Vacation Planner vs TripIt: Which Trip Organizer Wins in 2026?

If you have spent any time researching trip planning apps, two names keep coming up: Vacation Planner and TripIt. Both promise to bring order to the chaos of travel logistics, but they approach the problem from fundamentally different angles. TripIt, owned by SAP Concur since 2012, has built its reputation around passive trip organization, forwarding confirmation emails and letting the app assemble your itinerary automatically. Vacation Planner, on the other hand, is an AI-powered planning tool where an AI vacation expert helps you design the perfect personalised trip.

So which one actually deserves a spot on your phone or browser? In this head-to-head comparison, we break down every major feature category so you can make an informed decision before your next trip.

Quick Overview

Before we get into the details, here is a snapshot of what each app brings to the table.

TripIt has been around for over a decade and is a go-to for frequent business travelers. Its core strength is aggregating reservations from confirmation emails into a single, clean timeline. The Pro tier ($49.99 per year) adds real-time flight alerts, alternative flight suggestions during delays, fare monitoring, and seat tracking. It is available on web, iOS, and Android.

Vacation Planner is a newer, web-based platform powered by an AI vacation planning expert. It gives you personalised itinerary generation, a drag-and-drop itinerary builder, real-time budget tracking, and the ability to share itineraries with travel companions. The free plan covers core features, while the paid plan adds email sync for automatic booking imports. You can start planning at vacation-planner.app.

The key distinction is philosophical. TripIt organizes trips that are already booked. Vacation Planner helps you plan trips from scratch and manage them through execution.

Feature Comparison Table

Feature	Vacation Planner	TripIt (Free)	TripIt Pro ($49.99/yr)
AI planning	AI vacation expert	Not available	Not available
Itinerary builder	Drag-and-drop, fully editable	Manual entry through menus	Manual entry through menus
Reservation import	Email sync (paid plan)	Email forwarding to plans@tripit.com	Email forwarding + auto-import
Budget tracking	Real-time, category-based	Not available	Not available
Sharing	Share itineraries	View-only sharing	View-only sharing
Flight alerts	Not available	Not available	Real-time alerts
Alternative flights	Not available	Not available	Delay/cancellation suggestions
Fare monitoring	Not available	Not available	Price drop alerts
Carbon footprint	Not available	Not available	Per-flight tracking
Airport maps	Not available	Basic	Detailed terminal maps
Platforms	Web	Web, iOS, Android	Web, iOS, Android
Price	Free + Paid plan	Free	$49.99/year

Both apps have genuine strengths. The question is which strengths matter most for the kind of travel you do. Let us walk through each category.

Itinerary Building

This is the area where the two apps diverge most sharply.

Vacation Planner treats itinerary building as the core experience, powered by an AI vacation planning expert. Tell the AI your preferences, budget, and interests, and it generates a personalised day-by-day itinerary. From there, you can fine-tune everything using a clean drag-and-drop interface. Want to swap your museum visit from Tuesday morning to Wednesday afternoon? Just drag it. Need to restructure your entire second day because you found a better restaurant? Rearranging takes seconds. The combination of AI-generated plans and manual control gives you the best of both worlds.

TripIt takes a different approach. Its itinerary is primarily assembled from imported reservations: flights, hotels, car rentals, and restaurant bookings get pulled in from confirmation emails and arranged chronologically. If you want to add an activity that does not have a confirmation email (say, a hike or a visit to a free museum), you need to enter it manually through a series of form fields and dropdown menus. This process works, but it is noticeably slower and less intuitive than a drag-and-drop interface. TripIt was designed to organize what you have already booked, not to help you plan what you want to do.

Winner: Vacation Planner. If you want a tool that helps you actively design and rearrange your trip, Vacation Planner is the clear choice. TripIt’s itinerary is better thought of as a timeline of confirmations.

Reservation Management

Here is where TripIt genuinely shines.

TripIt has perfected the art of reservation import. You forward any travel confirmation email to plans@tripit.com, and the app parses the details (flight numbers, hotel addresses, check-in times, confirmation codes) and slots them into your itinerary automatically. It handles airlines, hotels, rental car companies, restaurants, and even concert tickets. For frequent travelers who receive dozens of confirmation emails per trip, this is a massive time saver. TripIt Pro takes it further with automatic email scanning if you connect your inbox.

