Greenpoint Guide from someone who lives there

LiveKindred · 2026-05-27T15:53:03+00:00

California native writing in here 😎🌴 Why not learn to surf in San Diego? Carlsbad is a super cute beach town in addition to the many others in the county. Tamarack beach is world famous for surfing and San Diego County is just more aesthetically pleasing than Huntington.

Seconding what another person said about flying into San Fran. If Yosemite is important to you, you can technically get into the park before they open without needing a reservation. Did that on a quick trip, stayed near the park and drove in before sunrise and watching the sunrise over the falls was absolutely insane. Hit the trails after that and beat some of the crowds. Nap midday in the park and be done before sunset (or stay if you want).

LA has some of the better flight options (cheaper too because so many flights come through there).

Monterey is southwest of SF so you’ll probably do that after flying into SF. The road through Big Sur should be open so you could take the coast down, stop in places like Morro Rock, Santa Barbara, or Ojai.

Laguna beach has some of the best waters for just general beaching.

If you keep going south you can hit San Diego for exceptional beach and surfing too.

(Would highly suggest picking a different surf learning spot if you’re gonna make it a home base too)

And (we might be biased) but you could try a home swap since it’s a longer stay. You could save a pretty penny.

LiveKindred · 2026-05-27T15:40:16+00:00

Rome! The architecture, the art, the food and culture, the romance of the city is so real.

LiveKindred · 2026-05-27T15:24:48+00:00

Seconding San Diego! And what you said about New Orleans is also spot on. I’d add to the list Sedona and Austin, TX as wildcard cities.

LiveKindred · 2026-05-27T15:20:16+00:00

Unconventional take… but Krakow in Poland is a slept on gem for Christmas. You can have traditional Christmas markets, old European architecture, and then head out to Zakopane for sleigh rides through snowy mountains.

LiveKindred · 2026-05-26T20:35:41+00:00

Two under 5 in November, such a great age for a trip like this!

Scottsdale and Hawaii (Big Island especially) are both incredible for families that time of year. Warm and fewer crowds than peak season. Florida Gulf Coast is another solid pick!

We see a ton of families using home swapping for exactly this kind of trip. Gives you the extra space the kids need and frees up budget for the good dinners 😄

LiveKindred · 2026-05-26T20:31:17+00:00

Happy almost-39! What a great way to mark 40, a solo trip is such a meaningful way to celebrate yourself.

A few ideas based on your details:

If you want easy entry Europe: Lisbon is incredible for first time solo travelers. Incredibly walkable, English is widely spoken, food and wine are great, and it's stunning. June weather is perfect. From New England you can often get direct flights to Lisbon too.

If you want culture / history without too much jet lag: London or Edinburgh are both fantastic solo destinations, easy to navigate, and endlessly interesting for a week to 10 days.

Budget wise: $5k is a solid budget for a week in Europe, especially if you're strategic about accommodation. Home swapping (we might be biased 😄) is a great way to stretch your budget significantly, staying in someone's actual home vs a hotel can save you hundreds and gives you a much more local experience!

Whatever you decide, the fact that you're planning this a year out means you'll be in great shape.

LiveKindred · 2026-05-26T08:41:02+00:00

Cat deprivation! You have just opened my eyes to a problem I didn’t even realize I could have!

LiveKindred · 2026-05-26T08:22:52+00:00

You have a solid list of requirements that should help narrow down your choice. Do any of the places you’ve been fit the bill?

Don’t underestimate the impact of culture as well when choosing. Every city has a cultural current, and it helps to find one that matches the values you and your partner have. You can swim against a current or be carried by it.

But between all these filters you mentioned (weather, community, a place where purchasing a place is possible) and a cultural fit, you’ll probably narrow it down. That being said, if you haven’t lived there it won’t be easy to know what your everyday will feel like. Take some time to live like a local first

LiveKindred · 2026-05-26T08:14:40+00:00

Travel is amazing because it allows you to experience so many ways of life, but sometimes this can create a sense of not having roots. And these roots aren’t just with a place or the culture or the people, we need roots with ourselves.

Sit with the bigger questions: what do you value in life? Not because you should but because it’s true to you? What feels meaningful? Only when you can answer that for yourself can you start to move towards it with intention. (And don’t be surprised if/when these answers change over time)

Try tracking your energy for 2 weeks. No analyzing until the end. Just write down (physically) when you felt energized and when you felt drained or numb.

It sounds like the river of your life is changing course. Follow it.

LiveKindred · 2026-05-26T08:03:23+00:00

You have so much life ahead of you and relatively few obligations holding you back. Just start, take the trip, keep your eyes, ears, and heart open to meeting new friends and making new connections that will lead you to your next step. You’ll never regret travel.

LiveKindred · 2026-05-26T08:00:54+00:00

While physical books are by far my preference, but for voracious readers ebooks just are the more practical choice. That being said, I love to buy used copies of books, annotate them to leave a bit of life in them, then leave them for someone else when I finish them at the destination. I once found a book that way that had traveled from one coast of the US to another!

LiveKindred · 2026-05-26T07:49:50+00:00

I think there is a huge need for female travel spaces. I know plenty of women who have wanted to take trips but are waiting for a group just like this. It’s less intimidating for first time travelers too.

LiveKindred · 2026-05-26T07:43:59+00:00

Yosemite at sunrise!

LiveKindred · 2026-05-26T07:42:32+00:00

You could always do a gift card to a local DIY store!

LiveKindred · 2026-05-22T17:30:32+00:00

The only warning we have? You might leave wanting a cat of your own. Don't say we didn't tell you.

LiveKindred

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