7 Important Vacation Planning Tips – How to Plan a Vacation You’ll Love

One of the things I love about vacations is looking forward to them.  Knowing that I have a trip coming up gives me a sense of anticipation, excitement and even joy in the planning.  It is such a good positive distraction to spend time thinking about an upcoming trip (read more about positive distractions here).  I am a type A person who loves to plan and organize so I may do more than most but I’ve had some amazing trips that I attribute to good planning and research.

I’m sharing seven important vacation planning tips with you so you can make the most of your next getaway and have a vacation you’ll love!

Tip #1: Make the Biggest Decisions First

Choices about where to stay and how to get there are usually the biggest decisions for a trip.  These decisions require the most thought and research because they are usually the most expensive.  It is important to make these decisions first because they can also be time sensitive to reserve.  Lodging reservations, airfare and ground transportation are always the first items on my vacation planning checklist.  

I take time to read reviews on places like tripadvisor.com, travel websites and blogs.  If possible, I talk to someone who has been there and get their advice.  A tip to keep in mind when reading reviews is to pay attention to the date of the review.  Sometimes a review will indicate “construction noise”, “lots of bugs” or particulars about the weather.  Compare dates of these reviews to the dates of your trip.  One person’s complaint or praise may be due to the particular timing of their trip and may not apply at all to you.

After the hotel, airfare and ground transportation have been booked, I often breathe a sigh of relief knowing that that major decisions have been taken care of. Once I get to about 4-6 weeks out from my vacation, I start to plan some of the other details of the trip.  To me this is the fun part! 

Tip #2 – Research Activities

If you are spending the time and money to travel somewhere, make sure you are experiencing everything there is to do and see.  Research activities to ensure that you are taking full advantage of the area and not missing out on anything spectacular.  The worst feeling is returning from a vacation and discovering you missed out on the thing everyone is talking about!

I’m speaking mostly from the perspective of someone who likes to travel to explore and experience adventure.  I like to make sure I am seeing the important places and taking advantage of the activities that are rated highest for the area. I like to see what makes an area unique. There are many people who travel to relax….to do nothing, to rest or to be catered to at an all-inclusive.  I think the same planning applies to both.  Even on a relaxing vacation, you want to make sure you research the amenities available to you.

I like to look up top attractions and activities on places like tripadvisor.com and tourism websites for the area.  I also take the time to read the hotel or resort website to see what activities they suggest.  Often a quick web search of “best things to do in …” will lead you to many websites, blogs and reviews that will help you.  Take the time to research these things and see what best fits your personality and goals of your vacation.

Tip #3 – Research Restaurants

I will admit that I am somewhat of a self-proclaimed foodie. I enjoy trying new and eating well.  My enjoyment of good food also applies when I am on vacation so I take the time to research restaurants at my destination.  Restaurants are often a great way to appreciate the location, the culture and the people of your vacation destination.  It is important to research restaurants especially if you are going somewhere new.  Some of our family’s favorite vacation memories are centered around a cultural meal, trying a new food, experiencing a fun restaurant or eating at a memorable location. 

As I read reviews and websites of an area, I take notes of restaurants that are mentioned.  If we stay at a VRBO or vacation rental, I like to read the restaurant recommendations of others who have stayed there.  Since we often travel with our children, I will sometimes even look at menus and prices to make sure the recommended restaurant fits our family.

A final tip for restaurants is to also find a nearby grocery store.  Whether you have a rental home with a full kitchen or a standard hotel room with a mini-fridge, picking up some groceries to have on hand can be extremely helpful.  We often pick up bottled water, drinks, shelf-stable breakfast items and snacks.  We’ve found that having these items on hand significantly cuts down on costs. It also helps for between meal downtime and long car rides.

Tip #4 – Make a Schedule

Once I have a good idea of activities, attractions and restaurants, I like to make a very general itinerary for our vacation.  I simply map out on a piece of paper the days that we will be on our vacation, including travel days.  Some vacations have lots of excursions, activities and meals planned and others are very low key.  I still find that laying out a schedule helps me to think through our time on vacation and make the most of it. 

I usually reserve the first day of vacation as a day to stay at the resort or hotel and check out our surroundings.  If time allows for this, it is a great way to relax after a travel day, unwind and change your body from the pace of life at home to vacation mode.  It also allows time to unpack, explore things nearby, collect any groceries and catch up on any missed sleep from the travel day. 

