How to Hire a Virtual Assistant for Travel Planning

The first time I hired a VA for travel planning, I thought the role was simple: “Book flights, reserve hotels, send me the itinerary.”

Two trips later, I had tight layovers, hotels far from meetings, and confirmations scattered across email threads. Nothing was technically “wrong,” but everything felt harder than it should have been.

That’s when I realized the real issue: travel planning isn’t booking work, it’s decision work.

Done poorly, it creates stress before the trip even starts. Done well, it disappears entirely.

Here’s the exact process I use now to hire a travel-planning VA who makes travel smoother instead of more complicated.

Step 1: Define What “Travel Planning” Actually Means for You

Most travel VA hires fail because expectations are vague.

Travel planning can include:

• Flight research and booking
• Hotel selection (location + convenience)
• Ground transportation
• Visa or document checks
• Calendar coordination
• Loyalty program optimization
• Itinerary creation and updates
• Rebooking during disruptions

And not all travel is the same:

• Executive business travel
• Conference-heavy trips
• Personal or family travel
• Multi-city international itineraries

Practical takeaways

• Decide what the VA can book independently vs. what needs approval.
• Clarify preferences before the first booking.
• “Just book something reasonable” leads to frustration fast.

Step 2: Hire for Judgment and Attention to Detail

Early on, I hired people who were great at finding deals. That wasn’t enough.

A strong travel-planning virtual assistant:

• Thinks through connections, timing, and fatigue
• Understands location tradeoffs
• Catches visa, baggage, and check-in details
• Plans buffers, not just the cheapest routes
• Anticipates disruption scenarios

What matters more than experience:

• Obsession with details
• Comfort double-checking
• Willingness to ask clarifying questions
• Calm problem-solving when plans change

Practical takeaways

• Cheap flights aren’t always good flights.
• Travel errors cost time, energy, and money.
• Precision matters more than speed.

Step 3: Document Your Travel Preferences Before You Hire

This step eliminated almost all friction for me.

Before posting the role, I write:

• Preferred airlines and seating
• Layover minimums
• Hotel standards (location, star rating, amenities)
• Budget ranges
• Loyalty programs to prioritize
• Red-eye rules
• How much choice I want presented

Example rules

• No layovers under 90 minutes
• Hotels must be within 15 minutes of meetings
• Present 2–3 flight options, not 10
• Always prioritize refundable fares when possible

Practical takeaways

• If preferences live in your head, mistakes are guaranteed.
• Rules save time for both of you.
• This doc becomes your long-term travel SOP.

Step 4: Use a Scorecard Focused on Travel Quality, Not Volume

I stopped measuring “trips booked” and started measuring travel experience.

Scorecard template

• Role: Travel Planning Virtual Assistant
• Scope: Business / personal/mixed
• 30-day outcomes:
  • Zero missed bookings or confirmations
  • Travel aligned with stated preferences
  • Clear, consolidated itineraries
  • Proactive alerts for changes or delays
  • Same-day rebooking when disruptions occur

Red flags I now watch for

• Booking without confirming preferences
• Missing time zone or date details
• Overloading me with options
• No contingency planning

Practical takeaways

• Fewer, better decisions beat fast bookings.
• Travel quality is measurable.
• Reliability builds trust quickly.

Step 5: Interview Using Real Travel Scenarios

I stopped asking “Have you booked travel before?” and started asking this:

• “How would you plan a 3-day, multi-city business trip?”
• “What would you do if a flight gets canceled mid-trip?”
• “How do you choose between convenience and cost?”
• “What details do you double-check before booking?”

I’m testing thinking, not tool familiarity.

Practical takeaways

• Calm explanations matter more than perfect answers.
• Overconfidence is risky in travel planning.
• The best VAs plan for things going wrong.

Step 6: Run a Paid Test Using a Realistic Trip

Travel planning is easy to test and should be.

My go-to paid test (45–60 minutes)

Provide:

• A sample trip (dates, city, purpose)
• Travel preferences
• Budget guidelines

Ask them to:

• Propose flight options
• Recommend accommodations
• Build a simple itinerary
• Explain the tradeoffs they made

Practical takeaways

• Always pay for the test.
• The explanation matters as much as the plan.
• You’ll immediately see judgment quality.

Step 7: Onboard With a Clear Travel Rhythm

The best travel VAs I’ve hired weren’t flashy; they were predictable.

My onboarding setup

• One booking process
• One itinerary format
• One communication channel
• Clear escalation rule: “If unsure, pause and ask.”

Operating rhythm

• Pre-trip confirmation checklist
• Day-of-travel monitoring
• Post-trip cleanup (receipts, records, notes)

Practical takeaways

• Predictability reduces travel stress.
• Visibility prevents last-minute chaos.
• Trust builds when nothing slips.

Summary: Hiring a Travel Planning VA Who Makes Trips Feel Easy

If I were starting again, I’d stop treating travel planning as admin work and start treating it like experience design. That means:

• Clear preferences upfront
• Outcome-based scorecards
• Scenario-driven interviews
• Paid tests with real trips
• Simple, repeatable workflows

My non-negotiables now

• Written travel preferences
• Paid test task
• Limited-option recommendations
• Proactive disruption handling
• Clean, consolidated itineraries

When done right, a travel-planning VA doesn’t just book trips; they remove friction, reduce stress, and make travel feel effortless again.