Vacation Planning Tips

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If you’re anything like me, part of the fun of travelling is the planning. From researching vacation spots and attractions, to scoping out that great deal on flights or accommodations – my love for travel is all about the process and not just the destination.

And during 25+ years of avid wander lusting, you do learn a few things along the way. With March Break approaching and visitors going through the roof to my blog posts on Big Island Snorkeling Spots, Barbados Snorkeling, Snorkeling Roatan Honduras and The Pros & Cons of Cruising, I thought I would share a few of my top vacation planning tips. As always, comments and your own suggestions are encouraged and highly appreciated.


There’s no getting around it. Money may be the root of all evil, but it is also the deciding factor in what kind of vacation you’re going to book. If you are budgeting $6000 for your family of 4 to take a trip during March Break, don’t waste your time searching for 2 weeks accommodations in Fiji or a week at the Hotel du Cap Eden-Roc on the French Riviera. Be realistic. There are still fantastic vacations to be had on a budget. And there are a few things you can do to ensure your budget stays modest.

If you have a flexible schedule, research flights and resorts using travel sites that offer “best price calendars” (Redtag, Air Canada Vacations, Expedia etc.). And if you can fly out mid-week, you can usually save some pretty decent coin.

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In particular for flights, if you can plan and book early, you are pretty much guaranteed the best price. Especially during the holidays, prices more often than not, go up significantly as the date approaches.

Speaking of booking early, here’s my opinion on last minute vacations. If you don’t have a specific destination and resort in mind AND you’re not trying to book a vacation during the holidays, there are some incredible last minute packages to be had a week or two out from your travel date. BUT, let’s say there is a specific island you want to go to during Christmas or March Break and there are also a handful of resorts you are hoping to stay at – don’t risk it.

I learned my lesson once before. A few years ago I held out for a last minute deal on a specific Caribbean island over Christmas and the good deal never came and I had to book a completely different destination – and didn’t get a deal there either. Since then, I’ve monitored last minute deals leading up to the holidays and the pickings are slim. Again, if you don’t necessarily need to travel during the holidays and you don’t have your heart set on a specific destination, booking last minute can be great. For me, I’d rather research and book early. I get what I want and it is generally at a very reasonable price. After all – time is money.

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But unfortunately for us as business owners, if we want to have a reasonable amount of peace and quiet to relax on our trips, we have to travel during the holidays. But traveling during the holidays comes at a premium price. If your schedule allows for you to travel just before or after holidays, you can usually save a bundle.

As devote foodies, I might be a bit hypocritical by suggesting this. Some of our trips like Palm Springs, San Diego and Hawaii ended up producing restaurant tabs that would choke a dozen donkeys. And don’t even get me started about our recent trip to Scottsdale with the floundering Canadian dollar doing us no favors. But sprinkled in with those top restaurants are cheap eats. And sometimes those smaller local joints have produced some of the most memorable and delicious meals we’ve had during our travels. So if you’re not staying at an all-inclusive resort and have to hit some restaurants during your travels, seek out those small local gems like burger joints, mom and pop pizza places and taco stands. You can save some money and sample some pretty awesome food in the process.

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Know what kind of vacation you want

Because sometimes you don’t feel like the over-indulgence of an all-inclusive resort or a cruise ship. We tend to alternate between all-inclusive holidays and condo rental type trips. I generally prefer our condo rental trips as I tend to eat less, drink less and I’m more active too. Having a condo with a full kitchen means you can eat a healthy breakfast (hold the bacon, sausage and pancakes with syrup) and pack a lunch for a day of hiking in the mountains or snorkeling at the beach. As well, after a busy day of activities, you can save a little money cooking a slow and relaxing meal back at the condo rather than eating at a restaurant every night which can quickly blow your budget.

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Research and plan your vacation activities in advance

There are a few benefits to doing a little planning before your trip. When I’m not traveling, I’m thinking about travelling. For me, researching my upcoming travel destination is what gets me pumped and primed to take on our next adventure. The more you know about the place your visiting, the more you will get out of your experience. And don’t limit your research to sources like Trip Advisor and Frommers. While they’re great, there is a ton of alternate sources of information out there.

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Things like tourism sites and especially smaller travel blogs can give you insider information that you may not come across on bigger travel sites. Some of my best off the beaten path hikes, snorkeling spots and restaurants were found on travel blogs. Find a few bloggers that share your interests and approach to life and use them as a resource. Don’t just read their posts – ask questions. Travelers love to talk travel. And for the budget-conscious (and shouldn’t we all be) – a little research can go a long way to finding more affordable and cost effective activities and excursions. I’m all about more bang for my buck. More money = more travel.

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Turn the pressure off

And finally, the whole point of travelling and vacations is the opportunity to relax, recharge and renew. So do your best to take care of all the little things like packing, exchanging currency and planning ample time to catch your flight so you are in the right frame of mind to embark on your vacation. Nothing starts a trip off on the wrong foot like last minute scrambling to find that missing passport or to catch the airport shuttle – I can speak from experience on this topic.

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And when you do take off, have an open mind. Don’t start a trip with sky high expectations for what the experience will be like – let the journey unfold organically. If you only have the opportunity to take a vacation once or twice a year, you can put a ton of stress and pressure on yourself and the people around you to make the trip extraordinary. Stress and pressure are not ingredients you want to include when travelling. Experiencing the unexpected with an uncluttered mind will always produce the most memorable travel moments. For now, back to the cage.