Easy Travel Planning Guide- Plan now for memories later

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Travel Planning can seem like an overwhelming task to take on by yourself. But planning a trip should really be a fun thing to do! This travel planning guide will help you navigate where to go on your vacation, where to stay, and what to do.

I truly believe there is nothing better than a planned trip on the horizon. Even if it’s just a day trip on a Saturday, and you are back in your bed that same night. You’d be amazed in what doing a little research will help you find, even within a few hours from your house.

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Aerial view of Miami

So, let’s dive into travel planning!


First step in travel planning

Where to get inspiration for your dream vacation

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Grand Canyon

There are many sources of where you can get inspirational ideas for a day trip or a dream vacation.

Maybe there was a commercial on TV of a beautiful tropical place.

Or maybe you got a detailed rundown of how amazing your neighbors road trip was to the Grand Canyon.

And just maybe you are driving next to an RV, jealous of their freedom… (um, yeah, totally me)

The thing is inspiration can come in many forms. And the trick is to write your dream locations down.

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Notes on iPhone

Maybe start a bucket list? I mean, lists are amazing. I use my lists function on my phone ALL the time. From shopping lists, trip itineraries, a bucket drink list… Yep, I actually have a drink list that I use when I’m stumped on what cocktail to get!

I love getting ideas from multiple sources to help me decide where to take my next trip. But one of my favorite sites to use when trying to get ideas is Pinterest. So many different ideas in one place!


Now comes the exciting part of travel: Research!

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Bayfield, WI

With a destination in mind, now comes the research. My favorite part! My hubby always kids me and says that I like the planning part just as much as the vacation. Yes, this is true, but I know it’s not everyone’s cup of tea. Don’t worry, I’ve got the shortcuts right here for you. 

At this point, you will start a new list in your phone (or on paper) to create your trip itinerary. Put the destination on top of the list and jot down things you want to do. Once you are done with your research, you’ll go back and fine tune the list and put things in timed order. 

Here’s what I look at to help me decide what I need for my trip. 


Weather plays an important part of your trip

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There’s an off-peak season for a reason. It may be cheaper, but you may also be swept away in a hurricane. You don’t want that. Do a simple google search, “what is the average weather for this location  ____ in this month____”

Furthermore, continue to check the weather up to the day you leave on your trip so you can plan and pack accordingly.


 How to find the points of interests, where to eat, and where to stay

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Map on iPhone

Look at a map of the destination (via Google Maps, the map on your phone, or an actual map) try different directions from place to place, this gives you context of how far away things are. Google Maps also has reviews and pictures that are super helpful. Another neat thing with Google Maps is you can input all your places and save maps for the future.

Use TripAdvisor 

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TripAdvisor

Another great place for tips and reviews is TripAdvisor. I always look at what ranks the highest for hotels, things to do, places to eat, and read the reviews. Using the map on the site is another great tool.

Pinterest

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Not only does Pinterest help you find your destination… It’s also great resource on what to do and eat and where to stay as it’s typically based on the writer’s personal experience.


Decide what you like to do on vacation

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The next important thing to determine is what you like to do on vacation. Here are a few popular choices on things to do:

  • Are you a museum person?
  • Do you like being on the beach, or hanging out at a pool
  • Visiting a winery/brewery
  • Gambling
  • Outdoor- Hiking, biking, skiing, surfing, parasailing
  • Guided tours
  • Sightseeing 
  • Is food your #1 priority?
  • Shopping
  • Nightlife/Clubbing
  • Hanging out on the balcony freely drinking cocktails without worrying about a dang thing (oh yeah)

Your search should include those things that you like to do.


Where to stay on vacation  

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Casa Marina in Key West

Where you stay will be determined by whether you want to be close to the action, and or, what you want to spend per night.

 I have found that location means -EVERYTHING 

It could make the difference between spending A LOT of time in transit from place to place (looking at you, Los Angeles) or being able to actually maximize your time at the places you want to visit.

I have to admit, when we first started traveling, I didn’t know what the heck I was doing. We stayed at some pretty questionable hotels that were farther away from our destination or just weren’t in a very good neighborhood.

We didn’t know any better and we were just excited to get away. But it’s a thousand times better/easier when you pick a good location to stay in.


Deciding what kind of accommodation you need

Determining what type of accommodation you need, will rely on a few factors. This next section will talk about whether to stay in a home sharing platform or a hotel. 

 Airbnb

  • Staying in an Airbnb allows you to rent on a home sharing platform- (basically, the people rent out their homes to you)
  • You can rent a whole house, tiny home, apartment or if you got the funds, even a mansion.
  • Pet friendly options– find one with a fenced in yard for your pup to run around or (shhh.. allow for more freedom to bark)
  • More beds to allow for more people (families or group trips), so you are not crammed in a tiny hotel room. 
  • A kitchen– so you can save money on food, or you crazy people that like to cook on vacation can do so. Or just having more counter space to rest your poptarts and chips… 
  • Rent a place that has a private pool (so cool)
  • Safest bet in a pandemic or a lovely option to avoid the people in normal times. The only tricky part is their cancellation policies are not always the best. It’s often 7 days or more when you can cancel before your trip. Be sure to look at this before booking.

Lady’s tips:

  • Be flexible on your dates of stay as prices can range widely from week to weekend. Booking during festivals/ big events will also drive up the price.
  • Utilize the price calendar on Airbnb site to determine the cheapest days.
  • If you have a credit card that offers points for travel, see if you can redeem for a gift card for Airbnb.

 Benefits to staying in a hotel

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Bellagio Hotel

Now that we know about staying in a home sharing property, here are the benefits to staying in a hotel.

