How To Have A Crazy Awesome Sister Road Trip

Posted by Dani on August 1, 2013

MOMA New York Exhibit
Last week was a fun week here at Lifeovereasy. We set off on a sister road trip. A double sister road trip, actually, because Nads and I brought along my 2 girls. That’s 4 sisters in 1 car for about 800 kilometers, from Toronto to New York City. The drive takes about 8 hours in normal human time, or 32 sister hours if you consider there’s 4 of us.

road trip map

And it certainly felt like 32 hours – 32 hours of fun, that is! Cause sister road trips are a blast. I highly recommend them. Even if you don’t have sisters, borrow someone else’s sister and give it a try. Jam a car full of sisters and head to New York City. Guaranteed fun, I promise. Especially if you have Nads along. She can even turn a Buffalo garage car-repair pit stop into fun. Which she did, but more on that later.

Now there are some things you can do to up your fun quotient. First of all, you have to have a Fun Mindset. You need to believe that everything can be fun. No matter what. And this is easier than you think. First of all, you’re away from home. You’re with a bunch of girls you love. You’re heading to New York City. What could be more fun than that? Just assume you will have a blast. Know that like you know the sun will come up in the morning, and that ice cream for breakfast is good for the soul.

If you are bringing a younger generation of sisters along, you have to lay the groundwork years before. Brainwash them from a young age to believe in the Sister Code. Nads and I have always been close, and when I had 2 girls we knew we had to make sure they were close too. Use any means to accomplish this – education, indoctrination, manipulation, bribery – whatever it takes. Great road trips are worth it.


Once you hit the road, there are lots of things you can do to make the trip extra fun. I’ve put together a few tips and tricks from my trip to make sure you have a blast. Feel free to pick and choose whatever works for you. You may not need to use all of these for one trip. Everyone’s fun formula is different. It’s best if you add some personal fun touches of your own. Some of mine are uniquely whacky, and only actually work if you have Nads and my girls in your car. In fact, on second thought, you might want to use some caution with these ideas. It’s up to you, and it’s all good. Don’t forget, you’ve decided you’re going to Have Fun No Matter What.


How To Have A Crazy Awesome Sister Road Trip

1. Don’t worry about how long the actual road trip takes, cause the trip is as much fun as the destination. Our trip down took about 15 hours instead of 8. That might be a little much, but no worries because It’s All Good. Keep telling yourself that during the 15 hour drive. Denial helps, too. No matter how long the trip takes, keep thinking it’s only about 8 hours.

2. Pack some healthy and tasty food for the trip. Actually, get your sister to pack it – much easier. This means that on rest stops, you can buy fun stuff like Venti Caramel Frappuccinos instead of wasting your money on real food. And stocking up on healthy eats during the drive means you can feel free to do things like go gourmet dessert hunting in New York, for things like Cronuts, cereal milk shakes, and frozen s’mores.

Milk Bar Williamsburg menu

3. If the air conditioner happens to break down during the sweltering drive, take a detour and check out Buffalo. Drive around remote streets looking for a mechanic. Find Stevie who owns the gas station, who only fixes Chevys but sends you to Dougie who fixes those foreign cars. Forget Stevie’s directions and drive around a while until you find a garage that has a Dougie in it. Hang out in Dougie’s air conditioned office for 3 hours while feeling deep gratitude for the miracle of modern air conditioning. While you’re waiting, spend your time making up games, taking funny Instagram pics, and twirling on the counter stools. Sign for any packages that happen to come for Dougie. Read the old issues of the local Buffalo paper that are lying around the office. Feel really impressed that those hardcore Americans publicly shame their criminals by publishing full names and addresses. Spend at least an hour reading about all the local petty criminals, where they live, and what they did.

4. When Dougie quotes an astronomical price to fix the a/c, calculate how many outfits and pairs of shoes that money would buy in New York. Remind each other that excessive sweating can be a great detox, thank Dougie for his time, and head out to find the I-90. Get lost on the way and wind up driving through a construction zone, where the bumpy roads miraculously fix the air conditioning. Know that this sister road trip is Meant To Be.

5. Head out toward NYC, stopping at a bunch of rest stops on the way since with 4 girls and lots of frappuccinos someone always has to pee. Keep the car running at all costs because girl logic says that will help keep the air conditioner going. If it happens to conk out at all, try to find some bumps to drive over.

6. Make sure you buy goofy things from the rest stops, like local maple syrup in a Statue of Liberty bottle.

maple syrup in a Statue of Liberty bottle

7. Get off the interstate in some tiny town to find a McDonald’s because someone needs a bathroom. Notice a large group of wholesome-looking, attractive teen boys leave the McDonalds with their milkshakes, pile into the back of a shiny red Ford pickup, and drive off into the countryside. Watch your 15 year old stare and declare she has found the American Dream.

8. At least 1 sing-a-long hour is mandatory. Make sure the kids participate at all costs because they may not yet appreciate just how fun a sister sing-a-long can be. Hide their i-Pods if you have to, or bribe them with another caramel frappuccino. Let them choose the playlist, and make sure the singing is loud. Include some great family oldies, like Lucille and Country Roads. Abba is also a sure winner.

