How do you plan your travels?
Some people love the freedom of vacation. They fly by the seat of their pants. Make no plans, not even hotel reservations (this would freak me out). Others like to have a general idea of where they are staying and what they want to see. And then some make an itinerary and plan every second of every day. I fall somewhere between having a general idea and having an itinerary. I like to have a good idea of what we will be doing but leave wiggle room for some spontaneous fun or an afternoon lounging at the beach or pool.
How do you pick where you are going?
Some people have bucket lists. They want to check off from a list. Every restaurant featured on Diners, Drive-Ins, and Dives. Every state or country. Others want to only hit tropical locals. We want to catch all the National Parks, MLB stadiums, and NHL arenas. I also have a deep desire to visit the Countries our ancestors came from. Plus, I want to stay in a hut over the ocean and to swim with manatees and otters. So many adventures out there to have!
So, how do you pick? And once you choose, how do you make those plans?
Start with your time and budget. How much vacation time do you get in the year? Do you have to use it or lose it? Does it roll over to sick after a certain amount? How much time does your spouse have available? Decide on how long your vacation will be and go from there.

Look at your budget. What can you afford? You do not want to go into debt to pay for a vacation. That may mean going places closer to home for a long weekend until you can save up for that trip to Europe or Asia.
If you have a week, how will you get there? Is it a road trip, or will you fly to your destination? How much gas will you need? Look at airline prices and rental cars versus public transportation costs. Once you’ve got your timeline and budget, decide where you are going.
This is the fun part.
You’ve got your length, you’ve got your budget, and now you’ve picked your destination! It’s time to figure out what you are going to do while there and start making your reservations.
Here are a few tips for saving money when planning your vacation:
- Use places like Costco or Sam’s Club. We used Costco each time we went to Hawaii. We priced out the hotel, airfare, and car rental through other travel sites. We saved thousands of dollars by using Costco packages.
- If you are going to a city that has a CityPass and you enjoy museums, zoos, and other attractions offered, take advantage! We have done the CityPass in NYC and Chicago and definitely got our money’s worth.
- If you fly a particular airline a lot, look into a credit card to earn mileage. We fly Delta and have their American Express card, which gives us two free checked bags and early boarding. We use the card for vacation expenses only and pay off the balance after each trip. This way, we know how much we spent and only have to track one card.
What to do while on vacation?
How do you decide what to do and where to go when you visit a new place? We prefer to find local restaurants to eat at, not national chains when we are in a new city. We spend some time ahead of our trip looking up places to try. This is especially important because of my celiac disease. We need to have an idea of several places that are safe for me.
There are tons of ways to find appealing restaurants. I usually start with google. Because of my dietary restrictions, I search for gluten-free CITY, but if you can eat anything, try searching near your hotel. Do you have a particular type of food you like? Google Pho and the city or vegan and the city. You can usually find blogs or newspaper articles with top X lists. Those are great places to start. And once you’re in town, ask locals where they like to go. A lot of hotels have concierges for this exact reason. Use the resource!
We usually try to eat a huge breakfast and then an early dinner. We typically head to places either near where we are staying or our destination. It doesn’t always work out that way, but we try to maximize our time and travel. Often we don’t have lunch. We may have an afternoon snack if we come across something. For example, in Hawaii, we usually have an afternoon shave ice break.
How do you plot and plan your vacations and travels?