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July 6: Up Island + Sunset in Menemsha

Up Island

Monday, July 6

departure TIMe: 4:30 pm

excursions:

Free Time: Edgartown

Private Tour: Up Island

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We've spent weeks learning about life in Australia. Who knows the answer?

What's one thing that's significantly different in Australia than in the U.S.?

Wrong answers are encouraged.

Summer travel season is officially here!

Curious—where is everyone headed this summer?

Drop your destination in the comments (or just the state/country if you’re keeping it a surprise).

I’ll go first: we had originally planned a

Everyone talks about the beaches, coffee, and kangaroos.

Nobody talks about:
Selling half your life
Wondering where that one important document disappeared to
Pet immigration paperwork that feels longer than a mortgage application
Realizing you've s

There’s something about June that always feels like the beginning of possibility.

Longer evenings.
Kids out of school.
Summer plans starting to feel real instead of hypothetical.
The world feels a little more open this time of year.

One th

Happy World Cycling Day 🚴&zwj;♂️

Cycling is one of the biggest sports in the world, and it’s been such a privilege over the years to experience it in a few really special ways.

We’ve been lucky enough to attend some incredible races in

We’re officially in the waiting chapter of our Australian adventure.

Jordan’s visa is currently in process, so we’re in that in-between space where so much is already set in motion, but nothing is quite “go time” yet.

Brittany was my dearest and best friend.

We were in such similar seasons of life — young working moms to little boys, always talking about the future. “One day when…”
When they’re older,
When things are easier,
When

Good golly, Miss Denali 😍

This is what “custom” actually means to us — not just choosing a destination, but shaping the experience around how you want to feel.

The Mitchell family had been to Italy before. They knew the highlights, the rhythm, the usual sto

Maybe that’s why Christopher McCandless’ journey into the wild still resonates so deeply with so many of us. Beneath the recklessness and the romance was something profoundly human: the desire to step outside the noise, to see the world w

Birthday shoutout to Jordan, the first mate of Land + See, and the reason this whole thing exists in the first place.

The one who pushed when things felt impossible, kept raising the ceiling on what we thought we could do, and never really accepted

Overplanning is the fastest way to miss the point of a trip.

We’ve done it both ways — the tightly scheduled version where every day had a checklist, and the looser trips where we left space for things to go wrong, change, or just&hellip

There are two types of travelers:

“I know exactly where I want to go.”
or
“I just know how I want it to feel.”

I work with both.

So whether you’re set on a destination…
or just craving something different&helli

Here’s what most people don’t realize:

Waiting doesn’t make travel easier—it limits your options.

Planning early means:
✔ Better accommodations
✔ More unique experiences
✔ Less stress
✔ More flexibility

It’s not about

It’s never just about the destination.

It’s about that moment when everything slows down…

You’re sitting outside with a glass of wine,
watching the waves crash onto a coastline you’ve only ever seen in photos,
and thi