How to Plan a Trip? 10 Step Guide to Expert Planning

Are you excited about the prospect of traveling, but don’t know how to plan a trip? I hear you, and you are not alone. Planning a trip can seem overwhelming and that is because no one is born knowing how to plan a vacation. But, I will let you in on a little secret: there is a system to planning a trip that makes it easy and fun. An easy, step by step, effective way to plan an amazing trip. So get ready to learn how to plan a trip!

Get ready, to follow the guide and think of all the things that are important not only to plan a memorable trip but also to personalize it to you. You will ask questions about your preferences and travel personality that will result in curating an unforgettable experience.

Planning a trip has never been easier; consider the many resources available at your fingertips. Pages and pages of information– that can actually be overwhelming to search through all the information to plan your trip. My 10 step guide to expert planning will save you from having to cross-check endless lists of sites to get the best options from trusted sources. Use free travel apps to help you plan your trip. Definitely read over the ultimate 22 free travel apps that will make planning your trip a breeze. I recomend you use it as a resource in combination with this guide.

Insider Tips from a Professional Traveler

Traveling has been a big part of my life. I have been traveling for decades for work and leisure. Yes, I am a professional traveler that has mastered the art of travel planning. I am thrilled to walk you through the easiest way to plan a trip. I will share insider tips that will bring you a step ahead in the travel planning process.

Pre-Planning Phase

The initial step in planning a trip is to answer a few essential questions. To personalize and curate an experience that you will love. After all, you are the ideal person to plan your trip (unless you have a travel expert on speed dial) because who knows you better than YOU to decide:

  • When to travel?
  • Where to travel?
  • How to travel?
  • Where to stay?
  • What activities to do?
  • Where and what to eat?

Imagine yourself living your travel daydreams. You deserve this trip and you can plan it, I will guide you along. Make your travel dreams a reality!

Island vacation

Define what type of trip you are planning

Ask your self the following questions:

  • Is it a vacation or a business trip? 
  • What type of experience do you want to get out of this trip?
  • Are you going to a city destination or a beach/outdoor destination?
  • Is it a quick trip or a long trip?
  • Do you have a budget?
  • Are you planning a luxury experience or are you looking for options to save?
  • Is someone traveling with you or are you traveling alone?
  • Is doing fewer things but doing them thoroughly more appealing to you than rushing to do as many things as possible?

Take some time to think about these questions and keep the answers in mind as you follow the 10 Step Guide to plan your trip:

The Planning Phase

1. Choose Your Destination

How to plan a trip? Choose a destination

Narrow your choices down and choose a destination. If you are undecided, do a quick search on each of the destinations you are considering to help you choose. Then use Pinterest or Instagram to find out top things to do in each destination and decide which one you want to experience. Or perhaps you are a step ahead an already know your destination. Where are you traveling to?

Insider Tip: I recommend buying a travel guide book, they are immensely helpful to plan a trip and researching the best things to do in the destination of your choice.

I like Lonely Planet travel guides, to start they give you an in-depth overview of the destination. Then includes all the information you need to plan your trip and much more. In addition to covering history, best dates to travel it also includes sample itineraries, accommodation options, cultural norms to observe, maps, etc. You can opt for the paperback and bring it with you for reference or buy the online edition for easy access on your mobile devices. An alternative is to visit your local library and search the travel section for guide books.

Once you choose the destination it is time to find out how much the trip will cost and how much is available to spend on that vacation.

2. Set a Budget

Set a budget

Now it is time to think about the budget for the trip. To set a budget, know how much big-ticket items will cost you (i.e, accommodations, flights, activities, entertainment, transportation, food, discretionary spending money, etc.) Add all of those expenses related to the trip and that will give you the cost of the trip to shape thee budget. The add discretionary funds to use for unexpected expenses, to give you a cushion and not worry if you end up spending more. You can asses if there are enough funds to cover the expenses for the trip or if you have to save a little bit more.

Furthermore, having an idea of what your budget is will determine the choices you make. If there is an unlimited budget and you have the freedom to do anything you want (a dream come true!), having a budget is still useful to keep track of your expenses.

After setting the budget we move on to choose travel dates.

3. Choose Your Dates

How to plan a trip? Choose dates

Choosing your travel dates is key and the dates you choose will impact the type of experience you will have. In fact, the dates not only impact your experience but your wallet as well. Before you ask for time off or book your flight, first read on to find out how the dates you choose impact on your trip.

How does seasonality affect your trip

First there is:

  • Peak Season or High Season: is the busiest most expensive time to visit. There will be a sea of people visiting and going to the same sights. Prepare yourself for long lines and to pay a premium for hotels, flights and entertainment activities. You will have to book/confirm your arrangements well in advance to guarantee your reservations. Or run the risk of things selling out.

Then there is:

  • Shoulder Season (s): these are the weeks leading up to the high season and those just right after the high season has ended. Not only are hotels and flights cheaper because it’s not high season, but there is less people. Best of all, the destination feels vibrant with a lot of activity but without the big crowds, it’s that sweet balance. