Build a Full Trip Itinerary with Claude (Cowork, Code & Design)
A complete all-in-one, customizable system for planning a full, day-by-day trip with Claude — from a single intake to a dynamic, updateable, customizable plan.
A complete all-in-one, customizable system for planning a full, day-by-day trip with Claude — from a single intake to a dynamic, updateable, customizable plan. This deck walks through every component: destination research, flights, points-aware lodging, the day-by-day itinerary, restaurants and reservations, packing, credit-card credits, and best-time-to-visit timing — plus the Cowork-vs-Code playbook (where chat shines for research, synthesis, and drafting, and where Claude Code wins for schedule generation, calendar sync, and packing lists). It's built around a fully worked, anonymized example: a two-week Spain trip across Mallorca, Ibiza, Granada, and Madrid. For anyone traveling soon — or tired of losing a Saturday to 47 browser tabs — who wants AI to do the heavy lifting and one shared source of truth. A companion prompt library will be added so you can run the whole workflow yourself.
What's included
Meet your expert
Ben L.
Lead AI Instructor | 4x Top Coach | Build Agentic Systems for Work & Life
• Stanford GSB Alum, Class of 2021 -- see relevant background & experience below: • Coaching | Advised 400+ admits into Stanford GSB, HBS, Wharton, Kellogg, MIT Sloan, INSEAD, Haas, and more (230+ Leland reviews), while teaching multiple courses through Leland • What I'm Doing Now | Based in NYC, building a publication 'Staying Human', working on a stealth, marketplace startup, coaching and playing chess profssionally, and advising a slate of Seed to Series C startups through Elevate LLC • Public Policy | Prior to Stanford, worked on the Policy Team for the Chicago Mayor's Office under Mayor Rahm Emanuel, focusing on 5G infrastructure policy, criminal justice policy, and citywide corporate/economic development deals • McKinsey | Before policy, worked at McKinsey & Co , with casework focused on job training for the formerly incarcerated and workforce development for at-risk youth • PE / VC / Startup Advising | After Stanford, worked in Bain's Private Equity Group on various due diliegences, managed deals with several venture capital firms, and advised multiple startups on growth and go-to-market strategy • Professional Writing | Speechwriting in public policy & political environments, Lead Editor for Nondisclosure (Stanford GSB's magazine) and Managing Editor for the Stanford International Policy Review • Additional Writing | Crafting op-eds, ghostwriting for major publications, developing a fictional short story collection, policy deep dives, a book on chess applications to life, and application essays of all sorts • GMAT / Test-Taking | Scored in the highest percentile of GMAT test-takers, but more importantly I've honed my ability to help others extrapolate top test-testing strategies in the areas they're weakest • Additional Coaching Details | 5+ years experience working with >750 individuals on essay writing and resume professionalization for top consulting firms, MBA programs, execs, and the broader job market • Interview Training | I was interview-trained with McKinsey, helping me give high-quality mock interviews for MBBs and any MBA program; I've also held 10+ events through Leland on interview prep for McKinsey's PEI and GSB's interview process in particular
