Tripsy
Tripsy is a bootstrapped two-person company that builds an Apple-only travel planning app (iPhone, iPad, Mac, Apple Watch), centralizing flights, stays, activities, expenses, and documents with email-import automation and a freemium Pro subscription for individual travelers, couples, and families.
- Company typePrivate
- Founded2018
- Headquarters—
- Headcount1–10
- GTM typeB2C
- OfferingSoftware
What Tripsy does
Tripsy LLC is a privately held, bootstrapped software company founded in 2018 and domiciled in the United States. It operates as a two-person team building a consumer travel-planning application natively for the Apple ecosystem - iPhone, iPad, Mac, and Apple Watch - distributed exclusively through Apple's App Stores. The product centralizes flights, lodging, activities, expenses, and travel documents into a single itinerary, automates ingestion of reservation emails from 700+ providers, delivers real-time flight delay and gate-change alerts, and supports calendar sync, multi-currency expense tracking with CSV export, weather forecasts, and granular trip-sharing with collaborators and view-only guests.
The underlying technology stack is fully native Apple (iOS/iPadOS 18+, macOS 15+, watchOS 10+) with iCloud as the cross-device sync layer and MapKit for map rendering. A custom MCP (Model Context Protocol) server at mcp.tripsy.app exposes trip data to Anthropic's Claude for AI-assisted itinerary reorganization and trip creation. Native importers exist for TripIt (free) and for the now-shuttered TripCase (Pro-gated). Distribution is product-led: freemium model with a generous free tier, paid Pro features offered as a $59/year subscription or a $299 family-shareable lifetime license.
Tripsy serves individual travelers, couples, families, and friend groups - with stated testimonials covering solo trips, four-month European itineraries, and group coordination - primarily targeting Apple users who want an integrated alternative to TripIt and TripCase. The company has no disclosed external funding, no enterprise customers, and concentrates its go-to-market on App Store visibility (4.9-star rating on 3,100+ reviews, Apple editorial feature), word-of-mouth through shareable trip links, and content marketing via its blog. Android and full-featured web versions are publicly listed as waitlists, representing the principal expansion vectors beyond the current Apple-only footprint.
Tripsy firmographics
Firmographics- Name
- Tripsy
- Legal name
- Tripsy LLC
- Website
- https://tripsy.app
- Company type
- Private
- Founded year
- 2018
- Operating status
- Operating
- Headcount range
- 1–10 employees
- Short description
- Tripsy is a bootstrapped two-person company that builds an Apple-only travel planning app (iPhone, iPad, Mac, Apple Watch), centralizing flights, stays, activities, expenses, and documents with email-import automation and a freemium Pro subscription for individual travelers, couples, and families.
- Ownership category
- akta.pro rank
Tripsy industry classification
Industry- Product category
- Travel Planning Software
- NAICS
- Travel Agencies (561510)
- akta.pro primary industry
- Itinerary Management & Trip Collaboration Apps (THALAMAE)
- akta.pro secondary industry
- Online Booking & Reservation Platforms (B2B/B2C) (THALAMAA)
Keywords
Tripsy business model
Business model- GTM type
- B2C
- Offering type
- Software
- Cost components
- Personnel, Technology or R&D, Operations, Marketing or Sales, Infrastructure
Revenue model
- Tripsy Pro Subscription: Freemium model with optional Pro subscription. Free tier includes unlimited trips, cloud sync, unlimited guests, search flights, expenses management, forwarding reservations, advanced travel stats, flight update alerts, document management, calendar feed, weather forecasts, TripIt importer, timezone changes, and data export. Pro features enhance the core travel planning experience.
- Annual Subscription: Annual subscription at $59 per year providing 1-year of Tripsy Pro access with all premium features.
