Four Cities You Can Conquer In Four Days

When I worked for Four Seasons Hotels in my early 20s, the best perk of the job was being hosted each year by one of their hotels or resorts for a three day familiarization trip. We jammed our carry-on bags full to bursting and on arrival, set immediately to moving through our packed itinerary, hopping between dining experiences, tours of the hotel and opportunities to see as much of the city we were in as possible. Those fast-paced jaunts to new places opened my eyes to the idea that travel didn’t have to be this once-yearly financially burdensome orchestration every time you wanted to see some place new. Since those days on the reservations team, I’ve spent four days or less in over 30 cities across North America and Europe and based on my experiences, I can confidently say that you can absolutely pack an entirely worthwhile vacation into a short stretch of time. These “fam” trips can be easy and budget-friendly and it’s definitely possible to see a lot of what’s on your bucket list if you’re strategic with the time you have.

As the world starts to slowly return to normal and we start thinking about reincorporating travel back into our lives, I wanted to share four cities that you can absolutely conquer over the course of a four day trip if you’re needing to escape your house, your spouse or your kids for an extended weekend away. Because traveling might still be a ways out, I included a list of movies and tv shows you can watch to get yourself pumped up for the day that you set off in the direction of your destination of choice!

1. New York City

Let’s kick it off with NYC, the ULTIMATE long-weekend getaway. While New York City can never truly be conquered due to the sheer amount of culture, attractions and experiences to be had there, it’s definitely one of the easiest places to visit on a whim for a few days again and again. It’s not the most budget friendly of locations - hotels are on average around $300 a night! - but there are a wide array of Airbnbs to choose from, and many people opt to stay in either Brooklyn or New Jersey to cut back on costs. If your finances and the lodging options available allow for it, I would opt to stay on the island of Manhattan for the sheer savings in time and cost of commuting back and forth. Food can be costly too if you’re not careful to read the menus in advance but it’s entirely possible to get the full New York experience on a budget. Here are some of the things that you can do with your time in NYC.

Bike or Row Your Way Through Central Park :: I know it sounds ridiculous to recommend going to a city only to spend time in nature, but Central Park is seriously one of the coolest parts of New York City. It is HUGE and will absolutely take you more time to explore than you anticipate but I promise it’s worth it. At the very least, be sure to walk The Mall - the famous stretch that’s lined with trees and benches. If you have time in your schedule to dedicate to this part of the city, I highly suggest setting aside half a day for renting bicycles to explore the lower half of Central Park or a row boat to paddle past the instantly recognizable Bethesda Terrace and Bow Bridge. At $14 per bike for two hours and $20 per hour for a row boat, it’s a budget friendly way to have an adventure in the city. Fair warning - the boats are old and squeaky but it adds to the charm and you’ll definitely feel like Prince Eric or Ariel gliding through the lagoon and won’t be able to wipe the smile off your face!

Walk the High Line :: Located on the west side of Manhattan, the High Line used to be an old railway that the city converted into a raised footpath that’s nestled in amongst the piers and buildings of Chelsea and the Meatpacking District. I love that it’s tucked in behind apartment buildings and shipping docks - it feels like an intimate glimpse into life in New York City. I highly recommend walking it at sunset - it’s on the west side of the city so you’ll end up with literally glowing views of the Hudson River. You can enter it at either Gansevoort Street in the south or 34th Street in the north - I recommend starting at the north entrance and exiting in the Meatpacking District where there are a ton of really cool bars and patios to kick back at for the evening’s meal or cocktail

Explore famous locations in Greenwich Village on foot :: Ghostbusters, Friends, Sex and the City and When Harry Met Sally are just some of the titles that have famous filming locations in the village that you’re sure to recognize. We did a walking tour in the area which I would highly recommend - it’s a beautiful spot with a lot of history, particularly for the LGBTQ community. Be sure to stop by the popular Big Gay Ice Cream shop where some of the cones are named after The Golden Girls.

Kick back in Bryant Park and peruse the New York Public Library :: This is a really pretty park to grab a drink or snack and sit on the lawn for a break. There are some gorgeous cafes to choose from and it has a view of the massive New York Public Library. If you’re into libraries, the NYPL is an incredible building to walk around inside or take a tour of.

