AI Prompts for Claude for Travel

Before I start researching destinations, help me get clear on what I actually want from this trip. Ask me a series of questions that help me articulate: what I am hoping to feel or experience, what I am trying to escape or reset from, what kind of pace I want, what has worked in past trips and what has not, and what constraints I am working within. I will answer each question honestly: [BEGIN]. Then give me a one-paragraph brief that captures what the right trip looks like for me, which I can use to evaluate any destination against.

I am considering a trip to [DESTINATION]. Help me evaluate it honestly against my actual priorities rather than its general reputation. My priorities for this trip are: [LIST IN ORDER: E.G. GENUINE CULTURAL IMMERSION, GOOD FOOD AND WINE, MANAGEABLE CROWDS, WARM WEATHER, WITHIN BUDGET, EASE OF GETTING AROUND]. For each priority, tell me honestly how [DESTINATION] scores and where it might disappoint someone with my expectations. Then give me your honest assessment of whether this is the right destination for what I am after, or whether I should consider an alternative.

I am planning a trip to [DESTINATION] and trying to decide when to go. The timing options I am considering are: [LIST MONTHS OR SEASONS]. Help me think through the trade-offs of each timing. What is the weather like in each period? How do crowds, prices, and the local atmosphere change across the year? What is the best and worst case for each option? What would most affect the quality of the specific experiences I want, which are: [DESCRIBE]? Give me a clear recommendation with the reasoning.

I am trying to choose between two quite different trip options. Option A: [DESCRIBE: E.G. TWO WEEKS IN JAPAN]. Option B: [DESCRIBE: E.G. A ROAD TRIP THROUGH SOUTHERN EUROPE]. Here is my situation: I have [X DAYS] and a budget of roughly [AMOUNT]. I am travelling [DESCRIBE WHO WITH]. What I most want from this trip: [DESCRIBE]. What I most want to avoid: [DESCRIBE]. Help me think through both options honestly. What am I likely underestimating about each? Which fits what I have described better, and why? Give me a recommendation I can commit to.

I have a trip plan I am about to book and I want to pressure-test it before I commit money. Here is the plan: [DESCRIBE: DESTINATION, DURATION, ROUGH ITINERARY, WHO WITH, BUDGET]. What are the most likely ways this trip disappoints? What am I probably assuming that might not hold? Are there any logistical issues with how I have planned this that I should fix before booking? Tell me the 3-4 things most likely to go wrong and what I should change or put in place to mitigate each one.

I want an itinerary for [X DAYS] in [DESTINATION] that is designed specifically for how I travel. Here is how I actually travel: [DESCRIBE HONESTLY: E.G. I LIKE SLOW MORNINGS, I EXPLORE BETTER ON FOOT, I CARE MORE ABOUT EATING WELL THAN SEEING SIGHTS, I HATE QUEUING, I LIKE TO FIND THINGS SPONTANEOUSLY RATHER THAN FOLLOW A STRICT PLAN]. Build me an itinerary that reflects this rather than a standard tourist version. Structure it around days with a clear anchor or two rather than a packed schedule, and leave room for the kind of exploration I actually enjoy.

I am planning a solo trip to [DESTINATION] for [X DAYS]. Help me plan it in a way that takes advantage of travelling alone rather than just treating it as a paired trip minus a companion. What are the genuine advantages of solo travel in this specific destination? What experiences are better done alone? What should I plan around the natural rhythms of solo travel such as flexibility, meeting people, and being open to change? Build me a solo-optimised itinerary with specific suggestions.

I am travelling with [DESCRIBE: E.G. MY PARTNER, A FRIEND, FAMILY MEMBER] who has a different travel style from me. My travel style: [DESCRIBE]. Their travel style: [DESCRIBE]. Our shared interests: [DESCRIBE]. Our potential conflict points: [DESCRIBE]. Help me design a trip structure that genuinely works for both of us rather than one person compromising the whole time. What principles should guide how we plan? How should we split the day or certain days? Build me a rough itinerary structure that balances both travel styles.

I want a trip that has enough structure to be efficient but enough flexibility that it does not feel like a schedule to execute. I am going to [DESTINATION] for [X DAYS]. My past trips have tended to be too [RIGID / UNPLANNED] and I want to correct for that. Help me design a trip framework that: locks in the things that genuinely need advance planning, keeps certain days or sessions completely open, and gives me decision frameworks for the spontaneous moments rather than just a blank space. Tell me specifically what to book in advance and what to leave open.

I want to combine [GOAL A: E.G. COMPLETE RELAXATION] with [GOAL B: E.G. CULTURAL EXPLORATION] in one trip to [DESTINATION OR REGION]. My trip is [X DAYS]. These two goals often pull against each other and I want to do both properly rather than neither. Help me design a trip structure that genuinely honours both goals: how to split the time, which part to do first and why, and how to transition between modes without one undermining the other. Give me a specific itinerary framework that makes this combination work.

