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How to Plan for a Vacation + Tips for a Stress-Free Trip

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It can be super exciting to start thinking about taking a fun trip for spring break or a summer vacation, but there are a lot of little details and planning that go into a successful vacation. To prevent yourself from becoming overwhelmed, here are the steps I take, and some basic tips I do every time I’m planning for a vacation:

CHOOSE AN EXPERIENCE

What do you want to do on your vacation? What are you hoping to get out of your trip? Choosing an experience before you choose your destination will help you stay on track with your vacation plans if you are unable to travel to your first destination pick. The key to not becoming overwhelmed in the beginning of your vacation planning is to make a solid decision, and feeling confident in that decision.

When you’re getting ready to plan a vacation, ask yourself what kind of experience you are looking for. Do you want to go surfing? Are you looking for nature hikes in the mountains? Do you want to visit a large city? Do you want to watch a performance/show? Whatever experience you are looking for will help guide you to selecting a destination.

RESEARCH + SELECT A DESTINATION

Research destinations that will accommodate the experience you want to have. If you chose that you wanted to relax at the beach for your experience, you’ve just narrowed down your options for a destination. Research all the destinations with beaches and try to narrow down your choice even more.

When I am planning a vacation, I really like to fully research the destination. I’ll look up photos of the place on Instagram, search for travel diary posts/blogs, and look up ratings online. Pick a destination that makes you excited.



ESTIMATE YOUR BUDGET

Once you’ve picked a place you love and are excited to visit, start planning what it would cost to visit there. Consider common expenses like flights, hotel, rental cars, food, and activities. You just need to get a rough estimate of what it would cost to stay at this exciting destination and then determine if you can afford it at this time.

If you had your heart set on going to Italy as your destination but you realize that flights for two would cost $1500 and that is more than you were thinking to spend, then maybe Italy isn’t the destination for you right now. Estimating the budget helps you get an idea of the cost for your vacation and will help you decide if that’s what’s right for you at the time. If it’s not feasible to go to your first destination pick at this time, select another destination that will give you the experiences you are looking for. Even though your initial plans may change, you won’t feel like you’re flip flopping around because you are sticking within your original experience. Put those more expensive destinations on your bucket list and you can plan to visit them next time you plan/budget for a trip.

Repeat the Destination-picking, and Budget-estimating steps until you select a destination with the experience you want at the price that seems reasonable for you.

RESEARCH THE AREA + ACTIVITIES

After researching destinations and selecting a place that seems reasonable for your budget, research the area more in detail. This is where you really want to dig deep and figure out where you want to stay, what hotels are well-rated, and what areas are the best. When is peak season?

I recommend starting by reading different blogs or articles to see what area is the best for your destination. For example, search in Google for “which island to visit in Hawaii”, or “best areas to stay in New York”. Check out the different articles for your destination and see what makes each area special.

Once you have an idea of what areas you like/want to stay in, research activities that are close by your area. You can research in Google, Pinterest, yelp, or blogs. If you really want to do a certain activity, is it near your hotel? If you aren’t renting a car, how will you get there? What will you eat while staying in this area? Are there restaurants you are interested in nearby? Will you need to uber or rent a car?

I really like to research every aspect of the trip and what we would want to do while we are there. I like to keep a running list of the activities I want to do/places I want to see in my planner. Once I’ve narrowed down all of the places I want to see/things I want to do, I plot the points in Google Maps and try to group things that are close in proximity. This way, I can organize my days and not need to drive/uber back and forth across town to do everything. If one of your activities is an outlier on the map, then maybe you would need to dedicate the entire day to that one thing and if you don’t really want to do that, eliminate it from your list.

Also, if you do decide to use Huber when you get to your destination (like we did in San Francisco), be sure to use code bend13689ue to sign up and get $5 off each of your first two rides.

PICK A DATE

If you are going on a spring break or a summer vacation (from school or work), then you may already know the specific dates that you want to take your vacation. If you have a job where you need to request time off, then look up dates on the calendar and figure out how long you can be gone and what dates work best. If you are requesting time off, make sure to do it in advance so it gets approved or so that you have priority over others. You may also want to request a couple of extra days off as buffer for when you go on your vacation so that you can re-aclimate to being home.

SET A BUDGET

When you estimated the budget earlier, you got an idea of how much this vacation would cost. Now, you need to tighten up those numbers and make sure that you will have enough money by the time your trip comes. Use a spreadsheet or your planner to document the cost of everything for your trip — flight/gas for your car, hotel, food, rental car/uber, passport, activities, miscellaneous/ souvenirs.