9. Stop at any huge outlet mall you pass on the way, even if there are only 45 minutes of shopping time left and you have to race through the massive complex. Trust that Nads will find you a bargain, because she always does. If you don’t have a Nads with you, just have faith and keep repeating “Final Reductions. Half Off The Lowest Ticketed Price” while you run around.

10. Eventually get to the Big Apple after what you tell yourself is only 8 hours. As you drive through the Lincoln Tunnel, make sure you play a New York themed song. Choose the classic “New York, New York” like we did, and let Frankie serenade you into the city.

11. Spend a whirlwind 5 days following Nads from cool neighbourhood to cool neighbourhood. Load up on bargains, Magnolia Bakery cupcakes, and various other goodies. See a show. Keep your eyes peeled for celebrities. If you do happen to bump into anyone famous, keep your cool but make sure at all costs to take a cellphone photo with as many sisters in it as possible. Eat a ridiculous amount of amazing food. Take 5000 photos. Collapse in bed at night in your cool boutique hotel off Times Square that Nads found for 2/3 off the regular price.

Times Square, New York City

12. After 5 days of this, it’s time for the trip home. Keep agreeing with Nads that you want to hit the road early, although you know that will never actually happen. Decide to make one more quick stop in Soho before you go. While you’re there, stop in at Mac Bar for 1 last gourmet mac and cheese. And you can’t really leave without visiting Jonathan Adler. Keep telling yourself that you’re going to leave early, but drop in for a second to check out the sale area at Anthropologie and buy a really cute dress. Wait while one of the girls scores a great straw fedora. And then take a last minute walk through Times Square to pick up some fun street art for one of the girls’ bedrooms you’re decorating. Take 45 minutes to figure out how to jam everything into a suddenly tiny trunk. It’s afternoon rush hour by the time you leave the city. You knew that was going to happen. No worries, ‘cause It’s All Fun.

Artists & Fleas market, New York City

13. Make one final coffee run before you hit the road. If you get stuck in line behind a family of 10 who order 14 special drinks, while away the 40 minute wait time by googling pictures of the new royal baby and checking out Kate’s post-baby appearance dress. Order the biggest drinks they have to get the most sugar and caffeine for your drive home. Don’t worry about having to pee in 20 minutes, you can deal with that later.

14. Keep having Fun with a capital F as you make the long drive home. Review all the highs of the trip: best shopping score, top NYC dessert, best meal, final verdict on the Broadway show Chicago, favourite neighbourhood. Make sure the girls know just how cool the Sister Road Trip thing is. Remember, indoctrination with the Sister Code will ensure many great road trips in your future.

15. After a few hours, stop for food in a small town and eat at the local supermarket. Feast on things like chicken salad on white bread, devilled eggs, and if you’re lucky, some kind of dessert that has chocolate pudding, Reese’s Peanut Butter Cups, and Oreo crumbs in it.

Band in a Bucket

16. After what feels like forever in the car, decide it’s time for another sing-a-long. If you have a couple of whacky fun sisters along like Nads and my youngest, they will pull out a surprise – the Band In A Bucket they secretly picked up at Toys R Us when no one was looking. Everyone gets their own instrument for this sing-a-long. AND YOU TOTALLY ROCK IT DOWN THE INTERSTATE. At least 150 kilometers of full-on singing and banging.

children's musical instruments

Don’t stop whacking the spirit bell that comes with it’s own mallet. The driver can groove with the egg shaker. The girls can alternate between tambourine, kazoo, and harmonica. Everyone totally kills it. If the car breaks down, there will be no problem earning enough for a night at a local motel. Give yourselves a band name, like the Travelling Wilburys Wheelbarrows.

buskers, New York subway

17. As you drive through customs back to Canada be honest about your purchases. The Customs Man will see 4 girls on their way back from New York City and know that you went shopping. Actually, if you didn’t buy as much as the Customs Man thinks 4 girls would have bought in 5 days, girl logic says you should lie and say you bought more. Just to be safe.

18. Roll into Toronto at some crazy hour like 3 in the morning. Understandably, your husband will have given up waiting and gone to bed. Annoyingly but predictably, your mother will be mad that you came home so late and didn’t call on the way. The only one who will be there to greet you happily is your giant fluffy dog. Doesn’t matter – you just had one Crazy Awesome Sister Road Trip.

19. Re-write Rules 1-18 next time you head out together, because it will be totally different. But no worries, it will still be Crazy Awesome.