I am planning a trip to [DESTINATION] in [MONTH/SEASON] and trying to decide how much to book in advance versus keep flexible. The things I am considering booking in advance: [LIST]. The things I am tempted to leave open: [LIST]. My travel style leans toward [PLANNING AHEAD / STAYING FLEXIBLE]. Help me think through the trade-offs for this specific destination and time of year. What genuinely needs advance booking to avoid disappointment? What is better left flexible? Give me a clear booking strategy rather than a generic answer.

I am staying in [DESTINATION] for [X NIGHTS] and trying to decide on the right type of accommodation. The options I am considering: [LIST: E.G. CENTRAL HOTEL, APARTMENT RENTAL, BOUTIQUE GUESTHOUSE, RESORT]. My priorities: [LIST: E.G. LOCATION, FLEXIBILITY WITH CHECK-IN, HAVING A KITCHEN, CHARACTER, VALUE FOR MONEY, FEELING IMMERSED IN THE LOCAL AREA]. Help me think through which accommodation type suits this specific trip and my priorities. Then tell me what to look for when choosing a specific property.

I am travelling to [DESTINATION] for [X DAYS] and trying to decide whether travel insurance is worth buying. My trip details: total cost including flights and accommodation roughly [AMOUNT], type of activities planned [DESCRIBE], any pre-existing health considerations [DESCRIBE IF COMFORTABLE], my home country's reciprocal healthcare coverage in this destination [DESCRIBE IF KNOWN]. Help me think through the actual risk-reward calculation for my specific situation and give me a clear recommendation on whether to buy it, and if so, what level of cover actually matters.

I am planning an extended trip of [X WEEKS/MONTHS] and want to avoid the burnout that often hits long travellers. My planned route or destinations: [DESCRIBE]. My past experience with long trips: [DESCRIBE IF ANY]. The things that tend to drain me on the road: [DESCRIBE]. Help me design a trip pace and structure that builds in the recovery, routine, and slower periods that make a long trip sustainable rather than exhausting. What are the common mistakes people make on long trips, and how do I build the antidotes into my plan from the start?

My trip plan has become too ambitious for the time I have. Here is what I originally planned: [DESCRIBE FULL ITINERARY]. Here is the time I actually have: [X DAYS]. Help me cut this down to something that is genuinely enjoyable rather than a rushed version of everything. Tell me your honest assessment of what to cut and what to keep. What can wait for another trip? What would I regret missing most? Design a tighter version of this itinerary that does fewer things properly rather than many things poorly.

I am visiting [DESTINATION] and food is one of my main priorities. Help me find genuine food experiences rather than tourist-trap versions. What are the dishes most specific to this region that are worth going out of my way for? Where do locals actually eat versus where they send tourists? Are there any food markets, specific neighbourhoods, or dining traditions I should build my days around? Give me specific enough guidance that I can actually find great food independently without relying on a bookings app.

I have [X DAYS] in [DESTINATION OR CITY] and I want to go deep in a smaller area rather than try to cover everything. I am most interested in: [DESCRIBE YOUR SPECIFIC INTERESTS: E.G. A PARTICULAR NEIGHBOURHOOD, A HISTORICAL PERIOD, A LOCAL ART SCENE, A FOOD TRADITION]. Help me design an experience around this specific focus that a typical tourist would miss entirely. What would a true enthusiast for this interest do with the same time? Give me a focused plan built around genuine depth.

I want this trip to [DESTINATION] to feel genuinely connected to the place rather than a surface-level tourist experience. I am not interested in staged cultural experiences. What are the practical ways a visitor can have real interactions with locals and develop a genuine feel for how life works here? Consider: where to shop, eat, and spend time like a resident, any community activities or local events worth seeking out, and how to approach conversations with people in this specific culture without being awkward or intrusive.

I have just returned from [DESTINATION] and want to reflect on the trip properly while it is still fresh. Help me run a travel retrospective. Ask me questions across: the best and most surprising moments, what did not live up to expectations and why, what I would do differently, what I learned about how I travel, and what I want to do or see next based on what this trip sparked. I will answer each: [BEGIN]. Then help me capture the key insights I should carry into how I plan future trips.

I am planning a trip to [DESTINATION] for [X DAYS] and I want to use the time away to make genuine progress on [GOAL: E.G. WRITING A BOOK, MAKING A CAREER DECISION, RECOVERING FROM BURNOUT, DEVELOPING A CREATIVE PRACTICE, THINKING THROUGH A MAJOR LIFE DECISION]. Help me design the trip so that the time and context actively support this goal, rather than just being a holiday where the goal gets squeezed in at the margins. What does the daily structure look like? What conditions should I create? What should I protect and what should I let go of for this to work?