Stippl is a good free trip organizer and a thin AI planner. On a 7-day Tokyo brief, its free AI returned three neighborhood bases and eight empty days; AI day plans are a Pro feature. Pick Stippl if you already know your trip and want one shared place for it. If you want the days written for you, look elsewhere.
- What it is: a trip organizer at stippl.io for web, iOS and Android, rated 4.6 from 486 US App Store ratings (October 20, 2026).
- AI on the free tier: a route of 3 bases and 10 sights in short paragraphs, with 0 stops scheduled.
- Building it yourself: about 10 actions per stop, and the free AI chat stops at 20 messages.
- Price: free; Pro is €3.99 a month or €24.99 a year, and an account is required.
- Strength: the shared trip shell, with a calendar, an expense split with settlements, packing lists and members.
- Oh-No Travel Index: 11 of 15 must-dos left unanswered or wrong, from entry papers to a packing list with flip flops (lower is better).
What does Stippl's AI make from a 7-day trip brief?
Stippl's free AI turned one typed brief into a route of three Tokyo bases in about 68 seconds, and scheduled nothing inside them. The brief, entered on October 19, 2026, asked for 7 days in Tokyo from November 16 to 22, for a couple, with USD 1,500 excluding flights, at a comfortable pace, on a first visit to Japan.
The route is sensible: Asakusa and Ueno (2 nights), Shinjuku and Shibuya (3), Odaiba and Tsukiji (2), each with one paragraph of suggestions. But the trip runs November 16 to 23, a day longer than the brief, moves hotels twice inside one city, and the badge read "20% ready" for the next six minutes.
Every day in the day-by-day tab shows a base, a temperature, an "+ Add" button and "No accommodation booked."
How hard is it to build the days in Stippl by hand?
Adding one stop to one day took 7 actions in Stippl on October 20, 2026, and giving it a time took 3 more, so a 7-day trip of about 20 stops is close to 200 actions. The steps for one stop:
- Open Day by day.
- Expand the day.
- Press "+ Add".
- Switch from the saved-ideas search to "Add new". The first box only searches saved places: "Senso-ji" there returned "No ideas saved."
- Type the place. The results for Senso-ji in a Tokyo trip included Sensō-Ji Paros, in Greece.
- Press "+ Add" on the right result.
- Close the panel. The stop arrives with "No time", a $0 price and status Pending; set From and To to schedule it.
Stippl shows each place's address and website, but no opening hours to schedule around.
The Ask AI chat is faster but capped at 20 free messages; the counter read "16 messages left" after four, which had added three places, all without times. One answer called Shinjuku Gyoen "a premier, tranquil hanami destination," a cherry-blossom outing, for a trip in November.
Is Stippl free, and what does Stippl Pro cost?
Stippl is free for building a trip by hand, and Stippl Pro costs €3.99 a month or €24.99 a year (shown as €2.08 a month, "Save 48%"), as of October 20, 2026. The US App Store lists Pro at $3.99, $24.99 and $34.99.
| Feature | Free | Pro |
|---|---|---|
| Route, day-by-day, calendar view | Yes | Yes |
| Shared expense tracker, members | Yes | Yes |
| Packing lists | Yes | Save and reuse |
| AI route of bases | Yes | Yes |
| AI chat | 20 messages | Not stated |
| AI day plans | No | Yes |
| Calendar sync, expense export | No | Yes |
| PDF export, ticket forwarding | No | Yes |
| Offline maps | No | Yes |
| Ads | Yes | No |
Pro's list leads with "AI day plans for every destination", the part the free account left empty. Pro's day plans were not tested for this review.
What are Stippl's limitations?
Stippl's main limit on the free tier is that its AI stops at the route. The rest:
- No cost check. The Budget tab is an expense tracker that started at €0.00, in euros for a dollar brief; the only guidance was "set aside roughly USD 60–70 per day for food and transport," with nothing on whether USD 1,500 covers the trip.
- A breakfast on closed days. The Odaiba and Tsukiji base suggests "a street-food breakfast at Tsukiji Outer Market" on Saturday 21, Sunday 22 and Monday 23. The market closes on Sundays and national holidays, and November 23 is a national holiday, which leaves the Saturday moving day. A venue scheduled while it is closed is the top fault in AI-planned trips: in a study of 356 AI-generated itineraries, 43% of 2,735 planned days carried a verifiable fault before correction, and a venue closed at its scheduled hour was the largest category.
