How To Organize the Perfect Cottage Getaway

In honour of my annual girls trip happening next weekend, which I sadly can’t make it too, I’m reposting the recap from last years epic cottage trip!
As you will read below, my friends know how to do it right when it comes to cottage weekend planning.
I’m so sad to be missing this years trip, especially after revisiting this blog.

Keep on reading if you want to know exactly how we plan the PERFECT cottage trip!



How To Organize the Perfect Cottage Getaway


My lifelong girlfriends and I make it a point to go away to a cottage every summer together. Sometimes it’s for someone’s bachelorette – and summers like this when no one is getting hitched, we just go for some recharging and girl-time.

This past weekend we went to Grand Bend to the sweetest little cottage. (Click here to view the property.) It was clean, cute, colourful and had plenty of sleeping space. We had amazing food, cocktails, themes (yes we as a group are notorious for hilarious theme parties wherever we go), and plenty of laughs.

The last night we were there, I was soaking it all in and I realized how much we truly ‘nail it’ as a group based on organizing and not putting too much onto one person. Really and truly the jobs are split evenly, so that there is never that one friend that’s doing everything and not having fun.
So, today’s blog is all about how to organize and plan the perfect cottage getaway. I’ve broken it down in to 5 easy steps with lots of pictures to inspire you!

Yes we are all 30-something going on 13 and prefer to have a ‘no boys allowed’ weekend – but this plan could also work for couples, multiple families or any group of friends!

1. Pick a Date (and Let It Go!)
We all eventually get to the age where not every single weekend ‘works’ for everyone. Trying to accommodate every single person is so frustrating and you are bound to hurt someones feelings. After a few years of trial and error we’ve now just started booking our summer cottage trip 6 months in advance.

The occasional year it doesn’t work out that way and we are still planning a month out. In that case, the best bet is just to book it and pick a weekend and everyone just has to work around it! No one wants to miss out on fun – so it always works out that even the ones that thought they couldn’t come, end up there.

Basically, you’ll never get it booked if you try to be a slave to everyone’s schedules. Book it and let everyone else work it out.

2. Make Teams and a Meal Schedule
This is by far the best thing we as a group have ever implemented for our weekend getaways. It keeps the morale high, the kitchen clean, your budget low and everyone well fed.

Here is exactly what we do:

  • Assign everyone to pairs or three’s (depending on how many people you have).
  • Assign each team a meal slot. This time we went from Friday at lunch until Sunday morning and there were 11 of us.

This was our schedule:
Friday: Lunch  – LAUREN & CLAIRE
Friday: Dinner – ANDREA & SUZ
Saturday: Breakfast – BRITTANY & HEATHER
Saturday: Lunch – ANGIE & DEB
Saturday: Dinner – ANGELA & JORDIE
Sunday: On-the-go-breakfast (bagels & cream cheese/fruit to take on the road) – ALANA.

  • Depending on how many people go and how long you are there for – you can change the number of team members. If you are going for a week with other families, maybe assign each family one full day. There are lots of ways to do it, but split the time evenly so time spent enjoying yourself and cooking is fair.
    Each team is responsible for fully preparing the assigned meal including buying groceries, cooking/serving the meal and clean up. We always include a signature drink too.

Here were the rules this time:

– Each team responsible for bringing groceries and feeding 10 people for their assigned meal + a signature cocktail/mocktail + clean full up.

– Kitchen must be left in perfect condition for the next team’s meal.

– You MUST bring home your leftover food, mix, sauces, etc. If you came with it, you leave with it. Bring Tupperware for leftovers.
(Note: We do this to avoid food waste. Also makes leaving and clean up super 
easy when everything in fridge is cleared!)

– Can everyone provide a gluten free option? There are quite a few of us this year. Even if it’s simple i.e.: burger (no bun is G-free)

Honestly, I can’t recommend this system enough. You get to put love and care in to one special meal and then eat like a Queen for the rest of the time. Also, the kitchen clean up is always the worst part, especially when cocktails are flowing. This guarantees it is taken care of!

