Canada: How to Combine Two Trips to Create a Guess Where Overnight Getaway

Canada: How to Combine Two Trips to Create a Guess Where Overnight Getaway

How to Combine Two Trips to Create a Guess Where Overnight Getaway

Craft the ultimate weekend getaway by combining two incredible road trips

Last year, we unleashed the phenomenon known as Guess Where Getaways, and boy, did it take off like a rocket! Our weekend escapades were an instant hit, with all slots selling out faster than we could say "adventure awaits!"

We had an absolute blast curating these itineraries for unforgettable weekend getaways. But here's the deal: coordinating accommodations and crafting customized trips turned out to be more time consuming than we thought. So, instead of focusing on exclusively curated weekends for two, we decided to give you the power to create your very own Guess Where Getaway!

Prepare for an epic road trip by combining not just one, but two of our jaw-dropping trips! We've cherry-picked the most ideal pairings and included our top accommodation recommendations.

Before you dive headfirst into the excitement, here are a few things to keep in mind:

  • Buckle up, because managing two back-to-back road trips is an adventure of its own! To make the most of your weekend, we recommend booking an extra day or two off work. Kick off your adventure on a Friday, and don't forget to reserve Monday as your well-deserved day of rest.
  • Most accommodations have a minimum stay requirement of two nights over weekends. So, we've handpicked these pairings with that in mind. Picture this: you'll follow your first Guess Where Trip itinerary on the way to your dreamy accommodation Friday, spend Saturday on your second roadtrip, then head back to your fantastic accommodation for your last night, leaving Sunday.
  • The order in which we suggest taking these trips is like a well-choreographed dance of driving distances, proximity to accommodations, and the availability to do the trip on a Friday, Saturday or Sunday. If you prefer weekday escapades, no problemo! Just make sure the "Available to Depart" section of the trip aligns with your desired days of adventure.

Get ready to unleash your inner road warrior and create memories that will last a lifetime. The time has come to unleash your inner road trip warrior and experience the road trip weekend of a lifetime! Let's do this!


Western Ontario

    The Funky Getaway

    We absolutely love this getaway, which centres around the funkiest motel you've ever seen.

    Penny's Motel

    When to go: Friday to Sunday, Summer or early Fall

    Best for: People coming from KW or the GTA. This can be done from London, Sarnia or Niagara as well, but the drive up will take longer.

    Bonus: This weekend is dog-friendly!

    : Penny's Motel

    Book two nights at Penny's Motel, and be sure to save room for dinner so you can visit their on-site restaurant, Après. The food is to die for, and the motel boasts a stock tank pool, bocci ball and Muskoka chairs surrounding a campfire.

    Friday: The Waterfall Route

    Explore a variety of waterfalls, charming towns, funky restaurants and several photo ops. Please note: waterfalls may dry up in extreme heat or drought.

    Saturday: Markets to Mountains

    From cute markets to mountainside hikes, Markets to Mountains provides you with all the stops for a cozy yet adventurous day trip.

    The Picture Perfect Getaway

    Free up space on your phone for the hundreds of photos you'll take on this weekend away.

    Flowers and Wine

    When to go: Friday to Sunday, June or July to see lavender in bloom

    Best for: People who love wine and flowers, coming from London, KW or the GTA

    Accommodation: Our recommendation is to stay close to the end of your second road trip (Funky Florals & Fine Wines) as this iconic town is the perfect location for a weekend away. We like this royal hotel, this inn on a vineyard, or this well-priced historic inn. These accommodations are about 90 minutes from the fourth stop of An Adventure is Brewing, but well worth the drive.

    Friday: An Adventure is Brewing

    This road trip takes you on the perfect summer adventure filled with lavender fields, funky hidden gems, beaches and unique wineries and breweries.

    Saturday: Funky Florals & Fine Wines

    This pretty little road trip offers quite a few hidden gems combined with some iconic attractions. Must enjoy: wine, food and flowers.

    The Paranormal Getaway

    Calling all paranormal seekers: this getaway combines two of our spookiest trips, filled with ghost stories and a stay at a haunted inn.

    Paranormal Getaway

    When to go: Friday to Sunday, September or October for the spooky feels

    Best for: people coming from London, the GTA, Niagara, or KW (please note, part of this trip takes place in Cambridge)

    Bonus: This trip is pet-friendly!

    Accommodation: Stay at The Barracks Inn, a boutique hotel believed to have been built to house British Soldiers fighting in the War of 1812

    FridaySpooky Sights & Ghostly Tales

    Spooky ruins, abandoned buildings, and haunted mansions make up this ghostly road trip. Perfect for history buffs & paranormal seekers! We've included an optional scavenger hunt with clues at each stop. This trip takes place in a busier city, so travellers may run into some traffic.

