Ask HN: How do you plan vacations?
Curious how other folks on here plan their vacations. Looking to get away during Christmas to somewhere warmer. Anybody have good tools, websites, or strategies that they would recommend?
Vision - I should be at the beach chilling right now
Strategy - Let me book a trip to the beach for Christmas today to get the best deals, when no one thinks about Christmas since it's January.
Design - I like to be free on vacation so I'd usually look for apartment rentals or even houses (airbnb or specific websites depends on the location). I try to avoid hotels so I don't have to leave the room every morning at the same time. I don't want to tip the hell out of my day as well while on vacation. I can make my own bed. I prefer having a kitchen where I can cook whenever I want. My own fridge, etc.
Execution - Budget is key, I start to look at how much I can afford. Then I split it into 2 categories - flight cost and room cost. If I fly very far I'd lower my room budget or look for places slightly outside of the tourist places, where I could easily get to whenever... If I fly domestic then I make sure to rent a very nice place. In terms of day to day expenses, I usually save a little bit of cash here and there from January until the trip. So it's not even budgeted and I have a pile of cash to travel with when the day comes.
Whenever a good deal comes up to somewhere that seems cool, I just book it. There is a chance I won't be able to make the trip work, but in the long term, the cost of periodically missing a $300 round trip to Europe or a $500 round trip to Asia is far lower than always paying $1000, and for me the spontaneity of going to new and exciting places sometimes last minute is absolutely worth it.
This can be very difficult to coordinate with my job, especially when the deals come up last minute, but we usually find a way to make it work.
Sometimes friends and I will want to go somewhere specific. Our usual strategy in this case is to not book anything because always one of us cannot 100% commit, or one of us has a hope in the back of our minds that a deal might come up. We almost always end up committing in the end, and a deal almost never comes up, so we normally end up paying the highest prices at the last minute. Though we do get lucky sometimes :)
As for choosing destinations: we're an outdoorsy friend group, so the combination of all of us reading nature and travel blogs / magazines, following Instagram feeds, etc. is enough to give us a bucket list. Usually travelling inspires me to visit more places. Whenever there's a really good deal on YVR Deals, I'll use that as inspiration to go somewhere new.
I am based out of SFO and have IFTTT set up to get a SMS whenever there is a new deal http://www.theflightdeal.com/category/flight-deals/sfo/. Works brilliantly. I have gotten deals like $525 RT to Nepal, $404 RT to Indonesia, $240 RT to Colombia and many more...
All of my vacation time is planned around going to Blackhat/BSides/Defcon. I book whatever the defcon hotel is for the full block of dates.
I choose a rough slot of time, and start looking flights. Cheapest flight decide the city, then room from booking.com. An excel sheet logs and guides my preparations for Visa Application, another one lists the documents required. One more helps me to pack the items/things.
I tend to use Skyscanner or similar for flights. This may help me choose the destination based on costs.
Hotels.com for hotels as they have a buy 10 get 1 night free offer.
Then Google for other things. Like skiing for example to find the best deals on lift passes and hire etc.
I used to do the whole lonely planet guide thing when younger and cram activities in. Now I prefer to go somewhere with a rough idea of things to do found on the net, and play it by ear.
Last holiday in Queenstown NZ I did 3 days with family of just hanging out. It's glorious not to be on a schedule sometimes.
Conversely I hate tours for this reason. Done them a couple of times and I dislike travelling with random people especially if they are heavy drinker loud types. I also dislike the forced 6am starts every day.
First I look at flights: what is affordable and when? Some dates are much more expensive than other dates.
Then I look at hotels and itineraries: What do I want to see? What is affordable near where I want to visit? Hopefully there isn't a convention that overlaps.
Finally I look at rental cars: Is it still affordable?
Recently I've used the packaged deals websites or through the airlines. It can be cheaper to get it bundled.
If any one of those factors (airfare, hotel, or car) is overpriced, then I look at a different place. It is usually conventions that disrupt my plans and cause spikes in the prices.
From there, Airbnb, atlas obscura, and google maps to find green areas nearby
Google "top travel destinations Christmas"
I think Thailand is a good one
Youtube "Thailand travel"