Vacation Planner offers email sync on its paid plan, which automatically reads your booking confirmation emails and imports the details into your itinerary. On the free plan, you add bookings manually, though the drag-and-drop interface makes manual entry faster and more flexible than TripIt’s form-based approach.

Winner: TripIt still has the edge here with its long-established and highly refined email parsing system. However, Vacation Planner’s paid-plan email sync is a solid alternative that narrows the gap considerably.

Budget Tracking

Money management can make or break a trip, and the two apps handle it very differently.

Vacation Planner includes a full-featured budget tracker at no extra cost. You set an overall trip budget and break it down into categories: flights, accommodation, food, activities, transportation, and miscellaneous expenses. As you add items to your itinerary, you assign costs and the budget updates in real time. You can see at a glance how much you have allocated, how much you have spent, and how much room you have left. For group trips, every collaborator can see the same budget view, which makes splitting costs and staying on target much easier.

TripIt does not include any budgeting features. Not in the free version, not in Pro. If you want to track your trip spending alongside your TripIt itinerary, you need a separate app. This is a significant gap for leisure travelers and anyone planning a trip with a fixed budget.

Winner: Vacation Planner. Built-in budget tracking is a core feature, not an add-on, and TripIt simply does not compete here.

Group Collaboration

Planning a trip with friends, family, or coworkers adds a layer of coordination that solo travel does not require. The collaboration tools in your trip planner matter.

Vacation Planner lets you share your itineraries with travel companions so everyone can see the full plan, including activities, accommodation details, and schedule. The AI vacation expert helps you build a comprehensive itinerary that you can then share with your group, keeping everyone informed without the chaos of group chats and screenshot exchanges.

TripIt also offers trip sharing with a view-only model. You can share your itinerary with travel companions so they can see the schedule, but they cannot edit it. For business travel, where one person typically owns the itinerary, this is fine. For group leisure trips, it means everyone depends on one person to make changes.

Winner: Tie. Both apps offer itinerary sharing rather than full collaborative editing. Vacation Planner’s AI-generated itineraries give it a slight edge; the AI does the planning work, and everyone else just needs to view the result.

Flight and Travel Alerts

This is TripIt Pro’s marquee feature set, and it is worth examining in detail.

TripIt Pro ($49.99 per year) offers real-time flight alerts that notify you of gate changes, delays, and cancellations as they happen. If your flight is delayed or canceled, TripIt Pro suggests alternative flights on the same airline and sometimes on competitors, helping you rebook faster. It also includes fare monitoring. If you have booked a flight, TripIt Pro tracks the price and alerts you if the fare drops so you can request a refund or credit. Additional travel intelligence includes detailed airport terminal maps, baggage claim carousel information, and carbon footprint tracking for each flight.

Vacation Planner does not currently offer flight tracking, real-time alerts, or fare monitoring. These features fall outside its core focus on trip planning and collaboration.

Winner: TripIt Pro. If you fly frequently and want proactive flight intelligence, TripIt Pro delivers features that no free tool matches. This is the strongest reason to consider TripIt, especially for business travelers.

Pricing and Value

Price is always a factor, and the gap between these two apps is significant.

Vacation Planner offers a generous free plan that includes the AI vacation planning expert, itinerary builder, budget tracking, and itinerary sharing. The paid plan adds email sync, which automatically reads booking confirmation emails and imports details into your itinerary, a major convenience for trips with multiple bookings.

TripIt Free gives you reservation import, basic itinerary viewing, and view-only sharing. It is a capable tool for solo travelers who just want their confirmations in one place.

TripIt Pro costs $49.99 per year and adds real-time flight alerts, alternative flight suggestions, fare monitoring, airport maps, seat tracking, and carbon footprint data. These are genuinely useful features for frequent flyers, but the price adds up. That is roughly $250 over five years for features that primarily benefit people who fly regularly.

For the majority of travelers planning one to four trips per year, Vacation Planner’s free plan delivers more planning functionality, especially AI-powered itinerary generation, than TripIt’s free tier. TripIt Pro’s value proposition is strongest for road warriors who fly weekly and need real-time flight intelligence.

