How do you plan vacations/get aways?

This is mainly wishful thinking right now, but with seemingly everyone making plans to get away somewhere taking a vacation has been on my mind. This is pretty open ended, but how do you plan vacations? Do you have a budget or goal amount you save for, or do you just make plans and try to keep the plans at a reasonable cost? Do you have a running list of places you want to go/things you want to do?

Our options were limited for a long time by having a baby/toddler, and even now I’m reluctant to plan a trip to, say, Hawaii with a six year old when he’d be just as happy going to a beach place we can drive to. Options are probably also going to be limited by availability this year since people are making up for lost time, but I need something more specific than “I’d like to take a trip somewhere sometime at least a few months from now.” With all that I figured I’d see how other people plan things. I’m sure I could google some article that would say how we Should do things (along with lots of helpful ads promoting various places we should spend our money on), but I’m looking for how real life actually works.


I think most of my plans start as a) wanting to see people (/attend weddings) b) wanting to do an activity (eg backpacking)…and maybe for the first time, soon: c) wanting to go to a place. Once I have a “core idea” we start contemplating the other pieces.

a) look up cheap flights at times we can take off work. Run them by hosts/targets. Iterate. Include lodging if necessary. If (destination) wedding, dates might be set but we have some flex around them for other activities.
b) theoretically planning backpacking with my mom right now. We decided Glacier sounds good. Dates are tied to mom’s planned vacay time. Need to look up flights/car rentals/routes/permits.
c) inviting in laws to where we had planned to do our canceled wedding. Dates are again tied to my mom’s vacay. Need to find a house to rent so in laws can book time off/tix.

Once you pin one moving piece it kind of comes together? I think at 6 years old there is an excitement to travel and new places and to the vacation mentality that we forget about as adults. I haven’t been to Hawaii but I know it has more than beaches and it’s different. But a great vacation doesn’t have to be far or expensive. One of my favorites as a kid was when we went up the Yuba River and hiked out to swimming holes and gorged on blackberries. It was way more relaxed than what we usually did. Disneyland was fun, but I was never into characters and Great America had better rides and wasn’t 5 hrs away. So… I think go for variety and try to stay chill and your kid will remember something fondly.

Budgeting caveat: I don’t really do buckets for anything. Most expenses we cash flow at the expense of adding to house fund or efund/general savings. If you think in buckets, staring with “what can we do on $X in our vacay fund?” makes more sense.


We’ve never taken a trip that wasn’t to visit family but might start doing trips just for fun so I’m curious to see what others say :slight_smile:

1 Like

We don’t really do buckets for anything but then I feel like the only acceptable vacation budget is zero dollars which we can only get close to if we stay with my parents/in-laws and that doesn’t really feel like a vacation. I know it’s bad logic, and yet. :roll_eyes:


When my kids were little I figured out a thing we could do/ place we would go where I would have less responsibility. A few times we got a cabin on the shore of a safe, shallow lake so I could lie on the beach and half pay attention while they splashed around and looked for interesting rocks, then the easiest possible dinner.
When they got older and I had more money we went to an all inclusive resort, with the same goal in mind.
Actual interesting travel didn’t happen until they were old enough to be helpful and independent.


We don’t really budget so much as “let’s try not to spend too much”.
We are lucky that, within reason, we can spend whatever we want, and not be too concerned about it when we get home, though maybe if we ‘overspend’ we might cut back on extras for a few months at home; but going into debt isn’t an issue.

There are a few ways I plan vacations.

The first is starting with the destination.
So like, I am going to Banff, what are my options. Then I look at what various priced vacations might get us, and decide where I am aiming at. I then obsess over where to stay, and plan detailed itineraries for each day to cover things we could do, as well as options for if we decide we don’t want to do them. When driving, I try not to be on the road for more than 10 hours a day, so I look at affordable hotel options along the way, or whether we want to extend a stop to see things in that area as well, and make it a true ‘road trip’. If we are flying, I start watching flights about 6 months out. I always try to book cancelable lodging in case I can’t find affordable flights.

