Sample Post Category: Travel

Every travel writer will tell you to visit New England in October. They are right about the foliage. What they leave out is that you will be sharing that foliage with three million other people who read the same articles, all driving up Route 100 in Vermont at the same speed as you.

Boston in April is the sleeper season. The city is coming back to life after a hard winter, the Public Garden’s tulips are ridiculous, the college students are jubilant and slightly deranged from having survived February, and the tourists are not there yet. Hotel rates are dramatically lower. Restaurant reservations open the week you ask for them. The Red Sox home opener is happening and people are wearing shorts and coats simultaneously in a way that is only Boston.

Walk the Freedom Trail. Do the Isabella Stewart Gardner museum on a rainy afternoon. Get a beer at Trillium’s rooftop. Take the T out to Cambridge and eat at any restaurant on Mass Ave. The city will feel emptier than it does in October, which is exactly the point. New England is at its best when the light is coming back, not when the leaves are falling. Come in April. Bring a jacket.

Camden, Maine is 90 miles north of Portland on the coast, and it is the small-town New England experience most people go looking for in Bar Harbor and do not find. Bar Harbor is fine. It is also overrun with tour buses by 10am from June to September. Camden is quieter, better food, more locals, one specific great bookshop and no fudge shops. This ratio matters.

Stay at the Whitehall for a night if the budget allows. Walk up Mount Battie in the morning for the harbour view that Millay wrote about. Eat lobster at Peter Ott’s (touristy but good) or at Long Grain (Thai food you would not expect in a Maine coastal town, run by a chef who moved back from New York). Browse The Owl and Turtle, which is one of the best independent bookshops in Maine.

What Camden has that Bar Harbor does not: a working harbor. The boats are lobster boats, not tourist boats. In September the schooners come in for the classic weekend and the whole town smells like pine and diesel. In October the leaves turn and the light is the light of every Maine painting you have ever seen. Two nights is exactly enough. Three, if you like sitting.

Millennium Park in Chicago is fine. The Bean is fine. But every visitor spends their first afternoon there, and then every visitor leaves thinking that is what Chicago parks feel like. Chicago parks do not feel like Millennium Park. Chicago parks feel like Palmer Square in Logan Square, and I would take a visitor there before I took them downtown.

Palmer Square is an oval-shaped little park with a jogging path, dog owners, families with strollers, and coffee shops within a block in every direction. It is entirely un-Instagrammable, which is why almost no visitors go. But the neighbourhood around it is where a lot of Chicagoans in their 30s actually live, and walking around it for an afternoon tells you more about the city than a whole day at the Art Institute.

The move: take the Blue Line to Logan Square. Walk to Sportsman’s Club or Lost Lot for a drink. Get pizza at Lula Cafe or breakfast at Longman & Eagle. Sit in Palmer Square with a coffee from Gaslight for an hour. You will understand Chicago as a place people love, not as a skyline you photograph. That distinction is the whole game with any city worth visiting.

I went to New Mexico because I had been putting off the Georgia O’Keeffe museum for a decade, and I ended up giving away half of the days I had planned to Chinese food and ceramic shops. That is the mark of a good trip — you go for one specific thing, and the state you did not know rearranges the itinerary.

Santa Fe as a base for two nights. Do the O’Keeffe museum first, before you drive out to Abiquiu, because the paintings and the actual landscape need to be seen in that order. Then take the winding road up to her ranch house. Reservations required, small groups, about an hour of guided walking. What she painted for 40 years is exactly what you see out of her studio window, and knowing that is the entire point of the pilgrimage.

The third day: drive north to Taos, take the high road (Highway 76) not the low road, stop at Chimayo for pilgrimage dirt and lunch. Taos is a small mountain town with a pueblo you can walk through and a Pueblo Peak that is almost too on-the-nose. The whole three days you will be at 6,500 feet and the sky will be the kind of blue that people from the East Coast do not believe exists. Drink water. Sleep more than usual. Do not skip the museum.

New York in July is the city at its worst. Ninety degrees on the sidewalks, ninety-five in the subway platforms, tourists in packs everywhere south of 42nd Street, restaurants operating at 40% capacity because half the staff is at the Rockaways. If you have never been, do not book a July flight. You will get a lopsided idea of what the city actually is.

The two windows I recommend: mid-October and mid-February. October is the New Yorkers’ favourite month for reasons that will be obvious the moment you step outside — light is amber, temperature is 60 degrees, everyone is in a wool coat and a mood. February is the sleeper pick. It is cold enough to keep tourists home but not brutal, museums are empty, you can walk into any restaurant, hotel rates are 40% of summer.

What you lose in February: outdoor everything. What you gain: the actual city. New Yorkers in February are chatty because everyone is bundled up and there are no tourists to compete for their attention. Bartenders remember you between visits. You can spend 20 minutes at a Whitney exhibit without someone standing behind you. If you can layer, do February. If you cannot, do October. Do not do July.

