Plan accordingly

Sometimes, you just gotta chill on vacation.

Sometimes, you just gotta chill on vacation and take in the sights from a comfy beachside chair …

When I was younger, my family would go to Disney World somewhat often and my dad would know precisely at what time and which restaurant we would be dining at and which theme park we’d be visiting on which day and for how many hours. There was a handy Word document (or maybe it was Wordperfect back then?) where you could follow all the, um, “action.”

While I inherited some of that zeal for “over-planning,” it’s a sharp contrast to Caitlyn’s travel style, which is much more of the “let’s-hang-out-on-the-beach-and-go-with-the-flow” approach to vacationing. We complement each other’s vacationing styles nicely and there can be a happy medium, of sorts, to planning a vacation without over-planning. Follow these steps:

1. Availability. When is you attraction open or when can you get reservations to your restaurant? I start here to form the basis of a skeleton itinerary. My itinerary might start off looking like this:

June 1

9 am – Breakfast: Cereal Bar

10 am – Bata shoe museum (opens at 10 am)
12 – Bloor Street shopping/get lunch wherever

4 pm – Film: Tiny at Scotiabank Theatre
Evening: Dinner at CN Tower; CN Tower observation deck

OK, so we have the outline for the day, but it’s not too overwhelming. It’s not like I’m saying which stores we have to be at which times between 12 and 4 p.m. Plus, we won’t really (I hope) spend four hours shopping, so that gives some wiggle room for seeing other things in the area … because that’s part of the thrill of vacationing – finding that hidden gem!

2.Pace yourself. The above day starts off with breakfast, eases into a little culture at the museum, picks up with some shopping and refueling at lunch and then the rest of the day is a little less active: Movie, dinner, observation deck at CN Tower (which is by our hotel). Similarly, you want to pace yourself if you’re taking a several-day or weeklong trip. For example:

May 30
9 am – Leave for train station in Montreal

10:10 am -Train leaves for Toronto

330 pm – Arrive at train station in Toronto
4 pm – check into hotel
5 pm – Walk to dinner at Sadie’s Diner

630 pm – Get to Rogers Centre for Blue Jays game

7 pm – Blue Jays game

10 pm – Take subway to Bloor Street for Greg’s Ice Cream
May 31
Sleep in!

10 am – Tim Horton’s for quick breakfast?

11 am – Kensington Mkt/Chinatown/lunch there

3-6 pm – Elmwood Spa

7 pm – Dinner at Earth Rosedale (GROUPON)

June 1

9 am – Breakfast: Cereal Bar

10 am – Bata shoe museum (opens at 10 am)
12 – Bloor Street shopping/get lunch wherever

4 pm – Film: Tiny at Scotiabank Theatre
Evening: Dinner at CN Tower; CN Tower observation deck

Note how May 30 is going to be a lonnng day – travel, ball game in the evening, ice cream after that – we probably won’t get back to the hotel until 11:30 or midnight. Conversely, the next day is much more chill, with sleeping in, the spa, an early evening and some flex time to do or explore other things throughout the day. June 1 is a mix of both – busy and relaxing. You don’t want to burn out two days into a 7-day trip.

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…and other times you gotta bust a move to get to places!

3. Figure out how you’re getting around. You’ll save yourself a lot of headaches, time and cell phone bill (especially if travelling internationally) if you plan out how you’re getting between places in advance. This info will also come in handy when you’re tired near the end of the trip and don’t want to walk aimlessly for 15 minutes looking for a non-existing subway station or bus stop. Your May 30 schedule might now look like this:

May 30

9 am – Leave for train station in Montreal (take taxi)

10:10 am -Train leaves for Toronto

330 pm – Arrive at train station in Toronto (take taxi)

4 pm – check into hotel

5 pm – Walk to dinner at Sadie’s Diner (WALK: right onto King, right onto Spandina, left onto Adelaide – it’s at Portland St)

630 pm – Get to Rogers Centre for Blue Jays game (Adelaide east to Spandina, turn right; turn left on Front – it’s at Blue Jay Way)

7 pm – Blue Jays game

10 pm – Take subway to Bloor Street for Greg’s Ice Cream (get on YUS subway at Union Station toward Downsview – get off at Spandina station; left on Spandina to Bloor)

If you’re feeling lazy and don’t want to come up with your itinerary, Fodor’s is known for making them for most every large city. Try this for a snapshot of what to do in NYC.

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