Passion can lead you to an amazing vacation itinerary
Travel Planning

How to Plan an Amazing Vacation Itinerary Anywhere

How do you plan an amazing vacation itinerary in any location? 

I am guilty of sometimes over planning and over scheduling (a person who loves travel planning OVER planning, no way!). After organizing numerous trips now, I feel like I have found a balance. We know how to plan just enough to keep us engaged and active, but not so much that we don’t actually stop to enjoy the moment. 

No matter where you are traveling to, big city or small town, mountains or countryside, we have tips to help you narrow the choices down. Read on to learn how to easily plan a great itinerary in any location. 

What Do You Love to Do?

Cafe with pastries

Start by thinking about what you love to do. Are you outdoorsy, do you love history, food, wine, beer? Pick the top 2 or 3 things you really enjoy, and research activities around those things. 

I’ve included a few ideas below to get your planning juices flowing. 

  • Love wine or beer? Find a tour to a few wineries or breweries, or a wine or beer tasting at a local bar. 
  • Love to be outdoors? Look for a bike tour, a lookout point, or a hiking trail in a park. 
  • Love food? Look for local food halls or markets, food tours, or a unique cuisine in the area.
  • Love History? Find historical sites, museums that interest you, or streets filled with historical charm.
Pro Tip: I use a number of sites to research these things. Usually I start with reading other blog posts I find on Pinterest about that location, to find out what they enjoyed. Check out Trip Advisor or Airbnb Experiences to find tours and reviews, or google local tour companies. I also order and read a local guidebook like Lonely Planet, Rick Steve’s, or Frommer’s a few months before my trip. 
 

Itinerary Timeline

Calendar vacation itinerary

A major factor in planning your vacation itinerary is how long you have in the location. A few days versus a few weeks can really change what you can fit in. 

Here are some ideas on what to schedule depending on the time you have. 

  • 2 – 3 Days – Focus on three main activities with some free time built in. In my experience, rushing to see all the things in one city just to say you saw them, leaves no time to truly experience the city or place. Spend a little time wandering, or sitting at a cafe and chatting with locals. 
  • 5 – 7 Days – You’ll have time to really dive into a location and get to know different neighborhoods, as well as hit major sites you want to see. Consider a day trip to see a nearby town or some scenery. 
  • Over a Week – Ahhhmazing! Who doesn’t love to have more than a week on vacation? Spend time in each area of town, and really get to know it. Plan a few day trips or even an over night stay or two in another city or area. 
Pro Tip: If you want to maximize your time to see things, organize sites in the order of location, and use mass transit to move between places. You could also rent bikes to ride around the city and get a little exercise at the same time. 

Time of Year

How to plan an amazing vacation itinerary around weather

Something to pay attention to when planning your trip, is what the weather will be like that time of year. Not only for what to plan, but also for what to pack. 

Things to consider when it comes to the weather: 

  • Indoor Activities vs. Outdoor – If you plan a tour in a city that notoriously has a lot of rain during that season, you may want to book a driving or bus tour, rather than a bike tour. The same goes for extreme heat or cold. Maybe you didn’t realize southern Spain can get up to 90+ degrees (32° C) in the summer. More reason to do that tapas crawl or visit a museum! 
  • Hours of Operation – Some attractions or historical sites changes their hours depending on the season. You see this a lot in Europe, once fall/winter hits and there are less daylight hours, the hours of the attraction are reduced.  
  • Holidays or Festivals – Definitely important to research this one! If the country observes a holiday and you are not aware, many things can be shut down. A festival could be really fun to join in on, but it could also drive up costs while you are there and add to crowding. 
Pro Tip: If you find yourself in the middle of a big festival or event you didn’t know about, make the most of it. Visit the vendors that set up, people watch from a cafe, or even try to attend depending on what it is. It could end up being the best experience you have! We were in Italy for their Labor Day and realized we were stuck in the town we stayed in, Montepulciano. We were supposed to leave and explore nearby towns, but it ended up being a fun day of waking up to a parade, and shopping at vendors along the narrow streets. (Memories we will never forget!)

Travel Budget

Budgeting for you amazing vacation itinerary

An itinerary would not be complete without considering the cost of activities. 

Once you’ve done research on what you would like to do in a city, check the costs and determine how much you want to spend. 

There are a few ways to lay out your activity budget. 

  • Spread it out – Do one activity that doesn’t cost too much money each day. If your main focus is food, you’re in luck because you have to eat everyday. 
  • Go all out on a big activity – Devote the majority of your budget to one big activity like a big food tour, or a tour out of the city to another town, or to wineries. 
  • Budget friendly – Luckily there are always lots of free things to do in a new place. A few ideas; site see, hike up to a view, spend time in a park, wander down alleys and streets and get lost, or people watch. Another great idea is to share food or drinks with your travel companion. That way you get to try more for less. 
Pro Tip: Find the experience(s) that excites you the most and base your budget around that. Don’t forget to remember all other areas you need to budget for like food, transportation, accommodations, and drinks. 

In the end, go back to my question above, “what do you love” and focus on what brings you the most joy. After all, that’s what travel is all about. 

Whether you have a tight budget, or want to splurge, I hope these tips help you plan an amazing vacation itinerary wherever you next trip takes you! 

Disclosure: This page may contain affiliate links, meaning we receive a commission if you decide to make a purchase through these links (we so appreciate your support), at no additional cost to you. 

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