Vacation Planning: How Early is Too Early?

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baby on beach at sunset

I’ve mentioned before that I’m not great at planning family vacations. Now that J is in kindergarten, though, the school year feels a lot more constraining on our schedule… and I realize it’s only going to get worse from here on out. In order to try to force myself to plan vacations, my husband and I just picked a few things we know we want to do, are divvying up the planning work, and we’re trying to block the year out ahead of time so we know what’s what, with school schedules and other major dates in there.

I’ve heard a bit about “year planning,” as well as about planning way in advance for some trips (I’ve read articles that suggest you plan Disney 9-12 months in advance!) — so I thought it might make an interesting discussion here. So: Do YOU plan your year in advance, including visits with far-flung relatives, vacations, mini-trips, date nights, etc? Do you go by the school year, calendar year, or something else? If you have grandparents far away do you try to visit them, have them visit you, or explore a new place together? Does this help you stalk ticket prices/hotel prices and the like, help you with planning (or outsourcing planning), or otherwise mentally help you plan? (For those of you who’ve been doing this a while, are there major pitfalls to watch out for?) I had found a summer planner earlier this year that really saved me this summer (I can’t find it now, of course), and we just had a nice discussion about the best planners and planning tools over on Corporette, so I thought we’d discuss here.

(A blogger’s blogger who I follow, Michael Hyatt, has a single Excel spreadsheet that looks awesome for planning your year — it’s from 2013 but you just have to update one cell to the correct date and it automatically changes the dates to the current year.)

Ladies, what say you — are you this ahead of the game? Does it make division of labor easier or harder for vacation planning, as well as for requesting work vacations and more? 

(Pictured: Private collection; all rights reserved.)

A baby sitting on the sand during sunset.

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It depends on the vacation. Disney, yes, you really do want to plan 9-12 months in advance. Dining reservations open 6 months in advance and there are some that are gone immediately. Reservations for fast passes on rides (that save you the 2-3 or more hour wait for the most popular) open 2 months in advance and are also gone immediately for the more popular rides. There are five of us, and we have to go during times school is out, so it’s more crowded. So, yes, I plan Disney 9-12 months in advance, and it pays off in that we just had a lovely trip with minimal waits.

If we are taking a vacation where we are flying and I want to use miles to book us all tickets, then I plan early because that’s how you get the cheapest mileage tickets.

If we are driving to a general location or state (e.g., Maine), then I plan closer to the trip. I may pick dates and put them on my calendar and book a place to stay, but you can be more fluid with the rest of it.

I don’t otherwise “plan my year.”

My job is relatively heavy-travel, so it’s important for me to plan personal travel and days off well in advance so I can protect them on my calendar.

I enter all school information on my work and personal calendars as soon as the school calendar is approved in the spring. Once my daughter’s sports and scout calendars are finalized in early fall, I enter all that information and then buy theatre and concert tickets to work around those dates.

We usually choose a vacation destination and timing about a year out. It gives us something to look forward to. I usually start stalking flights and hotels for good rates several months out, especially if I am planning to use points or miles.

Summers are planned in early January, including sleepaway camp, day camp, and weekend trips. We generally invite relatives to visit us for the holidays rather than traveling ourselves, and extend those invitations several months ahead of time.

It’s my last day at my current job, which I’ve had for 7 years and doing some reflecting on the way out. I just wanted to say how grateful I am for this community. I’ve tried to contribute as much as I can but ultimately I know that I have benefited much more than I could have ever hoped from a group of professional moms who are generous with advice and support, non-judgmental and really ‘get’ the struggles and joys of trying to make this juggle work. Thank you!!!

We tend to plan our vacations pretty far in advance. Before kids, our vacations mainly were (1) adding a vacation day onto a work trip, (2) traveling for other people’s weddings, bachelor/ette parties, and showers, or (3) to visit family. In fact, DH and I have been together for 12 years, and I’m pretty sure we’ve only taken 2 trips (including our honeymoon) that weren’t for one of those reasons. Now we’re mostly past the wedding phase–only two this year and so far only one next year–and our schedule revolves around when Kiddo is out of daycare (which is on a school calendar). But we’re still traveling to visit family, so really, nothing has changed.

Here’s a question – I would LOVE to take my kiddo on a week long beach vacation this winter. But I know that I would go crazy solo parenting for a week with no adult interaction, cooped up in the house during naps and after bedtime. I also know that I would go crazy traveling with my parents, and that trying to coordinate with other “mom” friends would likely be so complicated that it wouldn’t happen (I’ve tried before).

Are there communal parenting resorts? Or resorts that offer babysitters and also have communal activities (so, not couples isolating themselves but actually all the adults at the resort hanging out together)? I don’t even know what to call it….

We really enjoy national park trips too. We’ve been to yellowstone a few times. Staying in the park actual does require some planning – and I’ve heard of other parks (I think it was Yosemite?) that have lake houses and/or beach houses that sell out the day they open up. Our district has a fall break too and we typically (now that we are in the position to) plan a trip to one of our national parks then as well.