Vacation Planning: How Early is Too Early?

vacation-planning-a-year-in-advanceI’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.)


  1. 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.”

    • mascot says:

      Disney is its own special planning snowflake. We generally start that planning process about 6-7 months out. The good thing is that they have a super generous cancellation policy and you only have to put down a small deposit if you are staying at one of their resorts. You can also book a room and then modify the reservation later to take advantage of any specials that have come out.
      For other vacations, we book maybe a couple of months out and plan around the school calendar as much as we can.

      • Meg Murry says:

        Yes, I agree that trips like Disney are definitely their own special snowflake – although I know some families that plan all their vacations as if they were a Disney vacation (months and month ahead).

        This type of pre-planning is part of why I don’t think I’m ever taking my kids on a Disney trip – my husband is way too laid back to plan months out like this, and I’m not willing to do it 100% myself.

        • I tend to plan all my vacations quite a bit ahead, for reasons discussed above (i.e., Disney, planning flights), but also because I enjoy the planning. It’s fun for me. So, I don’t plan everything a year out, but I do start thinking things through and researching. It becomes a hobby. I am already loosely planning our 2018 vacation, because we want to go to Europe, and my kids will be almost 5, 10, and 10, so that seems like an undertaking!

    • CPA Lady says:

      Is 3 a good age for Disney? Or would you wait til 4? I’ve never been and would like to take CPA toddler, but I’m not sure what a good age is.

      • CPA Lady says:

        Oh, and my level of “vacation planning” is more along the lines of “planning not to take a vacation til my kid is 4 or 5 because every attempt thus far has been wretchedly miserable”. But I’m a crabby old Grinch. Except I will obviously make an exception for Disney because I wish I could be…. PART OF THAT WOOOOOORRRLLLD, and it doesn’t involve changing time zones.

      • mascot says:

        If you go before age 3, they are free. We did a trip at 4.5 and will do another one this year at 6.5. So many rides don’t have height restrictions and they really do cater to families. So that offsets some of the difficulties for traveling with littles. I thought our first trip was a great age because he was well past afternoon naps, could handle walking and standing in line, and could ride some of the bigger, faster rides. If this is going to be your only trip, I’d probably wait. If you are going to go several times, then I think 3 or 4 would be fine and it depends on your kid. My kid was not a great traveler at 3. There’s plenty to grow into (last time we were big into the Disney Jr. characters, now he likes Star Wars more so we will do more of those activities). I think one of the reasons that people get so nutty about planning is that it is a pretty expensive vacation and many people only go once. So they put a lot of pressure on themselves to make it perfect.

      • I think Disney at 3 would be fine, but I would wait a year or two if you think you may go to Disney once or twice while your kids are growing up. I grew up near Disney, and my parents live about 15 minutes away. We took our son twice before he turned one, and we’re planning to take him again right before he turns 2. (Kids under 3 get in free anyways.) But we also know that we’ll be back every 6-12 months, and the adults have done everything multiple times, so our trips are pretty low-pressure. If you want to go for a week, go to all the parks, “get your money’s worth” by doing all the things, I’d wait. From my observations, 5-8 seems like the perfect age. The kids that age last longer in the parks and have a little more patience and understanding for waiting in line, but still feel all the excitement and magic.

      • Mrs. Jones says:

        We just returned from a week at DisneyWorld. It was our 5-year-old son’s first trip, and it was a perfect age for it. He was tall enough to ride almost everything, and we didn’t need a stroller. I have no rational idea why people take infants/toddlers there, but obviously many people do. Definitely plan way ahead of time! And go October-March when it’s not too hot.

        • I can tell you one big perk of toddlers vs. kids. Toddlers can ride around in strollers. Kids have to walk. And thus complain about the walking and beg to sit on benches and wonder loudly what kind of “witchcraft” mom and dad are employing to be able to have so much energy.

      • We took my twins right before they turned 3 and my youngest was almost 3 when we went this summer. It’s a great age. Particularly at Magic Kingdom, they can really do almost everything. They understand what is going on and who the characters are. My kids were mostly interested in admiring them from a distance, but my youngest LOVED seeing all the princesses. I wouldn’t pick 3 for a “we are going once during their childhood” trip, but it’s a great age to go.

        We took my twins again at age 5, and they were 8 on our last trip. We hands down had the most magical time when they were just shy of 3. They are just so awed by everything.

        For a family vacation with a 3 year old, Disney is great for them being able to participate in and enjoy everything. You just have to be willing to go at their speed. I liked to plan days in 3 parts–morning, afternoon, evening. You can only be out with the toddler for 2 of the three. So, you can go all day and then crash early in the evening. You can get out early, take a nap in the afternoon, and go back out in the evening. Or you can get a late start (not recommended for park days but good for off days) and go in the afternoon and evening. I also highly, highly recommend a monorail resort with the littles. So, Grand Floridian, Polynesian, or Contemporary. It’s just so easy for Magic Kingdom and Epcot. Also, plan down days–days where you go to a water park or hang out at the pool or around the resort. It breaks up the crazy stimulation of Disney.

    • Quick note – I just got back from Disney for the second time (with a 15 YO and 9YO) and booked through costco, stayed at a Disney hotel (best price I found was using Costco). The fast/max pass you can only use THE DAY you are there – dining you can book 60 days (not six months) in advanced (unless I missed something) and you can book dining and do the Max pass through the app.
      I have also utilized this site for planning both of our Disney trips – I have loved it. We are going back when star wars land opens. I am honestly surprised at how much I loved Disney.

  2. avocado says:

    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.

  3. 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!!!

  4. 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.

  5. NewMomAnon says:

    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….

    • There are family summer camps that offer all-day childcare / children’s activities, but they are typically supported by college or HS aged counselors. I know of several universities that offer camps like this.

      During the winter, I think Club Med might have something similar?

      My preferred option would be to bring my nanny or daycare provider or favorite babysitter along for the week. I can’t remember how old your baby is, but definitely a more fun experience for you if you can leave him with someone he already knows and trusts. They could help you lug the gear through the airport, too — bonus.

    • JayJay says:

      I know some Hiltons and Westins in the Caribbean have “Kids Clubs” during the day. You may have to pay a little more, but you can drop of your kiddo and they’ll watch them, play games, entertain them for several hours, etc. That might give you a good sanity break. I don’t know the ages available, but I know the Hilton in Los Cabos where I was recently (on a couples trip) had an awesome looking kids club area. The Westin in Cancun also does (and the rooms have kitchens which is SO HELPFUL with kids). That might be a starting point?

      • NewMomAnon says:

        Last time I looked, the Kids Clubs started at 3 or 4 and the feedback was that folks didn’t feel great about leaving 3 year olds with the minimal supervision (kiddo turns 3 in Feb)…and it still doesn’t get to the need for adult interaction for me, because I would guess that most of those resorts are aimed at families or couples who plan to hang out in a big pack but not invite in stray singles. Maybe I just need to double down on the ‘rent a big house and invite friends with kids’ efforts. I’m basically looking for a singles excursion club that offers night time babysitting, and that seems unlikely.

    • Maybe a Disney cruise would fit your needs?

  6. 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.

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