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Your Ultimate Trip-Planning Guide From Start to Finish

The prospect of planning a vacation can be an exciting one; getting to see and experience new places and cultures can enhance your worldview and give you a much-needed break from reality. Of course, the actual process of planning a trip can be daunting. After all, there’s so much that goes into coordinating even a short trip! From deciding where to go to figuring out what to do while you’re there, coming up with your perfect trip itinerary will require some time, planning, and patience.

By following our step-by-step guide to trip-planning, however, you can take a lot of stress out of getting ready for your next vacation while still making sure all your bases are covered. From there, you can enjoy your travels to the fullest!

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Where Should You Travel?

The first step in planning any trip is deciding where to go. Sometimes, this is easy. Perhaps you have a destination in mind that you’ve always wanted to visit. Other times, deciding where to go can be a little tricky and there are some specific factors you’ll need to take into consideration to make the best choice.

Time of Year

The time of year may affect your travel plans in a number of ways. For example, if you’re planning a trip during the frigid winter months, then you may want to choose a tropical destination that will allow you to escape from the ice and snow. On the other hand, you may want to avoid visiting certain places during their peak travel seasons if you don’t like being around heavy crowds. New York City during the holidays, Rome during the summer or New Orleans during Mardi Gras are just a couple examples of busy destinations during peak travel times.

Time Available

If you’ll be taking time off work to travel, you’ll also need to think about exactly how much time you are comfortable with taking off and thus how much time you’ll have to enjoy your trip. Only having a few days to work with may limit your travel to somewhere relatively local, whereas a longer vacation may be the perfect opportunity to travel somewhere international.

If you’re limited on vacation days, you may be able to optimize your time off by dividing it between your “weekend” days. For example, if you have four vacation days to use and you’re normally off on Saturdays and Sundays, you can use vacation days on Thursday, Friday, Monday, and Tuesday to extend your trip to six days.

Your Preferences

Ultimately, where you should travel will depend on what most interests you. If you’re looking for a relaxing vacation where you do as little as possible, then a tropical beach destination may be perfect for you. If you’d prefer to explore a new culture and do a lot of sightseeing, then visiting a new major city may be a better choice. Don’t forget to also take into account any preferences from those with which you’ll be traveling when deciding on a destination.

How Will You Get There?

Once you’ve decided where you’ll be traveling, the next major step in planning your trip is figuring out how you’ll get there. If you’ll be traveling any substantial distance or if you’ll be going anywhere overseas, then flying is almost always going to be your best option. Flying will allow you to reduce your total travel time, which in turn maximizes the amount of time you have to spend exploring, relaxing, and taking in the sights.

Finding a Flight

Begin by searching for flights to your destination; if you have any flexibility with your departure and return dates, you may be able to save some money by flying on days that are less busy and not book an expensive flight. Most airlines have a calendar search feature that will show you rates for different travel dates so you can maximize your savings.

When searching for flights, it’s also a good idea to use third-party travel sites that will allow you to compare rates across different airlines. This can help you find the best rates so you can spend less money getting to your destination and have more spending money once you arrive.

After You Arrive

Don’t forget to factor in how you’ll get from the airport to your hotel or other destination once you land. Depending on where you’re traveling, the airport could be located quite a distance from your hotel, so you’ll want to plan accordingly. Check for airport shuttle services to your destination, which tends to be both convenient and affordable. Many airports also have a taxi line where you can wait with your luggage for a cab to take you wherever you need to go.

Ride-sharing services and rental cars are also viable options for getting from the airport to your destination.

Where Will You Stay?

Even if you don’t plan on spending a lot of time at your hotel during your trip, you’ll still want to set aside some time to find the accommodations that will best suit your needs. Whether you plan on staying in a hotel, Airbnb, hostel, or anywhere in between—there are some tips worth keeping in mind.

Finding Deals on Hotels

Third-party comparison sites are great for finding the best rate on a hotel at your destination. Just be sure to read some reviews from recent travelers to make sure the hotel you’re considering is clean and has all the essentials you’ll want during your stay. If you have rewards points to use, this can also be a great way to cut down on accommodation costs during your trip.

