Travel Planning

Airport-Specific Guidance

Provide context based on the airport:

Large/Complex Airports (require more buffer time):

• LAX, JFK, ORD, ATL, DFW, LHR, CDG - add 15-30min to connection estimates
• Note: Multiple terminals often require train/shuttle transfers

Medium Airports:

• Most US hubs - standard timing usually sufficient

Small Airports:

• Regional airports - connections typically easier, less walking

Key Information to Extract

From any flight itinerary, identify and highlight:

1. Departure time and airport/terminal/gate
2. Arrival time and airport/terminal (with time zone conversion)
3. Layover duration (calculate precisely, accounting for time zones)
4. Terminal changes (requires extra time)
5. International connections (customs/immigration time needed)
6. Airline changes (may need to re-check bags, different terminals)
7. Overnight connections (hotel needed)

Pre-Departure Checklist

Generate based on specific trip:

• Check-in timing: 2-3 hours domestic without PreCheck, 3-4 hours international
• Security considerations: PreCheck status, liquids rules, electronics
• Baggage strategy: Check vs carry-on based on connection times
• Documentation: Passport, visa, boarding passes
• Special items: Medical devices, batteries (carry-on only), restricted items

Day-Of Execution Guidance

When user is at airport or encountering issues:

• Delayed first flight: Calculate impact on connections, suggest proactive rebooking
• Missed connection: Explain airline obligations, rebooking process, hotel vouchers
• Gate changes: Help navigate to new gate quickly
• Security wait times: Estimate based on time of day and airport size

Road Trip vs Flying Analysis

When to Recommend Driving

Consider road trip when:

• Distance < 300 miles: Usually faster door-to-door when accounting for airport time
• 300-500 miles: Competitive if traveling with family/group or lots of luggage
• Multiple destinations: Road trip allows flexibility for stops
• Remote destinations: Poor flight options or expensive regional flights
• Travel party size: 3+ people can make driving more economical

Factors to Calculate

• Driving time: Distance ÷ average speed (typically 60mph highway, 40mph mixed)
• Flight time: Flight duration + airport arrival (2hrs) + transit to/from airports + layovers
• Cost comparison:
  • Driving: (miles ÷ MPG × gas price) + tolls + parking
  • Flying: Tickets × passengers + baggage fees + airport parking/rideshare
• Flexibility: Road trips allow spontaneous stops, schedule changes
• Fatigue: Long drives (6+ hours) can be exhausting; consider overnight stops

TSA and Customs Rules Quick Reference

Carry-On Restrictions

• Liquids: 3.4oz (100ml) containers in 1 quart-sized bag
• Electronics: Laptops, tablets must be removed for screening (unless PreCheck)
• Batteries: Lithium batteries, vapes, power banks MUST be in carry-on (fire hazard in checked bags)
• Sharp objects: No knives, scissors >4 inches, tools
• Prohibited: Firearms (without proper declaration), explosives, flammable items

Checked Bag Rules

• Weight limits: Typically 50lbs (23kg), fees for overweight
• Size limits: 62 linear inches (length + width + height)
• Prohibited: Lithium batteries, vapes, flammable items, compressed gases
• Valuables: Don't check electronics, jewelry, medications, documents

International Travel

• Passport validity: Many countries require 6 months validity beyond travel dates
• Visas: Check requirements for destination country
• Customs declarations: Must declare items over duty-free limits
• Agricultural restrictions: Many countries prohibit fresh foods, plants

Mode 2: Local Shopping Discovery

When to Use

• Finding authentic local products and makers
• Avoiding tourist traps
• Understanding quality indicators
• Brand comparisons
• Price expectations

Authentic vs Tourist Trap Detection

Red Flags for Tourist Traps

• Located in high-traffic tourist areas (airports, cruise terminals, hotel gift shops)
• "Hawaiian Made" stickers on items clearly mass-produced overseas
• Identical inventory across multiple shops
• Pushy sales tactics or pressure to buy
• Prices seem too cheap for claimed quality (e.g., "solid koa ukulele $150")
• No information about maker/origin
• Accepts only cash with no receipts or clear pricing (harder to dispute charges or return items)

Green Flags for Authentic Local Makers

• Located in residential/local neighborhoods, not tourist zones
• Staff can explain maker's background, process, materials
• Items show individual variation (hand-made vs factory)
• Reasonable prices reflecting actual craftsmanship
• Established reputation, reviews from locals
• Maker information visible (name, location, story)
• Willing to show workshop or explain process

Product Category Guidelines

Musical Instruments (e.g., Ukuleles)

What to look for:

• Solid wood vs laminate (look inside sound hole - solid wood grain continues through)
• Local wood species (koa for Hawaii, maple for other regions)
• Hand-made details (smooth frets, tight joints, quality tuners)
• Brand reputation (research the "Big 4" or equivalent for region)
• Setup quality (plays in tune up the neck, comfortable action)

Price expectations:

• Entry-level solid wood: $300-600
• Mid-range local maker: $600-1200
• High-end artisan: $1200-3000+
• If it seems too cheap, it probably is

Questions to ask:

• Where was this made?
• Is this solid wood or laminate?
• Who is the luthier/maker?
• What's the wood species?
• What's your return policy?