Make your way to the Top of the Rock :: While the Empire State building is world famous for its view and sheer height (and the final Sleepless in Seattle scene), the one downfall is that if you’re in it, you can’t see it. Head to the Top of the Rock instead and you’ll get a skyline view of the entire city inclusive of the Empire State building.

Land a spot in Jimmy Fallon’s audience :: This one’s a bit of a long shot but this was a totally awesome experience if you’re a Jimmy Fallon fan. Your chances of getting in to the audience are best with this show because you have two options: you can apply to be part of either the test audience or part of the live taping. Jimmy Fallon is the only one that tests his jokes on a live audience before the live taping, which gives fans two opportunities every day to be part of the show. We applied for tickets for both the monologue dry run and the live taping and we only got a response for the monologue dry run and I’m certain it’s because I thought to fill that request with references to the show - it was peppered with “Ew”, nods to the regular segments he puts his guests through, and mention of my favourite interview: the time he found out that he was on a date with Nicole Kidman and had no idea. I imagine it’s because they prefer to have an audience that knows and loves the show. You can apply for tickets here. Fair warning - you usually have to apply months in advance so be sure to check out the calendar and set a timer for when they go on sale. We booked a spot in advance of picking the date to travel there and ended up scheduling our trip around it instead of the other way around.

Grand Central Station :: I wouldn’t say this is a must but if you’re a sucker for breathtaking architecture, the main hall is well known for it's beautiful floor to ceiling windows. The best part of Grand Central Station in my opinion is the Pershing Square restaurant that’s located under the bridge that’s attached to the building. I have gone here every single time I’ve been to NYC. It has delicious food and is really atmospheric- it has an old timey NYC vibe and is reasonably priced. Also, they make a mean Shirley Temple. Perhaps a bit of a basic recommendation but I like what I like!

Honourable mentions :: baseball game at Yankee Stadium, walk the Brooklyn Bridge, see a Broadway show, 9/11 Memorial, Statue of Liberty and Ellis Island

What to watch before you go :: Definitely, Maybe; When Harry Met Sally; Someone Great; You’ve Got Mail; Elf; Big; Enchanted; Breakfast at Tiffanys

2. Paris

Paris is one of those cities that you know you’d like to travel to but you don’t realize just how much you’ll love it until you’ve seen it for yourself. It’s hands down one of the fanciest metropolises you’ll see in Europe. The architecture is high class at every turn and you’ll quickly realize how it earned its glamorous reputation. While it’s possible to do Paris in four days (I’ve done it in four days on two separate occasions), you have to be really strategic in how to use your time if you want to see as much of it as you can. It sprawls far wider than it appears on any map and what looks to be a block away, could equate to 20 minutes or more of walking. Getting comfortable with using the Metro or getting a ticket on a hop-on hop-off bus will ensure you get to where you want to go without wasting half of your time there trying to walk everywhere. Here are just a few of the things you can do with four days in The City of Light.

Stroll through Montmartre up to Sacre Coeur :: In my humble opinion, Montmartre is the best part of Paris. Narrow cobblestone streets, charming sidewalk cafes galore and breathtaking views of the sprawling city at every turn are what make it such a delight to explore. If you climb to the top of the hill at the right time of day, the angelic voices of the choir ringing out of Sacre Couer will have you wondering if you died and landed at the gates of Heaven.

Get up close and personal with the dead in the Catacombs :: Simply put, this is a very long tunnel filled with old human bones. It’s both super creepy and also oddly interesting? I wouldn’t recommend it for people who are claustrophobic or don’t want to be brushing up against human remains deep underground for the better part of an hour but this is definitely a unique and memorable experience.

Be creeped out by the carvings on Notre Dame :: As world renown as this church is, I personally don’t feel that it’s necessary to see the inside. The lines to get inside are long which equate to wasted precious time and, well, it pretty much just looks like an extra nice church inside. I’m not sure of the state of it since the fire so I can’t make any recommendations about going in purely to see the view from the top, but what I find most interesting about Notre Dame is the external façade - it’s intricately carved with saints holding their own heads and menacing gargoyles that guard over its perimeter. To take in the sheer magnitude of its architecture that makes the church world-famous, cross the bridge and take in the view from across the river or hop on a river boat tour down the Seine.

