How to Plan a Trip: 6 Simple Steps to Plan Your Dream Getaway

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Let me guess — you’re here because you want to go on an amazing trip, but don’t know the first step. Well, friend, you’re in the right place!

Over the last half year or so, I’ve developed quite the obsession with planning trips. I can’t necessarily say I’m an expert (I have a lot more learning to do), but gosh, I can plan the heck out of a trip!

In this post, I’m going to share with you my exact process for planning a solo trip. I’ll be sure to go into as much detail as possible so you don’t finish this post still feeling clueless, stressed, or overwhelmed. Because traveling is too fun to just give up!

Grab a cup of coffee, cuddle in your bed with your furry buddy, and whip out a pen & notebook. We’re about to do some serious trip-planning.

Ready, friend? Let’s go!

THIS POST IS ALL ABOUT HOW TO PLAN A TRIP.

THE SIX FUNDAMENTALS OF PLANNING A TRIP

• Why: Why do you want to travel? Are you celebrating a milestone, like a birthday or anniversary? Have you been working really hard at work and need a vacation? Have you constantly been seeing videos about a particular destination and are itching to go?
• Where: Where are you going? Is it domestic or international? Is it more of a tropical or urban destination? Have you ever been there before? Why are you interested in visiting? Who or what inspired you to visit?
• When: When are you embarking on your journey? Are you going in the next couple of weeks, or later down the line? During which season do you plan on visiting? Exactly what month do you want to travel?
• Who: Who am I traveling with on this trip? Is it a solo trip, family trip, couples trip, or group trip? How many people am I traveling with?
• How: How are you getting to your destination? Are you going to fly, drive, take the train, ride on a cruise ship, or take the bus? How long will it take to get there? What stops will you make along the way? How long is each stop? Do you plan on doing anything during that time?
• What: What kinds of things will you do during your trip? What attractions do you want to visit? What neighborhoods do you want to explore? What kinds of food will you eat? What interactions do you hope to have?

HOW TO PLAN A TRIP

STEP #1: GET INSPIRED

Before you start planning a trip, you’re going to have some sort of inspiration for the trip. Why do you want to take a trip? Why do you want to visit a particular destination?

There’s so many points of inspiration from a trip, but these are some of the most common ones you’ll experience:

• You saw someone post about their experience online. I get a TON of inspiration from people sharing their travels online, whether it’s on YouTube TikTok, Reddit groups, or one of my favorite travel blogs.
• You feel like you need a break from something. I’m going to assume — especially because you’re a 9-5 worker — you need a break from your job every now and then. And it’s not always a bad thing; sometimes you just need a nice weekend getaway to get a few extra hours of rest, sunbathe at the beach, or explore a new city. If it’s not your job you need a break from, it could be a multitude of other responsibilities, like family, school, a side hustle — anything!
• You’ve been itching to go on another trip. This is probably the one I personally experience the most besides seeing other people post about their trips. I am a travel nerd and I can’t go too long without feeling the burning desire to plan and go on another trip.

STEP #2: RESEARCH

This part, along with planning, is undoubtedly one of the more time-consuming steps to planning a trip. No matter where you go, you need to extensively research the destination.

Because there’s no feeling worse than arriving in your destination and having a completely different experience than you planned. Good, strong research can genuinely make or break a trip, so you need to spend a decent amount of time in this phase.

There are three distinctive and non-skippable aspects of a trip you need to research, so let’s dive into them!

THE THREE BASIC RESEARCH ELEMENTS

RESEARCH YOUR DESTINATION OPTIONS

Remember: at this point, unless you’ve got your mind set on a specific destination, you likely still don’t know where you’re going.

So, start with some basic research of a few different cities. I like taking both domestic and international trips, but I’m going to focus on domestic travel for this post since it’s your first solo trip.

Let’s say I see someone sharing a review of the hotel they stayed at during their solo trip to Miami, FL. But then a few hours later, I read a blog post where someone shares their favorite restaurants they ate at on their solo trip to New Orleans, LA.

