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Summer Road Tripping 101

I have loved road tripping since I was young … some of my fondest memories growing up were getting to drive to Slave Lake, Calgary, Edmonton, Kelowna, etc. and sing my heart out with my friends along the way. As you get older and everyone has grown up jobs, boyfriends and starts getting pregnant, engaged or married …. it becomes next to impossible to find time go on a road trip, let alone with your best friends. Getting all of these girls together (I have known them since I was 5) sent us right back into the good ol’ days. We couldn’t have asked for a better road trip if we tried!!! If you are lucky enough to be able to go on ANY type of road trip this summer … I wanted to share some important tips with you to make sure yours is just as great as ours!!!!

Roadtripping is SO fun in the summer because you can decide where to stop and WHEN (at your own leisure). If you see something cute or want to run into an antique shop or ice cream parlour … you can!!!! Better yet, if you road trip through the Okanagan you can stop at any vineyard or winery along the way and it will not only be picturesque but will also have SO much to offer … like tons of wine and lots of great food!!! Us girls had so much fun together … so without further ado read through these 6 simple steps before heading off on your next adventure ….

This summer, Joe Fresh and the Canadian Automobile Association (CAA) have partnered to help you hit the road and adventure through Canada. Up until July 24, you can enter our #HereComesSummer contest for a chance to win CAA memberships, Joe Fresh gift cards and Ultimate Dining Cards. You could even win the Ultimate Road Trip prize pack worth $5,000 in gift cards from Joe Fresh, Best Western, PC, Ultimate Dining Card and MasterCard. How to enter!?!?! Enter with your email address here:

summer road tripping in the okanagan jillian harris in the middle of the road in Osoyoos wearing poppy barley and joe fresh jillian harris' best friends hitch hikingokanagan road trip jillian harris in the middle of the road pregnant in joe fresh maxi dress jillian harris best friends in middle of road all wearing joe fresh

1. WHO To Go With: 

I grew up with these girls and each and everyone has their own little quirks and special additions to our group. We have travelled, road tripped, laughed and cried together so we all knew as soon as we were planning this that we would be a good fit to be stuck in a car with. If you are planning on wine touring I definitely recommend going with someone that is PREGNANT or volunteers to be a DD for one of the days!!! You want to be able to tour around without worrying about a driver … if you are wine touring I recommend staying overnight at one of the gorgeous wineries as well!!

Photo 2016-05-19, 1 57 08 PM jillian harris and friends walking down street in joe fresh jillian harris and friends summer road tripping in joe fresh shannon in joe fresh floral maxi dress jillian harris in joe fresh dress and melanie auld jewelry jillian harris in striped joe fresh dress and frye boots jillian harris pregnant with friends on road trip jillian harris in joe fresh and frye boots jillian harris and friends at jillian's kelowna home

2. WHAT To Wear:

It ended up being a cold and stormy weekend in BC, Canada but it was still muggy outside. We made a stop in at Joe Fresh before hitting the road and decided to dress comfortably while not sacrificing style. My go to outfit when travelling is an easy throw on dress that looks cute with a pair of sandals, boots or heels … you never know where the day or night will take you!!! This weekend we had to make sure our outfits looked cute with jackets and sweaters because it was still cold out. I wore my Joe Fresh grey striped tank dress one day and it was SO comfortable and cute … it was a little bit too cold to wear on it’s own for the road trip but it was easy to layer and pair with everything else that I brought to keep warm. I also wore my Joe Fresh black scoop neck maxi dress which was PERFECT for a cozy road trip with the girls and even looked cute with my bump (even though it’s not maternity). I love wearing Joe Fresh clothing for road trips because their items are so soft, affordable and comfortable. Everything is easy to pair together and the fabrics don’t typically wrinkle when you’ve been sitting for too long.

