If you’ve ever felt overwhelmed by the idea of planning a trip, you’re not alone. There’s so much to think about — where to go, what to do, how to fit it all in — and sometimes just getting started can be the hardest part.

I love trip planning. Like, really love it. I can happily spend hours falling down internet rabbit holes about restaurants, landmarks, hidden gems, and the best walking routes between them. I actually tend to try to cram in WAY MORE than I should, which can create some tension if I don’t communicate with my family about my ideas and get their input.  

Over time, I’ve found that doing the legwork before you leave can completely change the outcome of your vacation. You avoid the dreaded “what should we eat?” debates, don’t waste time zig-zagging across town, and make the most of your days. Of course, not everything goes according to plan — and that’s fine — but starting with a solid outline sets you up for a much smoother trip.

That’s why we’ve put together this guide: to help you create your own smart, well-organized trip plan without spending weeks glued to your laptop. It’s the same process we use for our own travels, and it works whether you’re going somewhere for a weekend or a month.

1. Pick Your Destination

This is often the trickiest part. The world’s huge, and there’s never enough time (or budget) to see it all. I’m always torn between visiting somewhere brand new or going back to a place that already has my heart.

When deciding where to go, start with a few simple questions:

What’s the vibe you’re looking for?
Do you want the buzz of a big city? Lazy days on the beach? Mountain hikes? Or a mix of everything? Pin down the type of trip you’re craving — that alone can narrow your list fast.

When can you go?
Your travel dates can make a big difference. If you’re off work in the winter and want warm weather, head somewhere tropical. If you’re escaping summer heat, aim for cooler climates or destinations in the Southern Hemisphere.

Consider peak vs. shoulder season
Some places are wildly crowded (and pricey) at certain times of year. If you don’t mind slightly less-than-perfect weather, traveling during shoulder season can save money, reduce crowds, and still give you a great experience.

Follow the deals
Sometimes the destination chooses you. I’ve booked trips I didn’t expect to take simply because I found an amazing flight deal (more on that in Step 3).

Go for a special event or experience
Anchor your trip around something unique — like a music festival, cherry blossom season, or a famous scenic drive that’s only open part of the year.

Need ideas? Here are some of our favorite places so far:

• Italy – Italy is a captivating blend of rich history, breathtaking landscapes, world-class cuisine, and vibrant culture, offering everything from ancient ruins and the canals of Venice to stunning coastlines and charming villages.

• Croatia – Croatia is a dazzling mix of crystal-clear Adriatic waters, medieval coastal towns, breathtaking islands, and rich cultural heritage, making it a dream destination for history lovers, nature enthusiasts, and beachgoers alike.  And they have some of the best waterfalls you’ll ever see in Plitvice National Park.

• Hawaii – Hawaii is a tropical paradise where lush landscapes, stunning beaches, vibrant culture, and year-round sunshine come together to create the ultimate destination for relaxation, adventure, and natural beauty.

• Utah – Utah is an adventurer’s dream, boasting otherworldly red rock landscapes, five stunning national parks, year-round outdoor recreation, and a unique blend of natural beauty and rich pioneer heritage.

• Boston – Boston is a vibrant city where rich American history, world-class museums, charming neighborhoods, and a thriving food scene blend seamlessly with a lively sports culture and beautiful waterfront views. Do the Freedom Trail, either on your own or guided; it’s incredible!

• U.S. National Parks – Favorites include Yosemite, Zion, Yellowstone, Bryce, Acadia, Mesa Verde, and Arches.

2. Set a Travel Budget

Once you’ve chosen where you’re headed, figure out how much you’re willing — and able — to spend. This includes the big stuff (flights, hotels, car rentals, taxis or Ubers) and the smaller daily costs (meals, gas, activities, tips, pet care, etc.).

We use a simple travel budget spreadsheet to map out each trip. It helps us balance splurges with budget-friendly adventures so we can keep traveling without putting a strain on our finances. You can get our free spreadsheet here.

3. Track & Book Flights

With your destination and budget in place, start watching airfare prices. We use a mix of free tools and paid alerts to make sure we rarely overpay.

Free Tools We Love

• Google Flights – Lets you track specific routes and get notified when prices change. The “Explore” feature is great if you’re open to different destinations.
• Skyscanner – Often finds fares other sites miss, especially for international flights.
• Scott’s Cheap Flights (free version) – Sends alerts for discounted fares and even rare “mistake fares.”

Paid Tools Worth It

• FareDrop – Lets you choose departure airports, destinations, and months, then sends targeted deal alerts.
• Hopper – Predicts whether prices will go up or down, helping you time your purchase.

Pro Tip: Whenever possible, we book flights using credit card points. It’s the easiest way to get “free” travel — just by paying for everyday expenses with the right travel rewards card.

4. Book Accommodation

Once flights are locked in, we jump on lodging. Popular spots can fill up quickly, especially in peak season.