Naked Cowboy, New York City


And here’s our Sister Car Band Sing-A-Long playlist, in case you’re looking for one. Now, this play list will make no sense to some people. But it worked for us, so here you go:

1. Ring Of Fire – Johnny Cash
2. Blurred Lines – Robin Thicke feat. T.I., Pharell
3. Burning Down The House – Talking Heads
4. 5 Days In May – Blue Rodeo (perfect for harmonica and kazoo solos)
5. Get Lucky – Daft Punk (this is where the egg shaker really kills it)
6. I Love Rock ‘N’ Roll – Joan Jett and The Blackhearts
7. Piano Man – Billy Joel (to wake up the harmonica player)
8. Wagon Wheel – Old Crow Medicine Show (Country music works particularly well with the Band In A Bucket instruments. No offence.)
9. Ho Hey – The Lumineers
10. Fernando – Abba
11. Halo – Beyoncé
12. Rolling In The Deep – Adele
13. Titanium – David Guetta feat. Sia
14. Brutal Hearts – Bedouin Soundclash feat. Cour De Pirate
15. Cecilia – Simon & Garfunkel
16. She Will Be Loved – Maroon 5
17. Girlfriend In A Coma – The Smiths
18. Daydream Believer – The Monkees
19. LIFEGOESON – Noah And The Whale
20. Like A G6 – Far East Movement
21. Temperature – Sean Paul
22. A Thousand Miles – Vanessa Carlton
23. 500 Miles – The Proclaimers
24. Cupid’s Chokehold – Gym Class Heroes
25. If We Ever Meet Again – Timbaland feat. Katy Perry
26. I Melt With You – Modern English
27. Heart Of Glass – Blondie

32 Responses to “How To Have A Crazy Awesome Sister Road Trip”

  1. Tasha says:

    Even if you don’t have sisters, borrow someone else’s sister and give it a try! Hahahahaha! Love it!

    I’m so glad my sister is at that age where she would find road trips fun! She’s turning 13 this September, not going to New York anytime soon with her (her dad would kill me for taking her out of the country) lol but I do plan on taking her to Banff next summer:) I would love to go to New York someday. Sounds like you had an absolutely riot! 😀

  2. So wish I had sisters after reading this post!! Sounds like you had an amazing time!!

  3. Wow, I REALLY wish I had a sister now!!! I’m so glad you stopped by my blog today so I could find you. I LOVE this blog. I’m looking forward to following all your adventures. I’m also going to find you on instagram and pinterest.

    • Dani says:

      Thanks so much Carol! I’m actually scared to follow your blog because your crazy awesome challenges will make me want to do something crazy like actually get fit, which will really interfere with my late night ice cream eating! Jokes 😉 – I love your blog and I’m looking forward to all the inspiration I know I will get. Thanks for dropping in, xo.

  4. That sounds like so much fun! My sister and I have never traveled together without our parents before. I’m pretty sure we would rip each other to shreds before we reached our destination. We love each other but fight like crazy in confined spaces. 🙂

    • Dani says:

      Nads and I occasionally go at it, too, but we try to move on quickly. The sister thing can be complicated, right? I decided a long time ago that she totally makes up for it, so I keep her ;). Maybe you and your sis can skip the road trip part and meet up in New York – might be more fun that way 😉

  5. MyDirt says:

    I don’t have sisters but I do have friends who are like sisters! Maybe I can talk a couple of them into a road trip next year? What a great trip. I love NYC. Thanks for sharing.

  6. WOW it looks like it was a blast!

    Since I don’t have sisters, the only thing I can compare this to is the time I went with these two sisters, their mom and me in the car from Toronto to Niagara Falls. It was awesome. It was 2001 and I was the only one that had a CD player in the rental car. We had a never-end Britney Spears marathon. It took us about a year to be able to listen to any of her music again.

    And, yeah, I would have love to see the naked cowboy man. Fireman, Police, etc…

    • Dani says:

      Haha, love that – Britney Spears overdose! Yes, it was a blast. And the Naked Cowboy was there every day to greet us 😉

  7. I don’t have a sister, but I’d borrow one in a heartbeat to hit the trails for NYC – have only been once, and would go back without thinking twice… Maybe not for the naked cowboy – but, does he ever leave? 😉

    • Dani says:

      I think NYC is a perfect girls trip destination – sisters or friends. And I think the Naked Cowboy is a permanent fixture in Times Square – he takes his job seriously 😉

  8. Oh that sounds like a SUPER COOL trip, awesome!!

  9. Tia says:

    Wow! Sounds like such an amazing time!! It has been WAY too long since my sister and I went on a road trip. I’m off to drink a bottle of wine and discuss this idea with her immediately.

  10. Love the play list!

    We love road trips as a family – wish I had a sister to take this one with!

    So fabulous.

  11. So. Much. Fun! Looks like you guys had a great time!

  12. paula schuck says:

    Wishing I had a sister now too. This looks like great fun!

  13. This was such a fun read! I went traveling with my sister once for 3 weeks and it was fun at first. .. After 3 days we annoyed the heck out of each other…. won’t be doing that again.

    • Dani says:

      Thanks Amy! I think maybe sister trips should have an expiry date – 3-5 days max should keep things in the fun zone 😉

  14. Crystal says:

    I love your playlist! Music can totally make a trip in my mind! Sounds like you had a great trip, it all makes me want to go back to NYC again!

  15. Love it! It sounds like so much fun… Now I need to find a “sister” to go on a road trip to NYC with me 🙂

  16. Hannah Teej says:

    The only person who will be happy to see you will be the dog.

    Totally legit. 🙂


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