Art and Crafts

What to look for:

• Artist signature or maker's mark
• Certificate of authenticity for expensive pieces
• Traditional techniques vs modern reproductions
• Local materials and motifs
• Gallery representation vs street vendor

Food and Consumables

What to look for:

• Made in [region] on packaging
• Small batch vs mass-produced
• Local ingredients
• Appropriate pricing (artisan honey costs more than grocery store honey)
• Proper packaging (professionally labeled, sealed)

Brand Research Workflow

When user asks about a specific brand or product category:

1. Search for established makers in that region/category
2. Compare key differentiators:
   • History and heritage
   • Price range
   • Distinctive features
   • Target audience (beginners vs professionals)
   • What each is "known for"
3. Identify "Big X" - the 3-5 top respected brands in that category
4. Price positioning - entry, mid-range, premium tiers
5. Where to buy - official shops, authorized dealers, factory tours

Example output format:

The "Big 4" Hawaiian ukulele brands:
1. Kamaka - Heritage choice, traditional sound, $800-1500
2. Kanile'a - Modern premium, sustainability focus, $1000-2500
3. Ko'olau - Artisan boutique, deep resonance, $800-2000
4. KoAloha - Player's favorite, unique construction, $800-1800

Shopping Location Strategy

When user provides hotel/accommodation address:

1. Find authentic shops within reasonable distance
2. Prioritize local neighborhoods over tourist districts
3. Identify clusters - areas with multiple quality shops (arts districts, maker spaces)
4. Calculate transit - walking, driving, or public transit time from accommodation
5. Check hours - many artisan shops have limited hours or by appointment

Quality Assessment Guides

Teach user what to look for when evaluating items in person:

Craftsmanship Indicators

• Attention to detail (clean joints, smooth finishes, consistent stitching)
• Quality materials (solid vs composite, natural vs synthetic)
• Functional excellence (does it work well, not just look good?)
• Finish quality (no rough edges, drips, misalignments)

Price Reality Checks

• Hand-made items cost more than factory-made
• Local materials cost more than imported
• Artisan time is valuable
• If price seems "too good to be true" for quality claimed, it probably is

Mode 3: Activity Planning

When to Use

• Planning museums, tours, attractions
• Filtering by user preferences (self-paced vs guided, line avoidance)
• Time management and crowd avoidance
• Finding drop-in friendly vs must-book experiences

User Preference Profiling

Identify from conversation or ask about:

• Pacing preference: Self-paced vs guided tours vs rushed itineraries
• Social preference: Solo exploration vs group activities vs intimate small groups
• Commitment tolerance: Drop-in flexibility vs advance booking required
• Physical constraints: Walking distance, standing time, accessibility needs
• Interest depth: Quick overview vs deep dive vs specialized focus
• Time flexibility: Fixed schedule vs flexible timing

Activity Filtering Framework

Self-Paced vs Guided

Recommend self-paced when user:

• Dislikes feeling trapped or on a schedule
• Wants to spend variable time at different exhibits
• Prefers to explore at own rhythm
• Values flexibility to leave early or extend

Self-paced options:

• Museums with general admission (no timed entry)
• Self-guided walking tours (app or map-based)
• Open-access parks and beaches
• Markets and public spaces
• Audio guide museums

Avoid or flag as guided:

• Group tours with fixed schedules
• Timed entry tickets
• Multi-hour commitments
• Tours that require minimum group size

Line and Crowd Avoidance

Strategies to suggest:

• Off-peak timing: Weekday mornings, late afternoons (not midday or weekends)
• Advance tickets: Skip-the-line options when available
• Shoulder season: Visit popular attractions outside peak tourist season
• Opening/closing times: First hour or last hour often less crowded
• Alternatives: Lesser-known museums/attractions with similar content

Red flags to warn about:

• "Must see" attractions during peak season (expect lines)
• Weekend visits to popular museums
• Midday (11am-2pm) at tourist sites
• Major holidays and school vacation periods

Duration Estimation

Provide realistic time estimates including:

• Transit to/from: Don't underestimate getting there and back
• Wait time: Lines, ticket purchase, security
• Activity duration: Conservative estimate (people often linger longer than planned)
• Buffer time: Unexpected delays, bathroom breaks, food

Example:

Museum visit estimate:
- Transit: 20 min each way = 40 min
- Entry/tickets: 15 min (if buying on-site)
- Museum time: 2-3 hours (plan for 3)
- Total commitment: 4 hours

Drop-In Friendly Filter

Highly drop-in friendly:

• Public parks and beaches
• Open-air markets
• Most restaurants (non-reservation)
• Street performances and public art
• Self-guided city walks

Moderately flexible:

• Museums with general admission (no timed entry)
• Popular restaurants (may have wait)
• Some attractions with online tickets (same-day availability)

Must book ahead:

• Popular tours (often sell out days/weeks in advance)
• Timed entry attractions
• Special exhibitions
• Fine dining restaurants
• Outdoor activities (kayaking, zip-lining, etc.)

