Trip & Itinerary Planning

Once flights and hotels are booked (see Flight Search and Hotel & Accommodation Search), the next problem is keeping all the moving pieces together. For events synced into your normal calendar, see Calendars & Scheduling. For maps and offline navigation, see Maps Offline & Nav. For deep journaling, the PWA section covers offline-capable web apps.

Two distinct jobs here, often confused: aggregation (forward a confirmation email, get an itinerary) and planning (collaboratively pick where to eat in Lisbon).

Self-host & FOSS first

• ★ ★ Hugo / Astro / Eleventy trip site — free OSS; static-site posts per day; the trip blog that survives forever.
• ★ Obsidian + Map View plugin — free; your trip notes plus a map of the GeoJSON in them.
• ★ Logseq / Trilium / AppFlowy / Anytype — free OSS notebooks; pair with manual ICS exports to your phone calendar.
• ★ OpenStreetMap-based maps — Organic Maps, OsmAnd, Magic Earth — free / OSS; offline-first; see Maps Offline & Nav.
• ★ Self-host trip planning stack — see Travel Self-Host Trip Planning.
• Open Source Polarsteps alternatives — OwnTracks + a static map renderer for "where I went"; Hauk for ephemeral location share. See Family Location Sharing.
• Custom Postgres + PostGIS — for the over-engineered.

Confirmation aggregators

• ★ TripIt — free + paid Pro (~$49/yr); ★ the original. Forward plans@tripit.com and confirmations parse automatically. Pro adds airline status alerts, fare-watch, mileage tracker, neighborhood safety scores. Free is fine for casual use.
• App in the Air — paid + free; flight-focused, gamified.
• Apple Wallet — free; auto-detects boarding passes and hotel confirmations from Mail; minimal but everywhere on iPhone.
• Google Travel (formerly Trips) — free; aggregates from Gmail; has been deprecated and re-launched twice — currently lives inside Google Maps "Trips" tab.

Collaborative trip planners

• ★ ★ Wanderlog — free + paid Pro (~$50/yr); ★ ★ the modern default for shared trip planning. Map view of all stops, drag-to-reorder, expense splitting, offline access on Pro. Strong web + mobile.
• TripHobo, Trip Planner AI, Sygic Travel (was Tripomatic) — older, less active.
• Roadtrippers — paid Plus (~$30/yr) + free; ★ for US road trips; "interesting things along your route" discovery.
• Mind My Trip — paid + free; itinerary + budget tracking.
• Notion / Obsidian / Logseq trip pages — free; for those who already live in their notes app. Shared Notion databases work well for groups.

AI-generated itineraries (2024–26)

The "describe your trip and get an itinerary" category emerged fast and is still settling.

• Layla (Skyscanner-owned), Mindtrip, Roam Around, Wonderplan, Curiosio, Vacay — paid + free trials. Useful for first-pass brainstorming; almost all hallucinate restaurant hours and museum closures — verify everything before booking. Treat as "intern who's never been there."

Route journaling / "where I went"

• ★ Polarsteps — free + paid Premium (~$30/yr); ★ for automatic route tracking — runs in the background, draws your line on the map, you add photos and notes. Premium adds offline maps, photo books, longer trip history.
• Found (was Found Trips) — paid + free; similar concept.
• Strava — paid + free; primarily fitness but a real travel-route record for anyone running / cycling on tour.
• Day One — paid (~$35/yr); journaling app with location tags; pairs well with Polarsteps for prose alongside the map.
• Drifters — newer; iOS-first.

Self-host / DIY (deeper)

See the Self-host & FOSS first section at the top of this page for the full FOSS stack — Hugo / Astro / Eleventy, Obsidian, Logseq, Trilium, AppFlowy, Anytype, OwnTracks.

Practical rules (2026)

• The aggregator (TripIt) and the planner (Wanderlog) usually want to be different apps — one is read-only and email-driven, the other is collaborative and editable.
• AI itineraries are best for brainstorming (give me 15 things to consider); they're worst at operational details (is this open Tuesday afternoon).
• Polarsteps and similar continuous trackers eat battery — leave them off in airplane mode for transit days.

Pick this if…

• Default FOSS / self-host trip blog: Hugo / Astro / Eleventy + OpenStreetMap.
• You already live in Notion / Obsidian / Logseq: stay there; export ICS for calendar.
• Track every step of a months-long trip (FOSS): OwnTracks + static map renderer.
• Forward me confirmations and shut up: TripIt free.
• Plan a trip with friends, see it on a map: Wanderlog.
• Track every step of a months-long trip (paid hosted): Polarsteps.
• US road trip discovery: Roadtrippers.
• AI brainstorm starting point: Layla / Mindtrip — but verify operating hours.