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Travel Tips· 5 min read
Conference Travel: What I've Learned From 10+ Events (2022-2026)
I've spoken at or attended conferences in Boston, Orlando, San Francisco, McAllen, and Hollywood since 2022. Four years of INBOUND alone.
I've spoken at or attended conferences in Boston, Orlando, San Francisco, McAllen, and Hollywood since 2022. Four years of INBOUND alone, plus Social Fest, Blockchain Futurist, and a handful of others. Some were 10,000-person productions with keynote stages and sponsor booths. Some were 200 people in a converted warehouse with folding chairs. The production value varied. The lessons didn't.
Hotels: Close Beats Fancy
The conference hotel is usually overpriced and sold out by the time you decide to go. The hotel two blocks away is half the price and ten minutes closer to the venue than you think. The goal is to minimize the distance between your bed and the first session of the day, because conference mornings start early and conference nights end late and the walk matters more than the thread count.
My best conference hotel stays across four years: The Verb Hotel in Boston (2022, near Fenway, rock-and-roll themed, more personality than anything in the Seaport). The Omni Boston Hotel at the Seaport (2023-2024, when I wanted to be inside the conference building without leaving). The DoubleTree by Hilton Orlando Airport (multiple Orlando trips, reliable, affordable, and the cookies are a real perk that I'm not too proud to admit I look forward to). Casa de Palmas in McAllen (2025, a 1918 building with a courtyard bar and tile work that had no business being this good for a first-year conference in a border town). The JW Marriott San Francisco Union Square (2025, central location, upper floors with Bay views).
Food: Leave the Venue
The conference lunch is a salad in a plastic container with a brownie. The conference dinner is a buffet with warming trays and rubber chicken. Neither is something you'll remember. The meals that actually matter happen away from the venue, usually at a restaurant someone recommended in the hallway between sessions.
Boston: Row 34 for oysters and beer. Eventide for the brown butter lobster roll. Giacomo's in the North End where you wait in line and the pasta comes in portions that could feed a family and you pay cash because they don't take cards. Three years. Three INBOUND conferences. These three restaurants were the constants.
San Francisco: The Mission district for handmade pasta at a place a local recommended. The Ferry Building Marketplace on a Saturday morning for almond croissants and coffee and a bench overlooking the Bay. Chinatown on Grant Avenue for dim sum and roast duck, $90 for five people, which in a city where a salad costs $22 felt like a loophole.
McAllen: Barbacoa breakfast tacos every morning from an unlisted spot. Cabrito in Reynosa across the border. The rental car smelled like barbacoa for the rest of the day. These are the conference meals I tell people about years later.
Orlando: A Thai place in a strip mall near the airport that a conference contact recommended. The pad see ew had real wok char. Nile Ethiopian on I-Drive.
Hollywood, FL: Kuro at the Seminole Hard Rock for Japanese. The wagyu nigiri is legitimately excellent casino restaurant food.
The rule: ask a local, not the concierge. The best conference meal is always 10 minutes from the venue in a direction nobody else is walking.
The Conference Itself: What Actually Matters
The hallway conversations beat the sessions. After four years of INBOUND and a dozen other events, the best content I've absorbed has been in the hallway between sessions, at the hotel bar after hours, and at dinner with people I met that morning. The sessions are the reason everyone's in the building. The conversations in between are the reason everyone comes back. If you're spending the whole day in sessions and eating lunch at your seat, you're optimizing for the wrong thing.
The recurring faces are the network. By INBOUND year three in Boston, I was recognizing people from year one. Hugs instead of handshakes. Conversations that picked up where they left off 12 months ago. A woman from Austin who I'd met in 2022 and who showed up in 2024 and we immediately started talking like we'd seen each other last week. That's when conferences stop being events and start being community. The first year is about learning. The second is about reconnecting. The third is about belonging.
First-year conferences have the best energy. Social Fest in McAllen (2025) was a first-year event organized by a local marketing agency and powered by the Mission Economic Development Corporation. The crowd was younger, hungrier, and more engaged than conferences ten times its size. People weren't there because their company sent them. They were there because they wanted to learn. Notebooks out. Questions specific. A woman in the front row of my session was photographing every slide. At most conferences that would annoy me. At a first-year conference it felt like someone capturing something they planned to use immediately. Those are the best rooms.
When INBOUND moved to San Francisco in 2025, the whole dynamic changed. In Boston, the conference took over the Seaport District. You'd run into INBOUND people at every restaurant and coffee shop within a mile. In SF, the conference was one of fifty things happening that week. The city didn't rearrange itself for us. We fit into it. Different energy. Not worse. Just different.
Packing for Back-to-Back Trips
In September 2025 I went from INBOUND in San Francisco directly to client meetings in Phoenix. SF layers and a jacket versus Phoenix shorts and sunscreen. No stop home in between. Two packing cubes solve this: one for conference clothes (collared shirts, good shoes, a blazer), one for casual (shorts, t-shirts, sneakers). Swap cubes, swap trips. One pair of versatile shoes that work with jeans and a blazer. Laptop charger in the carry-on, never checked. Aisle seat. Always.
The Local Conference
The Blockchain Futurist Conference at the Seminole Hard Rock in Hollywood, FL (2025) was 25 minutes from our apartment. No flight. No hotel. No suitcase. Drive there, speak, drive home, sleep in my own bed. The luxury of a local conference is absurdly underrated. If there's an event within driving distance, go. The barrier is zero and the upside is the same.
The Bottom Line
Go to the conference. Skip the boxed lunch. Find the taco shop. Talk to the person next to you at the bar. Go back next year and find them again. That's the whole strategy.