What It’s Like to Work With a Custom Trip Planner

Gabriella Steinhauser
Aug 12, 2025
3 min read

If you're like most people I work with, you’ve probably planned a trip before — and it may have involved 40+ browser tabs, a few headaches, and at least one “we’ll figure it out when we get there” moment.

That’s where I come in.

As a custom trip planner, I’m here to take all of that stress off your plate and turn your dream trip into a clear, exciting, low-maintenance experience. If you’ve ever wondered what it’s actually like to hire someone to plan your vacation — this post is for you.

📝 Step 1: Discovery & Intake

Once you reach out, I’ll send you a short intake questionnaire to gather the basics: where you want to go, when, your rough budget, travel style, and any must-haves or deal-breakers.

I also offer a free 30-minute discovery call if you'd prefer to talk things through — especially if you're not sure what kind of trip you want yet.

This helps me understand how you like to travel — and ensures your itinerary reflects you, not just a list of top-rated tourist spots.

🤝 Step 2: Contract & Payment

After we chat, if you decide to move forward, we sign a simple agreement that outlines:

What I’ll provide
What you’ll approve
My hourly rate and estimated time
Booking terms and your payment method

This keeps things transparent and clear from the start — no hidden fees, no guesswork.

🔍 Step 3: Research & Planning Begins

This is where the magic happens. I dive deep into building your ideal trip, including:

Flights or alternative routes
Accommodations that match your vibe and budget
Activities, experiences, and downtime
Transportation between cities
Points & rewards strategy (if applicable)
Dining recs, local tips, safety guidance, and more

Depending on your needs, I either book everything on your behalf with written pre-approval, or I provide clickable links and instructions so you can book each element yourself.

🗓️ Step 4: You Receive Your Itinerary

When everything is mapped out, you’ll receive a fully detailed itinerary, including:

Daily breakdowns
Reservation info
Maps, links, tickets, and backup plans
Budget summary
Pro tips specific to your destination

Whether you’re going to Italy, Japan, or a U.S. national park, you’ll have everything in one clean, easy-to-follow format.

📘 Step 5: Add-Ons (Optional)

Depending on your trip and preferences, you can add optional extras like:

🎒 A tailored packing checklist
📘 A Shutterfly photo book made after your return
💡 Help with budgeting or travel insurance

These are great for travelers who want every box checked, even the ones they didn’t know existed.

🌍 Step 6: After Your Trip

Once you’re back, I’ll check in to hear how everything went. If you opted for a photo book, you can send me your favorite pictures and captions — and I’ll create a gorgeous keepsake for you.

Many clients also refer friends, which means they get a $100 credit or gift card as a thank-you.

💬 What Clients Say

Here’s how past travelers describe the experience:

🗣️ “You saved me so much time and stress. Every day flowed perfectly.” 🗣️ “I felt like I actually got to enjoy the process instead of worrying about it.” 🗣️ “You thought of things I never would have. I’ll never plan a big trip alone again.”