Or, if I have a time I want to travel, say Christmas, I pick 4 or 5 destinations and start pricing out the options, comparing the available attractions, looking at the weather. Two years ago, we really wanted to go to Spain or Chile, but ended up in Portugal when all other options were weighed.

Sometimes I plan vacations a year ahead of time, other times I plan them with nearly no notice. (Though we haven’t done the no notice thing since we had kids. But I once booked a cruise on a weeks notice, forgot I was still in school and had a class…oops. I skipped it.) Whereas our Galapagos trip was booked like 24 months ahead of time, and it took us that long to save for it.

We like active vacations, so going to a resort and just hanging out has never been a thing for us. I plan A LOT of activities, some which are booked ahead of time, and some of which are backup plans. But I really like to know what we will be doing before we get there.

Even for things like hiking, I want to know the routes we are doing, and I want to know what the 2nd choice is if the trailhead parking is full for the first one.


I also want to add that as a family we’ve decided to place a lot of importance on travel.
We are trying to hit all 50 US states as a family, and my son is 2 and we’ve hit 12 together. (The kids have both been to 16, but not all at the same time.) Sometimes it’s to experience something new, sometimes to get to the place we are going, and sometimes just to check a destination off the list.

We are really really hoping to be able to travel internationally again soon. We had planned to do that a lot before my daughter starts kindergarten (next year), but that got quite derailed. So right now the family country list is just Canada and Portugal.

One of the main reasons for this is my husband had never been out of the state until he turned 16 (and went to Ireland with a school trip). He felt like his view of the world was very skewed because he hadn’t been exposed to anything else. He was very “Texas is the greatest place on earth, and nothing else comes even close”, and now he’s “Wow, lots of places in the world do things way better than us, and most places in the US are a lot more alike than different.”


That’s some truth right there.


One of my favorite things to do it plan a vacation!!!

We have a running list that Mr Pug and I add to anytime someone suggests a place. Plus I want to go everywhere anyway so it’s mostly about what Mr Pug is up for and what we can do with Puglet and that will change over the years.

I will usually pick a place that we’ve never been to and then see how much it will cost and then save for it. I don’t set an amount and then make a trip work within that amount. I am usually thinking about big trips a year out so like next summer we’re planning a trip to Colorado. We’ve also been talking about take a train across the country so maybe we’ll combine them, but it depends on if Puglet can handle 2 days on a train. Over the next year I’ll add points of interest to a google sheet for the trip so we get the most our of our stay.


I love trip planning! And taking trips!

The main question I like start with is how I want to feel on a trip? Where do I want to be on the adventure-serendipity-relaxing spectrum? I have 3 kinds:

  • Go do a specific adventure, like a through hike or one-way bike ride. Usually a thrill (high pre-planning)
  • Go to a cool place I don’t know well, explore (moderate pre-planning — figure out where to sleep ahead of time, read some websites/books for fun, maybe schedule 1-2 things, but mostly play things by ear once the vacation starts)
  • Go to a place I already know and love, do stuff I already know and love with slight variations (low pre-planning — book accommodation ahead of time, packing is easy, and usually only plan things 1 day in advance)

(For me, “book accommodation” is a pretty low bar. All it means is "I’m pretty confident I won’t be SOL on a place to sleep each night. This can equally mean “airbnb a house” or “book a camper van” or “pack the tent and stove and cooler, we know in this area we can snag a spot on the fly”.)

I try to balance my expenses over the course of several years, not a single trip. We talk about this in our annual financial conversation which usually happens around the new year. Some years have more big spendy flying trips, others more domestic/driving/camping. We also factor in work or family travel, which can be opportunities to plan vacations nearby. We have more cushion in the budget the past couple years but I also want to remember (and raise my kid to know) that moderately frugal or totally dirtbag adventures can sometimes be even more delightful.

