Every trip. Every story.

53 stories across 12 countries and 8 years of travel together.

53 stories

2026

Caribbean, Various · August 2026

Caribbean: The Cruise and the Keynote

Our friend Haresh turned 50 and celebrated by chartering a cruise from Antigua to St. Lucia and inviting about 60 of his closest friends. G and I flew into Antigua the day before and spent the night at Hodges Bay Resort & Spa, about ten minutes from...

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Fez & Marrakech, Morocco · February 2026

Fez & Marrakech: Morocco

Five nights. Casablanca to Fes. G and I, early February, a work trip that turned into one of the more unexpected travel experiences we've had.

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Phoenix, USA · January 2026

Phoenix: Back Again

Back in Scottsdale for client meetings. Three nights at the Hilton Garden Inn Scottsdale North, which is a Hilton Garden Inn near the Perimeter Center and does Hilton Garden Inn things. Clean room, decent breakfast, a pool I didn't use because January...

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San Luis Obispo, USA · January 2026

San Luis Obispo: The Question

I flew from Phoenix to San Luis Obispo on January 8th with a ring in my carry-on and a plan that I'd been working on for months. G thought we were going on a weekend trip to the Central Coast because I'd told her I wanted to see the Madonna Inn and...

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Various, USA · January 2026

Various: And the Rest

2026 kept going. A day trip to West Palm Beach on the Brightline in January, no overnight, just meetings and back.

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2025

Phoenix, USA · December 2025

Phoenix: For Work

Straight from San Francisco to Phoenix. No break. Different suitcase energy when you pack for a conference and a work trip back to back and the climates are completely different: SF layers and a jacket versus Phoenix shorts and sunscreen. The flight...

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Hollywood, USA · December 2025

Hollywood, FL: The Guitar Hotel

The Seminole Hard Rock Hotel & Casino in Hollywood, Florida, is about 25 minutes from our apartment. The Guitar Hotel tower is shaped like a guitar, which sounds absurd and is absurd and is also visible from the highway and lit up at night in a way...

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McAllen, USA · December 2025

McAllen, Texas

Four nights in McAllen, Texas. G came with me on this one. We were both speaking at Social Fest, the first social media conference in South Texas, held at the Mission Event Center about 15 minutes from McAllen. The conference was organized by a...

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New York City, USA · December 2025

New York: December 2025

Five nights in early December. Two hotels, two neighborhoods, two versions of the city.

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New York City, USA · November 2025

New York: One Night at The Ludlow

One night at The Ludlow on the Lower East Side in mid-November. Work trip. Quick in-and-out.

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Ottawa, Canada · October 2025

Ottawa in October

Quick trip home. Three nights, mid-October, staying with my mom. No hotel. G came with me.

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San Francisco, USA · September 2025

San Francisco: INBOUND Moves West

Fourth year speaking at HubSpot INBOUND. But this year the conference moved from Boston to San Francisco, which changed everything. Different city, different hotel, different energy. The Boston routine I'd built over three years was gone. Starting...

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New York City, USA · September 2025

New York: Ten Days

Almost ten days at The Beekman in lower Manhattan, late September into early October. Work trip that kept extending. You know the kind: you fly in for three days and then a meeting gets added and then another one and then you're buying underwear at...

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Halifax, Canada · August 2025

Halifax for My Brother's Graduation

My brother graduated from law school at Dalhousie University in Halifax, Nova Scotia. You go. There's no version of this where you don't go.

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Palm Beach, USA · July 2025

Palm Beach for July 4th

We took the Brightline from Miami to West Palm Beach for the long weekend. G and I, no agenda except the holiday and the beach. About an hour and a half on the train, which is even easier than the Orlando run. You barely have time to finish a coffee...

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Punta Cana, Dominican Republic · May 2025

Punta Cana with Mara

Four nights at the Hard Rock Hotel Punta Cana in mid-May. G was still on her Europe trip, so this was a getaway with my friend Mara. Sometimes you need a pool and a beach and someone who doesn't want to talk about work for four days. Mara is that...

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Dubai, UAE · April 2025

Dubai & London: G's Birthday Trip

G's birthday fell in April and she wanted to do it big. The plan was Dubai for a week, then I'd fly home and she'd continue through Barcelona and Rome before coming back. Nearly two months of travel for her, two weeks for me. Different appetites for...

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Orlando, USA · March 2025

Orlando with G (Brightline Round Two)

Took G to Orlando for a conference. Brightline from Miami, both of us this time. She'd never taken the train and spent the first 30 minutes looking out the window like a kid on a school trip, pointing at things (a heron, a cow, a water tower that...

