City Trip Smarts: Dos and Don’ts When Visiting a New City (with bonus London tips!)

Last week I returned from a very successful trip to London which made me wonder, “What makes me so darn amazing at going on and fully enjoying city trips?” I went over the things I do to prepare for a trip and the things I do once I’m at my destination and decided I might as well share them, because I know many people find holidays of any kind, but especially short getaways, stressful to plan and sometimes even hard to fully enjoy. (And if you’re not interested in general tips, I give some London-specific tips at the end of this post)

1. Define the goal(s) of your trip
Before you leave, ensure you know exactly what you want to get out of your trip and (this is key) be unapologetic about it. Too many times I’ve found myself running around a city like a headless chicken covered in fatigue and blisters just because I tried to see everything everyone told me I had to see. If you truly want to see all the landmarks a city has to offer: great! But if you want to go to, say, New York to eat your way through every food truck in Manhattan, own that! Don’t let other people or guidebooks dictate what you do. When your trip is over and you’re soaking your tired feet, you’re the one who needs to feel good.

Big Ben and Fireworks

2. Find the perfect travel partner
If you want to explore every inch of a city on foot when your buddy is of the hop-on-hop-off tour persuasion, you will run into trouble that may very well result in resentment at best and explosive fights at worst. I really enjoy doing my own thing without having to worry about other people’s feelings while on holiday, so I’ve gone on many solo trips. Recently, however, I’ve found a travel buddy whose interests (FOOD!) mesh well with my own, but who also enjoys going off on her own adventures. So when we travel together we may spend an afternoon exploring those things we find interesting but the other person finds patently dull (or not interesting enough to see twice: I’m looking at you, Tate Modern). Naturally, compromises can always be made, but don’t put yourself in a situation where you end up compromising on everything. Holidays cost a lot of money and feeling like your expenses were wasted because they were not ones you wanted to make will not give you that happy post-trip glow.

3. Make plans, but be flexible
Before I go on any trip, I make a list of everything I would like to do or see. For my recent London trip, I made this list on Pinterest. I haven’t found much use for that site yet, but drawing up a London pinboard was both excellent holiday foreplay and a great way of visualizing what I wanted this trip to look like. It’s important to be realistic though, and to be aware that you probably won’t get around to doing everything you want to do. After listing everything you’d like your trip to be, make sure you set priorities and don’t have more than one or two priorities per day. That way, you’ll be able to hit up your own personal highlights and any goodness that’s added to that is just a fantastic bonus.

4. Be local
With the powers of the Internet, it’s easy to look up which events, festivals, and other temporary things are going on while you’re in town. When I was in London with my mother in 2003, we left our hotel one morning to go to Highgate Cemetery. We never got there, because before we reached the Tube we had run into a massive demonstration against the war in Iraq. Public transport in the city had all but shut down and there was no way we would be able to do any of the things we had planned. It ended up being a great experience (we joined the march and I still cheer, “When they say “˜warfare,’ we say “˜welfare’!” to myself from time to time), but running into an event like that when you really have somewhere you very much want to be (and perhaps being of a different political persuasion) can muck up your experience. Conversely, there are a lot of fantastic local events that go on in every city in the world that you may not get to experience without proper planning (because you need tickets in advance or because you didn’t know they were happening until after the fact). If you visit a city like London or New York, looking up which big name actors are currently doing (off) Broadway or West End stuff can result in you seeing Cate Blanchett, Imelda Staunton, or Eve Myles in real life (these are all actresses doing plays and musicals in London while I was there).

5. Book accommodation that fits with your trip goals
When traveling solo, I spent a lot of time in hostels because they’re cheap and they allow you to easily meet people to do stuff with when you feel like being social. Two years ago I stayed in a hostel in Boston for a week, where I met a group of fantastic guys with whom I spent a lot of time exploring the city, making snow angels, and going on extremely ill-advised late-night hikes through snow banks. If I’d been at a hotel, I highly doubt I’d have enjoyed being mostly snowed-in as much as I did. This past trip in London, we stayed at EasyHotel South Kensington, which is part of the same company as EasyJet. It was cheaper than booking two beds in a 6-person hostel dorm, but you get what you pay for (which is really nothing more than a bed and a private bathroom). If I’d been in town to relax rather than spend the entire night wandering around the city and meeting up with friends, this might have gotten on my nerves. So if you’re one of those people who needs to be able to relax in the evening with a movie and an overpriced minibar drink, don’t scrimp too much on your hotel costs. Which brings me to the next tip.