- Lifetime Purchase: One-time lifetime purchase for $299 (one-time) that is shareable with family members, providing permanent Pro access without recurring payments.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Freemium | Free | Free tier with essential travel planning features |
| Subscription | Annual | Annual Pro subscription |
| One time/ perpetual license | Multi-year contract | Lifetime Pro purchase |
| Subscription | Monthly | Monthly Pro subscription (Brazil) |
Go-to-market motion1 record
Distribution channels6 records
Marketing channels6 records
Tripsy product offering
Product offeringCore offering
Tripsy is an all-in-one travel planner mobile application for Apple devices (iPhone, iPad, Mac, and Apple Watch) that organizes flights, stays, activities, expenses, and documents into a single itinerary. The app automatically parses forwarded reservation emails from 700+ providers, delivers real-time flight delay and gate change alerts, syncs with Apple Calendar, supports collaborative trip sharing with guest permissions, and offers AI-powered trip planning via a Claude MCP integration. It is offered on a freemium model with a Tripsy Pro subscription unlocking advanced features such as cloud sync, expense management, and weather forecasts.
Product overview
Tripsy is a unified travel planning platform built primarily for Apple devices (iPhone, iPad, Mac, Apple Watch), with a free core tier and a Pro subscription (available as monthly, annual, or lifetime purchase). The product suite includes the native iOS/macOS app as the central product, supplemented by Tripsy Pro (premium subscription unlocking cloud sync, expenses, flight alerts, calendar feed, weather, and export), the TripCase Importer and TripIt Importer (data migration tools for users switching from competing itinerary apps), the Tripsy + Claude AI integration (MCP-powered natural language trip planning via Anthropic's Claude), and Tripsy Book/Recap (annual travel statistics and summaries). Android and web versions are in development but not yet released.
Differentiator
Problem solved
Functional benefit
Brands
- Tripsy Pro: Premium subscription tier offering unlimited trips, cloud sync, flight updates, expense management, and other advanced features
- Tripsy Book
- Tripsy Recap
Products and services
- Tripsy Travel Planner App All-in-one travel planner native application for iPhone, iPad, Mac, and Apple Watch that organizes flights, stays, activities, expenses, and documents in one place for individual travelers, couples, families, and groups.
Quantifiable outcome
- Flight alerts detected increased by over 100% compared to previous releases with support for most airlines and airports worldwide
- +1 more outcomes
Companies that use Tripsy
Customer profileNamed customers5 records
Segments5 records
Ideal customer profiles3 records
Tripsy technology and API
TechnologyTechnology focussed Yes
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
Integration13 records
AI capability7 records
Feature10 records
Tripsy partnerships and signals
Strategic signalPartnerships
Three partnerships are on record, tiered core.
- TripCasecoreTripCase importer transfers all trips from TripCase to Tripsy before TripCase shutdown on April 1, 2025. Since TripCase did not offer an export function, Tripsy developed their own solution to help users migrate their trips including all activities and details.
- TripItcoreTripIt importer allows Tripsy users to import all their TripIt activities directly into Tripsy, including flights, hotels, car rentals, and activities. Users sign in to TripIt from within Tripsy, allow data fetching, and review imported trips. The integration helps users migrate from TripIt to Tripsy.
- Claude (Anthropic)coreClaude MCP (Model Context Protocol) integration allows users to connect Tripsy to Claude Desktop or Claude Code. Users can ask Claude to reorganize itineraries by location, add activities, discover experiences, handle last-minute changes, and build complete trips through natural conversation. Data stays controlled by the user through MCP connection rather than being sent to external services.
Scale indicators3 records
Recent moves1 record
Expansion highlights5 records
Tripsy competitors and assessment
Company assessmentBroad incumbents
- Skyscanner: Skyscanner is a global flight and travel search platform with itinerary and trip management features layered on top of search. It is a broader incumbent whose trip-planning surfaces overlap with Tripsy at the top of the travel funnel.
- Hopper: Hopper is a broader consumer travel app covering flights, hotels, cars, and price prediction. While its core is booking and pricing rather than itinerary management, it overlaps in the consumer travel-planning journey that Tripsy serves.
