Guy Trip Blog

Real itineraries for real men. Less fluff, more logistics.

Recent Posts

• The Spring Trip Verification Protocol: How To Book Spring Travel Without Getting Burned — Spring travel demand is high, but spring is the most unstable season for group trips. Here's the verification protocol I use to book spring travel without getting burned.
• The Charleston City Dossier: A Blueprint for Southern High-Low Excellence — A tactical blueprint for executing a 72-hour Charleston guy trip. From Kiawah's Ocean Course to the bourbon selection at Husk, here's how to navigate Southern hospitality without the tourist traps.
• The 2026 Shoulder Season Playbook: Why The Smart Planner is Abandoning Peak Season (And How to Do It Without Getting Burned) — The Points Guy's 2026 trends report confirms it: 16% of Americans are abandoning peak season. Here's the tactical playbook for shoulder season success—including the destinations, the gear adjustments, and why AI planning tools will burn you.
• The Kentucky Bourbon Trail City Dossier: A Logistics-First Playbook for Distilleries, Steak, and Not Getting Stranded in Horse Country — The Kentucky Bourbon Trail isn't one location—it's a 75-mile logistical nightmare. Here's the spreadsheet approach to distilleries, transportation, and steak without getting stranded in horse country.
• The Route 66 Centennial: Why 2026 Is the Year for the Ultimate Guy Trip (And How to Not Screw It Up) — 2026 marks Route 66's 100th anniversary—and every car club and Instagram husband in America is hitting the Mother Road. Here's the tactical blueprint to execute the ultimate guy trip without becoming part of the centennial traffic jam.
• The Sacred Art of the Master Itinerary: Why I Still Carry a Waterproof Folder in 2026 — Why a former construction PM still carries a laminated, waterproof itinerary folder in 2026—and why it has saved more friendships than therapy ever could.