6. Have a realistic budget and know where you can be flexible about it
You’ll often pay for your accommodation in advance, but all your other costs won’t become fully clear until you’re actually out there doing stuff and they’ll almost always be higher than you anticipated. If the Tower of London is on your must-see list, you need to be aware entry will cost you around $30. Access to temporary exhibitions at London’s free museums can be similarly costly. It’s best to be prepared for these things, so you don’t suddenly find yourself spending 80% of your daily allowance on one landmark or event (not leaving much room for food or transportation). But again, flexibility is key. When I was in London, I suddenly found myself queuing for the new hit musical Matilda (music and lyrics by Tim Minchin). I told my travel buddy I would absolutely not pay more than 40 pounds for a ticket, but when we got to the ticket booth we were told the only two seats left were 52 pounds each. The difference was about what we anticipated paying for dinner that night (sans drinks), so we decided to not have a real dinner to have a great theater experience instead. If you forgo your morning Starbucks and stick to hotel/hostel-provided instant coffee instead, you may suddenly be able to do something you hadn’t originally budgeted for.

7. Be in the moment
You’re in a different city! Doing things a lot of people may never have a chance to do! Having experiences that no other person will ever have in quite the same way! How cool is that? So yes, you may be lamenting your decision not to bring flat shoes and yes, you may not have seen one of the things on your must-see list and yes, you may not have had the money to go to that Cate Blanchett play. But the great thing about cities is that you get to stroll around them completely free of charge and there’s always something to see, if you just know where to look. I once popped into a church to shelter from a sudden summer shower to find a young man quietly playing his guitar in a pew. I must have sat there listening to him while the rain was pouring outside for at least half an hour; it’s a memory I’ll always cherish. If you can delight in just being in a different place, you won’t have much trouble looking back on your trip fondly (even if half the trip consisted of crying in police stations because your everything got stolen, which happened to me in Madrid in 2007. Maybe I’ll tell you about that sometime).

So, London? This was my fifth trip in as many years and my seventh trip since 2003. This means the pressure to see the big attractions is pretty much off, but to be honest, it’s never been truly on. It’s a city that feels like home to me, even though I haven’t spent a sizable amount of time there and I have to get reacquainted with it on each visit. I’m lucky to know a few local people I now call friends (thank you, Internet!) who have opened up their homes and shared their knowledge of great restaurants and stuff-to-do-and-see with me. I’ll now pass some of that knowledge, some of it theirs and some of it mine, on to you.

  •  Get an Oyster card. Seriously. Travelcards are great because they give you unlimited transport, but if you’re anything like me you’ll want to spend most of your time exploring the city by wandering around it anyway, and you won’t take the Tube more than three of four times a day, which makes the Oyster the more financially-savvy option. In addition, the Oyster card works in all zones, not just zone 1 and 2, which prevents that pesky red light you get when trying to leave a station that’s (whoops) in zone 3. Yes, you have to pay a 5 pound activation fee, but you’ll get to feel like a local swiping your card at the turnstiles (plus they have some really cute and/or nerdy Travel Pass holders at Forbidden Planet).
  • Go to Forbidden Planet if there is a geeky bone in your body. They have all the big-name and indie comics and graphic novels and tons of merchandise from movies and TV shows. Wind-up Daleks! TARDIS mugs!
  • If you’re a Whovian, you’ll also want to swing by Earl’s Court station, because just outside it is a real-life blue police box. Get your nerd on by posing with it. Come on. You know you want to!
  • And while you’re at Earl’s Court, pop into the Prince of Teck pub for a pint or two and some cheesy fries just across the road. It’s a lovely, friendly pub with lots of locals and extremely reasonable prices for London (2.20 pounds for a half-pint of Guinness).
  • If you want your food and drinks on the go and are in town on a Saturday, stop by Borough Market. They sell a fantastic raclette (melted cheese and potatoes, yum!) for 5 pounds and you can eat it picnicking outside Southwark Cathedral. If you go there at the end of the day, you can also get some good bargains (organic chai for 1 pound, whaddup!).
  • London isn’t London without some proper Indian food and Drummond Street near Euston station has fantastic vegetarian food for very reasonable prices (I think last time I ate there we paid around 15 pounds for dinner and a couple of beers each). If you want some spice before you catch a show, Punjab on Neal Street is very tasty (if not the cheapest option).
  • Other great areas for food that may be a little out of the way include Edgeware Road for Middle Eastern and Brixton for pretty much everything (Asmara in Brixton has fantastic Ethiopian and is also reasonably priced, though not as cheap as it was a few years ago). But don’t underestimate Chinatown either. Leong’s Legend on Macclesfield St. offers mouthwatering Taiwanese morsels and can fill your rumbly lunchtime belly up with enough dim sum and tea to last you all day for under 12 pounds.
  • After stuffing your face (I just really like food, y’all), you may want to spend a little time enjoying the great outdoors, which is also remarkably easy in London. Of course there are the parks (Hyde, St. James, Kensington Gardens), but don’t underestimate the relief of traveling a bit out of your comfort zone to Hampstead Heath or Kew Gardens. Though these places are touristy, yes, walking in a different direction than the crowds will easily land you in a place that may very well feel like it’s all your own. And on a clear day, the Heath will give you a much more relaxing view of the city than the overcrowded London Eye ever could.
  • Go see a show. And prepare! Many theaters have super-cheap tickets that they sell as soon as their box office opens at 10am. You may have to queue for a bit, but it may very well be worth it if at the end you snag a 25-pound first-row seat for Wicked or an 18-pound private balcony seat for Mamma Mia! And even if you’re not an early riser, you can easily find affordable tickets to some of the longer-running shows by stopping by the theater’s box office the day of the performance. If you swing by 30 minutes before the show starts, you may even get super-cheap great seats that they just want to fill. If you’re not terribly picky about which show you see, there are a million great budget options out there for you. But really, you should go see Matilda, because it’s fantastic (I gushed about it at almost as much length as this post you’re reading now on my own blog).

