How To: Plan a Long Weekend Trip

For years, I was always super keen on taking long holidays. Basically, I always wanted to use 5 or 6 vacation days to spend at least a week abroad. In the past couple of years, however, I've really come to love weekend trips and exploring more of my own country. I read a NYTimes article about vacations boosting happiness and the results indicated that taking several shorter trips actually make people happier than a couple of longer trips.

Why? Because the best part of travel is apparently the planning and the anticipation, which is something I can wholeheartedly understand. I mean, I have a countdown app on my phone which I check daily to see how many days I have until my next trip. I make Pinterest boards to get inspiration for my trip. I collaborate with my co-travelers on Google Docs and we're constantly texting and emailing and chatting about the trip right until we actually depart. I pin cool spots on a travel map. I start an entry in my travel journal. I'm always eager when it come to planning my outfits and making my packing list. There's a flurry of activity prior to the trip, all of which just stoke the flames of excitement.
I still love my longer trips, don't get me wrong, but when there's a cheap flight or when I start to get a bit bored and itchy, it's super easy to run off for a few days.

A weekend trip is a great opportunity to do a solo holiday, especially if you tend to shy away from being alone. It's a short timeframe, which means that even if you're not splitting the cost of lodging with someone else, it won't dent your wallet too much.

It's also a really great way to wrangle those friends who don't necessarily have the luxury to take longer breaks. This is also an opportune trip to go on with friends you inevitably start fighting with after a few days; if you get along fine for three days and then on the fourth day, you always quarrel, well, you should only travel with these people for a maximum of three days which makes a weekend trip the perfect situation.

That being said, it's obviously more convenient to go with someone who has a similar mindset because most of the time, these trips are a whirlwind. So, if you end up with someone who's maybe not as eager as you are, or on the opposite end of the spectrum: too eager, you might not have the best time.
Shorter trips are great for activities you enjoy but can't necessarily see yourself doing for a full on weeklong trip. For me, that usually means a more active hiking and/or biking trip. I mean, I love hiking and biking but I can't really imagine doing it for a week straight; I wouldn't enjoy myself.

Maybe you like lounging around at the beach but you can't see yourself spending a full on vacation by the sea; just go for a long weekend. Or perhaps you can only tolerate the hustle and bustle of a major city for a few days maximum; well, go on a city break.
For a long weekend trip where I'm taking a day or two off of work, I always like to depart on Friday evening and return on Monday or Tuesday. I love going to work on Fridays because everyone is in a great mood and we get to wear jeans. Plus, I love the perk of returning to a short week. If you take off Thursday and Friday instead, then you're returning to a full week of work after a relaxing trip, which is frankly kind of depressing.

If you're heading somewhere close by, you might not even have to take any days off work.

Also consider incorporating a paid holiday into your trip and you won't have to use vacation days at all.

The beauty of this type of trip is that it's really easy to plan way ahead of time but it's also a great last minute ditty, which means you can jump on cheap flights if you happen to stumble on them. Even if scheduling vacation time with work can be difficult, I think most bosses will be fine with giving you a day or two without much notice.
The destination is obviously the most important component here. I personally like to browse Pinterest, InstagramKayak Explore, and Skyscanner for inspiration; at the v. least, it's a great jumping off point. Brainstorm a little and consider if there's somewhere you've always wanted to go that wasn't necessarily special enough for a weeklong stint because now's your chance!

If you want to fly somewhere, keep in mind that a long weekend isn't much time so don't strive for anything too ambitious. (That being said, I once flew to Madrid with my family for a long weekend because the price of the flights was just too good to pass up. But it worked out perfectly because it was a small enough city that really worked for that shorter time frame.) Just keep in mind that if you're battling jetlag or you spend a full 24 hours of your long weekend traveling, you won't have as much time for the fun part; that destination might be better saved for one of your longer trips. Here are a few long weekend trips I took which required plane travel:
If you plan on going somewhere close to home, make sure that it's still far enough from home that it really feels like a break. Here are a few weekend trips I planned within relatively easy driving distance:
Or you could do something kind of in between; road trip a bit farther or take a train or bus to a place a couple hundred miles from home. Here are a few slightly farther, but still easily accessible destinations:
I've shared tips on creating an itinerary previously and I emphasize having a plan so that you're not wasting time faffing about in the hotel trying to figure out what to do. Well, that is doubly important on shorter trips because it's much easier to waste time when you don't have much of it.

In this scenario, I like to get pretty specific. I'll write down exactly where I want to go and the order in which each spot should be visited (the most logical route).

And in making an itinerary, make sure you keep an eye on the weather forecast so you can come up with a backup plan just in case. If it's meant to rain in the afternoon, rearrange your schedule so you're doing all of the outdoor activities in the morning and the indoor activities later on.

In addition to hotels and rental cars and flights and all of those crucial items, I recommend booking ahead for anything else you can. For example, if you need tickets to visit some monument or you need to reserve a spot on a tour, do this in advance. It will ensure that you get a spot (you'll regret it if you miss out on more popular sites or ones with limited access) and it will save you time if it's the type of thing where buying a ticket ahead of time allows you to jump the queue. And even if you can't necessarily jump the queue, you'd at least avoid the ticket lines.

This also applies to restaurant reservations. Don't waste time faffing around when you're there. Do it when you're bored at home. Just hop on Yelp or Tripadvisor and scope out where you want to eat.

Even if you're an over-packer, a weekend getaway is the prime opportunity to pack efficiently, especially if the trip involves a flight. Bringing a carry on not only saves you money, but it will save you time. Standing around baggage claim waiting for the conveyor to spit out suitcases is one of the most depressing wastes of time during travel.

If you're flying, make sure to check in to your flights ahead of time. You don't want to be one of those losers on standby for this trip. I mean, you never want to be one of those losers on standby for any trip, but especially in this case because time is so precious.
I'm blabbering on and on about how you have to be organized and responsible but in the end, the critical point is that you have to have fun. Because otherwise, what is the point?