How To Plan A Trip – 10 Simple Steps

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Planning a trip can be overwhelming, but if you break it up into these steps, you can spread out the work and hold on to your sanity! The Quick overview of the 10 steps are as follows (then I’ll dive in to tell you exactly how to approach each step). At the end, I’ll give you some tips on packing for your well planned trip!

• Start early
• Choose your dates
• Choose your location
• Do a quick price plan
• Research activities
• Choose and book your flight
• Choose and book your lodging
• Book activities
• Rent a car
• Make an itinerary

1. Start Early

Have you ever waited until the last minute to plan a trip? It can be pretty stressful. Often the best stuff to do, see, and places to stay are all booked up and you can really miss out. You will often end up spending more because the lower cost options are taken. So, do yourself a favor and start planning your trip as early as possible. I recommend AT LEAST 6 months. If you are going to a really popular tourist destination and you know you are headed there during their peak season, starting even earlier will provide you with the best options. For example, if you are going to the Grand Canyon in the summer, some of the coolest activities get booked up as much as a year in advance.

2. Choose Your Dates

If you have school age children like I do, this will really limit when you can go on a family vacation. Even you are wide open all year, you’ll need to narrow down your timeframe before you can begin to look at prices. You will typically get better prices if you can travel during off season (usually when my kid is in school). So, if you have that flexibility, use it to your advantage. Places will be less crowded and less expensive during the off season.

3. Location, Location, Location

Pick the place you want to go. I keep a bucket list of places I want to go in my notes on my phone. I also have a TON of places pinned on my Pinterest boards, so my issue is just in narrowing those thousands of places down to just one.

Think about your budget and what kind of vacation you want. Low budget beach vacation? Maybe head to a local beach. Here in Texas, we can go down to the Gulf of Mexico or fly to a beach in Mexico pretty cheaply. High budget beach? How about Hawaii? Are you looking for a luxurious romantic getaway? Head to Bora Bora. There are so many places to choose from.

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4. Do A Quick Price Plan

This is just to get a quick idea of the cost. I usually jump on Expedia for this because it’s quick and easy, but you could use any number of booking sites.

• Look up flights and see what the average price is for your dates. I always google the best airport to fly into for any given destination.
• Look up hotels. Again, just look at an average cost. Though I often choose to stay in and Airbnb or VRBO, I still start here to get an idea of the prices.
• Rental Car
• Any can’t miss activities. If you don’t even want to go to Hawaii unless you can do the helicopter ride around the island, then you better find out how much that will cost you before moving forward.
• Daily spending. There is no real rule here. It’s really about how much you can afford and what your spending habits are. You can do a quick google search for “how much spending money do I need in Hawaii” and you’ll get a few good articles to glance at that will give you a good idea of what things cost in a given area.

Once you have your quick budget, you can always change the dates or location to find something more in line with the budget you had in mind.

5. Research What You Want To Do

I LOVE Pinterest for this part! This research is the most fun part for me when I plan a trip. Before heading to Costa Rica, for example, I searched Pinterest for the best things to do with kids, best hikes, best beaches, etc. When I saw something I really liked, I pinned it on a Google map. This enabled me to easily see where everything was located and how spread out it all was. I also put out a Facebook post to my local mom group and ask for their “can’t miss” things to do/see in the area I’m headed to. They always give me great ideas!

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From here, you may need to narrow down a few things. If all but 1-2 are in a particular area, then that’s the area you will want to spend most of your time. In Costa Rica, we ended up spending 3 nights in one place (La Fortuna), driving 4 hours or so and then spending 3 nights in another (Manuel Antonio) to be able to see volcanos, beaches and wildlife.

6. Choose Your Flight & Book It

Choose the airport closes to the are where you will be staying. I always go through Chase Ultimate Rewards to book my flight because I have a Chase card that earns points. But again, you can use Expedia, Google flights, or go directly to the airline’s website to book your flight. I filter for the shortest duration. It costs a bit more, but I have motion sickness and I really hate to fly (yes…a travel blogger that hates to fly…the irony is not lost on me). I’m happy to pay a little extra for a shorter flight. You can read more about how I fly for free with points in the related posts at the bottom.