If you made it all the way to the end of this post, I applaud you! And after applauding, I’d like to ask you: what are your must-do’s when planning a trip? And what are some of your favorite hidden gems in cities you’ve visited?

By Nanna Freeman

Anglo-America-loving Dutchie with a grad student twist and a mad dash of self-mockery.

Sometimes I also write things here:

15 replies on “City Trip Smarts: Dos and Don’ts When Visiting a New City (with bonus London tips!)”

When I go to a new city, I tend to take the city busses.  I get on one bus and just ride it to the end and then on the way back, stop at something I might have noticed I liked.  I really enjoy the realatively free sightseeing trip.  ( in Amsterdam, I took the tram the same way.  End to End)

Lately, I have been a fan of the hop on, hop off city tours.  When I went to Chichago with a few Persephone Ladies, I really enjoyed it. It was cheap, the guides were mostly fun ( except the one who hated rich people, he was pretty negative).  We learned that if we like the guide, we should stay on the bus all the way through and then get off on the next round at our various stops.  I have done this type of thing in London too.  It really is the best way for people to get the tourist (like with wearing cameras and American Jeans and looking really out of place) experience. 

In Amsterdam, I stayed at the Flying Pig hostel in the Leidseplein. It was really a great experience, I got to go to the grocery store down the street, cook my own meals, and saved my money on the food for the attractions, like a canal tour, and Museum entrance fees. I felt like Tourist by day, Local by night.  Doing my laundry in the local laundrymat was also a nerdy treat!


Ah, yes. All the “During the Games, you’re probably better off walking” ads in the Tube where horribly depressing. I was there the weekend of the marathon and that already made it SO CROWDED on Saturday. I wouldn’t discourage anyone from going during the Games if it’s the only chance, but you’d definitely have a different experience that when you go at any other time.

It’s a few years since I’ve been in London, but the underground is just horrid even on an ordinary day. Can’t imagine what it would be like around the games.

Definitely would be worth checking out how things may be different to usual, like theatre shows (some are closing during the games, I think), for instance. Also, the country-wide torch relay is, I think, going to be interfering with some travel, too.

I have to admit, for as much traveling as I’ve done, I’m usually not the person with the power to do all the planning, so I tend to just go with the flow or manage to excuse myself from the rest of the group to do my own thing when I can. However, I will definitely be referring back to this from time to time in the future!

Great travel buddies are so hard to find, but so good when you’ve found one! I’m pretty wimpy when it comes to travel too (did you see how often I’ve been in London over the past few years? With that money I could’ve also gone to… I dunno, Morocco or something), but even when you go to reasonably familiar places there’s still a lot of new stuff you can see and do.

Great advice! City-travel is definitely my preferred way to go (beach vacations bore me!) I tend to travel alone a lot, and I find cities to be a great place to be if you are going solo – plenty of opportunity to both be solo and meet other people if that’s your thing. One of my solo travel tips is a safety thing: avoid being drunk in a place with which you are unfamiliar. I’ve never felt unsafe in a city, but I definitely advocate staying sober(ish) when going it alone in a big city, especially at night.

Oh yes, definitely. I think I’ve only ever had more than 2 drinks if I was with people I know OR if there was a hotel/hostel bar. And even then I’d never drink a ton. Especially at a hostel you’ll want to have your wits about you. Good tip!

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