And a week later, someone at my job mentions they want to visit Houston, TX to visit family and attend a concert.

I’m a painfully indecisive person by nature, so to really narrow down my options, I have to extensively research each one. I’ll usually start with the most compelling one.

In this case, let’s choose Miami since it’s winter and 41 degrees in Illinois as I write this. I’ll go on one of my travel planning resources — which I listed a few sections ago — and make a series of simple, yet insightful searches, like:

• best time to visit Miami
• things to do in Miami in February
• best hotels in Miami
• where to stay in Miami
• day trips from Miami

NARROW IT DOWN TO ONE DESTINATION

I know, I know: this part be can incredibly difficult, especially when you haven’t really traveled much.

After doing countless hours of research on numerous cities, I usually narrow it down based on price, weather, and the number of activities I can do. I’m very much a tourist and, since I’m a solo traveler who doesn’t have infinite time or money, I have to maximize every single minute and dollar.

So right now in my travel journey, I tend to lean toward places where I feel I’ll get the best bang for my buck.

Based on the list above (Miami, Houston, and New Orleans), I’d probably pick New Orleans for several reasons:

1. I’ve already been to Miami and Houston before and, as much as I’d love to revisit, I’m focusing on new cities for now.
2. I’ve been seeing a lot of NOLA restaurants on TikTok and YouTube that look irresistible. I’ve always known that New Orleans has an incredible food scene but man… seeing the food really makes my mouth water! I love to try some gumbo and beignets.
3. The weather is currently above 60 degrees in each city, so I’m not really taking too big of a hit in the weather department.
4. While New Orleans doesn’t necessarily have the same quantity or quality of hotels, they are considerably more affordable than the other cities.
5. It’s slightly more walkable than Houston. Neither city is exactly known for their walkability, but New Orleans is more walkable than Houston.

RESEARCH YOUR FINAL DESTINATION

Whew, you can take a deep breath now. Now that you’ve got a destination picked out, you can focus on researching that specific city.

You’ll want to educate yourself on everything possible so you’ll have a full, well-rounded understanding and idea of where you’re going.

Here are some basic things to research for every single city:

• Weather: Research your final destination and make sure you’re comfortable with the climate you’ll possibly encounter during your trip.
• Diversity: You need to consider all factors of diversity, including religion, economic status, nationality, sexual orientation, and more. No matter who you are, what you believe in, who you love, or what you look like… you need to research your destination to ensure it’s a place where you’ll feel comfortable.
• Friendliness of People: Nobody wants to visit a city where people seem generally cold and bitter. That’s makes for a painfully uninviting and unpleasant experience, so please make sure you research how friendly the people are in the city you’re planning to visit. Thankfully, with my NOLA example, Southerners are very friendly and hospitable.
• Cost of Living/Visiting: You can find this in many places, but Google is always your bestie for anything travel-related. I also write full budget breakdowns for each of my trips, so feel free to check those out as well. Knowing this information will give you a good idea of how much you’ll be paying for transportation, activities, lodging, food, and even some of those miscellaneous expenses you don’t really think about.

STEP #3: PICK YOUR DATES

Although it’s the first step, it’s going to look slightly different depending on whether you’re a beginner or intermediate-level traveler. Allow me to explain.

If you’re a beginner, you’ll likely start with your dates and then continuing planning with those dates.

If you’re a bit more advanced, you can certainly begin with your dates, but you also might start flight instead. Meaning you go on Google Flights and base your next trip on whatever flight deals look good.

For the sake of this post, I’m going to assume you want to start with your dates. If, however, you want to do it the other way, I share an alternate process a bit later.

Picking your dates can be a little tricky as a PTO or student traveler since you’re pretty limited on time. I suggest taking advantage of weekends, random work closures, and holidays to maximize your time.

STEP #4: MAKE A BUDGET

This technically can (and should) be the first step, but if you have a specific set of dates in mind, it probably makes more sense to do this second.