- A template packing list. For 12 to 14°C, it lists flip flops, heels, shorts and a tank top among 74 items.
Is Stippl good for a first trip to Japan?
Stippl scores 11 on the Oh-No Travel Index and cannot be scored on the day, because it schedules no days; MonkeyEatingMango scores 4. The index counts, out of 20, the "oh no" moments a plan leaves you to find: 15 must-dos it should answer and 5 faults it should not make, on the October 19, 2026 runs. Lower is better.
| # | Before you go | Stippl | MonkeyEatingMango |
|---|---|---|---|
| 1 | Entry papers | ❌ | ✅ passport and visa check |
| 2 | Airport to the city | ❌ | ✅ Narita Express or limousine bus |
| 3 | Where to stay | ✅ Asakusa or Ueno, then two more bases | ✅ Ginza, all six nights |
| 4 | Suica or Pasmo, and how trains work | ✅ the card only | ✅ tap in and out at the gates |
| 5 | Whether a JR Pass is worth it | ❌ | ❌ |
| 6 | Cash or card | ❌ | ✅ cash-only spots, 7-Eleven ATMs |
| 7 | SIM, eSIM or pocket Wi-Fi | ❌ | ✅ three options with prices |
| 8 | Etiquette and tipping | ❌ | ✅ no tipping, bowing at shrines |
| 9 | What to book ahead | ✅ teamLab Planets | ✅ teamLab, Kabuki-za, with book-by dates |
| 10 | Closures and holidays on your dates | ❌ | ❌ Mondays avoided, not explained |
| 11 | Weather and what to pack | ❌ flip flops and heels for 12 to 14°C | ✅ forecast and a packing list |
| 12 | Scams and tourist traps | ❌ | ✅ Roppongi bar touts |
| 13 | A day trip out of Tokyo | ❌ | ✅ Kamakura, as a swap |
| 14 | The must-do sights | ✅ Senso-ji, Shibuya, Meiji Shrine | ✅ the same three |
| 15 | The leaving day | ❌ | ✅ checkout time, Narita for the flight |
| # | On the day | Stippl | MonkeyEatingMango |
|---|---|---|---|
| 16 | Arrival day planned like a full day | Not scored | ✅ 2 stops after landing |
| 17 | Too much in one day | Not scored | ✅ at most 4 stops a day |
| 18 | A stop closed when you arrive | Not scored | ❌ Tsukiji at 4:30 PM, stalls shut |
| 19 | A day that doubles back across the city | Not scored | ❌ day 7 back to Ginza before the airport |
| 20 | The same place twice | Not scored | ✅ |
| Oh-No Travel Index (lower is better) | 11, plus 5 not scored | 4 |
A comfortable pace means at most 4 named stops a day, and a day doubles back when its order adds a train ride it did not need. Someone who has been to Japan before will not miss Stippl's gaps; someone on a first visit will.
Stippl vs MonkeyEatingMango on the same brief
MonkeyEatingMango planned all 7 days of the same brief, 18 stops each with a time and a cost, in about 95 seconds without an account; Stippl is the better organizer once a trip exists.
| Stippl | MonkeyEatingMango | |
|---|---|---|
| See the plan yourself | Private to the account | ✅ Open the plan, no account |
| Input | One text box, after sign-in | 8 tap cards, no account |
| Days planned | 0 of 8 (route only) | 7 of 7 |
| Stops with a time and a price | 0 | 18 |
| Trip length | Nov 16 to 23 | Nov 16 to 22 |
| Cost | Expense tracker at €0.00; "USD 60–70 per day" | Cost estimate for 2: USD 4,539 |
| Opening hours | None given for any sight | On stops found in venue data; ❌ Tsukiji had none (row 18) |
| Oh-No Travel Index (lower is better) | 11, plus 5 not scored | 4 |
| Shared editing, expense split | Yes | No |
| Offline | Offline maps on Pro | Downloads, $0.99 one-time per trip |
- Cost: MonkeyEatingMango does not ask for a budget; it estimates the cost for the group. Of the USD 4,539 for two, USD 2,120 is getting there from Los Angeles and USD 2,419 is the hotel, food, activities and local transport, above the brief's USD 1,500, with no warning, because it asks no budget. It names a hotel area and a price range, not a hotel.
- Opening hours: each named stop is looked up in real venue data and scheduled inside its opening hours when it is found. Tsukiji Outer Market was not found in venue data on October 19, carried no hours, and landed after the stalls close (row 18).