Our go-tos:

• Expedia.com – Great hotel deals and other things like rental cars.
• Airbnb – Perfect for longer stays, cooking meals, and feeling like a local.
• Booking.com – Great hotel deals and a wide range of vacation rentals.
• Tripadvisor – The best place to read unbiased reviews before committing.

5. Arrange Transportation

Will you need a rental car? Public transit passes? Train tickets? Figure this out early.

For rental cars, we often book through Expedia.com, or sometimes direct with the rental car providers.  You can also try rentalcars.com or Costco Travel (if you or someone you know has a membership — they allow the name on the rental to be different from the member’s).

If you’re using public transportation, check whether advance booking saves money — like it does for many European trains — or if you can buy on the spot, as is common in U.S. cities.

6. Dive Into Research

This is where the trip starts to come alive. We scour blogs, vlogs, Pinterest boards, review sites, and Instagram to build a list of must-do activities, restaurants, and experiences.

Some of our favorite planning tools:

• Google – Search “best things to do in ___” or “where to eat in ___” to find blogs and curated lists.
• Pinterest – A visual goldmine for discovering travel blogs and saving ideas in one place. Check out our Pinterest page here.
• Tripadvisor/Yelp/Google Reviews – Compare reviews to see what consistently gets praise.
• YouTube – My favorite way to preview an experience before booking it. Shameless plug, we have hundreds of travel videos on our YouTube page, so check it out!
• AllTrails – Essential for finding and mapping hikes anywhere in the world. The Pro version is definitely worth paying the annual fee if you love hiking!
• Instagram – Great for checking current conditions, crowds, and unique photo spots. Of course, if you’d like to follow us on our you can find it here!

7. Map It Out

Once we’ve got our list, we drop everything into Google My Maps to see where each spot is located. This helps us with the best road trip route or to squeeze in as much of a destination as we can in the time we have.

8. Build Your Itinerary

Using our custom Google Sheets template, we lay out each day with activities, meal spots, addresses, notes, and estimated times. We leave wiggle room for flexibility (especially if you have kids!), but this structure helps us fit in everything we want without feeling rushed.

9. Book Tours & Reservations

Once your itinerary is mostly set, it’s time to secure spots for anything that requires advance booking — especially popular tours, timed-entry attractions, and restaurant reservations.

Some things to lock in early:

• Guided tours – Food tours, walking tours, boat cruises, etc.
• Major attractions – Museums, observation decks, or historic sites with timed tickets.
• Outdoor experiences – National park permits, trailhead parking passes, or sunrise/sunset tours.
• Dining – If a restaurant is famous or notoriously hard to get into, book as soon as your travel dates are set.

Pro tip: We put confirmation numbers, addresses, and start times right into our itinerary spreadsheet so we have them handy offline.

10. Plan for Pets (If You Have Them)

If you’ve got a furry friend at home, figure out their care well before your departure. Whether it’s boarding, hiring a pet sitter, or having a friend check in, early booking ensures you’re not scrambling last-minute.

Things to confirm:

• Food supply for your trip duration (plus extra, just in case).
• Vet contact info in case of emergencies.
• Written care instructions so your sitter knows your pet’s routine.

11. Pre-Trip Prep

This is the stage where you handle all those little things that make the trip smoother. Depending on your destination, that might include:

• Notifying your bank/credit card company of travel dates to avoid fraud alerts.
• Printing or downloading important documents (boarding passes, hotel confirmations, tickets).
• Setting up a mail hold if you’ll be away for a while.
• Checking visa requirements and vaccination recommendations.
• Downloading offline maps and translation apps.

12. Pack Smart

We’re big believers in packing as light as possible — even for longer trips. It saves time, stress, and money.

Our go-to strategy:

1. Start with a list – We have a standard packing checklist we tweak for each trip.
2. Lay it out first – Seeing everything before it goes into the suitcase helps cut down on overpacking.
3. Mix-and-match outfits – Stick to a color palette so everything works together.
4. Use packing cubes – They keep your bag organized and make unpacking a breeze.

Bonus: Roll clothes instead of folding — it maximizes space and minimizes wrinkles.

13. Enjoy Every Minute

Once you’ve done all the planning, it’s time to let go a little. Not everything will go according to plan — and that’s okay. Some of the best memories happen when you least expect them.

While traveling:

• Be flexible if weather changes or something better comes up.
• Try at least one thing you didn’t plan for.
• Talk to locals — their tips often lead to the best finds.
• Take photos, but also put the camera down sometimes and just be there.

At the end of the day, the point of all this planning is to free you up to truly enjoy the trip — without stress, without wasting time, and without wondering what you should do next.

Final Thoughts

Planning a trip doesn’t have to be overwhelming. With the right steps, a bit of organization, and some smart tools, you can create an itinerary that balances structure with freedom — so you’re ready for the adventures you know about and the surprises you don’t.

Here’s to smooth travels, unforgettable moments, and maybe just enough spontaneity to keep things exciting.

Be sure to check out our YouTube channel to experience what it’s like to visit many places around the world!