Everyone tells you that the end of September is the ‘sweet spot’ for a honeymoon. They say the crowds have thinned out, the prices have dropped, and the weather is still perfect. They are mostly lying to you. Or at least, they aren’t telling you the whole truth because they want to sell you a package deal at a resort that smells like industrial floor cleaner.
I’ve spent the last six years obsessing over shoulder-season travel because I hate people and I’m cheap, but the end of September is a fickle beast. It’s the transition point where the atmosphere starts having a mid-life crisis. You can get a week of pure gold, or you can get stuck in a hotel room watching local news in a language you don’t understand while a Mediterranean hurricane (a ‘medicane,’ which is a stupid name) rattles the windows. I know people will disagree with me on this, but I think Santorini in late September is a massive mistake. I might be wrong about this for your specific week, but usually, the wind—the Meltemi—is so aggressive by then that you spend the whole time picking hair out of your lip gloss and chasing your expensive sun hat down a cliff. It’s not romantic. It’s annoying.
The Sicily obsession (and why it’s better than the Amalfi Coast)
If you are dead set on Europe, stop looking at Positano. It’s a vertical mall for influencers. Go to Sicily instead. Specifically, head to Ortigia or the Noto Valley. I spent 11 days there three years ago during the last week of September, and it was the only time a vacation actually lived up to the mental montage I had running in my head. The water is still warm because it’s been baking all summer, but the air temperature drops to that perfect 76 degrees where you can actually walk to a cathedral without needing a second shower.
What I mean is—actually, let me put it differently. Sicily feels like a real place where people live, whereas the Amalfi Coast feels like a movie set that gets folded up and put in a box on October 1st. In Sicily, the food is better and it costs about 40% less. I tracked our spending: we had a seven-course meal with a bottle of Etna Rosso for 90 Euros. In Positano, that gets you two Aperol Spritzes and a condescending look from the waiter. Stay at a place called Monaci delle Terre Nere if you want to feel like a sophisticated farmer. Or don’t. It’s expensive. But it’s the only place I’ve ever been where the ‘rustic’ vibe didn’t feel like a marketing gimmick.
The people are grouchy in a way that I find charming. They don’t care that it’s your honeymoon. They just want you to eat the pasta and shut up. It’s refreshing.
The end of September isn’t just a date; it’s a gamble with the gods of wind and rain. Choose your terrain wisely.
That time I almost ruined my marriage in Mexico
I have to tell you about my failure so you don’t repeat it. I thought I was smarter than the National Hurricane Center. In 2019, I booked a ‘bargain’ trip to Isla Holbox for the last week of September. I told my partner, “The rain only lasts for twenty minutes in the afternoon! It’s fine!”
It was not fine. It rained for four days straight. Not ‘tropical mist’ rain. I’m talking ‘the streets are now rivers of sewage-tainted sand’ rain. We spent our honeymoon huddled in a room that smelled like damp cardboard, eating Pringles from a mini-fridge because the town’s power was out and no restaurants were open. I felt like a total idiot. I had ignored the fact that late September is the absolute peak of hurricane season for the Caribbean and the Gulf. If you book a honeymoon in Tulum, Cancun, or the Bahamas during this window, you aren’t being savvy—you’re playing Russian roulette with your memories.
I refuse to recommend Sandals or any of those massive Caribbean all-inclusives during this month. I don’t care if they have ‘hurricane guarantees.’ A voucher for a future stay doesn’t fix the fact that you spent your wedding trip staring at a grey wall of water. Total scam.
The data on where it actually stays dry
I’m a bit of a nerd when it comes to weather patterns. I actually spent 14 hours over three days last year cross-referencing historical precipitation levels with average daily sunshine hours for about twenty different regions. I wanted to see where the ‘stability’ actually lives during the September 20th to October 5th window.
- Crete, Greece: It’s far enough south that it stays summer longer than the rest of Europe. Average high: 27°C (80°F). Rain days: maybe 2.
- The Cederberg, South Africa: If you want something different, this is the start of spring there. It’s dry, the flowers are blooming, and the air is crisp.
- Mauritius: Unlike the Caribbean, September is one of the driest months here. It’s a long flight, but the humidity is low (around 65% compared to Bali’s 85%).
- The Algarve, Portugal: Usually safe, but the water is freezing. If you like swimming, skip it.
Anyway, my point is that you have to look at the southern hemisphere or the very bottom of the northern hemisphere. Anything in the middle is a toss-up. I used to think the South of France was the move for late September, but I was completely wrong. The Mistral winds kick in and suddenly you’re wearing a light puffer jacket to dinner. Not exactly the ‘sundress and rose’ vibe you probably paid for.
A mini-rant about ‘Honeymoon Packages’
Can we talk about how much I hate the word ‘honeymoon’ when it’s used as a prefix for a price? As soon as you mention it to a hotel, the price of the room magically jumps by $100 and they throw some dusty rose petals on a bed that you then have to brush onto the floor like a weird chore.
I actively tell my friends to avoid anything labeled a ‘honeymoon suite.’ It’s a tax on your happiness. Buy a regular room at a better hotel. Use the money you saved to buy a bottle of wine that doesn’t taste like vinegar. I’ve bought the same $400-a-night boutique experience in Sicily three times now—I don’t care if there’s a cheaper ‘modern’ hotel down the road. I want the old stone walls and the smell of jasmine. I’m irrationally loyal to places that don’t try to ‘upsell’ me on romance.
The South Africa ‘Wildcard’
I know people think a safari is too much work for a honeymoon, but late September is literally the best time to go. I’m being serious. In places like Kruger or the Sabi Sands, the bush is dry and thin. This sounds ugly, but it means the animals can’t hide. They have to congregate around the few remaining water holes. You don’t have to ‘search’ for lions; they’re just sitting there, bored, waiting for a zebra to show up.
It’s also not a million degrees. You can sit in an open-topped Land Rover without getting heatstroke. It’s the most expensive thing I’ve ever done, but it’s the only trip where I felt like the money actually bought me something I couldn’t get anywhere else. Most honeymoons are just ‘your life, but with a better view.’ A safari is a different planet.
Just don’t book a ‘group’ safari. Being stuck in a van with six strangers while you’re trying to be all ‘newlywed’ is a nightmare. Private vehicle or nothing. Worth every penny.
I don’t know, maybe I’m too cynical about the whole thing. I just see so many people spending $10k on a trip to a place because an Instagram ad told them it was romantic, only to find out the ‘private beach’ is shared with a cruise ship. My advice? Go somewhere that doesn’t need a filter to look good, and for the love of god, check the wind speeds before you book anything in the Greek Isles.
Is it weird that I still think about that rained-out week in Mexico more than the ‘perfect’ trips? Probably. There’s something about failing together that actually makes for a better story. But still, go to Sicily. It’s easier.