Winner: Vacation Planner. A generous free plan with AI planning, plus an affordable paid upgrade for email sync, covers more planning use cases than TripIt’s free tier.

Which Should You Choose?

The honest answer depends on how you travel and what you need from a trip organizer.

Choose Vacation Planner if:

• You want an AI vacation expert to create personalised itineraries tailored to your preferences
• You want to share itineraries with travel companions easily
• Budget tracking is important to you and you do not want to use a separate app
• You want a generous free plan with core planning features and AI assistance
• You value a clean, modern interface with drag-and-drop functionality
• You primarily plan leisure travel: vacations, weekend trips, family holidays

Choose TripIt if:

• You are a frequent business traveler who needs real-time flight alerts and rebooking assistance
• You receive dozens of confirmation emails per trip and want them auto-organized
• You want airport terminal maps and baggage claim information at your fingertips
• You fly often enough that fare monitoring and alternative flight suggestions justify $49.99 per year
• You need a native mobile app on iOS or Android (Vacation Planner is currently web-only)

The Verdict

For most leisure travelers, Vacation Planner is the better choice. Its AI vacation expert covers the full planning lifecycle, from generating personalised itineraries based on your preferences to building a day-by-day plan, tracking your budget, and sharing the result with travel companions. The generous free plan makes it easy to get started, and the paid plan adds email sync for automatic booking imports.

TripIt remains an excellent tool for its specific niche: frequent flyers and business travelers who need passive trip organization built around confirmation emails and real-time flight data. If that describes you, TripIt Pro is worth the annual subscription.

But if you are looking for a tool that helps you plan a trip rather than just organize one, Vacation Planner is the stronger option in 2026.

Frequently Asked Questions

Is Vacation Planner free to use?

Vacation Planner offers a generous free plan that includes the AI vacation planning expert, itinerary builder, budget tracking, and itinerary sharing. There is also a paid plan that adds email sync for automatically importing booking confirmations from your inbox.

Can I use TripIt without paying for Pro?

You can. TripIt’s free version handles reservation import via email forwarding and gives you a basic itinerary timeline. However, features like real-time flight alerts, fare monitoring, alternative flight suggestions, and detailed airport maps are exclusive to TripIt Pro at $49.99 per year.

Does Vacation Planner have a mobile app?

Vacation Planner is currently a web-based application, which means you access it through your browser on any device. There is no native iOS or Android app at this time. The web app is mobile-responsive, so it works well on phones and tablets. TripIt offers native apps on both iOS and Android.

Can I import my TripIt itinerary into Vacation Planner?

There is no direct import feature between the two apps. However, you can use Vacation Planner’s AI expert to generate a fresh personalised itinerary for your destination, which also gives you the opportunity to add budget tracking and share the plan with travel companions, features TripIt does not offer.

Which app is better for group trips?

Both apps offer itinerary sharing rather than full collaborative editing. Vacation Planner lets you share your AI-generated itinerary with travel companions, while TripIt offers view-only sharing of its booking-based timeline. Vacation Planner has the edge for group leisure travel because the AI expert creates comprehensive, personalised plans that you can share with your group.

Does TripIt track expenses or help with budgeting?

No. TripIt does not include any budget tracking or expense management features in either the free or Pro version. If budgeting is important to your trip planning process, you would need to use a separate app alongside TripIt. Vacation Planner includes real-time budget tracking on its free plan.

Is TripIt Pro worth $49.99 per year?

It depends on how often you fly. If you are a frequent flyer or business traveler who takes multiple flights per month, TripIt Pro’s real-time alerts, alternative flight suggestions, and fare monitoring can save you significant time and money. For occasional leisure travelers taking a few trips per year, the free version of TripIt or a comprehensive free tool like Vacation Planner is likely a better fit.

Can I use both apps together?

Absolutely. Some travelers use TripIt to aggregate confirmation emails and track flights, then use Vacation Planner’s AI expert for the planning work, generating a personalised itinerary, managing the budget, and sharing the plan with travel companions. The two tools complement each other well since they focus on different aspects of the travel experience.