Never sleep at a hotel the night before an early flight if the hotel is less than 20 minutes from the airport. Sleep at the airport hotel — the one physically connected to the terminal — even if it costs more, even if you have to walk longer, even if it looks charmless. The 20 minutes you save in the morning are not the point. The point is that you are one variable away from missing your flight, and that variable is transport.

Transport is the failure mode. Uber cancellations at 5am. Metro that unexpectedly does not run until 6:15. A taxi rank that is empty when you thought it would be full. All of these have happened to me. The two flights I saved were both because I was staying inside the terminal complex and could walk to check-in in seven minutes when everything else fell apart.

The airport hotels also have soundproofed windows, know what an early breakfast is, and often have direct check-in kiosks in the lobby. The vibes are worse than a boutique hotel. The reliability is 10x better. For any flight before 8am, this is now my default. The 40 extra euros are the cheapest travel insurance you will ever buy.

Icelandair has a policy called the “Iceland Stopover” that lets you break a transatlantic flight in Reykjavík for up to seven nights at no extra fare. If you are flying between New York (or Boston, or Seattle) and most European cities, you can add three days in Iceland and it does not count as a separate ticket. It counts as a stopover.

I use this twice a year. It turns a flight into a mini-trip. Reykjavík in three days is not enough time to see Iceland — but it is enough time to remind yourself that a city exists at human pace, walk to the ocean at sunset, eat one really good lamb dinner, soak in a geothermal pool, and get on the next flight refreshed instead of destroyed. The cognitive difference between arriving somewhere after 8 hours in the air and arriving after 5 hours plus a three-day break is enormous.

The catch: you have to book with Icelandair as your primary carrier, and the stopover has to be either at the start or the end of the trip, not in the middle. Their website makes it slightly hard to find; the option is on the checkout page under “extras.” If you fly the Atlantic more than twice a year, this policy alone justifies choosing Icelandair over the big US carriers. It has changed how I plan.

The touristy New York weekend goes: Times Square, Central Park, a Broadway show, Empire State Building, a diner, dinner in the West Village. It is a fine weekend. It is also almost identical to what six thousand other people are doing at the same time as you. Here is one that stays across the East River and lets you meet a different city.

Stay in Cobble Hill or Long Island City — both are 15 minutes from Manhattan by subway or a good walk over a bridge. Cobble Hill is where locals under 40 actually live and eat. LIC is quieter, has better waterfront views of the Manhattan skyline than any Manhattan viewpoint, and no tourists. Skip the Strand queue and go to Books Are Magic on Smith Street instead — smaller, weirder, actually a working bookshop with old furniture and a reading nook.

Eat at Frankies 457 on Court Street if you can get a table, or Rucola nearby if you cannot. Both are Brooklyn restaurants that a local would take an out-of-town guest to, not a tourist trap. Do coffee at Devoción in Williamsburg — they roast Colombian beans in the shop, big space, no rush. And on Sunday morning walk the Red Hook waterfront, which has views of the Statue of Liberty most tourists never see because it is inconvenient to reach.

I am not going to tell you the name. That is not gatekeeping — three of you would go, tell your friends, and by 2028 there would be an Airbnb listing that says “charming rural retreat 3 hours from Boston.” What I will tell you is that towns like this exist across northern New England, and if you drive an hour off any highway in Vermont or western Massachusetts and pick one at random, you will probably find your version.

What I go there for: quiet mornings, bread that is different from all the other bread I eat because they use a specific local wheat, a general-store owner who remembers your name after two visits, walking paths that go through maple sugar bushes from the 1800s, and evenings where the only sound is dogs, distantly, agreeing about something.

The trick is that you have to be OK doing nothing. There is no museum. There are no events. There is a river you can walk to in 40 minutes and a lookout that is a 90-minute uphill hike. That is the entertainment. If you cannot sit with your own thoughts for three days, this trip will feel like being punished. If you can, you come back rewritten. I have done it four times now. I keep coming back because I keep needing it.

Kyoto in cherry blossom season is a fine idea if you enjoy queuing next to strangers for photos of trees. I did that trip in 2018 and left with pictures of my own arm holding a phone. Kyoto in November, when the maple leaves are dying, is a completely different city. Cheaper flights. Half the tourists. Better food, because the local restaurants are not overrun. Colder mornings, warmer scarves, a slower rhythm.

The maple season peaks somewhere in mid-to-late November, and it lasts about ten days. If you plan a two-week trip you will see it. The trees turn red-orange in a way that is genuinely worth flying for, and the light in Kyoto in autumn has a specific slant to it that makes everything look film-grain.

Practical: temples that are impossible in April — Kiyomizu-dera, Ginkaku-ji — are walkable in November. Ryokans that are booked a year out in spring will have availability. And a bowl of ramen at a counter with steam rising into the cold is a specific experience you do not get in warmer months. Go in November. Bring a coat that is warmer than you think you need. Reserve nothing except your first three nights.