Trip Planning 101: How to Book Flights, Stays & Activities in the Right Order

Planning a trip can feel overwhelming—where do you even start? Flights? Hotels? Activities? After years of traveling, I’ve figured out a simple system that takes the guesswork out of trip planning. By tackling things in the right order, you’ll save money, avoid stress, and make the most of your time away. Here’s my 7-step process to plan a trip like a pro—from booking flights to finding unique experiences you’ll never forget.

7 Steps to Plan a Great Trip

Step 1: Find Flights First

Flights are usually the biggest expense, so booking them first sets the tone for your budget and trip.

By booking flights first, you’ll know exactly how much of your budget is left for everything else.

My favorite tool is Google Flights. Click the “Explore” tab, enter your home airport, and you’ll see the cheapest round-trip tickets around the world. You can filter by travel dates or trip length to narrow your options. When I spot a flight within my budget, I book it and build the rest of my trip around it.

If you already know your destination, track flight prices. Google Flights lets you set alerts, while apps like Hopper and Going are also great. Hopper tracks flight trends and offers solid hotel deals, while Going emails jaw-dropping deals from your home airport. Going has replaced my weekly Google Flights searches, but I still love exploring the map for inspiration.

Step 2: Choose the Right Accommodation

Pick a stay that matches your travel style—whether that’s a hostel, hotel, or vacation rental.

Decide what type of stay matches your trip:

• Do you need space and a kitchen, or just a bed for the night?

• Do you want walkability in a city, or peace and quiet outside the crowds?

With friends in Europe, I book hostels near the city center. With family, I usually choose a vacation rental, even if it requires driving. My go-to platforms are Hostelworld, Airbnb, and VRBO. If you prefer hotels, check loyalty programs or use a travel credit card to earn points and discounts.

Step 3: Research Like a Pro

Use Pinterest, locals, and travel groups to uncover the best spots, hidden gems, and must-dos.

This is where the fun begins.

• Pinterest: I start here for inspiration, itineraries, and guides (I even found a self-guided Monaco walking tour this way). Save pins to a board for easy access.

• Locals: If you know someone in the area, ask them! The best tips I’ve received have been from locals. Social media posts or Facebook travel groups are also goldmines for recommendations.

• Google & ChatGPT: Once I’ve gathered ideas, I’ll ask ChatGPT to organize them into a time-efficient itinerary—especially useful for large cities where it’s easy to waste time doubling back.

  
  
  
  

Step 4: Book Memorable Activities

Invest in a few unique experiences that make your trip unforgettable (and support locals, too!).

If you’re on a budget, skip this step—most destinations have plenty of free things to do. But if you can, invest in a couple of unique activities you can only do there.

Two of my favorites were in Italy: a pasta-making class and a half-day tour through Tuscany’s wine country. Both were booked on Viator, my favorite activity platform. Airbnb Experiences is also back, offering authentic tours with locals—a great way to support the community.

Step 5: Build a Flexible Itinerary

Map out your days so you’re organized, but leave room for spontaneity and rest.

With logistics and activities set, start sketching out your days.

• In busy cities, I like to start early with the must-sees, then slow down in the afternoon before dinner or nightlife.

• In relaxed destinations like beach towns or mountain escapes, I spread things out and leave more downtime.

Even a rough outline helps everyone know what to expect (and what to pack). If you’re more Type A, a detailed, timed itinerary works too—no shame in maximizing your trip!

Step 6: Add Personal Details & Hidden Gems

Go beyond the guidebook by tasting local food, finding quirky spots, and bringing home meaningful souvenirs.

This step is optional but makes a trip feel special. Research local foods, hidden gems, and souvenirs unique to the region (like my Italian leather purse from Florence). Look for quirky finds like speakeasies, film locations, or

off-the-beaten-path neighborhoods. These little touches make a trip uniquely yours.

Step 7: Pack Up and Go!

Finally—pack your bags and go! While you’re away, eat lots of food, take tons of photos, and make as many memories as you can. Happy travels!