoo.
• Catch a race at the Buxton Speedway. 
• Relax on the water during a Walpole Island Waterway Tour.
• See a movie at the Boonies Drive-In Theatre.
• Experience the great outdoors in Chatham-Kent. Travel tip: Ontario Parks and beaches are very busy on weekends. Plan to visit on a weekday to avoid the crowds.
  • Rondeau Provincial Park ❄
  • Erieau Beach 
  • Erieau Boulevard Trail ❄ and the Erieau Marsh Trail ❄
• Try an Ontario's Southwest Signature Experience! To help you find the best of the best we've created our very own Signature Experiences. The following experiences allow you to get hands-on, learn the stories behind these experiences, and make connections with the host as well as our region:
  • Beyond the Vase - Tulip Experience at Hat Trick Farms ✿
  • Awaken Your Spirit; A Spirit Horse Encounter at TJ Stables