VACATION PLANNING TIPS

When it comes to planning a trip, I warp into type my A mode. While planning any vacation, I spend hours researching Tripadvisor, Yelp, Urbanspoon, Travel Blogs and travel guides (ie. Lonely Planet and Frommers). I make a list of must do activities, restaurants and attractions, put it all into a Google Map, colour coded of course, and then plan my itinerary based on geography.

My Favourite Research Resources:

  1. Trip Advisor – My favourite site to start listing attractions, finding hotels reviews and figuring out the best time to visit a city. The real photographs of hotel rooms and views are super helpful. My first step is to always read the most negative reviews first and then the most recent. This is useful before booking a trip and during the planning phase.
  2. Travel Wiki – I like Travel Wiki for popular cities. It’s a good starting point to get a general idea of the culture, shopping, attractions and geography. My favourite part of the site is how it outlines day trips and transportation. How to get there from the airport and transportation within the city. I use this site to research places I’d like to visit and before I get into detailed planning.
  3. The Library for Travel Guides – Lonely Planet is my prefered travel guide series, but I do like Frommers as well. Travel Guides are updated annually and you’d have to visit one location a few times to make purchasing a guide worthwhile. Once I’ve picked a vacation spot, I head to the library’s travel section. It’s even easier today with the Toronto library offering digital copies of most Travel Books for your computer or tablet, all free.
  4. Yelp and Urbanspoon – This is starting to get serious. Eating on a trip is serious business for me. There’s only so many meals you have in a city. I start with making a list of the best reviewed restaurants and grouping them into price range and cuisine. Then I start trying to eliminate anything that seems too touristy. I start to read local food blogs and narrow down my choices.
  5. Google – More recently, I’ve started to Google for travel blogs. My search string is usually “City I’m visiting Vacation Blog”. The results are great vacation recaps from bloggers with real experiences, pictures and advice.
The Google Map from my Weekend Trip to Boston last year

The Google Map from my Weekend Trip to Boston last year

Once I have a list of colour coded locations (restuarants, things to go, and shopping) all mapped out, I start to slot them into an itinerary. This is what works for me, and why my friends love to travel with me. I try my best to be a good boy scout (always prepared) without being a schedule nazi. I like losing track of time at the farmer’s market as much as being early for dinner reservation.

Two possible trip itineraries

Two possible trip itineraries

Tips for Planning an Itinerary that doesn’t feel Restrictive:

  1. Plan the fancy meals first, don’t forget to include time to get ready and travel time.
  2. What are your must do’s? Plan those first and space them out. Don’t try to do too much.
  3. Always have a back up. That super cool new burger joint you read about, closed due to a water leak, good thing you looked up 3 other restaurants in the area.
  4. Keep some time free. Don’t plan every single hour. What if you hear about a new bar that just opened, or want to go back to re-visit a beach. It’s nice to have a plan, but it’s also nice to have a bit of (planned) spontaneity.
  5. Stay flexible. It’s Day 2, 4pm and the only thing you want to do is take a nap, not walk a museum. So take the nap, you’re supposed to be enjoying your vacation, and a good plan would have a back up slot, point #4, if the museum was a “must do” from point #2.
Hanging out with some fish at the Boston Aquarium. When we went to buy tickets, the box office line was ridiculously long. We joined a shorter line for pick up tickets and bought tickets online while waiting.

Hanging out with some fish at the Boston Aquarium. When we went to buy tickets, the box office line was ridiculously long. We joined a shorter line for pick up tickets and bought tickets online while waiting.