Wanderlog and Tripsy get compared a lot, but they are built for different travelers. Wanderlog is a cross-platform, map-based planner for researching and routing a trip before you book. Tripsy is an Apple-native organizer for keeping a booked trip tidy on the road, and in 2026 it added an AI feature that changes the conversation.
If you are choosing between them, the deciding factors are usually your devices, whether you want to plan or just organize, and how much AI you want doing the work. Here is how they stack up.
Disclosure: MonkeyEatingMango is our own product, the tool behind this blog, so treat its entry below with appropriate skepticism. Wanderlog and Tripsy are described from their public pages, verified June 2026; verify current details on the live sites.
Quick answer
| If you want | Pick | Price |
|---|---|---|
| Cross-platform map planning, group editing | Wanderlog | Free + Pro $39.99/yr |
| A polished Apple app to organize booked trips | Tripsy | Free + $59/yr |
| A full day-by-day itinerary generated for you | MonkeyEatingMango | Free |
Want the plan written for you instead of building it pin by pin? Generate a free itinerary in a few minutes, no signup required →
At a glance
| Wanderlog | Tripsy | |
|---|---|---|
| Platforms | Web, iOS, Android | iPhone, iPad, Mac, Apple Watch |
| Android app | Yes | Waitlist (not released) |
| Core approach | Manual map planning | Manual trip organizing |
| AI | Pro assistant suggests places | Claude feature builds trips |
| Full itinerary generation | No | Via Claude conversation |
| Budget tracking | Manual entry | Manual entry |
| Auto currency conversion | No | No |
| Live collaborative editing | Yes | Apple users only |
| Offline access | Pro | Yes |
| Free PDF export | Pro | Pro |
| Price | Free + Pro $39.99/yr | Free + $59/yr or $299 lifetime |
Pricing: what's free, what's paid
Both tools have a free tier and one paid upgrade, but the lines are drawn differently.
Wanderlog Pro is $39.99/year, sold annually with a free trial, as of June 2026. The free tier is generous for planning: unlimited places, live collaboration, smart recommendations, and flight, hotel, and car import. Pro adds offline access, the AI assistant, route optimization, booking deals, Google Maps export, and auto inbox scanning for bookings. For the full tier-by-tier breakdown, see the Wanderlog pricing 2026 deep-dive.
Tripsy is $59/year, or $299 for a lifetime license, both shareable with family, as of June 2026. Its free tier covers unlimited trips, cloud sync, unlimited guests, flight search, expense management, and forwarding reservations by email. The paid tier adds travel statistics, flight update alerts, document management, calendar sync, and a 10-day weather forecast.
So Wanderlog Pro costs less per year, and its free tier does more of the actual planning. Tripsy's lifetime option is the counterweight: $299 once can beat an annual fee if you travel for years, and the family sharing softens the per-person cost.
Wanderlog: cross-platform map planner
Best if: you want to research and route a trip yourself across any device, and plan with other people in real time.
Wanderlog is one of the most popular trip planners for a reason. You drop places onto a map, drag them into days, and it calculates driving times between stops. It runs on the web and has native iOS and Android apps, so a mixed-device group can all edit the same trip.
Key features
- Map-based planning with driving-time calculations between stops
- Native iOS and Android apps plus a web app
- Live collaborative editing for group trips
- Flight, hotel, and car import on the free tier
- Pro AI assistant that suggests places to add to your plan
Limitations
- The AI assistant suggests places, but you still build the itinerary yourself
- Offline access, route optimization, and booking tools sit behind Pro ($39.99/yr)
- Budget tracking is manual, with no automatic currency conversion
- Some users report the app slowing down on very large trips
Pricing
Free, with Pro at $39.99/year. See the Wanderlog review and feature comparison for a deeper look at the workflow.
Tripsy: Apple-native organizer, now with a Claude feature
Best if: you live in the Apple ecosystem and want a beautifully designed app to keep a booked trip organized, with AI help when you want it.
Tripsy is built for iPhone, iPad, Mac, and Apple Watch. It is strong at organizing multi-transport trips, with flights, trains, ferries, and rental cars laid out on one timeline, plus iCloud sync, widgets, and full offline access. You forward booking confirmations and Tripsy files them into the trip.
The 2026 change worth knowing: Tripsy added a Claude integration that, per its page, can build an entire trip from a destination, dates, and interests, then reorganize and add to it through conversation. That moves Tripsy from pure organizing toward planning, though it leans on a separate AI assistant rather than an in-app generator. Verify what the feature includes on the live page, since it is new.