Another tip is not to plan too much on the day, or at least afternoon, before you leave.  It’s nice to have the time to pack up and to ensure that you are not spending two days in a row traveling (like a long car trip, etc.). 

We always like to save time for a special dinner out on our last night.  We discuss what we liked about the trip, what we would change and how it compares to other vacations.  It’s a fun way to wrap up a vacation by taking the time to talk about your favorite memories!

Here is a sample vacation schedule:

Saturday	Arrive 4 pm Drive to resort Dinner at resort
Sunday	Day at resort
Monday	8 am boat ride with lunch Dinner out
Tuesday	Morning at resort Afternoon drive to lighthouse
Wednesday	All day drive to north end of the island
Thursday	Hike in the morning Afternoon at the resort Dinner out
Friday	Leave for airport at 10 am

Laying activities out on a schedule helps to ensure that you have enough time to see everything you want to see.  Taking the time to think this through helps you choose activities and sights that are near to each other on the same day so you cut down on time in the car.  It also helps you consider when you have time for meals out and what you might need reservations for.  Which leads us right into the next tip!

Tip #5 – Make Reservations

If your vacation involves any activities, excursion, sites, tours or restaurants that require reservations, I recommend making them in advance.  Often people wait until they get to a destination to discover what the area has to offer and then try to join an activity or show up at a restaurant.  Many times this will work out just fine and the spontaneity can be fun! However, if you have a large group or a specific day or time that you want to do something, you may be disappointed with your options.  If you know you are planning to do something anyway, then making reservations before your trip provides peace of mind and leaves you one less thing to think about on vacation.

I’ll share an example from a vacation we took to Kauai where reservations were important.  For our one week on the island of Kauai, we knew that we wanted to do surfing lessons, participate in a top-rated luau and sail around the Napali coast.  For all of these activities, reservations ahead of time were necessary. The luau filled up early and we had a large group, surfing lessons were only available for specific days and hours, and the boat ride around the Napali coast was weather-dependent.  We booked the boat ride early in the week so that if it was cancelled due to weather, we would have a chance to reschedule.  For that particular trip, reservations were important and helped ensure that we were able to do our highest priority activities.

If you stay at an all-inclusive resort or VRBO home, then reservations are not as important.  However, be sure to check the reservation policy at your all-inclusive so you avoid eating dinner at 9:30 pm with little children. (Yes, this has happened to us!)

Tip #6 – Send Countdowns

I love the anticipation of an upcoming trip and my family does too.  When we have a trip approaching, I like to send countdown emails or texts to my family to help get them excited too.  I know that these countdowns are loved by my family members and really add to the fun of vacation planning.

I often just screenshot photos of our destination or of the weather forecast and send them along with how many days left until our trip.  If it is a place we have been before, I’ll send photos as memories from our last time there. I also check out the destination or resort on social media (like Instagram) to get get great photos and up-to-date happenings.

Tip #7 – Assess Gear

Finally, when all else is done, take time to consider any specific clothing or gear that you’ll need for your trip.  Going to a beach?  Make sure you have a swimsuit, water shoes and sunblock.  Going hiking?  Make sure you have a travel backpack and appropriate footwear.  Have some fancy dinners out?  Make sure you have nice clothes to fit the occasion.  If you are traveling with kids, this is a larger task because you have to make sure their clothes and shoes still fit from the previous season.  Most of the necessary items can be purchased once you are on vacation but you’ll save significant money buying them from home.

We usually have all that we need to travel, but I still have fun picking out something new for the trip!  I like to treat myself to a good book to read and a new piece of clothing or two.  When my kids were younger, I would always surprise them with a few new items for the plane or car ride.  It was fun for them to discover a new activity book, handheld game or fun snack just for the trip.

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Planning a vacation doesn’t have to be hard!  We have so many resources available with the internet that our greatest limitation is our time and effort.  Take advantage of your resources and enjoy the planning process.  The effort you invest ahead of time will help you get the most out of your vacation and help you see all the good that travel can bring!

I’d love to hear what you do as you prepare for a trip!  Drop me a comment and let me know what works for you.