Coffee and cheese plates at a Parisian cafe :: This is a quintessential Parisian experience. Pick a cafe, any cafe, and partake in the city’s most famous way of passing the time. Be sure to sit outside under the awning and face the street so you can people watch and develop an appreciation for Paris’ distinct street fashion.

Treat yourself to Ladurée macarons :: I’ll preface this by saying these are insanely expensive and the shop is as bougie as they come. And, they’re really, really delicious. This company has been making macarons since the 1800s so they know their shit. I’m fairly certain you can buy them individually but if you don’t care about the brand, there are some places up in Montmartre that we purchased macarons from that were also really nice.

Get lost at Versailles for a half day or more :: The Palace of Versailles is full to the brim with history - I’m of the belief that it’s an absolute must when going to Paris. If you’re not into touring palaces (this one is well worth it though, I promise), the grounds alone are an exquisite site to behold. There are mazes and terraces and gardens galore filled with sculptures and lattice-lined pathways that make it fun to get lost wandering around. There are a few cafes you can stop at for lunch too - that way you can say that you dined at Versailles. Now is probably a good time to mention that it’s going to become obvious that one of my favourite things to do in a place is rent bikes where it’s safe to ride them. I would recommend exploring the grounds on foot for about an hour or two and then hop on a bike to see the rest. It’s impossible to see it all no matter how much time you have but a bike will really help you cover more ground. That, and it feels way more like an adventure when you mix it up.

Tour the Seine River in a boat :: I remember this being a little bit pricey but it was a pretty cool way to see the city from a different angle. The bridges alone are such an interesting feature of Paris, and you’ll see parts of the city that you wouldn’t intentionally see on foot. I think it’s worth it, especially if you want to rest your feet after walking for hours on end.

See the Eiffel Tower at night :: You haven’t truly experienced Paris until you’ve seen the Eiffel Tower at night. The best views are from the river banks or the terrace of the Trocadero. You can go up the Eiffel Tower in an elevator or by taking the stairs but we skipped it the last time we went and didn’t regret it.

Buy a trench coat :: Because where better to buy a trench coat than the city that made them fashionable? One of the shops I’ve been to during both of my trips to Paris is the Promod location in Le Marais across the river from Notre Dame. They sell affordable coats that are really great quality - my $130CAD trench is still in close to mint condition 6 years later.

Honourable mentions :: The Louvre (set aside a 1/2 day), climb the Arc du Triomphe for incredible city views, Moulin Rouge (bizarro show), take a stroll down the Champes D’Elysees or around Le Marais

What to watch before you go :: Lupin; Emily in Paris; Midnight in Paris; Da Vinci Code; Moulin Rouge; Funny Face; Marie Antionette; Amelie

3. Charleston

Charleston, SC is the perfect place to go if you want to have a relaxing weekend away. Charleston, in my opinion, has the least amount of things to do of the four cities on this list, but that doesn’t mean it’s not well worth a visit. My sister in law and I went together and still reminisce about it all the time. It’s not the most exciting city as far as activities go (we couldn’t figure out why a candle making workshop was the number one thing to do at night until we got there) but it is full of grandeur and southern charm. It’s clear that the owners of the homes take their stewardship of the 300-year old homes very seriously. The monthly garden maintenance alone on the majority of the homes probably costs more than my mortgage payments. The city is known for the stately residences and its cuisine so if you’re down for simply walking around a really old city for four days to look at architecture and eat, Charleston is a good choice. We left so relaxed and totally inspired by the houses and gardens there. Here are some of the things you can do with a long weekend in Chucktown.

Marvel at the homes and gardens :: Seriously… don’t go to Charleston if you don’t care about seeing colourful hundreds-of-years-old mansions and gardens. This is the main draw, aside from the food. We never tired of walking back and forth across the South of Broad area (we managed it THREE TIMES in one day - this is a very walkable city) and found something new every time we did. The window boxes alone are seriously impressive and made me want to up my own window-box game immediately upon coming home.