One thing has not changed: Tripsy is still Apple-first. There is no Android app yet, only a waitlist, and the web option is a view-only public link companions can open in a browser, not a full editor. For a mixed-device group, that gap still matters.
Key features
- Polished native apps for iPhone, iPad, Mac, and Apple Watch
- Multi-transport timelines: flights, trains, ferries, rental cars
- Full offline access once a trip is downloaded
- Forward-to-import for booking confirmations
- New Claude feature that can build and refine trips in conversation
Limitations
- Apple-only for editing; Android is a waitlist, web is view-only
- $59/year is higher than Wanderlog Pro; the value is the $299 lifetime option
- The AI feature relies on Claude rather than a one-tap in-app generator
- No budget-aware planning or automatic currency conversion
Pricing
Free, with paid at $59/year or $299 lifetime. See the Tripsy review for cross-platform travelers for more on where it fits.
Where a free AI generator fits
Both Wanderlog and Tripsy expect you to build the trip, then help you manage it. Neither produces a complete, budget-aware day-by-day plan from a short form. That is the gap MonkeyEatingMango fills.
Disclosure: this is our own product, described the same way as the tools above, including its limits.
MonkeyEatingMango takes a different approach. You answer 8 quick questions about your destination, dates, budget, and travel style, and AI generates a full day-by-day plan in a few minutes, with estimated costs in your local currency and an embedded map per day.
We built it for the part neither Wanderlog nor Tripsy does for you: the first draft. Download the plan as a PDF, export it to Google Sheets or Excel, and customize from there. It is free, with no account required.
Its limits are honest ones: no drag-and-drop planning workspace like Wanderlog, and no on-the-road organizing like Tripsy. It generates the starting point; those tools manage the trip. For a focused list of AI generators, see the best free AI travel planners for 2026.
Which one should you pick?
- Choose Wanderlog if your group uses mixed devices, you want to plan and route the trip yourself, and you want live collaboration. The $39.99/year Pro is the lower annual price.
- Choose Tripsy if everyone is on Apple devices, you mostly want to organize booked trips beautifully, and the new Claude feature or the $299 lifetime license appeals to you.
- Choose a generator like MonkeyEatingMango if you would rather skip the building entirely and start from a complete, budget-aware itinerary you can export and edit.
Many travelers use two of these together: generate a plan, then organize the bookings in Wanderlog or Tripsy once the trip is real. For more matchups, see the 11 best Wanderlog alternatives and the 10 best Tripsy alternatives.
See what a generated plan looks like: 7-day Japan itinerary or 5-day Paris itinerary.
Frequently asked questions
Which is cheaper, Wanderlog or Tripsy?
Wanderlog Pro is $39.99/year and Tripsy is $59/year, as of June 2026, so Wanderlog Pro is cheaper annually. Tripsy also sells a $299 lifetime license shareable with family, which can work out cheaper over many years. Both have free tiers, and Wanderlog's free tier covers more planning features. Verify current rates on each pricing page.
Does Tripsy work on Android?
Not yet. As of June 2026, Tripsy runs on iPhone, iPad, Mac, and Apple Watch, with an Android version on a waitlist rather than released. There is a web view: you can generate a public link to a trip that anyone can open in a browser, including on Android, but it is view-only, not a full editor. Wanderlog has native iOS and Android apps plus a web app.
Does Wanderlog or Tripsy generate a full itinerary with AI?
Both have an AI angle, but they work differently. Wanderlog's Pro AI assistant suggests places you tap to add to a plan you build yourself. Tripsy added a Claude integration that can build an entire trip from a destination, dates, and interests through conversation. Neither generates a complete, budget-aware day-by-day plan from a short form the way a dedicated generator like MonkeyEatingMango does.
Should I use Wanderlog or Tripsy for a group trip?
Wanderlog is the better fit for a mixed-device group: native iOS and Android apps plus a web app, and live collaborative editing. Tripsy can share a view-only link that opens in any browser, but only Apple users can edit the trip. If half your group is on Android, Wanderlog avoids the gap.
Is there a free alternative to both?
For manual map-based planning, Wanderlog's own free tier is generous. For an AI-generated day-by-day plan, MonkeyEatingMango creates a full itinerary with real costs, maps, and free PDF, Excel, and Google Sheets export, with no account required. It solves a different problem than either Wanderlog or Tripsy.
Disclosure: MonkeyEatingMango is our own product. Wanderlog and Tripsy are described from their public pages, verified June 2026; pricing and features change, so confirm current details on the live sites. Last updated June 2026.
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Photos from Wikimedia Commons, used under Creative Commons licenses