Boston is one of those cities that just feels alive when there’s an event happening — and there almost always is. Whether it’s tens of thousands of flags fluttering on Boston Common in May or confetti raining down during a North End feast in August, Boston knows how to celebrate.
Here’s my guide to the best Boston festivals and holidays — from patriotic moments that will give you goosebumps to foodie events you’ll be talking about for years.
If you’re in Boston for Memorial Day weekend, make your way to Boston Common. Every year, Home Base volunteers plant 37,000 flags on the Soldiers and Sailors Monument hill — one for each Massachusetts service member who has died in the line of duty since the Revolutionary War.
It’s quiet, powerful, and absolutely breathtaking. If you’re a photographer, go early morning or at golden hour to catch the soft light across the sea of flags.
Patriots’ Day (the third Monday in April) is uniquely Boston — it commemorates the battles of Lexington and Concord and doubles as Marathon Monday. The Boston Marathon is the world’s oldest annual marathon, and even if you’re not running, being part of the cheering crowd is an experience.
Head to Boylston Street near the finish line or plant yourself in Brookline or Newton to catch the runners tackling Heartbreak Hill.
Boston takes Independence Day seriously — and what better place to celebrate than one of the birthplaces of the Revolution?
Head to the Charles River Esplanade for the Boston Pops Fireworks Spectacular. It’s an all-day event with live music, picnics, and one of the best fireworks shows in the country.
Boston’s North End is already basically Italian Disneyland, but during St. Anthony’s Feast, it levels up. The last weekend of August, Hanover Street is closed to traffic and filled with food stalls, confetti parades, marching bands, and crowds of hungry locals and visitors.
This is New England’s largest Italian festival, and it’s been going strong for over 100 years.
What to eat:
Arancini (fried rice balls)
Italian sausages with peppers & onions
Zeppole (Italian fried dough)
And, of course, a stop at Mike’s or Modern Pastry for a cannoli
Pro tip: If you want a quieter North End experience, avoid this weekend — but if you want to be in the heart of the party, this is the time to go.
If you’re visiting during August, don’t miss my guide to If you’re visiting during August, don’t miss my guide to St. Anthony’s Feast in Boston’s North End—it’s one of the city’s biggest annual celebrations.St. Anthony’s Feast in Boston’s North End—it’s one of the city’s biggest annual celebrations.
The third weekend of October brings Head of the Charles, the largest two-day rowing event in the world. Even if you don’t know the first thing about crew, it’s a beautiful excuse to spend the day along the river, sipping cider and cheering as boats glide by with the fall foliage in the background.
Boston does cozy winter vibes really well. In December, Boston Common is lit up with a massive Christmas tree and holiday lights, and Faneuil Hall Marketplace hosts Blink! — a light and sound show. Add in ice skating on Frog Pond and hot chocolate from Tatte, and you’ve got a Hallmark-movie-level evening.
Boston knows how to throw a festival. Whether you’re standing in awe of 37,000 flags on Memorial Day, eating your way through St. Anthony’s Feast, or bundled up watching fireworks over the Charles, these holidays and events let you experience the city at its most alive.
Plan your trip around one of these celebrations, and you’ll leave with a camera roll full of photos, a stomach full of food, and maybe even a little confetti in your suitcase. For an up-to-date list of annual events, check out BostonUSA’s official event calendar. Planning your trip around the seasons? Read my Best Time to Visit Boston guide to see which festivals align with the best weather
Here’s the thing about Curaçao that nobody talks about enough there’s really no bad time to go. 🌤️ Outside the hurricane belt. Mid-80s nearly every day of the year. Colorful buildings no matter what month it is.
But there IS a difference between going in peak season vs. shoulder season, and it shows up in your wallet, your beach chair availability, and how long you’re waiting for a table at dinner.
Full breakdown of every season, what to expect, and when I’d personally go linked in bio.
I wasn’t expecting much. I just needed dinner. 🍽️ Kome ended up being one of the best meals of the entire trip.
Wood-fired everything. A menu that actually makes you read it twice. A vibe in Pietermaai that feels nothing like a tourist restaurant and everything like somewhere locals actually go. I didn’t rush. I didn’t check my phone. I just ate, start to finish, and enjoyed every single second of it.
If you’re in Curaçao and you only have one nice dinner make it this one.
#curaçao #travelling #travelvlog #musttryrestaurant #visitcuracao
Renting a golf cart in Bimini was genuinely one of the best decisions we made the entire cruise, and if you have a stop there, I cannot recommend it enough.
✨ Off the ship and behind the wheel within minutes
✨ Multiple beaches, food stops, and random pull-offs
✨ Zero tour schedules, zero waiting on strangers
✨ Just the island, at your own pace
Honest caveat: if you prefer a guided experience with everything planned out, a tour might suit you better. But if you like doing your own thing? This is it.
Everything you need to know about renting, where to go, what to budget, and our favorite stops, is linked in bio. 🔗
50 miles from Miami. Feels like a different planet. 🌴
One day in Bimini looks like: golf cart before 9am, Bimini bread still warm from the oven, water so clear it looks fake, and a conch stand where the guy knows everyone’s name.
No itinerary needed. But I made one anyway because that’s just who I am. Linked in bio
#bimini #biminibahamas #travel #travelblogger #visitbahamas
If you go to Bimini and don’t get conch salad… what are you even doing? 🐚
I’m not exaggerating when I say this ended up being one of my favorite parts of the whole trip. It’s a local staple, and after talking to enough people on the island, I realized fast, Bahamians have very strong opinions about where to get the best one.
So we made it a mission.
We tracked down the three spots that kept coming up over and over again, and I tried them all so you don’t have to guess.
Full breakdown is linked in bio. 🔗
#travel #travelblogger #bimini #bahamas #conchsalad
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