Rent bikes and ride around South of Broad :: I told you there was a running theme here. The day that we rented bikes and rode around the lower half of the city was my favourite day of the whole trip. It can get really hot in the city and you’ll be doing a lot of walking otherwise so it’s a great way to cool off and take a load off your feet. To rent bikes, download the Holy Spokes app to reserve a ride. You’ll get a code that you can use at any HS bike hub (they are all over the city) and you can even “hold” your bike reservation if you want to park it to get a bike to eat. It’s $8 per hour or $20 per bike for a day pass.

Research where you want to eat and book ahead for dinner :: As soon as you know you’re heading to Charleston, book any places you’re set on eating at ahead of your arrival. Charleston is a really small town with a handful of really famous restaurants and it can be damn-near impossible to find a spot. There were some places we couldn’t even book ahead for three days in advance. Some of the places that we ate at that came highly recommended are listed in this post about Charleston. There are far more than we managed to get a seat at so do some research because this will be one of the highlights of your trip.

Hunt for ghosts on an evening walking tour :: Once we figured out that there wasn’t much to do in Charleston at night other than eat, we decided to book a historical ghost tour that ended up being really fun. We got to see parts of the city that we hadn’t seen yet and learn stories about real-life pirates and fatal duels. It was actually pretty scary at times - we ended up sleeping with coffee grounds beside the bed to keep the boohags occupied!

Daydream about being a student at College of Charleston :: This campus is a dream to walk around. You don’t need a ton of time here but it’s worth seeing, mainly because of the buildings and the landscaping. It’s unlike any college campus I’ve seen before - certainly wildly different from the Hogwarts-esque University of Toronto that I attended. Fun fact: some scenes from The Notebook were filmed here as part of Sarah Lawrence College that Allie attended.

Educate yourself about the South’s dark history at Boone Hall or Magnolia Plantation :: Both of these locations do a respectful job at communicating the true history of the enslavement that the owners/enslavers of the plantations perpetuated in order to create massive wealth for themselves. Boone Hall has the original slave cabins still standing all down the front lawn (The Notebook left these out while filming the scenes of Allie’s house). The history of the families who were held captive there are shared and you can step inside the cabins to learn more about the despicable treatment and living conditions of the enslaved. As much as I don’t want to describe either of these places as being nice to look at, Magnolia does have some of the most incredible gardens I’ve ever seen. It goes without saying that if you decide to attend either, treat attending these as a sobering educational experience instead of as a source of entertainment.

What to watch before you go :: The Notebook; Southern Charm (like a terrible bus accident you can’t look away from); The Patriot; Dear John

4. Edinburgh

I have been to a lot of European cities and there isn’t one anywhere else that’s quite like Edinburgh. There is something in the air there - it’s full of magic and history and long-standing tradition and together, they permeate your senses. The most enchanting part of the city is the glimpses between buildings and down alleyways of the medieval castle that sits on top of a craggy dormant volcano hundreds of feet about the city. Edinburgh is very walkable- we didn’t use public transportation at any point during our four days there and managed to see a ton. Almost everything you want to see is within a reasonable radius of the castle. I found accommodations there to be a little higher than mid-range, mostly due to the exchange rate, but it’s got a lot of options through both hotels and Airbnbs that can make a stay there more affordable. If you’re a Harry Potter fan, you'll absolutely delight in this city - it inspired much of the scenery and the characters from the first novel and on. Pack your most practical pair of shoes and prepare to fall in love with this multi-tiered, gothic city.

Hike up Arthur’s Seat :: One of the seven hills of Edinburgh. many guides will say this is a walk but this is a near vertical climb at points. I’ve been to Edinburgh twice now - the first time we didn’t hike the seat and the second time we did. I would say that it was a fun activity to do and the views at the top are entirely worth it. Be sure to wear sturdy shoes and bring a bottle of water with you - it more than counts as grueling exercise rather than a leisurely walk. (As a matter of fact, leave your fancy footwear at home if you travel to this city- you won’t make it more than 10 paces without hitting cobblestone or having to walk at a 45 degree incline.) Plan your route to Arthur’s Seat in advance so that you end up walking down one side of Edinburgh through the university to get to it and up along the backside of Holyrood Castle at the bottom of the Royal Mile on the way back (or vice versa depending on where you’re staying or aiming to go afterward).

