Walking the ridge trail above Sete Cidades on São Miguel

THE CIRCUS WAGON

Trips, adventures & the things we don't want to forget.

Our trips, the long version

Latest Chronicles

The full stories from our trips, the ones that don't fit in a caption.

Walking the ridge trail above Sete Cidades on São Miguel
Azores · 2026

The Azores Chronicle

A fog diversion, two bonus days in Lisbon, and five and a half days on an island we fell completely in love with.

Colby working from a hammock in Puerto Pilón
Costa Rica · 2022

The Costa Rica Chronicle

Ten days, one manual pickup truck, and a country we were not quite prepared for.

The list we text our friends

You're going there?! Okay, you HAVE to…

Every time a friend tells us they booked a trip somewhere we've been, we end up texting them the same things: where to stay, what to see, and what we'd skip. So we put it all in one place.

Looking down into the Sete Cidades crater
São Miguel, Azores

Our São Miguel Guide

Sete Cidades, the hot spring that runs straight into the ocean at Ponta da Ferraria, Furnas, and the drive to Nordeste.

From our tripsRead the guide →
Breakfast with hydrangeas at Pico do Refúgio
São Miguel, Azores

Pico do Refúgio

A 400-year-old farm on the north coast and the best breakfast yogurt of my life. We'd book it for a week.

From our tripsRead the guide →
Jake in the outdoor thermal pool at Octant Furnas
Furnas, Azores

Octant Furnas

Our splurge night. Thermal pools fed by the hot springs, robes, loungers, and the cozido cooked in the ground.

From our tripsRead the guide →

Everything here is somewhere we actually went and paid for ourselves. If it's on the list, we loved it.

See the Full List
Meet Colby & Jake

Two New Yorkers, a 1987 sailboat, and too much stuff.

We live in New York City, but we're home maybe 30% of the time. The rest of it we're skiing, sailing, seeing family, or on a plane somewhere. Our motto: what you do for a living should be the least exciting thing about you.

Why The Circus Wagon? It's the name of our boat, and we named her that because we always have too much STUFF. We're not influencers. Social media never quite captures the moments that matter to us, so this is our alternative.

Colby and Jake at Caloura on São Miguel
Colby & JakeCaloura, São Miguel
From our camera roll

Mostly Colby's Fujifilm X-T50. Jake's Canon R5 shots are better, but they're stuck on his hard drive.

The ridge walk above Sete Cidades
Sete Cidades
Gorreana tea fields rolling down to the ocean
Gorreana
Jake heading out to surf in Puerto Pilón
Puerto Pilón
Jake photographing the No. 12 tram in Lisbon
Lisbon
A hydrangea lookout in Nordeste
Nordeste
The Circus Wagon with her sails up
The Circus Wagon, sails upOur boat
On the water

A 1987 Hunter 28.5 named The Circus Wagon

We found her on Facebook Marketplace. She's a little dumpy and definitely not the newest, but she makes us happy. We keep her in Noank, Connecticut, near Jake's family.

From Noank we sail out to Block Island, Fishers Island or Napatree Point. Our first trip was the big one: from Port Ewen down the Hudson, past the Battery, and through Long Island Sound to Mystic. More than 30 hours.

First voyage

Port Ewen to Mystic, more than 30 hours. We put the sails up after the bridges, right at sunset.

The boat

A 1987 Hunter 28.5. Not the newest, a little dumpy, and we love her.

Winter storage

Somehow it costs more than the summer mooring. Every year.

Jake's films

Mostly from the sky

All drone footage is courtesy of Jake. He shoots on his DJI Air 2S and Canon R5, and turns the best parts of each trip into a short.

Portugal from Above, Lisbon to the Azores
Lisbon to the Azores, PortugalShort

Get a note when a new trip goes up.

You're in! See you on the next adventure.

Hmm, that didn't go through. Double-check your email and try again.