How to Plan a Trip When You Hate Planning

Delegate the hard decisions to constraint-based shortcuts: fix your destination and dates first, then use pre-made itineraries and booking tools that do the thinking for you. The less you decide, the less you have to plan.

Pick your destination and dates before anything else. You need exactly two constraints to eliminate 80% of decisions. Choose a place someone you trust has recommended (not a long decision-making process). Pick dates that are already locked in your calendar—a long weekend, a week between two work projects, or a school break. Write these down. Do not revisit them. Everything else flows from these two facts.
Use a pre-made itinerary instead of building one. Go to sites like Rough Guides, Viator, or Withlocals and search "3-day itinerary [your city]." Pick the first one that sounds tolerable. Do not read five options. One itinerary decision, not ten. You're outsourcing the sequencing to someone who has already done the work. If it says "Day 1: Museum, lunch at X, evening walk," that is your plan. Follow it.
Book accommodation near the starting point of your itinerary. Look at where Day 1 begins. Find a hotel or Airbnb within walking distance or a 5-minute transit ride. Do not optimize for the perfect neighborhood. Close to your first activity saves you one decision. Use Booking.com or Airbnb, sort by price (low to high), pick something with 4+ stars and reviews mentioning "clean" and "location." Book it.
Arrange transport to and from your accommodation only. You need to get from the airport/train station to your hotel, and from your hotel back. That is your transport plan. Book an airport shuttle, ride-share, or taxi for both directions. Do not plan how you'll move around the city yet—your itinerary will tell you, and you'll figure out one leg at a time when you arrive.
Handle documents and visas in a single sitting. Check if you need a visa by entering your nationality and destination at iVisa.com or your country's travel advisory website. If yes, use iVisa or TravelDocs to file it—they handle the legwork. Get a photocopy of your passport and keep it separate from your passport. Set a phone reminder for your vaccination requirements (if any) two weeks before travel. Done. Do not reopen this task.
Prepare a minimal packing list based only on weather and duration. Check the weather for your destination during your trip dates. Pack for that weather plus one versatile layer. Bring enough underwear and socks for half your trip length plus two pairs (wash halfway through). Put the packing list on your phone notes. Pack the night before you leave. Do not overthink it.
Create one document with your key info and share it. Put your flight/train confirmation numbers, hotel address, travel insurance policy number (if you bought it), and one local emergency contact in a Google Doc or Apple Notes. Share it with one person at home. You now have a backup if something gets lost. This takes 10 minutes.

What if the itinerary I pick is bad?: It probably won't be. Most published itineraries for popular destinations are tested and solid. If you get there and hate something, skip it and sit in a café instead. You're not locked in. Permission to deviate is built in.
Should I plan activities in advance or book them when I arrive?: Pre-book anything with set times (museum tickets, organized tours, restaurant reservations). Book experiences that don't have strict times (walking tours, casual meals) when you arrive. Your itinerary will tell you which is which.
What about travel insurance?: Buy a basic policy from Allianz, World Nomads, or your credit card provider the day you book your flights. It costs $20–50 for a short trip. Do not overthink it. Pick one, buy it, move on.
How do I stay in touch with people back home without planning it?: Get a local SIM card or an international plan from your phone provider before you leave. Text one person a photo every evening. That is your communication plan.
What if I get lost or something goes wrong?: You will not be the first person lost in this place. Ask a local, use Google Maps offline (download it at home), or sit down and figure it out. Most travel "emergencies" are just surprises that become stories. You have resilience you don't know you have yet.