How to Plan a Bespoke Trip Without a Travel Agent

Because you know yourself better than anyone else.

Planning a trip is hard. It takes time and commitment. While this is not the only way to plan a bespoke trip, I want to give some insight into what I have done to plan trips.

1. Start with a Feeling, Not a Destination

Instead of asking where, ask what you want to feel. Do you crave stillness or stimulation? Seaside breezes or mountain air? Gourmet indulgence or creative inspiration? Let the emotion guide your destination.

Example: Instead of saying “I want to go to Italy,” say “I want to spend slow mornings surrounded by olive groves.” That might lead you to a private villa in Tuscany instead of Rome.

2. Research Research Research

This is THE most important step of your travel itinerary. It is important to start planning your trip 6 months to a year out. Every time my family has traveled, we have booked the villas 6-7 months before our departure. It takes time to research each house, restaurant and activity. The best method for research is truly social media. Looking at blogs such as mine, TikTok videos and Pinterest boards will help make your dream become reality. It takes a long time to research the hole-in-the-wall restaurants or find the villa perfect for you.

3. Book Experiences First, Then Housing

Start with what you want to do, then find a stay nearby that enhances it. Let the experience anchor your trip. Make sure you don’t spend half of the day in the car driving from place to place. When traveling to Mallorca this past summer, we booked a winery tour and beach club that was super important to my family. We did this step first before booking our villa.

I have only used Airbnb, but sites such as Withlocals and GetYourGuide are great for initial browsing as well. But, don’t stop there—many bespoke vendors operate off-platform.

4. Build in Spontaneity and Splurge Strategically

The beauty of planning your own trip? Freedom. Leave a few afternoons or full days open for whatever catches your eye—a local festival, a hidden beach or that tiny café you pass in the morning. Being stuck on an hour-by-hour itinerary leaves no room for spur of the moment experiences. And remember, You don’t need a limitless budget to create a bespoke experience. Choose 1–2 luxury moments—like a private catamaran tour or a Michelin-starred dinner—and balance the rest with charming but cost-effective options.

5. Enjoy your trip!!