Even if you find a great deal on a travel website, it’s never a bad idea to contact the hotel directly and see if they can match or beat a deal you found online.

Other Accommodations to Consider

Hotels are a practical option for many travelers, but they’re certainly not your only choice. Consider looking into other options that could help save you money or provide you with a more authentic experience. Renting out an Airbnb, for example, often allows you to immerse yourself in the center of your destination while also enjoying many of the comforts of home. A hostel, on the other hand, can provide you with a centralized location while saving you money in the process.

How Will You Get Around?

The best way to get around will depend not only on your destination but what you plan to do once you arrive as well.

Booking a Rental Car

If you want to have easy access to a personal vehicle throughout your trip, then renting a car is likely to be your best option. Most major airports will have rental car facilities so you can easily pick up your vehicle once you arrive and then drop it back off when you come back to the airport for your return trip. A rental car is a convenient way to get around, but you may need to factor in additional costs, such as fuel and parking.

Using a Ride-Sharing Service

If ride-sharing services (such as Uber or Lyft) are available at your destination, this can also be a great way to get around without needing to rent a vehicle yourself. Ride-sharing services are ideal if you’ll be traveling to a populated city or area, as availability of rides should be plentiful. This may not be as reliable of an option if you’ll be traveling to a smaller city or rural area. If ride-sharing services aren’t readily available, taxis are a similar and more viable choice.

Public Transportation

Any major city will have public transportation options available, though these can range greatly from one destination to the next. Subways, public buses, trains, and trams are all options to look into. Many of these options will run on a set schedule and also tend to be very affordable. Public transportation can sometimes be crowded and schedules aren’t always the most reliable, but it can be a great option for getting to other local destinations on a budget.

Getting Around By Foot

Some destinations are pedestrian-friendly, so you may be able to see and do a lot by simply getting around by-foot. This is most likely to be the case in a large city, where you can easily walk a few blocks from your hotel to a local restaurant, museum, or other attraction. If your hotel is farther out from the city, you may still need to take a cab or other means of public transportation into the city; from there, however, you can more-or-less walk to your destinations throughout the day.

Where Will You Eat and Drink?

While you probably won’t want to plan out all your meals ahead of time, it’s a good idea to have a general idea of where you may want to eat and drink during your trip.

Check Out Top 10 Lists

A great way to get a feel for some of the best bars, restaurants, and eateries at your destination is to check out some online “top 10” or similar lists, which are often published by reputable travel websites. This can help you get a better idea of what’s available and what some of the “must-see” places are to try local food. Many of these lists are also broken down into different categories so you can find options that suit your tastes.

Ask for Local Recommendations

Another way to find great food and drink options at your destination is to simply ask around. If you know people who have traveled there before, don’t hesitate to ask for recommendations. If you’ve already booked a hotel, you might also consider calling the front desk/concierge and asking for local food recommendations. Whether you’re looking for a great coffee shop to enjoy your morning cup of java or want to make dinner reservations for a special night out, local experts will know all the best places.

What Else Will You Do There?

Just as you wouldn’t want to plan every single meal for your trip ahead of time, you probably won’t want to plan your entire itinerary of activities, either. Still, having a few “must-sees” on your list and a handful of other options to choose from will help you make the most of your days at your destination.

Research Tourism Websites and Guides

Official tourism websites and travel guides can be excellent resources for learning about local attractions. Often times, these guides are broken up into categories (such as food/drink, museums, parks, etc.) so you can explore options that align with your interests.

Look Into City Passes

All those excursions, museum passes, and visits to other attractions can really add up and eat away at your budget. If you’re visiting a major city, look into saving money with a “City Pass” or similar option that will provide you with discounted or free access to certain destinations during your travel dates. These will cost more money up-front, but they’ll save you cash in the long run if you plan on doing a lot of sight-seeing and “touristy” activities at your destination.

Don’t Forget to Make Reservations

Keep in mind that getting tickets to certain attractions may be difficult during peak times of the year, so it may be helpful to make reservations or buy tickets for some attractions ahead of time. Yes, this will require a little more detailed planning on your part—but it will be worth it to not miss out on a “must-see” attraction.