- Where it falls short: no shared editing, no expense split, no offline maps.
Open the full MonkeyEatingMango plan for this brief: all 7 days, the map and the cost estimate, with no sign-in. Check it against the claims above. For other Japan routes, the Japan travel guide and the 7-day Japan itinerary start from the same data.
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Plan a trip →What are the alternatives to Stippl?
Five other planners received the same Tokyo brief on October 19, 2026, and each one plans more of the days than Stippl's free tier; none of them splits shared expenses the way Stippl does. They run A to Z below, with MonkeyEatingMango, the product behind this blog, last and scored the same way, and each tool's Oh-No Travel Index (lower is better).
| Planner | From the brief | Free | Paid, as of October 2026 | Oh-No Travel Index |
|---|---|---|---|---|
| iMean | Prose days in a chat | 1 message a day | From $6.99 a month, billed yearly | 5 |
| Plantrip | ✅ 7 dated days, train fares | 3 plans a month | Plus $3 a month or $30 a year | 11 |
| Stardrift | ✅ 7 dated days, 2 stops each | ✅ Free, with an account | None published | 10 |
| Wanderlog | In a chat; the trip stays empty | 10 AI messages | Pro from $39.99 a year | 8 |
| MonkeyEatingMango | ✅ 7 timed days, every stop costed | ✅ The full plan, no account | $0.99 per trip, for downloads | 4 |
1. iMean: one rich answer, then a daily limit
For a traveler who wants more than a route, iMean's first answer covered neighborhoods, ten priced hotels and a map. The free plan then allows 1 message a day, and a few facts were out of date. Read the iMean review.
2. Plantrip: a full plan from one text box
Plantrip filled all seven days from one typed brief in 92 seconds, with the train line, minutes and fare for every leg, the part Stippl leaves to the traveler. Its busiest days hold five sights plus meals. Read the Plantrip review.
3. Stardrift: dated days in a shared trip
Stardrift is the nearest to Stippl's shared trip: collaborators can edit it, and bookings import from Gmail. Unlike Stippl's free AI, it scheduled seven dated days of two stops and priced three hotels. Read the Stardrift review.
4. Wanderlog: an organizer with a stronger AI chat
Wanderlog works like Stippl, a trip organizer with an AI beside it, and its chat wrote a careful week with a budget that adds up to USD 1,500. The plan stays in the chat, so each stop still goes into the trip by hand. Read the Wanderlog review.
5. MonkeyEatingMango: a timed plan with no account
MonkeyEatingMango returned seven timed days with a cost on every stop and no sign-in. It has no shared editing or expense split, the two things Stippl does well. Open the Tokyo plan.
How was this review done?
Stippl received the brief word for word on October 19, 2026; MonkeyEatingMango, which has no free-text box or budget field, received the same trip through its 8 cards. Each plan was scored on the Oh-No Travel Index with every named venue checked against its official opening days. Stippl ran on a free account in a desktop browser and MonkeyEatingMango signed out; the screenshots come from those runs.
Who should pick Stippl?
Stippl suits a traveler who already knows the trip and wants one shared place for the route, the calendar, the packing list and who paid for what, and groups splitting costs get the most from it. A traveler who wants each day planned with times and prices will spend the week filling in Stippl's empty days by hand.
To see a full day-by-day plan for your own dates, start a trip on MonkeyEatingMango.
Disclosure: MonkeyEatingMango, the product behind this blog, also plans trips and appears in the comparison above. Stippl facts were read off the live product, its website and the US App Store on October 19 and 20, 2026.
Last updated October 2026.
Written by Shobhit Shrivastava · Founder
Related reading
Stardrift AI Review 2026: Is It Free, and Is It Any Good?
Stardrift turned one message into a dated 7-day Tokyo plan in about 90 seconds, with real hotel prices and an honest budget warning. It left the practical part of the trip to you.
Plantrip AI Review 2026: Is It Free, and Is It Accurate?
Plantrip turned one typed brief into a full 7-day Tokyo plan in 92 seconds, with the clearest train directions of six planners tested. It also packed the days and scheduled a garden on the day it closes.
iMean AI Review 2026: Is It Free, and Is It Accurate?
iMean's first answer to a 7-day Tokyo brief answered 11 of 15 must-dos, the most of the five outside planners tested, with neighborhoods, ten priced hotels, a map and a budget split. The free plan then allowed no follow-up, and several facts were out of date.