Where I would want to be every month of the year
I’m a lifelong New Yorker with no plans to leave. But I’ve long dreamed of taking a year (or more) where I could travel the world and be in what I consider the best place to be at any given point in time. It’s somewhat inspired by an ad I saw in the New York Times Magazine for a cruise ship called the World Yacht that would serve as a full or part time residence; sailing the world to find the best weather and most ideal locales for its residents year round. The idea of having a permanent place that would move to places with great weather & great events is attractive but it’s hard to get past the cruise thing, which still somewhat terrifies me. Nonetheless, the idea of imagining myself as the cruise director and not limiting myself to accessible locations for a large vessel is a fun place for me to daydream about.
But before getting into it, some things about myself that play into it along with my thinking:
I prefer warm weather, sometimes even bordering on the verge of hot — particularly if good beaches are nearby. Someone else who’s into skiing would come up with nearly diametrically opposite answers here
Sporting events drive a lot of my thinking. It’s not just that I would want to necessarily go myself, but it signals a season and location where a lot of people want to me. The major touring sports, the PGA Tour, Formula1 & the Pro Tennis tours (ATP & WTA) seem to factor this into their planning; not just so playing conditions are ideal but also so they stage events at attractive locales that can draw a mobile (and I suppose therefore wealthy) crowd. I’m excluding events like the Super Bowl, the World Cup or the Olympics because they rotate locations and recently, politics & money for event organizers are superseding attractiveness for visitors
I live in a big city so I’m biased to be near them as opposed to more remote locations. This is not the dream list for a surfer but then again that’s not my jam anyway
Friends and family are important to me and play a part in a lot of this thinking. As a result even if I were to want to be somewhere for a particular month of the year, traveling back to major holidays or being close to them definitely factors into my thinking
January - Melbourne, Australia
Not kidding with the hot thing. After the excitement of the holidays and the dead of winter starts to kick in, nothing reminds me that there will eventually be summer more than watching late night Australian Open tennis on TV from Melbourne. It’s a great international city that seems like a really fun place to start the year. Formula1 also kicks off its season in Melbourne as well, albeit later in their summer (March next year).
February - Cape Town, South Africa
One of my favorite cities in the world and the weather is perfect in February, a month where it seems most people are in hibernation mode. The PGA tour bounces between sleepy Arizona and Southern California locales; both are kind of meh for me although I have heard good things about Palm Springs. Meanwhile, Cape Town is full of fashion, arts and sporting events, plus it’s a beautiful city with fantastic fine dining, history, proximity to to great hiking and an amazing wine country. I think I’d want to be there.
March - South Florida
If you asked me, March is THE time to be in South Florida. There’s still quite a bit of baseball spring training to take in(although most teams are now in Arizona), plus the PGA tour makes its traditional Florida swing with four stops during the month. March is Florida in its peak season with most ideal weather. It’s not quite the dead of winter when you can catch some cold days, even in Miami, but it really hasn’t warmed up yet and gotten too humid, nor do you have to worry about hurricanes. And have I mentioned the beaches? Both St. Pete Beach and Miami Beach are among my favorites in the world. Only downsides are that the days can be a little short and I’m not the only one with this idea; the spring break crowds are borderline out of control. I like Miami a lot, but would probably make my home base at the Breakers in Palm Beach. It’s a little more central and a very welcoming resort for all — if you can afford it
April - Houston, TX
This is a little bit of an unusual one because Houston typically doesn’t have any significant events during that time (except sometimes a golf tournament as a Masters warm-up) but I went to college there and it is the perfect month to be there from a weather standpoint. So sitting out and watching some Rice Owls baseball games are all good by me — the Astros are another story. The days start getting consistently warm, the worst of the spring pollen (which is a real thing there) is done, yet the bad humidity of the summer doesn’t come until mid-May. I happen to love Houston as a great international & livable city. it may not be there most visually appealing but it is at its best in April and I’d still like to spend some more time there. Plus it’s reasonably close to the Masters and other major golf tournaments when the PGA tour swings through other locales if H-town misses out.
