When planning a trip, it’s easy to feel overwhelmed. There are so many decisions to make!
Over the years, we’ve planned dozens of trips ranging from big family vacations to romantic getaways and whirlwind multi-city adventures. Through trial and error (and a few “oops, I forgot to factor in the three-hour drive to the airport” moments), we’ve found a process that keeps us organized while leaving room for fun and spontaneity.
Here’s our personal step-by-step guide to planning a trip:
Step 1: Decide Where to Go
If you already know your destination, congratulations! You’ve cleared the biggest hurdle. If not, here’s my process for narrowing it down:
First, I think about who I’m traveling with. A trip with kids and grandparents is going to look very different from a couple’s escape or a getaway with friends.
- Family trips: Accessibility (wheelchairs, strollers, walkers), kid-friendly hotels, and activities for all ages are top priorities.
- Couple trips: I focus on romantic spots; adult-only resorts, private dinners, scenic boat rides, or unique tours we’d both love.
- Friend trips: The vibe is completely different. Are we sharing an Airbnb or booking separate rooms? Will we cook, eat out, or do a mix? Group-friendly activities like hikes, boat rentals, or all-inclusive resorts work best.
Then I think about what type of trip we want: hiking, lake, beach, city, or a mix. On our Northern Italy trip, we managed beach (Cinque Terre), lake (Lake Como), and mountains (Dolomites) all in one go. Some places naturally combine categories, like a lake in the mountains (Lake Lure, NC) or a city in the mountains (Denver, CO).
Finally, I look at how much time we have. For a long weekend, domestic trips are usually easier (but don’t rule out close international spots like Bermuda or the Caribbean from the East Coast). For a week or more, international becomes more appealing. And while you might assume domestic is cheaper, that’s not always true; sometimes Mexico or the Caribbean can be less expensive than Miami.
Step 2: Set Your Budget
Budgeting is flexible; you can make almost any destination work if you’re willing to adjust. That could mean shorter stays, simpler accommodations, or skipping pricier tours.
I break my budget into:
- Flights (or gas if driving)
- Accommodation
- Transportation (Rental cars, Trains, Trams, Metros, Uber, etc.)
- Food
- Activities (Tours, Boat rentals, Snorkeling, Wine Tastings, etc.)
- Miscellaneous (souvenirs, tips, parking, etc.)
Step 3: Pick Your Dates
Time of year matters, both for weather and pricing. Are you locked into certain dates, or can you be flexible?
If you’re traveling for something seasonal, like cherry blossoms in Japan or heather season in Scotland, you’ll need to plan around those dates. I also love shoulder seasons (spring and fall) for lower prices and fewer crowds.
Step 4: Do the *First* Round of Research
This is when I start looking at flights, accommodations, and transportation. NOT to book yet, but to get a feel for costs and availability.
Flight tips:
- Don’t just trust Google Flights. Some smaller or regional airlines don’t appear there; check their websites directly.
Accommodation tips:
- Explore all options: hotels, hostels, Airbnbs, VRBO, all-inclusive resorts, and private rentals.
- Check prices on different days, rates can change drastically over weekends or even within a single week.
Step 5: Plan Activities
This is one of my favorite parts. I gather ideas from:
- YouTube (“6 Days in Budapest,” “Top 10 Things to Do in Austin”)
- GetYourGuide & Viator for tours
- Airbnb Experiences for unique options
- Recent blog posts & vlogs for up-to-date seasonal info
I’m not huge on TripAdvisor’s “Top Things to Do” (too touristy), but it’s fine for a general overview.
Always double-check which days your activity is available. It sounds obvious, but when you’re juggling dozens of plans, it’s easy to overlook that the villa you’re dying to tour is closed on Sundays; the only day you’d planned to be in that area.
Step 6: Lock It In
Once I’ve got the big picture:
- Book flights (starting with the longest or most expensive leg)
- Book accommodations (the good ones fill up quickly, especially in summer)
- Book activities (especially ones with limited spots)
Step 7: Plan (and book) Meals
Are we at an all-inclusive? Cooking in our Airbnb? Eating out every meal?
With a smaller budget, I mix groceries with budget-friendly restaurants. For a splurge, I’ll research Michelin-starred or foodie-approved spots and book early.
One of my favorite ways to get ideas is watching YouTube videos titled “Best Food in [Destination]” to see the dishes before I go. I also use Google Maps to search restaurants and filter by cost and rating, whether I’m looking for a fancy date night spot or a quick, casual bite between activities.
If possible, book at least one to two months in advance, especially for popular spots, because the best places fill up fast. And if you’re after a truly elevated dining experience, I always recommend checking the Michelin Guide for your destination.
Step 8: Make a Loose Itinerary
I drop everything into a calendar (activities, meals, and travel days) without over-scheduling. I group stops by location to avoid zig-zagging across a city, and I use Google Maps to check travel times.
I have attached our FREE Downloadable Itinerary Template below as a helpful guide:
Step 9: Pack Smart
Only bring a carry-on and a personal item for multi-city trips.
- It saves time (no baggage claim), money (no checked bag fees), and stress (no lost luggage).
- Be mindful; many budget airlines abroad have stricter carry-on size rules than U.S. carriers.
- We love our Gieury carry-on backpack; it’s super lightweight, fits way more than you’d expect, has smart compartments for shoes and a laptop, and even comes with a USB charging port for travel convenience!
Use space-saver bags.
- I’ve packed winter coats, multiple dresses, and still had room to spare thanks to these.
- Bring Downy Wrinkle Release spray and roll your clothes to minimize creases.
Plan outfits you can re-wear in different ways.
Step 10: Enjoy the Adventure—You Planned Like a Pro
Once all that’s done, you’re ready to go; and that’s when the real adventure begins.