I budget for travel in a “Luxuries” mega-category, so it competes with home upgrades, sports toys, and fun clothing (e.g. not repair costs or replacing things that are worn out/wrong size) for $$.

Let’s see how this goes as my kid gets older, but I’d like to subscribe to the idea that vacations are as much for you as for your child. Ideally everyone has fun and is able to recharge their batteries in various ways, not just the kiddo. If Hawaii is what does it for you, and your kiddo would also enjoy it, then hell yeah!


For me it depends.

All the trips

The first trip I planned was because I really wanted to surprise my husband with a vacation for our 5 year anniversary. I chose a cruise because it was basically the only way I could afford to do a big trip, and I still saved up for over a year! We got to island hop a bit and everything was included and we had such a blast. Our lives were really tough day-to-day at that time so not having to do anything was amazing.

The next trip I planned was for our honeymoon and that was also budget driven. I really couldn’t spend very much so I knew it would have to be driving distance I chose Niagara Falls because neither of us had been and I thought it sounded kitschy and fun and romantic and it was close. It blew us away! It was so much more impressive than I imagined. The vineyards up there were also beautiful and so unexpected. Also, the uncle whose backyard we got married in went there with my aunt on their honeymoon like 60+ years prior, so it was special.

The next trip was the first really big one I planned and that was Iceland. We had money gifted from the wedding so it was the first time I could really choose anywhere. I’ve dreamed of going to Paris my whole life and that was my top pick. My husband always goes with what I want but I knew his top pick would be Iceland. I picked Iceland! Part of the reason was because I wanted him to be happy but it was also because I was worried I might not be able to handle an Iceland trip in a few years, so it might have been my only chance. It was AMAZING. I planned for over a year and did a detailed road trip plan. We did the ring road and then some (even the remote western fjords), saw the northern lights many times, and hiked to a remote hot springs. It was mind blowing and otherworldly.

We took a small trip to Oregon too, nearly forgot about this one. That was purely to go see the eclipse, which was worth it. It was actually a really cheap trip because my uncle had a vacation house out there and I had cc points so it was pretty much just rental car and food, which I cooked. A+

The next trip was Portugal and I saved up for that for over a year. I really wanted to go to Paris but it was so expensive at the time and Portugal was really affordable. It was a disaster. I tried to plan a similar road trip to Iceland but it didn’t work at all for a variety of accessibility reasons. Basically, we were lied to about the van’s accessibility and so I ended up in an absurd amount of pain and couldn’t do anything. The beaches were almost all inaccessible too, so I could only look down at them and not actually get to them. Not fun!

Upcoming trips are Miami Beach and Paris! The Miami Beach is like the least planned I’ve ever done a trip. Randomly the other day my husband asked what I wanted to do for our anniversary in September and I thought about it and was like: Miami! Haha, that was the level of thought that went into it. I think he thought I was going to say dinner or something, but f-it, lol, he was instantly on board. We had to cancel a trip to New Orleans due to Covid so we’re making up for lost time.

Paris will require some serious saving! I’m hoping we can go for our next anniversary in 2022 and I already started saving. I’ll plan a few restaurants and outdoor markets and boutiques but not do a daily itinerary. The biggest thing that stops me from saving money on travel is my need for direct flights and comfort at the destination. It’s just not realistic for me to add transfers to save money because I literally won’t be able to do anything when I get there. I feel like I pay a lot more to be close to things too, so I can minimize car time for the same reason.

I really like domestic travel in addition to international. It’s a lot easier and I feel like there’s so much I still haven’t seen here. I think we have so much diversity in different regions! I want to see the grand canyon and the redwoods and I want to stargaze in the desert and go to Hawaii and Alaska! And Utah! Utah looks gorgeous. I also want to go to Singapore, Italy, and Greece. Oh and I want to take a fancy river cruise through Europe and maybe a really fancy train through the alps or himalayans.


This is an excellent question!

