7 Best Trip Planning Tips

"Life is short & the world is wide"

We're well into our second lockdown and I can’t help but daydream about walking down the aisle.. the plane aisle that is. We have a trip to Hawaii waiting in the wings whenever travel bans are lifted and saying I'm anxious to rebook is an understatement. One of my favourite perks of being childfree is the freedom to travel. Now I'm not an especially organized person but when it comes to trip planning I'm in my element. I quickly realized through planning this Hawaii trip that it’s not a skill everyone possesses, so here are my 7 best tips to make your next trip a breeze to plan! 1. Do. Your. Research. - Start by researching all the things you want to do or see and restaurants you want to eat at. (Pinterest is a great place to find lists of popular tourist locations as well as local 'insider' spots.) Gather a lot of information, like more than you need and too much to process a lot. You want to go in with all the information you can at the beginning and whittle things down. There's nothing worse than travelling 24 hours to Thailand and realizing you aren't going to be able to go to the elephant sanctuary. (yes, this lesson was learned from experience.) 2. Manage Expectations - If you're planning a week long trip (8-10 days), I would recommend choosing a maximum of 5 must do activities. You want to plan in flexibility in your schedule. We can never bank on good weather and you don't want to risk being so busy that you don't get to enjoy the activities you've planned. A hike could only take you 3 hours but a nice afternoon nap afterwards can eat another 3 hours. Unexpected illness like stomach bugs or heat exhaustion or, as mentioned, a surprise afternoon nap need to be taken into account within the schedule. After your must do list is made, make a list of 5 "if we have time items" to fill in any empty spaces in your schedule. If the hike finishes early and you have a free afternoon, refer to your secondary list for something to fill the time.

3. Book Your Lodging - Don't book your lodging until you figure out your must-do items. Location is important, especially if you're travelling somewhere you won't be renting a car. Say you're going to New York and four of your 'must do' activities are in Manhattan, but the last item is in Staten Island, a day trip to the island is easier than travelling back and forth everyday, so paying a bit more and booking in Manhattan is going to make your trip a lot better. When shopping for a hotel keep in mind that you won't be spending a lot of your time actually in your hotel. We love the idea of the fancy place, the hot tubs and gym access and sauna and perks but how often will you really be there? It's important to book somewhere that at least has a comfortable bed, a bad night sleep isn't worth the savings, but spending an extra $200 a night on an extravagant suite isn't necessarily worth it. Opt for comfort and convenience and forget about luxury or extras. 4. Make A Budget, but Plan For Extra - A budget is important, always. As the wise Dave Ramsey says "A budget is telling your money where to go, instead of wondering where it went." This rings true in life and on vacation. We can so easily slip into spontaneous spending and wonder how our credit card bill came in with a few unexpected zeros on it. Do you have to buy all 3 meals in a day? Can you find a grocery store near by and cook some of your meals? Are you renting a car and have to pay for gas, or will you have taxi fees? Does the location require you to tip? All of these things need to be considered in your budget. We should also always assume we're going to spend more than we think. Dinner prices can easily be underestimated once you add an extra cocktail or two. Maybe you forgot to pack toothpaste or your bathing suit string snaps when you're putting it on. Accidents can and will happen. Sometimes it's worth spending a bit of extra money to take advantage of an activity or picking up a one of a kind item, just make sure your budget is prepared.

5. Go Out For Dinner - And as we're talking about budgets, plan at least one fancy dinner out. Find a restaurant with great reviews and fancy food and enjoy! You're on vacation after all and hotel lobby food will only sustain you for so long. Wherever you're going, it's likely a different, unique cuisine and it's worth enjoying local talented chefs cook you an authentic cultural meal!

6. Don't Buy Crap - I love collecting souvenirs from our trips. In Canada we've been as far west as British Columbia, as far east as Prince Edward Island and even travelled across the world to Thailand. It's fun to bring something home, but more often than not your souvenirs end up in a trash bag. If you want something to remember your trip by, buy something you'll actually use going forward. We've transitioned to buying Christmas ornaments as souvenirs and it's been a great decision for us! I personally love Christmas (more than any human should) and as I decorate the tree I get to reminisce about all the amazing places we've been blessed to travel to. They don't take up much space and they actually get yearly use. Other things that can be used regularly are pieces of art, jewelry or even a purse or backpack. Don't buy something just to buy something, be intentional. 7. Spend Some Time Apart - Don't be afraid to spend a day on your own. My husband loves booking a round of golf wherever we travel, but I don't golf. I take the time that he is golfing to recharge my introvert soul and get some much needed quiet time. I’ll hangout in the hotel and read, walk around or take advantage to do an activity I know he’d rather not be forced to do. If you like shopping or tanning or horseback riding or insert your thing here and your partner doesn't, take the day to do that thing. You can plan to meet up for dinner after and share stories about all the fun you had. We don’t spend 24/7 together in real life, and we don’t have to on vacation either.


Don’t let the stress of planning a trip stop you from going on one, because I promise it’s always worth it!


Travel isn’t always pretty. It isn’t always comfortable. Sometimes it hurts, it even breaks your heart. But that’s okay. The journey changes you; it should change you. It leaves marks on your memory, on your consciousness, on your heart, and on your body. You take something with you. Hopefully, you leave something good behind.” - Anthony Bourdain