A retrospective on running an AI-augmented two-week holiday entirely from a phone.

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The setup, or: why my Mac stayed in Haarlem

I really, really wanted to bring my laptop on holiday. Two weeks in Puglia with the family — wifi, sunny terrace, a glass of Primitivo, terminal open. Pure poetry. My wife disagreed. Her reasoning was something along the lines of "this is a holiday, not a working session" — ok, fine, fair.

But I'm not built to disconnect cold turkey. So the compromise was: the Mac stays at home, on, with the lid open and two remote-control sessions running — one Claude Code, one Claude Code (because backups). Plus syncthing, plus VPN, plus a launch agent or two to make sure nothing falls over while I'm a thousand kilometres away. Plus a caffeinate -d running so the screen never sleeps and the machine stays reachable. The first night of the trip, the very first test was: can I still open a session? Yes. Sigh of relief, glass of Primitivo.

And then everything happened from my phone. Every conversation, every file, every patched binary — typed on a small touchscreen, while sand sat in my keyboard.

What I actually used Claude Code for

The plan was modest: a few day-trip PDFs, a fallback in case I needed something off my Mac, and the occasional secret work task my wife wouldn't notice. That's not how it played out.

We rented a holiday house through Novasol. Things went… not well. The pool was closed. The Wi-Fi was down for nine days. The dishwasher was broken from arrival. The drainage flooded the bathrooms on day seven. The walls were crumbling with saltpeter from a wet winter. The kitchen, billed as a "fantastic living kitchen", lacked a corkscrew (we opened a wine bottle with a screw).

So my "fun productivity tool" became my "let's make sure we still get a refund" tool.

A non-exhaustive list of things I asked Claude Code to do, all from a phone:

• Combine four separate boarding-pass PDFs into a single, clean document for my wife — instead of forwarding her four emails she would never find again
• Read the entire WhatsApp thread with the local key holder, build a timeline, and produce a structured PDF complaint dossier for Novasol (in two languages, with quotes, photos and a chronology)
• Cross-reference a 2-star Airbnb review by a previous guest two weeks before our arrival to prove the issues were known and structural, not weather
• Draft and re-draft customer-service emails — first too soft, then too aggressive, then about right
• Fix my WhatsApp MCP bridge when it broke (twice). Once because WhatsApp updated its protocol mid-vacation and the Go binary was outdated, once because the /api/download endpoint hadn't been implemented in the fork I was using. We patched the Go source, rebuilt, restarted the launchd service, and downloaded all media for the dossier, all from a phone in a beach restaurant in Pulsano
• Generate full day-trip PDFs for Lecce, Alberobello, and Monopoli — with walking routes, parking spots, lunch picks, gelato shops, fun facts about saltpeter and trulli construction, and everything tied to deeplinks into Google Maps
• Re-route a planned beach day when it turned out the spunnulate karst pools we wanted to swim in were thirty minutes the wrong direction
• Cross-reference the morning weather forecast with our activity options every day — Grotte di Castellana on cold days, Alberobello when sunny, indoor museums when windy. A trivial-sounding task, but having it done in seconds with full context saved a lot of bickering
• Surface lunch and gelato spots filtered by "works for nine people, including a pregnant one and a four-year-old, in a town that goes silent at 13:30 for siesta" — which is not a query Google does well
• Translate a parish-festival schedule from a small-town Italian government website, including the strange Italian custom of daytime fireworks (loud, no colour, just to announce the saint's procession)

The actual poster Claude translated for me — patron saint festival in Galatone, complete with 1pm fireworks and a cardinal flying in for Sunday mass.

• Run the OAuth 2.0 device flow by hand to recover access to my Gmail, because the Mac was remote and I couldn't open a browser on it. Step 1: generate the auth URL from the laptop. Step 2: paste it into WhatsApp. Step 3: open it on my phone. Step 4: copy the failed-redirect URL back into the chat. Step 5: terminal command exchanges the code on the laptop. Too bad Claude had to be restarted before the new keys could take effect — and you can't restart a remote-control session.

The unexpected joy: songs

Once a few of the family chats got the hang of "Jeffrey just goes to his phone and a polished result appears," they started asking for more creative things.

We made:

• An italo-disco lament in mock-Italian about everything that didn't work in the house. The chorus is "No gas! No water! No lights! No wifi! No dishwasher! No pool! No livingroom, solamente niente, oh!" My kids now sing it at full volume in the car
• An upbeat tropical-house "Vacation in a Trullo" beach banger
• A nighttime italian drama ballad called "Casa Spasimato Tragedia"

For the kids to be able to sing along, every Italian phrase in the lyrics was rewritten phonetically into something a four-year-old can read out loud — "trulli" became "troelie", "andiamo" became "andiajamo", "ciao amore" became "tjauw amore". They sing it perfectly. They also have no idea what any of it actually means.