- Google Travel: Google Travel consolidates flights, hotels, and itineraries from Gmail confirmations directly into Google services. It competes with Tripsy's core email-parsing-to-itinerary value proposition but as part of a much broader free consumer offering.
Direct peers
- TripIt: TripIt, owned by SAP Concur, is the most-established itinerary management app and the primary direct competitor to Tripsy. Both apps parse confirmation emails into organized itineraries and Tripsy even offers a dedicated TripIt importer to capture switching users.
- Roadtrippers: Roadtrippers is a trip planning app specialized in road trip routing, stops, and discovery. While more focused on driving routes than general travel, it competes in the same consumer trip-planning category as Tripsy.
- Wanderlog: Wanderlog is a cross-platform trip planner app with itinerary building, road trip routing, expense tracking, and collaborative planning. It targets the same consumer travel-planning use case as Tripsy with broader platform availability including web and Android.
- Sygic Travel: Sygic Travel is a trip planner and city map app that helps travelers build itineraries with attractions, routes, and offline access. It competes with Tripsy on itinerary management and map-based trip visualization.
- TripCase (Concur): TripCase was a direct itinerary management competitor to both TripIt and Tripsy before it was discontinued on April 1, 2025. Tripsy's dedicated TripCase importer was built specifically to migrate users from this direct competitor.
- TripHobo: TripHobo is an online itinerary builder that lets travelers create day-by-day trip plans with bookings, maps, and recommendations. It directly overlaps with Tripsy's core itinerary-construction workflow for leisure travelers.
Emerging players
- App in the Air: App in the Air is a flight tracking and travel assistant app with itinerary, status, and miles tracking features. It overlaps with Tripsy on flight-centric itinerary management and real-time flight updates for frequent flyers.
Market position
Strengths5 records
Weaknesses5 records
Competitive moat5 records
Key risks6 records
Key highlights7 records
Customer concentration
Tripsy social profiles
Digital presenceTripsy compliance and trust
Trust signalCompliance2 records
Tripsy financial estimates
Financial estimateRevenue estimate
Valuation estimate
Tripsy leadership team
Management profileNumber of profiles
Tripsy funding detail
Funding detailFunding overview
Funding rounds
Investors
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
Tripsy M&A and investment
M&A and investmentM&A
Investments
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about Tripsy
What does Tripsy do?
Tripsy is an all-in-one travel planner mobile application for Apple devices (iPhone, iPad, Mac, and Apple Watch) that organizes flights, stays, activities, expenses, and documents into a single itinerary. The app automatically parses forwarded reservation emails from 700+ providers, delivers real-time flight delay and gate change alerts, syncs with Apple Calendar, supports collaborative trip sharing with guest permissions, and offers AI-powered trip planning via a Claude MCP integration. It is offered on a freemium model with a Tripsy Pro subscription unlocking advanced features such as cloud sync, expense management, and weather forecasts.
Is Tripsy a public or private company?
Tripsy is a private company. It is classified as founder individual operated bootstrapped and is currently operating.
When was Tripsy founded?
Tripsy was founded in 2018. It employs 1 to 10 people.
How does Tripsy make money?
Three revenue lines are on record. Tripsy Pro Subscription is the primary driver. The others are annual Subscription and lifetime Purchase.
Who are Tripsy's main competitors?
Broad incumbents on record are Skyscanner, Hopper and Google Travel. Direct peers are TripIt, Roadtrippers, Wanderlog, Sygic Travel, TripCase (Concur) and TripHobo. App in the Air is listed as an emerging player.
Does Tripsy have an API?
No public API is recorded for Tripsy.
What industry is Tripsy in?
Tripsy's product category is Travel Planning Software. Its primary akta.pro industry code is THALAMAE, Itinerary Management & Trip Collaboration Apps, with a secondary code of THALAMAA, Online Booking & Reservation Platforms (B2B/B2C). Its NAICS code is 561510.