Maddy Douglass

Knitter, lawyer, and safer beauty advocate in San Francisco. 

Loves coffee, crafting, and cheese plates.  


How to Take a Vacation

(Psst - We're changing things up a bit here at madeleine|blogs! In lieu of weekly High Five for Friday posts, I'll be doing a monthly roundup at the beginning of every new month about the previous month's activities that may not have made it onto the blog. Check out next week's August roundup on Friday, 9/05!) For now, please enjoy this travel post...


Everyone wants to go on vacation. Show me one person who doesn’t, and I’ll immediately break down that wall of fear and denial. I am a lawyer, you guys! Anyway, let’s just assume, everyone wants to go on vacation. You want time off from the hustle and bustle of work, to see things that are new and different from your everyday life, to relax on a beach with a mai tai. Regardless of your motivation, travel can be for everyone.

The problems start cropping up right around the time that you actually plan that travel. How will you get the time off from work? What will you bring? Will you be able to speak the language?

I present to you: Maddy’s (Very Introductory) Guide to Taking a Vacation.

1. What you want to see

The first step in taking any trip or vacation is deciding what your goal will be of the overall trip. Is it to relax and decompress? Do you want to pack as much sightseeing into your schedule as possible? Figure out whether you want to rest or explore (or a combination of the two) and then determine the location that fits the bill. See if you can get a great fare to Hawaii for several days, and just spend your time out on the beach. Or, alternatively, take a quick trip to New York City, and see a show after walking around Soho or the West Village for the afternoon. If you're going international, make sure you plan out which sightseeing spots are most important to you - or would you rather sit back and enjoy Italy like a native, relaxing at cafes and listening to the chatter around you?

Keep in mind that you can sightsee anywhere, and you can relax anywhere. It’s all up to you.

Regardless of your plans, it doesn't hurt to brush up on the language and local customs. You don't want to offend anyone unintentionally, and though many places speak English, it's nice to be able to say at least a few phrases in the native tongue. I've found the Duolingo app is great for practicing basic grammar in different languages, and the Lonely Planet and Rough Guides series are great for traveler's tips!

Of course, sometimes you have to go on vacations that are planned for you – family trips, a friend’s wedding, etc. If that is the case, problem solved! You already know what you’ll be seeing and doing! Skip ahead to number 2...


2. Where to Stay

This step relates heavily to number one in that, if your goal is to sightsee, it might make more sense to stay in an area that is closer to the museums and parks and restaurants you intend to visit. If you already know you’ll spend much of your time in the historical section of a city (as my family and I did in Montréal recently), then it would make more sense to stay there and be able to walk out your door every morning already in the area you want to explore!

If, on the other hand, you want to relax and occasionally go out for a walk or two, maybe stay in a less bustling neighborhood, or rent a house or apartment from someone in a more residential area. Most cities have pretty good public transit (and there are always cabs) so you aren’t locked into an area once you check in to the hotel or hostel or apartment. It’s all a matter of perspective, and planning.

Of course, sometimes financial constraints can come into play, but you can find great deals nowadays on the internet for lots of places that you wouldn’t ordinarily think were very affordable. Give it a try! (Also, sign up for Airfare Watchdog alerts if you want to travel somewhere but don't have a set time in mind... they're great!)


3. How to Pack

Once you know where you’re going, and what your activities will likely be, you can begin packing. It sounds obsessive, but making a list of every thing you’re going to bring can be truly helpful. Once it’s all written down and checked off, you can stuff the list in a suitcase pocket and double-check it before leaving your vacay destination – no forgetting shirts in drawers or cell phone chargers in the socket for you! I also tend to cross things off the list that I end up not bringing, so I don’t have a panic attack over a black shirt that never even made it into my luggage.

The key to packing is “editing.” Edit edit edit. Unless you are an expert packer (in which case, congrats!) most of us don’t wear some of the things that we bring on our travels, and those items are only taking up extra space that could be filled with souvenirs, or could turn your checked bag into a lighter (cheaper!) carry on bag.

Take a good look at what you’ll be doing. Will you be walking around? Pack one pair of comfortable walking shoes, maybe sandals or flats. Will you be going to dinners? That same pair of comfortable flats can sometimes double with a dress for a nicer look. If not, pack only one pair of heels that can match most of the things you’re bringing. Will you need pants? Pack one pair of jeans and some different tops to alternate – the key here is to mix and match. You can create so many different outfits from the simplest pieces, instead of bringing your entire closet. I love this post from A Cup of Jo on this very subject.

Once you think you’ve figured out your suitcase situation, go back through and be real with yourself. You probably won’t wear that lime green blazer while you’re in New York in November – put it back. It’ll be there when you come home.


4. Get your ducks in a row

Finally, you have to handle your business. You can’t just peace out of your office with a smile and a wave – besides just letting your boss know that you’re going to be out, let anyone else with whom you work closely know of your plans. Tell the team whose project you’re managing who else they can reach out to with questions. Set up a vacation response on your office email.

Be professional, and remember to organize things so that your workplace will still be running smoothly in your absence. They won’t replace you while you’re gone, and they’ll be happy to receive you back when you return.

Obviously the tricky part of going away on a vacation is the nitty gritty details: finding those cheap airfares; booking a hotel on discount that satisfies your brother, your mother, and your cousin’s needs; figuring out whether you can squeeze that last maxi dress into your already stuffed valise. But if you keep these maxims in mind, you can get through it just fine.

And finally...don’t forget to send me a postcard!


Have any helpful travel tips? Leave them in the comments!

Some excuses, and some pictures.

NOLA & The Flamingos | HOT SPOT