🎧 Listen to the songs:

• Casa Spasimato — Italo-Disco Lament — LINK
• Vacation in a Trullo — LINK
• Casa Spasimato Tragedia (ballad) — LINK

Suno generated the music; Claude wrote the lyrics and the style descriptors. Writing the lyrics was almost free — every shared experience the songs reference was already in Claude's context, so we didn't have to brief the AI on anything. No wifi, no dishwasher, no pool writes itself when those have been the running theme of an entire vacation. The kids' favourite is the lament. My favourite is the ballad. My wife mostly tolerates them.

Two unsung pieces of the setup

Obsidian + Syncthing. Every note Claude touched on the laptop — the day diary, the planning doc, the complaint dossier draft, the song lyrics, this blog — was instantly available on my phone. Obsidian on the Mac, Syncthing in the background, Obsidian on the phone, no cloud, no fuss. Claude wrote a paragraph to my journal; my phone vibrated forty seconds later. The Mac generated a 7-page PDF; it was browsable on the beach by the time I'd finished my espresso. This is the part nobody tells you about: the AI is the first half of the workflow, the sync layer is the second half.

WhatsApp as a fallback transport. Reception in Puglia ranged from "two bars of 4G" to "HSDPA from a 2009 phone" to "nothing at all". The Claude Code remote-control app didn't always load. So a recurring pattern was: ask Claude to do something on the Mac, then have it post the result to my own WhatsApp — drafts, PDFs, Maps links, song lyrics. WhatsApp's offline cache is fierce. I could read a polished Novasol draft on a beach with no signal, mark it up in my head, and reply via the app the moment a single bar reappeared. Treat WhatsApp as a second display you carry in your pocket.

Things that broke, and what I learned

The WhatsApp bridge. Twice. The fix the second time was upstream — somebody had skipped implementing a download endpoint. I read the Go source on a 6-inch screen and dictated the patch to Claude. We compiled, restarted, downloaded the media. Then a third patch later in the trip: I noticed photos sent in the same second were overwriting each other on disk, because the bridge generated filenames from a timestamp with second-resolution. Quick fix — prefix each saved file with its message-id hash. Re-download. The dossier had four distinct wall-damage photos again instead of just one. Everything is just code, somewhere.

Gmail OAuth. Refresh token expired about an hour into the trip. The standard "open the consent page in a browser" flow doesn't work when your laptop is sitting on a desk in another country. The two-step PKCE-with-state-on-disk dance worked fine — but only because Claude Code can persist state between separate command runs. That's the kind of thing I genuinely couldn't do as a one-liner.

An accidental journal. I never set out to keep one. But because every plan, every booking, every restaurant pick, every complaint and every song happened through Claude, my context ended up being a complete chronology of the trip. By day twelve, asking Claude to summarise our holiday into a diary was a single sentence. The journal wrote itself, as a byproduct of using the AI for everything else.

My own assumptions. I started the trip thinking my workflow was AI helps me write things faster. Halfway through I realised it was AI lets me coordinate fragmented systems from a single conversational interface. WhatsApp, Gmail, Google Drive, Maps, Suno, the local SQLite database in the WhatsApp bridge, my own Obsidian notes, a half-built Go binary, and the Novasol complaints department — all of those got composed live, from a phone, from a Trullo with terrible reception.

If a colleague had asked me beforehand whether you could realistically run a 14-day, complaint-heavy, multilingual, two-family holiday with five children entirely off your phone via remote-control to a Mac and an AI coding agent, I'd have said theoretically. After this trip: yes, very practically, and somewhat compulsively.

What I would do differently

• Maybe bring a proper Bluetooth keyboard (if my wife lets me). Phones are not built for prompting full PDFs into existence
• Pre-warm everything before leaving. OAuth refresh tokens, MCP servers, the WhatsApp bridge, the launchd plists. The first hour of vacation is not when you want to discover that something has expired
• Don't update macOS the day before vacation. Don't anything the day before vacation. Freeze the system, trust your past self
• Trust the holiday more. Half the things I dragged Claude into could have been a notebook and a glass of wine
• Tell my wife less about all this

A footnote on context. By the time we landed at Schiphol, my conversation context was at 91% of the 1M-token limit. Apparently a 1M context is enough for one Italian holiday — including dozens of song-lyric iterations and many, many drafts of complaint letters to Novasol. Just barely.

Closing thought

The single most useful thing I did all holiday, technically, was generating a 7-page bilingual PDF dossier with embedded WhatsApp screenshots, an Airbnb cross-reference, and a chronological timeline — entirely from a beach chair in Marina di Pulsano while my four-year-old buried my feet in sand. The complaint is still under review.

The single most useful thing I did all holiday, humanly, was singing No gas, no water, no light, no wifi with my kids on the way to a fornello pronto in Cisternino while a wood fire roasted bombette twenty meters away.

Both required Claude. Only one required Italian wine.