Explore Free Things to Do

If you’re on a tight travel budget or are simply looking to get the biggest bang for your buck, don’t forget to research free attractions at your destination. A quick online search should yield plenty of results for local sights that won’t cost a thing, including parks and festivals. Keep in mind that many museums also offer free or heavily discounted admission on select days of the week or month.

How Do You Need to Prepare?

Now that you have a better idea of where you’ll be going, how to get there, and what you’ll be doing once you arrive, it’s time to turn your attention to preparing for your trip.

Do You Need a Passport and/or Visa?

If you’ll be leaving the country to travel, you’ll need a passport and possibly a travel visa as well. Take some time to familiarize yourself with the documentation requirements for getting to your destination (and back). If you don’t already have a passport or if yours is near expiration, make sure you have enough time to obtain one before your trip; there are expedited processing services available, but you’ll need to pay additional fees.

Even if you already have a valid passport, make sure you know where it is! If you haven’t used it in a while, don’t assume you’ll be able to find it the day you leave for your trip. Find it and secure it now to avoid last-minute panicking.

Look Into Immunization Requirements

Certain vaccinations/immunizations may be recommended or even required based on your travel destination, so do your research and schedule vaccination appointments ahead of time. Specific vaccination requirements or recommendations will vary based not only on your destination, but your health, age, and recent vaccines as well.

Purchase an International Phone/Data Plan

If you’ll be traveling internationally, your current phone network and/or data plan may not work during your trip. Depending on your phone carrier, you may be able to purchase an international data plan so you will continue to have phone, text, and Internet access during your trip. Take some time to consider whether this is something you’ll need and if you’re comfortable paying for it.

Keep in mind that some hotels and other public areas may have free Wi-Fi, which can help you stay in touch with loved ones back home and have access to social media and/or e-mail. If you’ll be staying in a more rural area, however, access to Wi-Fi may not be guaranteed. In some cases, it may be more economical to purchase an inexpensive cell phone at your destination and use a pay-as-you-go plan during your stay.

Consider Purchasing Travel Insurance

Any time you travel, it’s a good idea to at least look into purchasing a travel insurance policy especially if you are traveling with children. Specifically, travel insurance can give you added peace of mind and protection during your trip by covering expenses related to unexpected events, such as:

  • inpatient or outpatient medical treatment
  • trip cancellation or delay
  • a missed flight or connection
  • lost or damaged luggage

Travel insurance policies are generally quite inexpensive, especially when you consider all that they cover. If you haven’t done so already, take the time to explore travel insurance options and choose one that best suits your needs.

How Will You Make Purchases?

Unless you’ll be traveling domestically, you’ll need to have a plan for making purchases during your trip in a foreign currency. There are a number of options available to you, but there are a few things you’ll want to consider before you decide how you’ll handle purchases during your trip.

Research Exchange Rates

Start by familiarizing yourself with the local currency at your destination and its current exchange rate; this will give you a better idea of how to translate dollars into whatever currency you’ll be paying with. Also, keep in mind that transferring money overseas can subject you to additional fees by your bank. It is not uncommon, for example, for a bank to take an additional 5% commission when you take out money at your destination, so plan and budget accordingly.

If you plan on using a credit or debit card during your trip, make sure you won’t be subjected to any foreign transaction fees or similar costs. Depending on where you’ll be traveling, it is possible that some major cities and tourist destinations (such as resorts) may accept United States currency—but you’ll want to confirm this before you travel.

Carry Your Money Safely

Always have a plan for carrying your cash and other valuables securely when you’re a tourist in a new town. Unfortunately, pick-pockets and thieves will prey on unsuspecting tourists, so leaving your money in a backpack, purse, back pocket, or other easily accessible location is not recommended. Consider investing in a money belt or similar accessory that will allow you to carry your cash and valuables more securely and out-of-reach of would-be thieves.

