Winston AI

Conversational-First Interface

Built around a natural chat interface where users can ask questions, search for travel options, plan trips, and manage tasks simply by describing what they need. Rather than forcing users into rigid workflows, Winston adapts to how people naturally communicate — making planning faster and less stressful.

End-to-End Trip Planning

Create trips with destinations, dates, and budgets. Organize flights, lodging, meals, activities, and transportation into day-by-day itineraries. Store confirmation numbers, booking details, and documents. Track spending against your budget — all manageable through conversation or direct interaction.

Calendar-Aware Coordination

Integrates travel and daily schedules into a single view. Upcoming trips appear alongside personal events, daily schedules provide context such as location and timing, and users can quickly check what's coming up without digging through multiple apps — acting as a daily organizer that understands time, place, and commitments.

Memory-Driven Personalization

Remembers personal preferences like seating and food choices, important facts and dates, habits and frequently visited places, and favorites such as restaurants, airlines, or hotels. Users never need to repeat themselves — over time, Winston becomes more personalized, improving recommendations and decisions automatically.

Group Coordination & Expense Splitting

Plan with others through shared trips, group decision-making polls, and automatic expense tracking with cost splitting. Clear settlement summaries show who owes what — reducing friction when coordinating travel or activities with friends and family.

Alerts, Reminders & Real-Time Awareness

Price monitoring for travel-related items, reminders for upcoming plans, and notifications about changes or important updates — all in a centralized notification history. Focused on relevance, not constant interruptions.

Voice-First Interaction

For moments when typing isn't convenient, Winston supports full voice interaction. Speak naturally to ask questions or make plans, receive spoken responses alongside text, and seamlessly switch between voice and chat — useful while commuting, traveling, or multitasking.

Human, Calm & Trustworthy

Intentionally designed as a helpful companion, not a noisy chatbot. Every suggestion is transparent and explainable, personal preferences and boundaries are respected, and the experience is built for long-term usefulness — helping users stay organized, confident, and prepared without adding cognitive load.

Winston AI is an intelligent personal assistant that handles trip planning, schedule management, group coordination, expense splitting, personalized recommendations, price alerts, and daily organization — all through natural conversation. Instead of juggling multiple apps, you describe what you need and Winston handles the rest.

You can create trips with destinations, dates, and budgets — either through the trip interface or simply by telling Winston in conversation. It organizes flights, lodging, meals, activities, and transportation into day-by-day itineraries, stores confirmation numbers and documents, and tracks spending against your budget.

Yes. Winston remembers personal preferences like seating and food choices, important facts and dates, habits and frequently visited places, and favorites such as restaurants, airlines, or hotels. You never need to repeat yourself — over time, Winston becomes more personalized and improves its recommendations automatically.

Winston supports shared trip planning with friends and family. Create groups, share invite codes, track shared expenses with automatic cost splitting, and use polls for group decisions on dates, destinations, and activities. Clear settlement summaries show who owes what — reducing friction when coordinating with multiple people.

Yes. Winston shows upcoming trips alongside personal events in a single calendar view. Daily schedules provide context on location and timing, so you can quickly check what's coming up without switching between apps — acting as a daily organizer that understands your time, place, and commitments.

Yes. Winston supports full voice interaction — speak naturally to ask questions, make plans, or manage tasks, and receive spoken responses alongside text. You can seamlessly switch between voice and chat, making Winston useful while commuting, traveling, or multitasking.

Yes. You can set price alerts to monitor flights and hotels to your favorite destinations. Winston notifies you when prices drop below your target, and monitors multiple routes simultaneously — so you never miss a deal.

When traveling with a group, you can add shared expenses as you go. Winston automatically calculates who owes what and provides clear settlement summaries — eliminating the awkward math and follow-up conversations after a trip.

No. Winston is intentionally designed as a helpful companion, not a noisy chatbot. Every suggestion is transparent and explainable, personal preferences and boundaries are respected, and the experience focuses on long-term usefulness — helping you stay organized, confident, and prepared without adding cognitive load.

Winston sends price drop alerts, trip reminders, flight status updates, group activity notifications, and calendar reminders — all in a centralized notification history. The focus is on relevance, not constant interruptions.

Winston AI is available on iOS and Android, putting a personal concierge in your pocket that handles trip planning, schedule management, group coordination, and daily organization from anywhere.

Winston AI is built for anyone who wants to plan trips, stay organized, and coordinate with others without juggling multiple apps. Whether you are a frequent traveler, a busy professional managing a packed schedule, or someone planning a group vacation with friends, Winston handles the logistics so you can focus on living.