May - Rome, Italy
I went to Rome for the first time last year and instantly fell in love. The food, the history, the sights, the architecture, the ease of walking…I could do it all! And it’s not just me who wants to be there, it’s traditionally the time for the Rome Open, the major clay court warm-up to the French Open at Roland Garos & a Formula1 Race in Imola. Plus, it’s really close to pop over to Monaco for the big annual race
Back-up option: New York is the one City that I could easily pick for two different months. The weather here really comes into its own through the month (but can be inconsistent) and there’s a lot of big events going on, with the Met Ball headlining the first Monday of the month, both baseball teams starting to warm it up, (hopefully) playoffs for the Knicks & Rangers and Fleet Week over Memorial Day weekend
June - Paris, France
The only place on the list I’ve never been, but c’mon it’s Paris and the “business” end of the French Open at Roland Garos is in June. The days are ridiculously long, the weather hasn’t gotten quite too hot and so I can think of a better of time to be in the City of Lights.
July - London, England
For very similar reasons why I’d want to be in Paris in June, I’d want to be in London in July. Ridiculously long days, temperate weather and the biggest golf and tennis tournaments of the year with Wimbledon at the start of the month and the Open Championship somewhere in Northern England or Scotland later in the month make this a great time to be London-based. Plus every other year there’s a World Cup or a European Championship and to say England gets worked up about those tournaments is an understatement.
Back-up option: OK so let’s say the Knicks or Rangers make a deep run, then I’d probably want to stay in NY for June, which is still great and do France instead in July. The Tour de France is a showcase of the country in the summer and I’d love to see it!
August - North Fork, NY
Though I live in New York City and always want to be based here, but the North Fork is my happy place. Lots of relatives are around, the weather is also quite bearable all year (Cutchogue gets the most sunshine of any town in New York State), I feel fully relaxed on the beaches and Peconic Bay, plus there’s wine country, some solid golf courses and fantastic restaurants. Yes, all of the A-listers are in the Hamptons, but I’m North Fork people.
September - NYC
Without a doubt, September is THE time to be in New York. The weather is PERfect. The humidity of the August typically gives way to crisp, dry days in the upper 70’s and low 80’s. I’m not the only one who’s clued in to this. Typically the US Open, Fashion Week & the UN General Assembly pack the City in quick succession, plus the MLB pennant race comes down the wire and there’s almost always some drama for the NY teams. September’s also the start of football season and just about the only month of the year when I’d like to be out at an NFL game. If I lived this life I’d be sure not to give up my place in the City. Hotel rates shoot to the moon in September in NYC.
October - San Francisco, CA
As an Oakland Athletics fan of my youth, it always struck me that even though the days were getting short and cool in the northeast, it always looked sunny and pleasant in the Bay Area in October and I was right. The weather in SF is a real oddity. As Mark Twain once joked, “The coldest winter I ever spent was a summer in San Francisco,” but as the fall comes in October the winds reverse and come off the land, warming the weather, drying the air and pushing the fog out sea so the City shines. Aside from perhaps some post-season baseball (I guess the Giants will be the only option soon) there isn’t a lot going on events-wise in SF. Formula1 is winding down in the Middle East and the PGA Tour is pretty much over. I was there for a visit last year and can vouch
November - Buenos Aires, Argentina
November means late spring in the Southern Hemisphere so after picking South Africa in February it’s only fitting I pick a spot in South America and Buenos Aires is my favorite so far. It’s a great walking city with a deep culture that mixes European and Latin America, diverse neighborhoods and this is a time of year when one of most beautiful cities in the world in full bloom. It’s also generally quite inexpensive so you can ball out on a reasonable budget. Plus it’s a short flight to great beaches in Punta Del Este, Uruguay
December - Hawaii
This is actually a tough one because of the holidays. Naturally the pull of being home in the Northeast to be with family is appealing so that would naturally be my default but otherwise, it’s actually hard to find much because so much of the world slows down in December. Sure, it’s mid-season in the indoor professional sports, the NFL has crucial games to determine the playoffs and the fervor of the European Soccer season starts to hit its peak around the holidays, but otherwise, it’s pretty dead with most of the global tours winding down at the beginning of the month. So naturally my instinct is to head to the Equator and enjoy the true treasure that is Hawaii. I’ve never gotten to explore the islands aside from Oahu — which was great — but doing some island hopping is really appealing. One downside to visiting in December is that the days are on the shorter side and it is the rainy season but the worst weather in Hawaii beats just about anywhere else in the world in December!