  • Some offer Room service (yaaasss) 
  • Some have a coffee shop ❤️/ restaurants
  • You can search for a hotel that has an Indoor pool/ hot tub 
  • Workout room 
  • Some have free continental breakfast 
  • Some are pet-friendly
  • Use TripAdvisor to find the hotel and use the filter function for the amenities you want but be sure to book directly on the hotel’s website
  • More strict cleaning procedures in place.
  • Cancellation policy is typically more flexible/ not as far out (always book a cancellable room- especially now in the pandemic)

Lady’s tips:

  • Book directly on the hotel’s website, do not book on an OTA (online travel agency, like Expedia or Hotels.com.) Its normally cheaper and easier to deal directly with the hotel if you need to make changes
  • Sign up for the hotel’s loyalty program or email listing for deals to be sent to you.
  • Be flexible in your days, (use pricing calendar or if there isn’t one, play around with the dates) the price can vary widely day to day. 
  • Avoid booking when events or popular festivals are going on.
  • If you have a travel credit card, use points for partial or totally free stays.


Here are some other accommodations to consider

  • Hostel– Which is good for cheap stays, you may have to share a room/bathroom with other travelers. Popular with solo travelers. Check out: Hostelworld

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  • Camping- If you like being one with nature- it’s cheap if you already have the necessary equipment, ie: tent, sleeping bag, flashlights, etc. check out: KOA campgrounds

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  • Rent an RV- Be the king of the road and travel in style by renting one of these bad boys from Cruise America

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♦ How to get to your destination 

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This part talks about how you will get to your destination, and also tips for renting a car. 

Do you like the journey and have a little more time? Then a road trip, or maybe a train journey would be right for you.

But, if you want to just hurry up and get there already, plane travel is for you.


Will you need a rental car or just do Uber/taxi (or both)

Uber

Uber… the best invention ever. They have gotten me out of a pickle a few times and it’s super easy to use the app on your phone. They may not be in rural areas though, so the more remote you are, the more you may want to consider renting a car. Hailing a taxi is another option that’s convenient if they are available in the area. 

 


Road Trip/Renting a car

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Renting a car– I know I said not to use an online travel agent for hotels earlier but is worth it for scoping out car rentals. It’s able to pull multiple rental agencies in one area and it’s typically pretty cheap. I usually use Expedia. You can always go directly to the car rental website to compare prices and book with them directly if it’s cheaper. 

Another popular car rental site is Turo which is like AirBnB but for cars. 

Just be sure to pick the option that allows you to cancel if need be. 

Lastly, when you pick up the car, make sure to not pick to pay for gas upfront as it’s almost never worth it- but make sure you fill the tank before you drop the car off


Train travel

Traveling by train is such a neat way to travel. You get to kick back and relax, while being able to look at the scenery passing by. 

In the U.S. the popular train is Amtrak.

Be sure to check out whether you want to save money by having a regular seat, or if you want to splurge and get a sleeper car. 


Plane travel

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  • Google flights is the best way to pull multiple flights into one area to see what’s cheapest.
  • You can also go directly to the airlines website to book.
  • Do not use an Online Travel Agent for flights (like Expedia) it can be really complicated to change/cancel flights, and we need all the flexibility we can get right now. It’s usually more expensive this route as well.
  • Flexible days is KEY to a cheaper flight.
  • Use Pricing Calendar to determine the prices.
  • If you want to pick your seat, you may have to go a step up from economy and pay a little more money. Very important if you want to sit next to the person(s) you are traveling with. 
  • Nonstop is the easiest way to fly, and worth the little extra money- Avoid stopping.
  • If you must stop (some locations may not have a direct route) Make sure the stop or layover is at least an hour to give yourself time to get to the next gate.
  • Be courteous of people standing in line waiting for security at the airport. Get everything organized, shoes off, liquids in plastic bags, laptops outbefore you get to the bins. Don’t be those people doing it last minute and making those behind you silently scream at you in their heads. 
  • Check with your credit card company before you leave to let them know you will be traveling.
  • If you have a travel credit card, see if you can use the points for free flights.

Packing tips

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  • If you are checking a bag, pack your swimsuit in your carry on. For most people, this is probably the hardest thing to replace if your bag gets lost. The same goes for your valuables and cash as well as medications, keep these with you. 
  • Bring gum/snacks and magazines from home to avoid the high prices at the airport. 
  • I cannot stress this enough, bring comfy shoes! A light jacket is also good to bring even when going to a warm place. Places love cranking up the air conditioning. 
  • Put everything that you can in your carry-on bag (like a purse or other small items) so you avoid losing things and also counts as one bag -aka- normally free if it fits under the seat.

Safety Tips 

  • Use your best judgement at night. Avoid alleyways. Try to be in more populated areas. Avoid suspicious people, or overly friendly people.
  • Don’t keep all of your cash in one place. Separate it in different areas. Maybe invest in a money belt.
  • Use credit cards for purchases, not your bank card. This way, your money in the bank won’t be lost (if stolen) and it’s easier to stop and reverse charges on the credit card.
  • Take a picture of your driver’s license/passport and email it to your personal secure email and another person you can trust so if they get stolen you can have back up.
  • Let somebody at home know what your flight/hotel information is and what your general itinerary will be.
  • Be cautious about flashing too much money or wearing lots of expensive jewelry. 

In Summary

Use the list/note function on your phone, (or write it on paper) make a list of your dream travel places. Also use it make out your itinerary.

Use maps to determine where things are and do your research. 

Your most expensive parts of travel will be getting there, and where you stay. Play around with the pricing calendars to get the cheapest prices on both. 

The most important thing is to BOOK IT. Just do it! Travel while you can and make those memories!

 

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