I like to go to a travel site and plug the trip into my cart to get real numbers (including taxes) for everything. I usually check hotel prices through Priceline.com, but I am not actually booking my trip at this point. Enter your destination into the search below to get a price for your accommodations for your vacation dates:

Once you have your hotel costs figured out, research your flight cost. I use Google Flights to check multiple airlines, but again, I am not booking anything at this point.

After you know the prices of all your major travel functions, you can firm up your budget. Make sure you include food, uber, and miscellaneous expenses/souvenirs — any expenses you will have + a small buffer. Take the grand total of how much your vacation will cost and divide that amount by the number of months you have until your trip. This will tell you how much you need to save each month in order to afford your trip. Obviously the further in advance you plan your trip, the more time you have to save.

For example: if you are going on a trip to Hawaii in July, and it’s March now, you have four months to save for your trip (March – June). If your trip costs $3500, then you need to save $875 each month in order to afford your trip.

But if you started planning for your trip in December, you would have seven months to save for the same trip and you would only need to save $500 each month in order to afford your trip. Plus, you can sometimes find better deals by booking in advance, so it definitely benefits you to start planning for your trip early.

I recommend never vacationing on credit. Ever. If you don’t have the money right now, then don’t go on vacation right now. Vacations are luxuries, not necessities — you can have an amazing time off having a “staycation” at home or somewhere less expensive. Putting vacations on credit will just cause anxiety about whether you can afford it or how much more debt you’ll have when you get back and look at the bill. You want to be able to relax and enjoy your vacation; make sure everything is in your budget and that you have the money before you go on a trip.

MONITOR PRICES

While you are saving towards your trip, you can continue to research for your vacation. Keep monitoring the prices for your flights and/or hotels to see if they have gone down. Google Flights lets you track certain flights and they’ll email you if the prices change.

Sometimes prices go up and sometimes they go down. It can be a little risky to try and hold out for the lowest price, but don’t let a sudden spike in price cause you to panic and make a purchase prematurely. You obviously want to watch for the lowest price to come back around, and also want to be sure you book before your hotel sells out. Certain destinations have a peak season and hotels can fill up. This is another reason why it really benefits you to start your planning/research in advance.

Personally, I book my hotel as early as possible as long as the price of the hotel is within my budget. So if I had researched and estimated that hotels in the area usually went for $200/night then that’s what I put in my budget. So later, when I am monitoring the prices of my favorite place and I see that it went down to $175/night, I’ll book it right away because it’s within my budget/less than I had budgeted. I would hate to have my hotel sell out on the dates that I want since that would throw off all of my other plans.

With flights, I constantly monitor the prices as well, and check different sites to compare. Flight prices fluctuate a lot though so I don’t rush to book anything until I’ve been watching the trends for a while. Again, if it’s within/under your budget you may want to consider booking a flight when you see the prices drop.

BOOK YOUR TRIP

After monitoring the prices of flights and hotels for a while, book your trip to lock in your rate. If there are other expenses you need to book, do that as well (i.e., concert tickets, rental car, admission to an event).

If your tickets are refundable, you may want to continue monitoring the prices to try to secure a better deal if it comes up. Otherwise, don’t worry about the prices changing after you’ve booked. At that point, it’s all about preparing for your vacation day.



PREPARE FOR YOUR VACATION

Basically immediately after I book my trip, I start a countdown until we leave. I like to have a fun trip to look forward to and I write it down each week in my planner. It’s just a fun way to celebrate the trip even more. I use my Erin Condren planner for basically everything and it’s so much fun counting down towards a trip.

Next, I like to get a rough idea of what I want to do each day. This is where I take that list of all the locations we want to visit and things we want to do and the Google Maps information on where all the attractions are located, and I’ll plan out what activities we will do each day. This may seem excessive, but I just want to ensure we are efficient with our time. Obviously, I’m flexible if plans change or if we decide to do something differently; this just gives us a good itinerary of everything.

As you get nearer to your vacation, check the weather forecast for that time. This will help you better plan for what to pack. I like to write everything about the trip in my planner (confirmation numbers, flight numbers) so I have everything in one spot. And then while we are on the trip, I use my planner to decorate/memory plan what we did that day and sort of scrapbook our trip. It is so fun to look back on. Get $10 off your first Erin Condren order through my link when you create an account.

I hope these tips were helpful for you in planning your next vacation. If you learned something that you can use in your vacation-planning journey, share this post on Pinterest!

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