I have a huge list of places I want to see, and tend not to want to repeat destinations (exception: if Boyfriend hasn’t been there and really really wants to go).

I usually start with some rough parameters when narrowing it down - like, when I settled on Cape Cod it was someplace I haven’t been/that is pretty and has scenery and water/relatively inexpensive flight/Boyfriend doesn’t care about going there as this was a solo trip/good weather in July.

When we went to Los Angeles, it was someplace that’s warm in early April/and has a beach/that we haven’t been to/that has Things to Do/and is not a usual beach tourist destination like Florida/and isn’t too expensive to fly to.

Being able to fly directly with no layovers is also pretty important to me, as I’ve lost entire days off trips due to sitting in some airport. So if it’s super expensive to get there without taking a bunch of short hops (looking at you Southwest!) then I’d really need convincing to choose that destination.

If I’m planning a big bucket list trip then I just shovel savings into my “vacation fund” like a madwoman, sometimes to the exclusion of other goals. This is how we did Maui in February 2020. If it’s a smaller trip, like a long weekend, then I generally just try and keep flight/hotel inexpensive but not terrible.

As I get older I seem to be prioritizing scenery that’s different from the Midwest, over experiences. Beach, mountains, desert, tropics.

Re Hawaii… I found the flight to be punishingly long and very unpleasant even though it was nonstop - and I am not six. And you’re farther east than I am.


Re: Hawaii, we went for our honeymoon. Instead of flying direct we flew from Boston to San Francisco then drove up the coast to Seattle over a couple days then flew to Hawaii did a lot of island jumping (five total) over 14 days. Then flew to Oregon for a few days then home. It was a lot of flying but I think it was good for us because I would not be happy seating in couch for a 12 hour flight and Mr Pug is far more frugal and would be unlikely to upgrade to first class, though I did get him to do Mint on JetBlue for one flight (it was amazing)

Yeah I think Hawaii will be when Kiddo is older (maybe 10?). Even aside from cost I don’t really want to fly with him for another couple years. Or road trip. He just does not do well sitting down for long periods.


On our flight to Ecuador, there were kids literally running laps around the plane. I think culture will depend if that’s acceptable to flight attendants and passengers though. We didn’t have any yet, but on long trips, I walk the aisle with them

I’ve found flying way better for fidgety kids than driving. They can stand up and walk around a bit. They can lay down across an adult lap. At with toys on the tray table. We let ours watch movies on in flight TV, but not in cars (typically). We also eat more on planes than in cars. Although, I’m lucky my kids seem to do pretty well with both.

For me it kind of depends on the purpose of the vacation…

  • Visiting family–I might suggest something but generally plan to go along with whatever their plans are, and costs tend to be limited to getting there (which I use cc miles for most of the time) and possibly tickets to an event or a dinner out. When sibling or extended family are hosting I definitely offer to treat to something of their choice, parent on the other hand tries to pay me back if I buy a round of drinks at a ballgame so mileage varies.
  • Activity trips (skiing, mountain biking, etc.)–generally done with friends and whoever’s organizing tries to find a reasonable shared lodging option and then we carpool if feasible and split food and cooking among the group since the focus is generally whatever activity plus game nights or something in the general vicinity in the evening. A couple friends have kids now which does limit some of this, but generally it’s pretty low-cost.
  • Bucket-list type trips to places I want to visit–I keep an eye out for reasonable flights that work with airline miles but am a lot less careful about picking and choosing activities once I’m there since it’s unlikely I’ll ever go back and I don’t want to miss things that I’ll regret. These are pretty rare though, and I usually start putting aside money to cash flow it the year I plan on going.

I fondly remember ski trips where 4 or 5 families would rent a large house, kids over 5 got the loft/basement where the big bunkbed and sofa bed were, parents and small kids got a bedroom per family, shared meals, snow play, billiards, movies from the VRBO hosts collection, board games, spooky stories, fireplaces.

Maybe kids in question are too young for a bit but don’t give up on these trips!