How I Plan My Trips: A Step-by-Step Travel Planning Guide

Monica Henry
Mar 19
3 min read

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Planning a trip is one of my favorite things to do! There’s something exciting about researching destinations, booking flights, and crafting an itinerary that balances adventure, relaxation, and exploration. With several upcoming trips on my calendar—including Amelia Island, Las Vegas, and a Greece & Turkey combo trip—I thought it would be the perfect time to share my step-by-step process for planning a trip. Whether you’re a meticulous planner or someone who loves spontaneous travel, these tips can help make the experience smoother and more enjoyable!

✈ Step 1: Choosing a Destination

Sometimes I choose a destination based on a lifelong bucket list dream, while other times, it’s about taking advantage of a great flight deal or an upcoming event. When planning, I consider:

✔ What type of experience I want (beach, city, adventure, cultural, etc.).

✔ The best time of year to visit.

✔ How easy it is to get there and move around.

💡For my upcoming Greece & Turkey trip, I wanted a mix of history, culture, and breathtaking coastal views. It’s been on my bucket list for a while, and this year felt like the perfect time to make it happen!

🏨 Step 2: Research & Booking Accommodations

Once I have my destination, I dive into researching the best hotels, Airbnbs, and boutique stays that fit my budget and travel style. I look for:

✔ Proximity to key attractions.

✔ High traveler ratings and reviews.

✔ Unique stays that enhance the experience.

💡 For Las Vegas, I have been multiple times and always end up staying at The Venetian because it’s on The Strip, is designed like a mall, and is both elegant and beautiful. I still checked reviews on Expedia to compare options, but The Venetian remains my go-to choice for its perfect blend of convenience and luxury.

📅 Step 3: Creating an Itinerary

I like to have a rough itinerary that includes must-see sights, food spots, and downtime for exploration. My approach:

✔ Prioritize 2–3 must-do activities per day.

✔ Leave room for spontaneity (some of the best experiences are unplanned!).

✔ Research tours, transportation, and logistics in advance.

💡 For Amelia Island, I’m planning a mix of relaxing on the beach, exploring historic sites, and indulging in fresh seafood. Below, I have included some pages from my South African travel itinerary.

💰 Step 4: Budgeting & Saving for a Trip

Budgeting is key to making sure I enjoy my travels without stress. Here’s how I stay on track:

✔ Setting a budget for flights, lodging, food, and experiences.

✔ Using travel rewards and credit card points for savings.

✔ Looking for free or low-cost activities to maximize the experience.

💡 I have five different Amex cards, each offering great benefits depending on my trip needs. For my Greece & Turkey trip, I used the Amex Delta Reserve Card to take advantage of flight perks and lounge access. I also love using my Amex Business Platinum Card for its amazing travel rewards and statement credits—it’s a game-changer for frequent travelers!

🎒 Step 5: Packing & Travel Essentials

Packing smart makes travel so much easier! I always consider:

✔ The climate and planned activities.

✔ Packing cubes for organization.

✔ Must-have items like a portable charger, travel pillow, and comfortable shoes.

💡 I never leave home without my Solgaard Lifepack Backpack—it keeps everything organized and is perfect for airport travel!

🔜 What’s Next?

Now that my next few trips are in motion, I can’t wait to share more about my experiences in Amelia Island, Las Vegas, and Greece & Turkey. Stay tuned for detailed travel guides, itineraries, and must-see recommendations! If you have any trip-planning tips or favorite destinations, drop them in the comments—I’d love to hear from you!

📌 What’s your travel planning style—structured itinerary or go-with-the-flow? Let’s chat below!