How to Plan the Perfect Travel Itinerary - Real Vacation Planning That Actually Works

Perfect trips don’t just materialize. Even the most relaxed, sleep-late, do-nothing getaways take clarity, planning, and structure; without it, everything slips into wasted time and logistical noise. A good itinerary isn’t about control - it’s about momentum. It’s about knowing where you’re going and why, so you’re not constantly checking your phone or arguing over dinner reservations in the back of a taxi.

You don’t need a hyper-stuffed schedule or a spreadsheet of backup plans; what you do need is a clear sense of pace, flow, and geography. A trip that feels effortless is always the result of one that was thought through.

1. Start With What Matters Most to You

Don’t start with flights and budget, start with the thing you care about most. The one element that is your driving force to choose this destination at this time.

If you're a foodie: build everything around your highest-priority meals. Research which restaurants take reservations and how far in advance you need to book; see which spots have tasting menus or limited seatings, and plan the rest of your schedule around those. A destination dinner in a tucked-away wine cellar is going to dictate where you stay, how you move through the city, and whether you need to adjust your arrival time.

If you're obsessed with the perfect hotel or resort, that’s where your planning begins. Maybe you're looking for a historic property in the center of town, a boutique spa resort in the hills, or the best oceanfront view within reach of your budget. Filter by dates, plug options into your custom Google Map, and monitor availability early. The best rooms go fast - especially in high season - and once you're locked in, everything else becomes easier to arrange.

If you're an outdoor adventurer, figure out which trail days require early starts or special permits. 

If you're chasing design, plan around museum schedules, gallery openings, or interior-access hours. 

If shopping is your priority, research market days or drop dates for local designers, and when the biggest sales are. 

If you’re going for a specific event - a festival, sporting final, seasonal market, or once-a-year celebration - book it before anything else. Get the tickets, confirm the dates, and secure the most convenient lodging you can afford. Major events drive up prices, sell out early, and anchor the rest of your timeline whether you plan for it or not. Your itinerary should be built around that fixed point, not squeezed in around the edges.

If your goal is to spend as much time in the water as possible, lock in proximity to beaches, boats, and surf conditions before you book anything inland. And for tropical places, and ocean-focused trips, it is almost always worth it to book during high season. While you can often get great deals and less crowds during shoulder and low seasons, you have a much higher chance of losing a lot of your trip to storms, or even getting stranded or into a dangerous situation. (I once got stuck on an island in the Maldives during a cyclone for an additional 5 days - which sounds like a dream except we weren't able to actually do anything, and we lost power, wifi, air conditioning, and had to move to a room on higher ground and literally could not get home.)

Everyone plans differently because everyone travels differently. Start with what you're most excited about and reverse-engineer the rest. You’ll end up with a trip that reflects your priorities - not just someone else's highlight reel.

2. Research Beyond Google

Before booking flights or picking a hotel, start with the foundation: figure out what you actually want to do once you land. Skip the auto-generated lists and go deeper. Read long-form travel blogs that feel personal, not paid-for (👋🏼). Look for specificity - not “best cafes in Paris,” but which arrondissement, what time of day, why that spot instead of the one next door.

Start saving posts on Instagram that are geotagged, not just aesthetic, and scan TikTok for real walk-throughs and restaurant reviews - Tiktok's search has been updated to be pretty incredible at giving you exactly what you're looking for now. Use Pinterest for visual mapping; it’s often better for neighborhoods and street energy than any formal guide. Prioritize voices that feel real, grounded, and up-to-date - and ignore anything that feels like it’s been SEO’d into oblivion.

Your goal isn’t to collect every possible option. It’s to find a few that match the version of this trip you actually want to have.

And remember - everything AI gives you is pulled directly from blogs, and 90% of the time you will get better information going directly to the source.

3. Plot Everything on Google Maps - Before You Book Anything

Once you’ve built a rough list of places, star them all on Google Maps. Some people love to color-code by type - food, nature, design, experiences - and add notes on hours, reservation policies, or any relevant detail that might change your day, but I just start simpler by just adding them all to my Starred Map. This helps get a visualization of where you want to go, and you can look around where points are clustered and start to preliminarily plan your itinerary and hotels from there. 

This map becomes your entire planning base. It shows you how far things are from each other, how long you’ll spend in transit, and whether your dream hotel is actually in the middle of nowhere. You’ll start to see natural groupings emerge - days that can be built around a neighborhood, a coastline, a market - and immediately spot the outliers that don’t make sense logistically.