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3. WHAT To Bring: 

Another good thing about driving is you can pack whatever you want and however much you want!!! I’m sure you all know by now my love for over packing …. and well I just say I like to be ready for anything. BUT some must haves when you go on a road trip … WATER, phone, charger, sweaters/scarves (it was cold in Canada still so these were KEY!!!!), camera , sunglasses (I picked up the heart sunglasses in store at Joe Fresh), map, bag, hat, comfy shoes … I usually go for my birks or my frye boots but Joe Fresh has some AWESOME sandals that are so comfy, I’ve linked them for you HERE!!!

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4. HOW To Get There: 

We drove Highway 97 from Kelowna to Highway 3A in Osoyoos. It is SO pretty because the entire drive is along the lake. Once you Hit Penticton it then starts to go through the mountains, orchards, and vineyards which is SO SO gorgeous as well. Definitely make sure you have a vehicle that’s large enough for everyone because as crazy as it sounds … it’s so fun to have everyone crammed in together for hours on end!! It’s part of the adventure …

Photo 2016-05-21, 10 37 37 AMPhoto 2016-05-21, 7 10 27 PM Photo 2016-05-21, 4 54 26 PM Photo 2016-05-21, 2 44 35 PM Photo 2016-05-21, 2 22 58 PM Photo 2016-05-21, 1 12 52 PM Photo-2016-05-19,-3-37-56-PM Photo 2016-05-21, 2 27 34 PM Photo 2016-05-21, 2 19 57 PM Photo 2016-05-21, 2 18 47 PM Photo 2015-05-23, 1 05 15 PM Photo 2015-05-23, 9 47 05 AM Photo 2015-05-24, 8 34 43 AM Photo 2015-05-23, 1 36 40 PM Photo 2015-05-24, 1 21 29 PM Photo 2016-05-21, 2 22 06 PM Photo 2016-05-21, 2 19 00 PM Photo 2016-05-21, 2 24 56 PMPhoto 2016-05-21, 6 05 56 PM

5. WHERE To Go: 

My best friend Shannon and I started in Vancouver and made our way to Kelowna where we met the rest of the girls. From there we road tripped through the Similkameen Valley stopping at fruit stands, wineries, scenic spots, and lakes along the way. If you are in the Okanagan and are able to take this SAME road trip from Kelowna to Osoyoos some of our favourite stops were: The Hatch Winery, The Grist Mill, Burrowing Owl and Nk’Mip winery.

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6. WHAT To Listen To: 

Having a perfectly curated playlist is an absolute necessity. Especially if you are going on a long road trip and are in and out of service … nothing is worse than running out of good music or better yet not having any at all!!! Here are some of the best songs from our playlist …

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Our outfits from left to right: Brown Pants | SandalsBeige Cardigan | Silk Tank | Jeans | Khaki Maxi Dress | Floral Maxi Dress | Striped Tank Dress

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Outfits from left to right: Striped Dress| Straw BagSporty Tank Dress | Knit Top | Brown Pants | Pink Tank Top | White Pants | Green Top | Jean Skirt | Blue Hat | Black Maxi Dress | Straw Hat

I hope you all get a chance to go on a summer road trip …



Leave a Reply

      1. Indeed it did work now. Fingers crossed.
        BTW, wearing JF dress at work today…their dresses are the best!! Cheap and chic. What more can a girl as for!

  1. Great pictures as always Jillian. Is your favourite lens still the 50mm or are you now using a 35mm? I tried to zoom in on your camera but I can’t tell. Keep getting those great angles!

  2. So I follow you on snapchat and I see that you are always looking for good vegan food. If you haven’t tried Larabar, it is a must…vegan and lots of delicious flavors, perfect for road tripping or keeping a snack in case you get hungry!

  3. Where are your boots from Jillian?? I don’t see a link on here for your short black adorable boots.)

  4. Where was the beautiful place with the pool overlooking the vineyard? It looks incredible. Just got back from a road trip to Kelowna and I’m already researching places to go and stay next year!

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