How to Plan the Epic Vacation Itinerary
Without Losing Your Mind
If you’re reading this, chances are you either drew the short straw and got stuck planning the family vacation again, or you genuinely love spreadsheets, schedules, and crafting the ultimate trip. Either way — I’ve got you covered so you can have an epic vacation itinerary.
After 30+ years of planning everything from family getaways and wine weekends to multi-generational mother-daughter trips, I’ve learned what works (and what absolutely doesn’t). This guide will walk you through my go-to steps for building a vacation itinerary that makes everyone happy.
👉 Check out my Viator shop here for curated experiences I’ve loved.
For a ready-made set of ideas, check out my Ultimate Guide to 9 Best 10-Day US Road Trips.
Not sure where to go next? Add one of these 10 hidden travel destinations only ultimate travelers know to your itinerary.
Disclaimer: This post may contain affiliate links, which means I will earn commission if you purchase from my links. This comes at no additional cost to you and helps me continue creating free and valuable content. Thank you!
Step 1: Know Your Travel Crew
First things first — who’s going?
This one matters more than you think. If it’s a solo trip, you can skip this part (you already know you’re fabulous). But if you’re wrangling a crew, understanding what type of travelers you’re working with is critical.
You might be traveling with:
- The Must-See-It-All Explorer – Can’t-miss a landmark or risk “wasting the trip.”
- The Chill & Sip Crew – Just here for the food, wine, and naps.
- The Adrenaline Junkie – Wants to cliff dive before breakfast.
- The Spa Seeker – Prioritizes facials over famous sites.
The sooner you identify your group’s style, the easier it is to find balance and avoid becoming the dreaded Vacation Dictator.
Check out my post to help discover what type of traveler you are and top destinations to go to!
Step 2: Do Some Light Research
Hopefully you’ve chosen your destination — if not, check out my travel guides on Rome and the Cinque Terre, Ireland, or Tenerife. Once your location is locked in, it’s time to dig into the details.
Start with this quiz to discover your ideal destination based on your personality and travel style.
Start with questions like:
- What are the top things to see and do?
- What’s the local food scene like?
- Which neighborhoods are best to stay in?
I usually begin with the official tourist site (search “[City Name] tourism board”). Then I send a quick group text to my fellow travelers with a few highlights and ask what sounds good. Easy crowd-sourcing to get to an epic vacation itinerary loved by all!
Tip: Be sure and get insurance for your trip! Check out Forbes best overseas travel insurance companies for 2025.
Next stop? Pinterest.
It’s my go-to for curated travel blogs and real-life tips. I search those same questions and save my favorite pins to a board. Way more organized than 42 open Google tabs. (And hey — follow me on Pinterest while you’re at it!)
Step 3: Choose Where to Stay (Seriously — This Matters)
Here’s a hot take: Your lodging location can make or break your trip.
Even the most beautiful hotel won’t make up for a 45-minute commute to everything you want to do. Ask me how I know… (Yes, there was a sketchy alley in Paris involved.)
Hotel vs. Short-Term Rental?
Check with your group again. Here’s a quick breakdown:
Hotels:
- Built-in amenities (pool, gym, concierge, restaurant)
- Ideal for first-timers or those who want convenience
Short-term rentals (like Airbnb or Vrbo):
- More space to spread out and relax
- Better for groups or longer stays
- Often more character (hello rooftop terrace!)
Use filters to narrow your search — I like “Superhost,” 4+ stars, and 50+ reviews. Always read reviews. One person’s “tiny shower” is another’s “authentic European experience.”
🧳 I use Booking.com for hotels and Airbnb or VRBO for rentals. Most of them let you create a wish list and share with your group (yep, back to that group text!).
Step 4: Find Things to Do (Without Overwhelming Yourself)
Time to sprinkle in the fun for your epic vacation itinerary. I rely on two tools here: Visit A City and Viator.
Visit A City — The Unsung Hero of Travel Planning
If you haven’t heard of Visit A City, bookmark it now, you will thank me later. It offers:
- Pre-built itineraries by city and travel style (packed vs. relaxed)
- Ability to add your hotel address for a custom schedule
- Opening hours and map-based planning
- Downloadable, shareable itinerary options
It’s an excellent research tool — and for some, it might be all you need!
Viator — My Not-So-Secret Weapon for Activities
From wine tastings to whale watching, Viator has it all. I’ve used it around the world and always recommend starting here.
Not sure what to book? Ask your group:
“What’s one thing you really want to do on this trip?”
Maybe it’s a cooking class in Rome, a sunset cruise in Maui, or ziplining in Costa Rica. Once you have your top picks, you can start building around them.
Some activities — like hop-on-hop-off tours — double as transportation and sightseeing. These are especially great for large cities like London or Paris. And trust me, your feet will thank you.
👉 Check out my Viator shop here for curated experiences I’ve loved.
Step 5: Time to Book It
Now that you’ve got your stay and your must-dos, start locking it in:
- Book hotels or rentals through your preferred platform.
- Reserve tours and activities through Viator.
- If you’re the group organizer, book for everyone and Venmo request their share. This avoids the dreaded “we got different time slots” mess.
Step 6: Pull It All Together
Once everything is confirmed, I use the TripIt app to organize my epic vacation itinerary. It’s my ride-or-die itinerary tool. Just forward your confirmation emails to pl***@****it.com and the app builds a shareable itinerary with:
- Flight info
- Lodging and confirmation numbers
- Activities and times
You can also add your travel companions to view the itinerary. No more “what time is our flight?” texts every hour.
iPhone users — use Apple Wallet to store tickets and passes. It’s so convenient.
Final Tips From a Seasoned Planner
🗣 Talk to your travel crew. Get their input. It’ll make the trip better for everyone.
🧘♀️ Be flexible. Not everything will go to plan, and that’s okay.
😴 Don’t overschedule. Leave space to breathe and enjoy where you are.
✈️ No major plans on Day 1. Let everyone acclimate, wander, and sip some wine.
📆 Leave room for spontaneity. Some of the best things we’ve done were booked day-of through Viator!
Be Sure and Check Out My Recommended Travel Essentials
Compression Packing Cubes – Keep your things organized.
Expandable Travel Tote – I could have used this when in Tenerife for all the shopping I did!
Quiet Loop 2 Ear Plugs – Great for the airplane!
Travel Charger – A must have and I love the size of this one!
Cooling Hat – For summer travel to keep your head cool.
Swiss International Luggage Set – Get a solid luggage set that is tested and proven!
Ready to Plan?
Planning a vacation doesn’t have to be overwhelming. With the right tools (and the right mindset), you can build an unforgettable trip and epic vacation itinerary that feels both organized and relaxed.
Have questions? Drop them in the comments or message me on Instagram @mywinewalk. And if you use any of the tools above — especially Viator — I’d love to hear what you booked!
🍷 Cheers to stress-free planning and unforgettable travel.
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