Not too long ago, I wrote about a great day trip to the Hamptons. In that post, I mentioned excitement to venture back to the end of Long Island for a more extensive trip, and I'm happy to say the task was accomplished this past weekend.
It was a welcomed return, and I was just as excited this time as I remember being when we pulled out last summer. I also feel a little more seasoned in my New York summer travels, which made it easier to know how to plan for a full weekend with friends. It was super cool to have friends in our travel group who'd never been to the Hamptons.
I love to travel and take in the charm of other towns. That being said, it was definitely a treat to venture out there again. There was time to rest, time to reflect, and time to just hang with friends, new and old. I'm a big proponent of getting out from the normal flow of life and doing it with friends, so I hope you'll find this helpful, encouraging you to venture somewhere yourself.
Plan in advance.
While spontaneous trips are fun, this is certainly an experience that should be planned before peak season. I've heard of groups booking Hamptons-homes as far out as January (to escape winter's bitter grip if just for a moment), but we were able to secure a spot roughly six weeks before we left. While our pickings were slim, we considered ourselves lucky to have discovered a gem of a home in Hampton Bays.
TIPS AND LOGISTICS
Get your party to commit to dates and budget before booking a place. Trust me, this helps so much—especially if you use Airbnb.
Rent a car. Yes, you take the train or bus, but it's better to have a car for getting around. This also ended up being a cheaper option per guest as well. (We rented from a spot near LGA to avoid navigating NYC rush-hour.)
Get groceries at Stop and Shop. Again, it's a cheaper option and makes for a fun activity to prepare meals. It's such a rare thing when living in NYC anyway, so I was stoked to make this happen over the weekend. (I recommend doing this for breakfasts and dinners and eat out for lunch if you want the local treats, too.)
Have a rough timeline of how to spend the weekend, but leave room for surprises. On Sunday, we drove out to the lighthouse in Montauk. We didn't know visitors could climb to the top of it. (We didn't research it enough I guess, ha!)
Bring cash. Certain places (especially for parking) only take cash. The food spot along Main Beach in East Hampton also only took cash even though they had pretty fancy-looking cash registers.
You can do it, too.
Sure, the beach isn't for everyone, and not everyone lives in NYC. That's okay! This weekend getaway can be replicated almost anywhere.
Whether you're with friends or family, I highly encourage this type of trip. You get out of your comfort zone and are provided with key times for community and conversation. (You also might find yourself in the middle of a rad sing-a-long in the car—thanks, Ryan!)
We were certainly on a budget, but with proper planning, you can do this without feeling like you cut yourself short. Just look for ways to pursue your passions (sports, art, architecture, cooking), and find a place to relax outside your usual flow with those you care about.
Lastly, before I drop a large amount of photos below, I'll leave you with this final thought: be real. Yes, traveling with friends is a blast, but it's also a humbling experience. People enjoy different things and have their own ideas of how to best vacation. Just make sure to communicate intent, including all parties in the decision, but then act. Accommodate people in the best way possible and care of each other's needs. It's amazing how life giving and God-honoring this practice can be.
As always, feel free to comment below if anything catches your eye. Also, I love talking about traveling and creating space in community, so please don't hesitate to reach out as questions come up.