    Saturday: Historic Haunts

    If you're a fan of ghost stories and unusual attractions, this trip is for you! We've rounded up the spookiest attractions for a 'Haunted History' route.


    The Romantic Getaway

    This centrally-located trip is great to take from many different areas. You'll enjoy a quiet, relaxing weekend with your own private outdoor jacuzzi, located by a conservation area.

    Romantic Getaway

    When to go: Friday to Sunday, Year-round

    Best for: Couples coming from Barrie, London, the GTA, Niagara, or Sarnia. This trip takes place close to KW, which is why we don't recommend choosing this one if you are from the area.

    Accommodation: This modern-day bed and breakfast will leave you feeling relaxed and replenished. Or, treat yourself to this hotel and spa.

    Friday: The Small Town Charm Trail

    You know those towns that are described as 'blink-and-you'll-miss-it'? They often have the most amazing hidden gems! Get to know a few small pockets of Ontario with this surprise road trip.

    Saturday: Local Markets & Picturesque Towns

    One of our best-selling trips, and for a good reason. Filled with charming towns and a year-round market, there is plenty to choose from to fill your day.



    The Woodsy Getaway

    Explore one of Canada's best-known and most beautiful regions on this weekend away in Muskoka. Natural beauty, serene charm, and amazing hikes, this trip is one for the books.

    When to go: Friday-Sunday/Monday, year-round (but we're partial to Fall)

    Best for: Active groups, couples, and families traveling from the GTA, Barrie or Kingston. If you're up for a slightly longer drive, you can also kick off your adventure from Niagara, KW, London, or Ottawa. In such cases, we suggest turning it into a 4-day weekend by doing your Guess Where Trips Saturday and Sunday rather than Friday. This way, you can make the most of your getaway without feeling rushed.

    Bonus: This trip and our accommodation recommendation are pet-friendly!

    Accommodation: This inn feels more like a cottage-y resort, and has something for everyone: hotel rooms, glamping tents, and even an airstream if you book far enough in advance!

    Friday: Weird & Wonderful Things

    One of our best-selling trips takes you north towards beautiful sights, unusual attractions and secluded waterfalls. 

    Saturday: Muskoka Meandering

    Muskoka Meandering is the perfect way to escape from the hustle and bustle of the city and immerse yourself in nature while enjoying delicious wines and beers, beautiful scenery and lookouts, and charming small towns.


    Nova Scotia

    The Acadian Getaway

    Discover the charming towns, hidden gems and views of Nova Scotia, just outside of Halifax.

    When to go: Friday to Sunday, June to September

    Best for: Halifax natives and visitors, or anyone in the Southwest Nova Scotia 

    Accommodation: We love this inn and its proximity to the historic waterfront.

    Friday: Coastal Crawl

    Get out of town and feel the ocean breeze in your hair. This trip perfectly combines iconic Nova Scotia views with small town hidden gems. 

    Saturday: Valley Views

    Down in the valley where the green grass'll find charming towns, get lost in lush vineyards, take in vast views and hike scenic trails on this countryside road trip. 


    British Columbia

    The Sweet and Delectable Getaway

    Tasty treats, great drinks and farmyard animals await on this charming weekend away from Vancouver.

    When to go: Friday to Sunday, May to October

    Best for: Anyone traveling from the Vancouver area, this getaway is more fun for adults than kids.

    Accommodation: A fairy-tale-themed B&B

    Friday: The Taste Trail

    This road trip will take you to some funky eateries, family farms, wineries, cideries and a whole lot more. To offset the treats, we've included a few whimsical hikes to end your day.

    Saturday/Sunday: Flora, Fauna & Farms

    This trip will take you to some wonderful countryside spots, historic farms, an animal sanctuary, funky eateries, lookout points and so much more. The short driving distance from the city and accessible locations make it the perfect family-friendly trip.

    Note: If you're traveling from Vancouver, do this second road trip on the last day of your getaway, as it will lead you home. 


    More Getaway Ideas 

    Interested in a weekend away with just one trip? Here are some great ones that end in some fantastic areas (accommodation recommendations are emailed post-purchase).


    Wine Time & Hidden Gems - clicking here will spoil the end location

    Markets to Mountains - clicking here will spoil the end location

    Funky Florals and Picturesque Towns - clicking here will spoil the end location


    The Long and Unknown Road - these fairytale cottages are worth the trip

    The Rocky Mountain Route - clicking here will spoil the at the end location


    Secrets on the Scenic Route - clicking here will spoil the end location

    As always, feel free to connect with us over email or Instagram if you need any trip recommendations. Happy travels!


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    Tags: Getaways