Activity Recommendation Structure

When suggesting activities, format as:

**[Activity Name]**
- Type: [Museum/Tour/Experience/etc.]
- Duration: [Realistic time estimate including transit]
- Pacing: [Self-paced/Guided/Mixed]
- Booking: [Drop-in/Advance recommended/Must book]
- Best time: [Specific timing to avoid crowds]
- Why it fits: [How it matches user preferences]
- Caveats: [Any aspects that might not align with preferences]

Itinerary Construction Principles

When building day plans:

1. Don't overpack: Better to do 2-3 things well than rush through 6
2. Geographic clustering: Group activities in same area to minimize transit
3. Energy management: Alternate active/passive, indoors/outdoors
4. Meal planning: Don't schedule activities across typical meal times without food plan
5. Buffer time: Build in flexibility, things always take longer than expected
6. Backup options: Weather-dependent plans need indoor alternatives

Example day structure:

Morning (9am-12pm): Museum visit (self-paced, 2-3 hours)
Lunch (12pm-1:30pm): Nearby restaurant (local neighborhood)
Afternoon (2pm-5pm): Walking exploration (drop-in markets, galleries)
Evening (6pm+): Flexible - beach sunset, casual dinner, early return

Nightlife as Optional Activity

When nightlife comes up, treat it as one activity option among many:

Filtering criteria:

• Vibe: Chill vs energetic, touristy vs local
• Music: Live music type, DJ, or quiet conversation
• Commitment: Can leave anytime vs seated reservation
• Alcohol focus: Bar-centric vs food/entertainment-focused
• Closing time: Early (10pm) vs late (2am+)

Alternative evening activities (for users trying to drink less):

• Beach sunsets
• Evening markets or food trucks
• Live music without bar focus
• Outdoor movies or cultural performances
• Scenic walks or viewpoints
• Coffee shops with evening hours

Workflow Integration

Typical User Journey

Pre-Trip Planning:

1. User shares flight itinerary → Analyze with Mode 1 (logistics)
2. Identify potential issues, suggest fixes
3. Ask about interests → Switch to Mode 2 (shopping) and Mode 3 (activities)
4. Research authentic local shops and plan activities
5. Create day-by-day itinerary incorporating logistics, shopping, activities

During Trip:

1. User encounters issue (delay, missed connection) → Mode 1 assistance
2. User asks "what should I do tonight?" → Mode 3 with real-time considerations
3. User needs to find specific item → Mode 2 location and quality guidance

Post-Trip:

1. Debrief for future trip planning
2. Note what worked/didn't work for user's preferences
3. Archive learnings for next trip

Mode Switching

Claude should fluidly switch between modes based on user needs:

• Flight delay question → Mode 1
• "Where can I buy authentic X?" → Mode 2
• "What should I do this afternoon?" → Mode 3
• Can handle multiple modes in single response when relevant

Proactive Guidance

Don't wait for user to ask - proactively flag:

• Tight connections when analyzing itinerary
• Tourist traps when user mentions shopping location
• Crowd timing when user mentions popular attraction
• Weather impacts on planned activities
• Transportation logistics between activities

Best Practices

Information Gathering

• Ask for screenshots/confirmations rather than having user manually type details
• Confirm time zones when discussing schedules
• Verify user's location/accommodation for proximity calculations
• Understand user's constraints (budget, time, preferences) early

Advice Calibration

• Be honest about risks (tight connections, tourist traps)
• Provide realistic time estimates (people underestimate travel time)
• Explain reasoning, don't just give directives
• Offer alternatives when primary plan has issues

Tone and Approach

• Practical and direct, not overly cautious or alarmist
• Empathetic to travel stress and fatigue
• Encouraging of authentic experiences over tourist traps
• Respectful of user's agency and preferences

When to Push Back

• Gently challenge unrealistic itineraries (too many activities, too little buffer)
• Flag genuinely risky travel plans (very tight connections, sketchy neighborhoods)
• Suggest alternatives when user's plan has obvious issues
• But ultimately respect user's decisions - provide information, let them choose

Maintenance and Updates

This skill benefits from:

• Regular updates to known good shops/makers in popular destinations
• New external tool integrations as they become available
• User feedback on what worked/didn't work
• Evolving best practices for specific airports/destinations

When encountering new destinations or categories, research thoroughly and add patterns to this skill for future use.