The Pre-Trip Planning System for Solo Travelers Over 50

I'm an engineer. Or I was, for 30 years. Which means I approach everything—including travel—like a project with variables to control, risks to mitigate, and outcomes to optimize.

When I took my first solo trip at 55, I researched the hell out of it. I built spreadsheets. I created systems. My wife looked at my three-ring binder of printed confirmations and maps and said, "Marcus, you're going to Iceland, not Mars."

She was right. But also, that binder saved me when my phone died on day two.

Seven years and 20 countries later, I've refined my pre-trip planning system. It's not sexy. It's not spontaneous. But it works. And at our age, when you're traveling alone and managing everything from medications to money to transportation, having a system isn't optional—it's smart.

Here's the framework I use. Adapt it to your needs. Ignore what doesn't serve you. But trust me: a little planning up front means a lot less stress on the road.

Phase 1: The 90-Day Planning Window

I start planning 90 days before departure. Not because I need three months to book a flight, but because breaking the process into phases prevents overwhelm.

Days 90-75: Destination Research & Decision

• Identify 3-5 potential destinations

• Research visa requirements (some take 6-8 weeks)

• Check CDC health advisories and required vaccinations

• Review weather patterns for travel dates

• Assess physical requirements (elevation, walking distance, terrain)

• Read recent traveler reviews on forums (I use TripAdvisor and specific 50+ travel groups)

Key Tool: I create a simple comparison spreadsheet:

• Destination

• Visa needed? (Y/N)

• Vaccinations required?

• Average daily walking distance

• Average temperature

• Flight cost estimate

• Accommodation cost estimate

• Overall difficulty rating (1-5)

This takes emotion out of the decision. You're comparing data, not daydreaming.

Days 75-60: Major Bookings

Once I've chosen a destination, I book the big three:

1. Flights - I use Google Flights to track prices, set alerts, and book when the price drops to my target

2. First 2-3 nights accommodation - Book the arrival city and maybe one more. Leave flexibility after that

3. Travel insurance - Non-negotiable at our age. I use a comparison site and always get medical evacuation coverage

Insurance Reality Check: Standard travel insurance often caps age coverage at 65-70. If you're older, you need specialized coverage. I use Allianz or Seven Corners and pay more, but it's worth it. Read the fine print on pre-existing conditions—this matters at 50+.

Days 60-45: Health & Logistics

This is the phase younger travelers skip. We can't.

Medical Preparation:

• Schedule doctor appointment 6-8 weeks before departure

• Request 90-day prescription refills (explain you're traveling)

• Get copies of prescriptions with generic drug names

• Carry doctor's letter explaining medical conditions and medications

• Research hospital locations in destination city

• Verify your health insurance covers international emergencies (most don't—that's why you have travel insurance)

Document Organization: I create a digital folder with:

• Passport scan

• Driver's license scan

• Credit card numbers and international phone numbers

• Insurance policy details

• Prescription information

• Emergency contacts

I email this to myself and print a copy. Redundancy is your friend.

Days 45-30: The Deep Dive

Now I get into the details that make or break a trip.

Accommodation Strategy: I don't book everything upfront. Here's my system:

• First 2 nights: Booked and confirmed

• Days 3-7: Research options, save links, don't book

• Week 2+: Complete flexibility

This gives structure without trapping you. If you love a place, stay longer. If you hate it, move on.

Transportation Research:

• Download transit apps for destination

• Screenshot routes from airport to hotel

• Research taxi scam alerts (yes, this is real in many places)

• Check if international driver's license is required

• Evaluate car rental vs. public transit vs. private drivers

Days 30-14: Technology & Money

Phone & Connectivity:

• Contact your carrier about international plans

• Consider buying local SIM (I use Airalo for eSIMs—game changer)

• Download offline maps for entire destination

• Test all apps before you leave

Money Management:

• Notify credit cards of travel dates

• Order small amount of local currency ($100-200 USD equivalent)

• Identify ATMs in destination (I use Charles Schwab debit—no foreign transaction fees)

• Set up mobile alerts for all cards

• Photograph credit cards (front/back) in case of loss

Apps I Actually Use:

• Google Maps (offline maps)

• Google Translate (download language packs)

• XE Currency Converter

• Trail Wallet (expense tracking)

• TripIt (consolidates confirmations)

Days 14-7: Final Preparations

Packing System: I use a modified packing list I've refined over years. At 50+, I pack:

• Medications (double what I need, split between carry-on and checked bag)

• Compression socks for flights

• Good walking shoes (broken in)

• Layers, not bulk

• Small first aid kit

• Copies of important documents

The Two-Week Test: Two weeks before, I set out everything I plan to pack. Then I remove 30% of it. We always overpack.

Final Logistics:

• Confirm all reservations (call if unsure)

• Check flight status 24 hours before

• Complete online check-in

• Set up auto-pay for bills at home

• Arrange mail hold

• Give someone you trust your itinerary

Days 7-1: The Mental Game

The logistics are handled. Now comes the psychological preparation.

I've learned that anxiety before a solo trip is normal. Even now, I get nervous. Here's my system:

The Night Before:

• Pack carry-on with essentials

• Charge all devices

• Set multiple alarms

• Review first 24 hours of itinerary

• Get to bed early (you won't sleep well, but try)

The Morning Of:

• Arrive at airport 3 hours early for international flights

• Eat something substantial

• Stay hydrated

• Don't drink alcohol before or during flight

Phase 2: The On-Ground System

First 24 Hours Checklist:

• Text someone that you arrived safely

• Test local SIM/data

• Locate nearest ATM, pharmacy, grocery store

• Walk the neighborhood in daylight

• Eat something and hydrate (jet lag makes this easy to forget)

• Set up WhatsApp or communication with folks back home

Daily Rhythm: I've learned I need structure, even when traveling. My system:

• Morning: One planned activity or destination

• Afternoon: Flexibility (explore, rest, whatever)

• Evening: Plan next day's logistics

This prevents decision fatigue while maintaining spontaneity.

The Reality Check

Here's what took me years to learn: no system is perfect. You'll forget something. Something will go wrong. A reservation will be messed up. But having a system means when something goes wrong, you have a foundation to work from. You have backup plans. You have documentation. You have structure.

The younger travelers at my hotel might laugh at my spreadsheets and my three-ring binder. But I've watched them panic when their phone dies or they can't find their confirmation email.

Meanwhile, I'm sitting in a café with a printed map, sipping coffee, exactly where I planned to be.

The Bottom Line

When you've prepared for problems, you can relax into the experience. I'm not suggesting you need my exact system. But I am suggesting that solo travel at 50+ requires more preparation than it did at 25. Your body is different. Your needs are different. Your tolerance for chaos is different.

Build a system that works for you. Refine it with each trip. And trust that the time you invest in planning pays dividends in peace of mind.

Now go book that trip. And make a spreadsheet about it.

You'll thank me later.