PRO TIP: If you really want to save on flights, try Scott’s Cheap Flights.Try a 14-day free trial and you’ll get a taste of the amazing deals! Learn more HERE.

7. Choose A Place To Stay & Book It

You can use any site you booking site for this. I primarily use Expedia, VRBO and Airbnb. Just look around a little and choose the place you like in the location you are happy with. Make sure to look at reviews and look for hidden fees before you book. Read my related post about Airbnb/VRBO listed at the bottom for more information.

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8. Book Extra Activities

You could choose to wait until you arrive to book various other activities you have planned, but I always recommend booking in advance. I’ve shown up without booking in advance only to find that the awesome thing I wanted to do was all booked up. Learn from my mistake and book it now.

9. Rent A Car (if needed)

Usually, I like an mid-sized SUV for my family of three. I drive an SUV and my husband drives a truck in our day to day lives, so anything smaller just feels wrong. I usually rent through Expedia. I like that I can see customer ratings. Make sure you pay attention to the location of the rental car company. Sometimes they may be a ways from the airport. Just make sure you are aware of that in case you are on a tight schedule.

10. Make A Simple Itinerary

I like to list out what we are doing each day. Not a minute-by-minute Grizwold ”European Vacation” style itinerary, just a simple list of the things that are scheduled for each day – flight departure & arrival times, hotel check in & check out times, scheduled activities, and a list of other possible things to do in the area. This just helps me remember what we have planned for each day. I intentionally leave A LOT of dead space because we like to stop when we see something cool. You also may hear of something to do or see in the are from the locals. You want to make sure you have plenty of time to just enjoy yourself.

Now you have everything you need to plan the trip. But, what will you pack? How many times have you forgotten to pack something? If you’re anything like me, you’ve lost count. Many times this is only a minor inconvenience, but sometimes it can be a real bummer and a costly mistake (ever had to buy sunscreen at an all-inclusive beach resort – $$$ yikes)! So, I’ve put together this vacation packing list. It’s sure to save you time now & headaches later. READ MORE. Also, be sure to check out ‘Packing Hacks You Never Knew‘ for some great packing tips & tricks.

Want to know where to look to find the best deal on your flight? Head on over to How To Find Cheap Flights. I did a price comparison on many of the most popular flight search engines and the results will surprise you!

Until next time…

Until next time…

About The Author

My mission is to inspire and empower families to prioritize travel now, creating unforgettable memories and deeper connections with their loved ones.

I provide guidance and practical solutions to help busy parents integrate travel into their lives, fostering joy, fulfillment, and stress-free adventures. Don’t wait until it’s too late; the time to travel is now.
Learn more about me & My Travel Obsession here.

My Favorite Travel Booking Apps & Websites

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⭐MY TRAVEL OBSESSION:

• Products & Services – My Travel Obsession's travel planning products, services, and freebies!
• What To Pack – See all of my personal favorite travel items.
• Travel Resources – Resources that I use most when planning, booking & traveling.

🏡FOR FINDING GREAT PLACES TO STAY:

• VRBO – My #1 recommendation for family-friendly lodging options.
• Expedia – My favorite for hotel bookings.

🚗FOR CAR & RV RENTALS:

• Discover Cars & Sixt – My favorite sites for rental cars worldwide.
• Turo.com – Rent a car from an individual owner – It's like VRBO for cars!
• RVShare – Rent an RV for your next family road trip!

🚁FOR ACTIVITIES, EXCURSIONS, & TOURS:

• Viator & Get Your Guide – The best sites to find and book activities & excursions.
• Gypsy Guide – An AWESOME audio tour app. ALWAYS check to see if they have a tour available.

🩺FOR TRAVEL INSURANCE:

• SafetyWing – The lowest-cost travel insurance out there. Several options starting as low as $42 for 4 weeks of coverage.

✈FOR FINDING GREAT FLIGHT DEALS:

• Going (formerly Scott's Cheap Flights) – My #1 recommendation for saving big $$$ on flights. Sign up for a free 14-day trial.

🥾FOR HIKING:

• AllTrails – THE APP for hikers. I recommend paying for the pro version so you can use the navigation feature while hiking.

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