Especially for a road trip or any travel where I will be moving around a lot, this is the most important part - I play around with driving directions between different points and areas to figure out the best general route and which places can be paired together well. It's important to look at driving directions and not just map plots, because even though some places appear close together on a map, sometime there is no road that connects them and they can actually be hours apart. I like to roughly write out a general itinerary for a road trip based on the easiest travel times, and plan hotel bookings from there. 

4. Book Accommodations That Match Your Itinerary - Not Just the Photos

Where you stay should support your trip, not complicate it. You can find a beautiful hotel almost anywhere - but the right one is the one that fits your mapped-out geography. Stay close to the things you care about; walkability is worth more than a rooftop pool you’ll only use once.

Think in terms of access: metro lines, ferry docks, walkable cafes. If you're driving, try to book a hotel that includes parking to make your life easier, if you're going to get around via train, you will thank yourself every day to be only a few minute's walk from the train station. If every meal you want to eat is on the opposite side of the city from your Airbnb, the glow of the space will fade quickly once you’re stuck in a cab twice a day. There’s a big difference between staying in a hotel located on Charleston’s King Street and booking something outside the city, for example.

5. Hunt for Smart Deals, Not Just the Lowest Price

Saving money matters, and it is always worth looking into deals, but cutting corners can often cost more later. Once you know where you want to stay, compare rates across multiple platforms: Hotels.com, Expedia, direct sites. Use tools like Hopper to track prices or find off-peak windows. For longer stays, or smaller properties, call directly and ask about discounts you won’t see online.  

Avoid falling into the deal-chasing spiral; booking a hotel you didn’t want just because it was $30 cheaper is a fast way to ruin the trip you already spent hours building. Travel is full of trade-offs - just make sure the ones you’re making are worth it.

This is also very true of flights, while a flight might be the cheapest option; having to take multiple legs, long overnight layovers - or layovers so short that you have a high chance of missing your flight or your bag not arriving, or arriving at the worst possible time takes away so much time from your trip and can feel like a grueling place to start. I usually set my parameters with as few stops as possible, layover times of at least 2 or 3 hours for international flights (especially in airports like London Heathrow that are notoriously chaotic), and desired arrival times and find the best flight deal from there - spending the extra $100 or $200 is almost always worth it. 

My rule in general is that if you're traveling more than 4 time zones away, it is always best to land in the afternoon or evening, so not only can you check in straight to your hotel, you don't have to stay up through an entire day to adjust to the time zone. Most travelers have fallen into the trap of arriving in Europe from the US at 7AM, on an uncomfortable flight, and had to wait until 3PM to get into your hotel room and fight through an entire day of being a zombie before you can sleep. Life is so much better when you can get to sleep after your arrival and start your first full day fresh. 

6. Don’t Pack Every Day to the Brim

The fastest way to ruin a trip is to overpack planning your vacation. Instead of creating a minute-by-minute rundown, build your days around one or two solid anchors: a reservation you’re excited about, a hike, a museum, a market. Leave everything else open.

Downtime isn’t wasted time - it’s what allows the trip to breathe. You won’t always know what you’ll want to do until you’re there, which is why you need room for shifts, for detours, for staying longer somewhere unexpected. Structure matters, but flexibility is what turns a plan into a memory.

However, this really comes down to how much you enjoy doing - I am someone that loves to go go go, and as a photographer I am always trying to get up before sunrise to get the best light and cities with no crowds (Almost all of the shots of popular places with no one around are taken just as the sun is coming up - it's usually the only way.) However, Brandon will only tolerate so much of that before he goes on strike and forces me to stay at the hotel, so you have to find the balance that's right for you and your group. 

7. Itinerary Planning Isn’t About Control - It’s About Flow

A strong travel itinerary isn’t a rigid checklist. It’s a framework that keeps you grounded while letting you move freely. When you’ve already made the big decisions - what’s worth seeing, where you’re sleeping, what area to explore each day - you’re not stuck re-deciding every hour. You’re just there, moving through it, present.

And if you're going to an area with lots of hotel options or outside of a popular season, it can be highly worth it to book hotels as you go and let your plan change as you experience the destination - this has lead to some of our more amazing travel experiences and given us the opportunity to see things that we would have missed after talking to locals while we are in the area. However, this can also lead to missing out on things that matter to you if reservations are unavailable, so take this on a case by case basis. When we took a road trip through Albania, we booked most of our hotels as we went as there were plenty of options, for The South of France in July, we booked everything ahead of time because things get booked up FAST, and sometimes your only available options are incredibly expensive or.... not great. 

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