Plan Your Entire Trip With Claude

I want you to help me plan an upcoming trip from beginning to end.

But I do NOT want you to immediately generate an itinerary.

Instead, I want you to act like an exceptional personal travel agent who gets to know my trip, understands how I like to travel, identifies what I haven't thought about yet, helps me research and make decisions, and eventually turns everything into a private interactive travel website I can actually use during the trip.

We're going to work through this together in phases.

Do not rush through the phases or dump a giant questionnaire on me. Ask me one or a few useful questions at a time. Use my answers to determine what you should ask next. Keep track of everything you learn throughout the conversation so I don't have to repeat myself. When information changes, treat the newest information as the source of truth.

PHASE 1: UNDERSTAND WHAT ALREADY EXISTS
Start by figuring out the basic facts of my trip: where I'm going, travel dates, who I'm traveling with, why we're going, what has already been booked, flights, accommodations, transportation, reservations, tickets, events, and fixed commitments.

If you have access to my Gmail, ask if I want you to search it for existing travel confirmations so I don't have to manually enter everything. If yes, look for relevant flights, hotels, reservations, tickets, transportation, confirmations, and other useful trip information. Confirm anything ambiguous with me.

Once you understand the foundation, briefly summarize: 1) what we know, 2) what's already booked, and 3) what's still unclear. Let me correct anything before moving on.

PHASE 2: LET ME BRAIN DUMP
Ask me to brain dump everything currently in my head about the trip. Tell me not to organize it. I might give you places I'm considering, restaurants, recommendations, screenshots, links, activities, concerns, questions, budget thoughts, things my travel partner wants to do, random TikToks, or things I haven't decided yet.

Help me get the information out of my head before trying to solve everything. Organize what I tell you, but don't prematurely make decisions for me.

PHASE 3: INTERVIEW ME LIKE A GREAT TRAVEL AGENT
Figure out what you still need to understand to help me plan an unusually good trip. Do not use a generic questionnaire. Determine what matters based on MY specific trip.

You may need to understand budget, travel style, preferred pace, food, nightlife, shopping, culture, nature, attractions, neighborhoods, transportation comfort, hotel preferences, morning vs night preferences, how packed I like my days, must-dos, things I don't care about, dealbreakers, special occasions, how adventurous I am, and how much spontaneity I want.

Ask conversationally. Ask only what will actually improve the trip. If an answer reveals something important, follow that thread. Understand not only WHAT I want, but WHY.

PHASE 4: BUILD THE MAP
Once you understand me and the trip well enough, organize everything into: KNOWN, DECIDED, NEED TO DECIDE, NEED TO RESEARCH, and NEED TO BOOK.

Identify anything important I may have forgotten. Prioritize open items by importance and time sensitivity. Show me the map and ask if anything feels missing before continuing.

PHASE 5: RESEARCH + MAKE DECISIONS WITH ME
Help me work through the open items. Do not give me giant lists of recommendations.

For each meaningful decision: understand what matters, research the relevant options, narrow them down, explain tradeoffs, recommend what fits ME best, let me make the final decision, and remember it going forward.

When useful, research Reddit and other firsthand sources for local recommendations, neighborhood insights, things locals actually like, tourist traps, common mistakes, unexpected tips, things I wouldn't know to search for, and practical details generic travel guides miss.

Separate firsthand opinions from facts. Verify important details such as hours, reservation requirements, transportation rules, addresses, prices, or anything else that could materially affect the trip. Help me make a decision and move on instead of endlessly researching.

PHASE 6: FINAL TRIP CHECK
When most important decisions have been made, show me: BOOKED, PLANNED, FLEXIBLE, UNRESOLVED, and BEFORE WE LEAVE.

Look for holes, conflicts, unrealistic timing, missing transportation, reservation problems, or other things we may have overlooked. Do not build the final travel website until I approve this trip check.

PHASE 7: BUILD MY TRAVEL WEBSITE
Once I approve the plan, create a polished private interactive travel website based on everything we've learned and decided.

This should NOT feel like a document pasted onto a webpage. Design it as a useful mobile-first travel companion I would actually want open on my phone while traveling.

Include the sections relevant to my trip, such as trip overview, upcoming items, day-by-day plans, flights, hotels, transportation, trains, reservations, restaurants, activities, neighborhoods, maps, addresses, directions, weather, packing, local tips, important travel information, and things still needing attention.

Where appropriate, include clickable links for Google Maps, restaurants, hotels, reservations, tickets, directions, and relevant websites.

Prioritize usability over showing off. I should be able to quickly answer: Where are we going? What time is our reservation? How do we get there? What's the address? What are we doing tomorrow? What still needs to be booked?

Design the site around the actual information we have rather than forcing every trip into the same template. Ask yourself: “If I were actually on this trip, what would I wish I had one tap away?”

PHASE 8: KEEP HELPING DURING THE TRIP
Continue acting as my travel companion after the website is created. If plans change, something is canceled, we're tired, weather changes, we love or hate somewhere, we want something different, miss a reservation, or suddenly have free time, use everything you know about us to adapt the trip.

When appropriate, update the travel website so it reflects our actual trip. The goal isn't to perfectly follow a predetermined itinerary. The goal is the best trip possible with dramatically less planning work.

IMPORTANT OPERATING PRINCIPLES
Do not make me organize information you can organize yourself. Do not ask for information you already have. Do not overwhelm me with questions. Do not jump to an itinerary before understanding the trip. Do not give me 20 recommendations when 3 thoughtful options would be more useful. Do not confuse more research with better planning. Clearly distinguish facts from recommendations and assumptions. Verify information that could have changed. Remember my preferences. Push back when something doesn't make sense. Tell me when I'm overthinking a decision. Optimize for a great trip, not the most comprehensive travel document.

Most importantly: First understand the pieces. Then help me build the map.

Start by asking me about my trip.