Two staff members at The Points Guy recently turned their personal city loyalties into a direct experiment. One lives in London and the other calls New York home. They agreed to trade places for two days, each planning the other’s itinerary without input from the visitor. The goal was simple: experience the rival city through fresh eyes and compare notes across everyday travel categories. ([1])
The Setup Behind the Swap
The idea grew out of casual office debates about which city offers the better short break. Rather than argue from memory, the pair decided to test their preferences in real time. The London resident flew to New York while the New Yorker crossed the Atlantic. Both had only 48 hours on the ground and strict instructions to build an itinerary that highlighted what each city does best. They booked hotels that could be reserved with points and miles, choosing neighborhoods known for walkability and local flavor. The experiment stayed deliberately short so the focus remained on first impressions rather than exhaustive sightseeing. Transportation, lodging, food, nightlife, and activities formed the scoring framework from the start.
Food and Drink Discoveries
Each editor sampled signature dishes and a few unexpected finds. In New York the London visitor tried classic pizza slices and housemade pasta. In London the New Yorker tasted fish and chips alongside the city’s unofficial national dish. Both also sought out hidden spots, including a 1940s-themed speakeasy and a mystery comedy venue where the lineup changes nightly and the audience never knows what act will appear. These meals and outings became central to the final tally. The editors noted how each city balances quick, iconic bites with more intimate neighborhood experiences. The short timeframe meant they could not exhaust every option, yet the contrast in pacing and presentation stood out immediately.
Neighborhoods, Hotels, and Getting Around
Location choices shaped much of the experience. The pair selected areas that offered easy access to both tourist highlights and quieter residential streets. Hotels booked with loyalty points provided comfortable bases without requiring cash outlays. Transportation comparisons covered everything from subway reliability to walking distances and the feel of each city’s public transit at different times of day. The editors tracked how quickly they could move between planned stops and whether the neighborhoods delivered the promised mix of energy and local character. Small details, such as the ease of finding a late-night option or the quality of a morning coffee stop, influenced their notes as much as the headline attractions.
What the Categories Revealed
At the end of the two days the editors scored each city in the agreed categories. Transportation, lodging, neighborhoods, dining, nightlife, and activities all received separate marks. The exercise highlighted clear strengths on both sides while also exposing the limits of judging any major city in such a compressed window. The results remain open to interpretation, which is exactly the point of the exercise. Large, layered cities like London and New York resist quick verdicts. The swap simply supplied new data points for an ongoing conversation that travelers continue to have every time they plan a city break. The experiment also underscored a practical takeaway: even a brief, well-planned visit can shift long-held assumptions. Whether the final tally favored one side or ended in a near tie, the real value lay in the fresh perspectives each editor brought back to their home city.