Before you get any further, you have to figure out how the heck you’re going to afford this thing! Because even though you want to have the time of your life, I’m positive you don’t want to break the bank doing so.

I like to including categories in my solo travel budgets:

• Flights
• Accommodation
• Local Transportation
• Activities + Experiences
• Daily Spending
• Travel Insurance
• Unexpected / Flex

STEP #5: BOOK YOUR FLIGHTS

No matter where you’re going, what you plan to do there, or how long you plan to stay there, one of the first things you need to book are your flights.

You may be unaware, but flight prices change as fast as the weather in the Midwest (which is insanely unpredictable, I must say). And there’s really no “best” time to book other than as soon as you can afford your flights.

I always use Google Flights and Skyscanner to search for flights, and then book them directly on the airline’s website. Many travelers use third-party booking platforms like Expedia and while you often get better deals, I prefer booking direct.

If you need help booking a flight, check out this YouTube video from Portable Professional. Megan takes you through the exact step-by-step process to find a reasonably-priced airfare.

STEP #6: BOOK YOUR ACTIVITIES

You expected me to tell you to book your hotel next, didn’t you? Well, you aren’t the only one who thought that.

When I first started traveling on my own, my hotel was the second thing I secured in my trip-planning process. But then as I planned more trips, I realized that you need to base your hotel on your activities — not the other way around.

Personally, I do quite a bit of research using the aforementioned apps to make a list of things that sound fun and interesting. The list usually grows fast, with all sorts of activities like museums, parks, observation decks, events, and more.

Many travelers like to drop pins on Google Maps any time they find something interesting, like a restaurant, coffee shop, hidden gem, or boutique store.

I just recently started doing this myself and I’ve found it to be a nice addition to complement my written lists. The written lists are great, but it’s nice to have a visual to look at.

Whether I’ve already been to the destination slightly changes my plans. For example, I’ve already been to DC several times, so I probably wouldn’t be too quick or eager to see the Lincoln Memorial.

I don’t narrow anything down until I’ve officially started making my itinerary, so I won’t really go into too much more detail right now.

STEP #7: BOOK YOUR HOTEL

Up until this point, I’ve been specifically talking about hotels because I usually recommend them for solo travelers.

Not only are they safer (you usually have 24-hour staff and security) and technically a better bang for your buck but with the crazy fees Airbnb likes to charge nowadays, you’d probably be better off just spending a bit more on a hotel.

You need to choose something central that allows you to walk to nearly everything on your itinerary. Here at The Solo Solstice, we greatly value walkable cities – especially as budget-conscious travelers. In fact, I only recommend a car-heavy city if it’s worth the financial, legal, and physical hassles that usually come along with renting a car.

Let’s say I’m planning my first solo trip to Chicago. I want to walk around the Art Institute, eat a good meal at Sweetwater Tavern & Grille, take some selfies at Millennium Park (can’t forget the iconic Bean!), and see a concert at Soldier Field.

I’ve been to Chicago four times already, so I have a few hotels in mind:

• Hilton Chicago
• Le Meridien Essex Chicago
• citizenM Downtown Chicago
• Courtyard by Marriott Chicago Downtown/River North

These properties are excellent choices because they’re all budget-friendly and no more than a 30-minute walk, train ride, or bus ride from these places.

I’m telling you. Once you get into the habit of planning your activities and THEN your accommodation, you’ll feel farless constrained.

You also don’t want to be in a rush to book your accommodations because it’s one of the only travel expenses that you thankfully don’t have to pay upfront.

As long as you book it, you can wait as late as check-in to pay for your stay. And as a solo + budget-conscious traveler, it’s nice to focus on expenses that aren’t as high as something like a hotel or Airbnb.

STEP #8: START PACKING

This is when things really start to feel official because you’re grabbing your suitcase and thinking about what you’re going to fill it with.

I highly suggest packing a capsule wardrobe (I have a post coming soon) and traveling carry-on only. Packing will take far less time and you won’t have to spend money to check your bag.

