Do you all remember last year, when I was invited by Visit St. Maarten to come to their amazing island? I spent a week exploring the history of both the Dutch and French sides, and experiencing some of the culture of the world’s smallest divided landmass. It was amazing, and you can check out my guide here. (That guide has also been my most read article since its publication!)
Well, apparently I impressed them and they were pleased with my work. Because I’m on my way back to work with them a second time! This time, I’ll be starting with a few nights on the French side of Saint-Martin (excuse the title of this article; it’s for the sake of not writing out all of the names into a thing that will run three lines long), then hopping over to the Dutch island of Sint Eustatius before ending back on the Dutch side Sint Maarten.
Before we get into the itinerary itself, I do have to offer some major thanks to the board and staff of Visit St. Maarten, to the government of Sint Maarten, to historian Jay Haviser, to WinAir, and to the hotels arranging my stays. I understand how much effort goes into putting this itinerary together, and the trust in me that it will be worthwhile with the content I produce. I take that incredibly seriously and will work hard to justify your faith. (I am not naming hotels at this point for safety/doxxing reasons, just as I don’t give specific dates, but will do so when articles are produced.)
The itinerary is below. As of this writing, the places are set. I am still waiting for a couple of specific activities/meetings/interviews to finalize, but those will all be fully arranged by the time I arrive (I hope!). As always, some basics can change based on weather, or the exigencies of travel and life, so please don’t hold me 100% to this. Articles are slated to begin mid-July, so if you want closer looks before then, please follow me on Bluesky (it’s like Twitter but without the hate and fascism).
Day One – Los Angeles to Grand Case, Saint-Martin
It’s a red eye flight to the east coast and then a hop down to the island, where I will rent a car and head to the French side of Saint-Martin.
Days Two and Three – Grand Case
While Marigot is the capital of the French side, Grand Case is its touristic center. I’ll be exploring that via French culture – and food! – here, enjoying pristine beaches and stunning sunsets in the process. This is France; it is literally a full department of France. And that distinction is what I’ll be writing about.
Day Four – Grand Case to Oranjestad, Sint Eustatius
WinAir is the easiest way to connect between islands in this part of the Caribbean, and they are flying me from Sint Maarten down to the Dutch island of Sint Eustatius. I will be profiling the airline and the experience for those considering similar island hops from a base in St. Maarten.
Days Five and Six – Oranjestad
Sint Eustatius is new for me. I’ll be exploring its history, both the colonial – this was the most important Dutch island during colonial times – and the Jewish history of the island. I’ll also be talking about one specific event in 1776. (No spoilers yet.)
Beyond that, we will see what modern Statia, as it’s known, offers. What is life like on this tiny island? I can’t wait to find out!
Day Seven – Oranjestad to Philipsburg, Sint Maarten
My return flight on WinAir (thank you again!) back to St. Maarten, and my drive into the capital Philipsburg will occupy only part of the day, so I can’t wait to relax with the rest. I’ll also be taking a stroll down the town’s art walk with a local artist!
Days Eight through Eleven – Philipsburg
You might be wondering what else a small town – even though it’s the capital – like this has to offer? Well, a lot! I’m meeting with some organizations that will offer insights into sustainability on a small island. I’m learning about (and writing a profile of) Peter Stuyvesant and his life prior to arriving in New Amsterdam (now New York City). And I’ll be celebrating Sint Maarten’s Flag Day with an exploration of the symbols of the island and discussions around the idea of a unity flag for the two sides.
I’ll also be seeing friends I made last time, eating amazing seafood, and enjoying just how wonderful this island is. They call it the Friendly Island for a reason.
Day Twelve – Philipsburg to Los Angeles
It’s sad to say goodbye, but I have a plane to catch and a connection to make to head back to California.
So that’s the trip! I expect somewhere between 7 and 10 articles, depending on how things go, plus an update to the full guide I linked above. It’s a lot, and it’s an ambitious timeline to get it all done within a few weeks of my return, but I’m honestly just super excited to share it with you.
Don’t forget to follow on Bluesky for some photos from the islands before articles come out!
For those who like maps (me!), here is one of the trip. The two flags at the top represent Grand Case (to the north) and Philipsburg (south). Oranjestad, Sint Eustatius is the bottom flag. It’s still very close.
