Plan The Perfect Vacation

Top Tips For An Organized Trip

Plan The Perfect Vacation

Fairly early on in our relationship, my husband did a very sweet thing for me… he planned a surprise weekend getaway. He wouldn’t tell me a thing about where we were going. But Friday morning, while I was at work and getting excited about leaving that night, a courier arrived at my office with an envelope for me. Inside was a detailed agenda of the weekend ahead. So charming and so organized! I was hooked.

That was the first of many trips he has planned for us. Whether we’re taking off on a road trip to the States or flying out West, he always figures out how we’re going to get there and what we can do while we’re there. Since it is travel month here at YMC, I asked him to share some of his secrets…


In my wife Jen’s very first Yummy Mummy blog post, she wrote that “feeling totally out of control and completely disorganized really freaks me out.” I don’t get that freaky myself, but I can appreciate the sentiment. And like her, I get more pleasure in planning and organizing than most. My favourite thing to plan? Vacations! Whether we’re travelling by air or by car, here are some of my top tips.

Once all the dates are decided, the fun begins. Researching flight deals, hotels and rental cars online with the usual suspects (, Travelocity, etc.) and then narrowing things down to a few options is a great place to start. Next, it’s time to read online reviews (TripAdvisor, Google, etc.) and see if the photos and descriptions of those hotels are too good to be true. Following up with phone calls to the providers themselves to ask for even better rates takes it to the next level. Don’t hesitate to ask for a better deal than they are offering online. The worst they can say is no. PLANNER’S TIP #1: And when it comes to hotels, when traveling with children, try and try again to book a hotel with a pool – wearing out the kid before we have to get in the car for yet another long drive is priceless.

Next comes filling in the blanks:
>> Research restaurants by meal (brunch downtown, lunch off the highway, dinner near the next hotel) and budget. Using Google, or better yet, fun sites Food Network’s Diners Drive-ins and Dives’ list and Chowhound can get mouths watering before the packing even starts. PLANNER’S TIP #2: Look up what each region’s signature food might be (for example, do not even think about stopping in Pittsburgh without eating a Primanti Brothers sandwich).

>> Look up fun things to do with kids. Search for the city name + “kids” to find well-known touristy spots and hidden local gems that your kids will love. PLANNER’S TIP #3: Children’s museums and farmers’ markets are our friends. Don’t forget to read reviews and see what fellow tourists and locals have to say – you want to make sure it’s worth the time and money.

>> If there are any sports fans in the family, be sure to seek out any major or minor league sports teams that are playing while you’re in town. PLANNER’S TIP #4: Major league games might be more heralded but minor league events are usually more affordable and much more family friendly.

Ok, we have our travel details and food and activity options. The next step is what I suspect actually got my wife to fall in love with me. The red folder. It’s a simple 2-pocket red folder but it contains so much:
1. Print-outs of each reservation confirmation.
2. Maps showing directions from each stop to the next.
3. Lists of our selected restaurant and tourist stop options along with their addresses (with maps) and phone numbers.

Planning complete? Check! Getting out the door with a smile on everyone’s face? That’s for another post, another day. Suffice to say, I just hope that everyone else out there has a control freak for a partner that loves to pack as much as mine.


And if you were wondering… We drove down to Pittsburgh for a Rufus Wainwright concert and then headed a bit further south to West Virginia (where I went to school) to see some friends that I hadn’t seen in years. One of the sweetest parts… he planned the whole thing with my friends down there when he hadn’t even met them yet. Yes. He’s a keeper!