WHY SHOULD I LEARN TO PLAN MY OWN TRIP? CAN’T I JUST HAVE A TRAVEL AGENT DO IT?

Even if planning trips isn’t really your jam, I still think it’s important to learn how to do so. There’s nothing as rewarding as spending hours, days, weeks, or even months planning every aspect of a trip and finally executing everything.

Seriously — I think I enjoy planning trip more than actually going on one! I might just have to become a travel agent someday…

Speaking of which, you can totally work with a travel agent to plan your trip. You can usually get some great perks, like upgraded flights or late hotel check-out.

But like I said, I do think you should learn the process yourself. Then, once you get the hang of it, you can think about handing off some of the work to a professional.

MY FAVORITE TRAVEL PLANNING RESOURCES

• Google Flights: a free website you can use to find flights all around the world. Enter your dates + your origin airport (like ORD, MIA, JFK, or LAX) and leave the destination airport blank. You’ll find some great deals as long as you’re flexible with your dates and budget.
• Skyscanner: slightly more detailed and user-friendly version of Google Flights. Great if your travel plans are extremely flexible and you’re planning far enough in advance for the best deals.
• Travel Blogs: amazing resources for finding popular activities, hidden gems, restaurants, chill spots, and more. My favorites include A Passion and a Passport, Bon Traveler, Wheatless Wanderlust, and Practical Wanderlust.
• Get Your Guide & Viator: excellent platforms for unique experiences, tours, and excursions in various destinations around the globe, often at discounted rates. All of your bookings live in one unified space.
• TikTok: incredible resource for activities, hotels, restaurants, day trip ideas, stores to shop at, and more during your trip.
• Reddit: my go-to resource for unfiltered travel advice and stories from travelers who have been to the places you plan on visiting. Super honest and detailed opinions, giving you trustworthy advice to plan your trip.

I plan to write a post full of all my favorite travel planning resources, so stay on the lookout! I’ll be sure to update this post once that goes live.

COMMON MISTAKES TRAVELERS MAKE WHEN PLANNING A TRIP

• Overpacking their itinerary: look, I know it’s tempting to add all kinds of tourist attractions, parks, and coffee shops to your itinerary, but you need to be realistic — even if it’s your first visit. You’ll quickly learn that I prefer a more moderate and real-life approach to travel. Instead of mindlessly adding things to your itinerary, I suggest picking one anchor activity (think of this as the main experience of the day) per day, along with a handful of other activities in the area.
• Not taking travel time into consideration: this is something I see and witness far too often. Please, please, please think about how long it’ll take to get from one stop to the next on your itinerary. And while we’re on the topic, you’ll also want to remember that you might spend longer at one stop than you originally expected.
• Skipping tourist activities: just because it’s popular or a bit more on the expensive side, that doesn’t mean it’s a tourist trap or isn’t worth experiencing. So go see the Bean in Chicago, the Eiffel Tower in Paris, or Lombard Street in San Francisco!

I’m writing a full guide on this topic, so stay tuned! I’ll be sure to add a link to it when it goes live.

FINAL THOUGHTS: HOW TO PLAN A TRIP

Goodness — this was a long post, wasn’t it? I’m glad you made it to the end.

Now that you’re done reading, I want you to go back through the post and carefully follow each step. I know everything can get overwhelming really fast, so it’s important that you stay patient.

Like I mentioned earlier, there are other ways to get the information in this post, so feel free to check out those resources.

If you have any questions, comments, or concerns, don’t hesitate to reach out! Simply comment on this post, send me a DM on Instagram, or email me at demarcus@thesolosolstice.com. I’d love to chat!

ABOUT DEMARCUS

DeMarcus is a Midwest-based travel content creator and the founder of the solo travel blog, The Solo Solstice. He began his solo travel journey in December 2025 and since has been creating practical, in-depth travel guides for a like-minded community of first-time solo adventurers.

Visit the About Page to learn more about DeMarcus, and visit the Ethical & Responsible Tourism Page to learn more about his efforts to promote responsible tourism.