Take in the views from Calton Hill :: If you plan your walk back into the city and aren’t feeling too jelly-legged, you can walk straight down Arthur’s Seat, wind through the neighbourhoods behind the palace and walk straight up to Calton Hill, another of the 7 hills with fantastic views of the city. These views are better than the ones on Arthur’s Seat in my opinion, because you’ll be staring straight down Princes Street with the castle in the near distance and a view of the most bustling street in the city. If you only have time for one hill, make it this one. It’s a bit of an odd place but there are some interesting monuments at the top to see and there’s a tower you can climb as well. From there, walk down through the ancient graveyard if that’s your thing (it’s mine for sure, there are some really old and quirky graves in Scottish graveyards) and along Princes Street. There are lots of nice shops on one side (one word: Primark! I bought a fleece sweater there made of plastic water bottles) and Princes Street Gardens on the other. Some of the best views of the castle are from within the gardens.

Cozy up in a pub on Rose Street behind Princes :: Whether you follow the route I describe above or find your own way there, make a point of snagging a seat at one of the pubs on Rose Street that’s tucked in behind Princes. All the pubs have live music, tight quarters and stone walls - everything you imagine a cozy Scottish pub would be and more. Be prepared to stand or share tables with some new friends - preferably with an Innis and Gunn in hand. I imagine it’s the closest thing on earth to the nectar of the gods.

Peruse Victoria Street :: You’ll know you’ve set foot on Victoria Street when you feel like you’ve suddenly happened upon Diagon Alley. The colourful shops and winding road are rumoured to have inspired the street in the Harry Potter books and films. The most unique part about this street is the terrace that trails all along the top of it. If you walk along the terrace and turn left onto the next street over, you’ll find yourself on the Royal Mile with the entrance to the castle at the top. The Royal Mile is mostly a tourist attraction with lots of souvenir shops, pubs, and beautiful closes which is basically a fancy word for an alleyway that takes you down to another street level or into a courtyard with shops and homes. One of the closes has the most gorgeous sunset views of the Scott Monument and another takes you to Jamie’s print shop from Outlander. The closes are definitely worth taking some time to explore.

Go underground in Real Mary King’s Close :: Speaking of closes, there’s an ancient, fully intact neighbourhood that’s buried deep beneath the city streets that is open to the public. You can take a tour of the dwellings that were closed off during the plague (with people still inside them!) and get a feel for what life in Edinburgh was like only a few hundred years ago. Hint: it was nowhere near as leisurely as it is today. I loved this tour. How often do you get to go underneath a city’s streets to view ancient homes and alleyways? Rumour has it that Mary Queen of Scots hid there for a time.

Soak up some inspiration at The Elephant Room :: (I would like to preface yet another Harry Potter reference by acknowledging that I do not share or condone JK Rowling’s recently vocalized opinions about transgendered women in any way. It’s a hard thing to let go of something completely that has had such an enormous impact on our generation. I don’t believe that “canceling” someone is as black and white as the online world would like for us to believe.) If you’re a Potterhead, head here for breakfast or lunch and ask for castle views, if possible. Rowling used to sit in the back room and look out over the castle and Victoria Street while penning the novels. I didn’t know this until after I left, but apparently if you check out the bathrooms, they are covered in HP fanfare and quotes written by Potterheads the world over. You can also buy some local artwork at the front of the cafe if you don’t want to eat there.

Unearth Tom Riddle in the Greyfriars Kirkyard :: Again, if graveyards are your thing- this is a really cool one. There are a few headstones that inspired HP characters and is said to be extremely haunted by a number of ghosts - including a dog named Greyfriar’s Bobby who visited his owner’s grave every day for fourteen years until his own death. If you’re in need of some luck, you can pat the nose of his statue just outside the graveyard at Chambers Street and the George IV Bridge.

Honourable mentions :: The Witchery for high tea or apps, Edinburgh Castle, Dean Village, Cockburn Street, Circus Lane, Innis & Gunn taproom, pub crawl

What to watch before you go :: One Day; Harry Potter and the Philosopher’s Stone; Brave (not set in Edinburgh but a wonderful movie based in Scotland); Men in Kilts on W Network/Starz

I read recently that there is just as much or more joy in planning a trip as there is in actually taking it, which I totally agree with - writing this post alone was food for my soul! I hope this list gave you a good place to start thinking about where in the world you decide where to explore next. Happy planning!