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Orlando, USA · February 2025

Orlando via Brightline

This time I took the train. Brightline runs from Miami to Orlando in about three and a half hours, which is roughly the same as driving but without the I-95 to Turnpike to I-4 gauntlet that makes every Orlando drive feel like an endurance test. The...

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2024

Las Vegas, USA · November 2024

Las Vegas: Vegas with G

Late November. G and I flew to Vegas together for the first time since 2020. No conference. No event. No reason except we hadn't taken a trip that was just ours in a while, and Vegas was easy: direct flight from Miami, three hours, and the Palms...

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Boston, USA · September 2024

Boston: INBOUND, Year Three

Third year at HubSpot INBOUND. Back at the Omni Boston Hotel at the Seaport. Same hotel, same skybridge to the convention center, same harbor view from the upper floors. At some point a conference stop becomes a routine, and the routine has its own...

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Nassau, Bahamas · August 2024

Nassau

Three nights at the Graycliff Hotel in Nassau, Bahamas. I was there to speak at an event. The speaking was a day. The rest was the Bahamas.

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Orlando, USA · July 2024

Orlando in July (The Nice One)

The JW Marriott Orlando Bonnet Creek Resort & Spa is a different Orlando entirely. Bonnet Creek is a resort complex tucked between Disney properties, with a lazy river, multiple pools, a spa, and grounds that feel more like a vacation than a work...

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Short Hills, USA · May 2024

Short Hills

One night at the Hilton Short Hills in late May. Work trip. G flew out the same day, which turned a routine overnight in New Jersey into something better.

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Orlando, USA · April 2024

Orlando Again in April

One night at the Hyatt Regency Orlando. Quick in-and-out. The Hyatt Regency is connected to the Orange County Convention Center by a skybridge, which means you never have to go outside, which in April in Orlando is a feature. The hotel is massive....

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Orlando, USA · January 2024

Orlando in January

Five nights at the Wyndham Orlando Resort International Drive in mid-January. Conference. The Wyndham is a conference hotel and it does conference hotel things without pretending to be anything else. Large lobby, pool with a waterslide that nobody...

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2023

Ottawa, Canada · December 2023

Christmas in Ottawa

We flew home for Christmas. Toronto Pearson to Ottawa, which is one of the shortest flights in Canada (about 55 minutes in the air, longer if you count the time you spend taxiing at Pearson because Pearson is a mess). Or you drive, which is about...

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Boston, USA · September 2023

Boston: INBOUND Again

Second year in a row at HubSpot INBOUND. This time at the Omni Boston Hotel at the Seaport, which had the advantage of being directly connected to the convention center. You walk from your room to the keynote stage without going outside, which in...

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Vienna, Austria · August 2023

Vienna: Back Again (With a Side of Prague)

We went back. Three weeks in August and September. G flew from London, I flew from Miami, and we met at the airport in Vienna like two people arriving at the same idea from different directions.

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London, UK · July 2023

London: G Stops In

G went through London in late July on her way to Vienna. Two nights. She'd been wanting to try Mama Shelter in Shoreditch, one of those hotels that markets itself as a lifestyle brand but actually backs it up with a good room and a lively ground...

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Venice, Italy · June 2023

Venice and Lake Garda

A friend was getting married in Venice in late June and we turned it into a week. Four nights in Venice, then we rented a car and drove to Sirmione on Lake Garda for another four. The wedding was the reason for the trip. Italy was the reason for...

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Scottsdale, USA · May 2023

Scottsdale: G's Birthday

G has a rule about her birthday: she leaves. Doesn't matter where. The point is to not be home, not be working, not be doing anything that resembles a regular Tuesday. Some years it's a big trip. Some years it's a weekend somewhere warm with a pool....

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Columbus, USA · April 2023

Columbus for a Wedding

Someone you care about is getting married in Columbus, Ohio. You go to Columbus, Ohio. That's the whole calculus.

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New York City, USA · February 2023

New York in February

There's a specific kind of cold that only exists in New York in February. It's not the temperature (Toronto was colder, always). It's the wind. The buildings create corridors that funnel it down avenues at speeds that make your eyes water and your...

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2022

Boston, USA · September 2022

Boston and Vegas: INBOUND and Everything After

The first week of September I was in Boston for HubSpot INBOUND, speaking at the conference. INBOUND is one of those annual events that takes over an entire convention center and half the hotels in the Seaport District for a week. Marketers,...

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Palm Beach, USA · July 2022

Palm Beach for the Weekend

Two nights at the Eau Palm Beach Resort & Spa in early July. No occasion. No event. Just one of those weekends where G looked at me on a Thursday and said "we should go somewhere" and by Friday afternoon we were checking into a resort 45 minutes...