Take Advantage of Rewards

If you have access to a travel rewards credit card with no foreign transaction fees, you might consider using this for all your trip purchases for the added convenience and travel rewards points. This will also save you the hassle of needing to exchange currency while rewarding you for the purchases you were going to have to make anyway.

If you don’t already have a travel rewards credit card, look into applying for one prior to your trip. These can especially come in handy if you do a lot of traveling, as you can earn extra rewards points for purchases like airfare, meals, hotels, and other transportation.

Give Your Bank a Heads-Up

If you’ll be using a credit or debit card at any point during your travel, make sure to give your bank a call to let them know about your travel dates and plans ahead of time. Otherwise, any purchases you make abroad may trigger a “fraud alert,” which can cause your account to be frozen. If your bank knows you’ll be traveling ahead of time, you can avoid being locked out of your account and unable to use your card(s).

What Should You Pack?

It’s time to pack for your trip! What should you bring and what should you keep in mind as you pack? We’ve got some tips worth keeping in mind as you bust out that suitcase.

Research the Local Climate

Before you pack a single item of clothing, consider what the climate and weather will be like at your destination. If you’ll be visiting a destination during the cooler months of the year, then you’ll want to bring plenty of clothes that can be easily layered to stay comfortable. If you’ll be visiting a city during the warmer months, make sure you have lots of light and breathable clothing, as well as sun protection and perhaps a swimsuit or two!

Factor in Planned Activities

Don’t forget to pack based on the activities you have planned, too. For example, if you’ll be doing a lot of walking and sight-seeing at your destination, then a pair of comfortable and supportive walking shoes is a must. If you’ll be going on any excursions (such as hiking), then don’t forget the bug spray or a backpack for your daily essentials (snacks, a change of clothes, etc.).

If you’ve made reservations at any nicer restaurants, check to see if a dress code is in place. It’s never a bad idea to pack one or two formal outfits for your trip, just in case.

Consider Your Accommodations

If you’ll be staying at a hotel or other location with easy access to laundry, then you may be able to pack a little less and simply plan on doing a load of laundry during your trip. This can be a great way to save on your baggage costs while packing more lightly in the process. You’ll also want to consider whether you’ll have easy access to a clothes iron, as this may also affect the type of clothing you pack.

Pack Essentials in a Carry-On

If you’ll be checking any baggage with your airline, there is always a slight chance that your suitcase won’t arrive at your destination with you. Airlines make mistakes. This, again, is where having travel insurance can come in handy, as a travel insurance policy will cover costs related to buying clothes and other essentials when your baggage is lost.

To avoid being stuck without the things you really need when you land, however, it’s best to pack some basics in your carry-on luggage. This includes at least one change of clothes, chargers for your devices, toiletries, and any prescriptions you need to take. Note, some airlines have specific carry-on luggage size requirements, so make sure to review these baggage policies before you get to the airport.

Before You Leave…

You’re almost ready to embark on your trip! Before you leave, there are a few last things you may need to get in order.

Make Copies of Important Documents

If you lost your wallet or passport during your trip, you could have a hard time getting through customs or even getting on the plane for your return trip. To expedite the replacement of any lost documents, it’s always a good idea to make photocopies of important documents (including your driver’s license/ID, passport, and/or visa) before your trip. Keep copies of these in each of your bags, just to be safe.

Hire a House-Sitter

If you have pets that need to be checked on, plants that need watered, or mail that needs to be brought in, be sure to hire a house-sitter before you leave.

Print Copies of Your Trip Itinerary

Whether you’ve thoughtfully planned out every last detail of your trip or have only loosely planned your vacation, it’s smart to print out a few copies of your itinerary so you can refer to it as needed. Be sure to include the details for any of your flights (including flight numbers and departure times) as well as the dates and times for any reservations you’ve made. It’s not a bad idea to e-mail a copy to yourself so you can store your itinerary on your phone or tablet as well.

Have a Safe Trip!

If you’ve completed everything in this guide, you should be more-or-less ready to embark on your next travel adventure. Yes, a lot of time and effort goes into planning a trip—but we think you’ll find that it’s well worth it when you’re able to enjoy your traveling to the fullest.

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