3. Odds & Ends
To prevent drinking and driving or anyone having to leave the fun when you realize you forgot something, assign all odds & ends before getting there.
Send a reminder note about BYO-beach towel, booze, sunscreen etc.
Then also assign the essentials. We did it by team this year. The cottage we went to already had condiments but we needed to assign the following items:

  • Bag of ice (assigned to every team so we had 5)
  • Packs of Toilet Paper (assigned to 2 teams)
  • Packs of Paper Towel (assigned to 2 teams)
  • Garbage Bags (assigned to 1 team)
  • Recycling Bags (assigned to 1 team)

4. Team Themes!
If you’ve followed our girls getaways over the years you will have noticed one thing for sure – there are always silly costumes, multiple themes and way too many giggles.
Each team will usually have a themed dinner. It can be something simple like ‘Italian Night’ or ‘Beach Picnic’ or it can get wild and hilarious like ‘Electric Circus’ or ‘High School Throwback’.
Regardless of what you do, themed dinners always add so many laughs, keep the excitement up and the pictures always end up being ON POINT!

This year Jordie and I did a Slumber Party theme and it was more magical then I could have imagined. There was something about the love of our friends, the cotton candy coloured sky and the nostalgic meal that was just so beautiful. We even played ‘Women & Songs’ in the background. If you were a teen in the 90’s early 2000’s this takes you right back to slumber parties back in the day. One of the girls even teared up. Love, nature and beauty – they just give you all the feels!

As I’m sure you would assume, I have zero chill when it comes to getting things done and making them into my vision. I truly get so happy when I plan a cute theme and I can’t help but pull out all the stops.
This time around it was all about the table setting. I spent a lot of time making it as cute and ‘girl party’ as I could. Since it was a sleep over theme – the food was is much easier than in previous themes I’ve done – so I focused my attention on really bringing the theme to life.
You can keep it simple or go all out. It’s truly the thought and delicious food that counts.

Here are some pictures and descriptions of what we did for our theme to inspire yours:

The outdoor table setting. Looked absolutely stunning against mother nature’s cotton candy sky.

We did a custom mug with balloons on a stick coming out of it to create look of helium ($1 for 8 sticks at dollar store, mugs from
We also put bowls of candy to keep with slumber party theme, and all the ladies were allowed to fill their mugs with candy. We served pizza, popcorn and salad for our meal. Our signature drink was pink bubbly with pink cotton candy on top and a cute pink paper straw. We also had Women & Songs playing in the background and asked all the girls to wear cute colours or PJs to dinner.

The hosts, one of my best friends Jordie and myself.

This picnic table was perfect to add to our theme!

The babes ready to dig in!

I made this banner before we left and set up a little photo booth as well.

Could this night end up any more perfect? This was the sunset over dinner. We ended up going down to the water and setting a timer on the camera to get this shot. Was WORTH the effort!!

We ended the night with a round of The Girlfriends Game!


5. Theme Inspo & Social
We always come up with a hashtag for the weekends we are away. For our 30th birthday trip we went to Niagra-on-the-Lake so we chose #NOTL30 and it was a great way to group all of our hilarious photos and themes.

For your teams theme dinner – Pinterest, funny things you’ve done in your past and you favourite food or interests can all be great inspiration for the perfect theme.

To help this journey along, here is a list of all the beautiful and wacky themes we have done over the years. Keep scrolling past the list for pictures.

  • Mexican (a variation of this for a bachelorette was ‘Sex Mex’ with sexual names for all the food.)
  • Italian
  • WWE (yes, wrestling… scroll down for epic pics)
  • Beach Picnic
  • Trailer Trash
  • Electric Circus
  • High School Throwback
  • Barbie Party
  • Flamingo
  • Canadian Brunch
  • Backyard BBQ
  • Slumber Party
  • 90’s Hip Hop

However you plan your weekend away, I hope our amazing cottage weekend system serves you well!

This was the wrestling theme! I cry laughing every time I see this picture. My sister is the best ?

The WWE Menu.

Trash theme! Taco Salads out of Doritio bags, trucker hats and tattoos!

Canadian Bacon theme! Oh, Canada! ?? Beach Picnic gives the best pics!

Floaties make the theme!

I know not everyone loved high school. But we really did! LOL. This was one piece of a really elaborate theme we did one year for Meghan’s Bachelorette. It was a hit!

Fancy themes like wine and cheese are always great for lunch!

This night included some lip syncing and Fresh Prince of Belair throwbacks! 90’s hip hop ?

Italian theme night over my bachelorette. The covered the table in that brown paper you can write on… such a hilarious idea to go with the Italian theme!

Sex-Mex Mexican theme!!