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Miami, USA · May 2022

Miami: Iris Comes to Town

G's mom Iris flew over from London in late May and we needed a place where she could stay with us that wasn't our apartment (love Iris, love our apartment, love both more when there's space between them). We booked an Airbnb on the 22nd floor of the...

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Toronto, Canada · April 2022

Toronto: G Goes Back

G went back to Toronto in mid-April for about two weeks. She stayed at The Drake Hotel on Queen Street West, which is one of those hotels that functions more like a cultural outpost than a place you sleep. Art on every wall, a live music venue in...

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2021

Nashville, USA · August 2021

Nashville for Three Days

I flew Southwest from Fort Lauderdale to Nashville in early August for a conference. Three nights at the Hyatt Place Nashville/Opryland, which sits out near the Gaylord Opryland complex about 15 minutes northeast of downtown. It's a Hyatt Place. You...

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Cancún, Mexico · August 2021

Cancún: A Friend's Birthday

A friend was turning a year older in late August and decided to celebrate by booking an all-inclusive in Mexico and telling everyone to show up. About a dozen of us did. Two nights at the Finest Playa Mujeres by The Excellence Collection, about 30...

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New York City, USA · July 2021

New York: G at The Ned

G went back to London in mid-July. Two nights this time. Family again, but she also wanted to stay somewhere she'd been wanting to try, so she booked The Ned in the City of London.

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Alaska, USA · May 2021

Alaska: G's Birthday on the Frontier

While I was somewhere between a moving truck and a mild existential crisis about Florida, G was in Anchorage watching glaciers calve into turquoise water. We have different approaches to life transitions. Hers involve mountains.

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Miami, USA · April 2021

Miami: G Goes First, I Follow With the Cat

G flew from Toronto to Miami in late April to start setting things up. Scouting apartments, figuring out neighborhoods, handling all the advance work that makes a move actually land instead of collapsing on arrival. I stayed behind to close out our...

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2020

Los Angeles, USA · November 2020

Los Angeles: Four Weeks at the Sunset Tower

The Sunset Tower Hotel was built in 1931 on the Sunset Strip in West Hollywood. Art Deco. Curved walls. Original moldings. John Wayne lived here. Howard Hughes kept a suite upstairs. Bugsy Siegel had an apartment. We checked in for nearly four weeks...

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Niagara Falls, Canada · October 2020

Niagara Falls

The drive from Toronto to Niagara Falls takes about an hour and forty minutes on the QEW, and for most of that drive you're looking at flat Ontario farmland thinking about nothing. Then you round the last bend, the highway dips toward the gorge, and...

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Vienna, Austria · August 2020

Vienna: Five Weeks in the City That Became Ours

G had been to Vienna before. Multiple times. She knew it the way you know a city you keep returning to. Every time she came back, she'd tell me about the coffee, the architecture, the way afternoons seemed to stretch without anyone getting anxious...

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Darmstadt, Germany · February 2020

Darmstadt: Two Weeks in Germany

We were in Germany for two weeks in February handling the AV and streaming for Miss Germany. Not something I'd have predicted being on my calendar, but that's how these things go. Someone needs the production done right, you're the team that does it...

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Las Vegas, USA · January 2020

Las Vegas: Before the World Stopped

Five days at the Palms Casino Resort in late January. We were in town for an influencer event, the thing where brands fly people out, put them up, and hope the content writes itself. The event was fine. What I remember more clearly is the hotel, the...

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2019

New York City, USA · December 2019

New York: December in the City

I was in New York for a few days in mid-December. Some things I needed to take care of. The kind of trip where the reason fades but the city sticks.

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Los Angeles, USA · August 2019

Los Angeles: Visiting G's Sister

Every city has a version of itself that exists in movies and a version that exists in real life. LA has about seven of each. The LA you see in films (palm trees, convertibles, sunsets over the PCH) is real, but it accounts for about 15% of the...

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Dubai, UAE · May 2019

Dubai & Seoul: Through Dubai to Korea

We'd been together for maybe five months when G booked a flight from Toronto through Dubai to Seoul for her birthday. A month-long trip. I wasn't going. We were new enough that a month apart felt like a test, but also not so new that I was going to...

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New York City, USA · March 2019

New York: Nora's Birthday

G's sister Nora is one of those people who lights up a room without trying. Their mom Iris wanted to come too but couldn't make it work, so the trip was the three of us. When it was Nora's birthday in late March, there was no debate about where to...

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Ottawa, Canada · January 2019

Ottawa: Home

Ottawa is where I'm from. It's not a city you go to. It's a city you go back to.

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