Step-by-step Trip Planning Guide!

Picture this: you’ve saved up the PTO, your busy work season is winding down, and it’s the perfect time to take that vacation you’ve been waiting for. But the problem is, you want your trip to be relaxing, fun, educational, and a great bonding experience with your destination and those you’re traveling with.

Which sounds like a lot of work to plan, and you’re not even sure where to start.

Well sis, you are not alone – I’ve totally been there!

And over the last many years of trial and error and planning TONS of different trips for groups, couples, friends, and solo travelers, I’ve compiled an ultimate trip planning guide to give you the tools and confidence to plan the perfect trip for YOU!

So I’m giving you permission to steal my strategies – take them and start planning that dream trip TODAY!

Step 1: Choose Your Destination

Maybe you already have a dream destination in mind for your trip. Or maybe you have so many destinations you want to explore that you can’t decide.

Either way, it’s important to be intentional about choosing your destination. It’s what determines the setting, flavor, and tone of your whole travel experience!

Ask yourself and those traveling with you…

What KIND of experience do you want to have? Are you looking for adventure or relaxation? A place to warm up or cool down?

Are there specific activities you want to do or bucket list items you want to check off?

Your answers to these questions can help narrow down location options and help you identify a focus or goal for your trip moving forward.

Step 2: Getting There

Now that you’ve selected a destination, you need to figure out how to get there!

Keep in mind that arriving at your accommodation may require multiple types of transportation (a train or bus ride from the airport, a ferry from the coast to the island). Consider each leg of the journey and make reservations accordingly, especially your first time arriving somewhere.


For closer destinations, camping trips, or road trips, taking a car is the way to go. Make sure to include gas costs in your trip budget if you decide to drive.

Train Travel

Transportation by train isn’t always the fastest way to travel, but it can be really fun and more affordable than flying.


Here are a couple of my favorite tools to help you find affordable flight options:

Google Flights: My number one tool every time I fly! This website compiles flight data from dozens of major airlines to show you the best options. You can even set a date or flight tracker to send you notifications when prices change.

Hopper: Keeps track of flight prices like Google Flights, but also tracks, freezes, and predicts trends for hotels, car rentals, and homes.

Step 3: Where to Stay

Where you stay on your trip is an important part of your travel experience! Now is a great opportunity to look back at the goals you set for your trip.

What kind of experience do you want to have?

What kind of housing will help you have that experience?

Here are some examples to consider:

If you need a break from the fast pace of life to recharge, look for a cabin or beach house away from the city.

If you’re just visiting for a weekend and want to visit lots of museums and restaurants, consider staying in a hotel or apartment at the heart of your destination.

If you’re looking for an authentic, immersive cultural experience, find a rental home in a neighborhood where you’ll live, shop, and play among locals.

Step 4: Getting Around

So you arrive at your destination, unpack your suitcase, and you’re ready to start your adventure!

But how are you getting to and from the activities on your itinerary?

Start by mapping out how far away each item is on your itinerary. Google Maps can help you familiarize yourself with distances and give you a better idea of feasible transportation options.

If you’ll need additional forms of transportation to get around besides walking, here are some resources I suggest using:

Google search: Websites for most cities will list suggested modes of transportation for their area. Some offer a CityPass or something similar that grants unlimited access to public transportation and free/discounted admission to certain attractions.

Ask locals: If you can contact a trusted source who lives in your destination full-time (search on Facebook or Instagram), they can give pointers for the transportation they use on a daily basis.

Step 5: Building Your Itinerary

Now we get to the really fun part – planning the play!

It’s especially important when organizing your itinerary to remember the goals and vision you set for your trip. The activities you plan will solidify the memories, growth, and bonding you experience during your travels.

Here are some tips to get started:

Research local event calendars. These events are authentic cultural experiences that will help you connect with your destination.

Think about activities you love to do already. Do you love libraries, history, sports, good restaurants, or museums? Incorporating these things into your itinerary can bring a sense of safety and familiarity, especially in a place that is very different from your hometown.

Consider whether you want to explore on your own or pay a guide to show you around. Both options have pros and cons: exploring on your own offers greater flexibility and lower prices, but you have to do a lot of research ahead of time. Paying a tour guide may be more expensive but it’s also a more efficient use of time.

Let’s Get Started!

With these tips and tools at your fingertips, you’ll be well on your way to planning your next unforgettable trip!

Find the full Ultimate Travel Planning Guide HERE! There are dozens more tips and recommendations in this guide to help you on your trip planning journey – and it’s totally FREE!

So what are you waiting for, sis? Let’s get planning!!

Additional Resources

If you’re looking for some extra help with planning the trip of your dreams or just don’t have the time to take care of logistics yourself, I’m your girl! 

Click here to sign up for a FREE trip planning discovery call! I’ll walk you through your vacation goals and vision, and from there, I’ll do the research FOR YOU to find the authentic experiences in your destination that will fit your vision perfectly.

Check out my post “5 Steps to Making Mindful Travel Memories” to find my tips for staying present and connected as you travel.

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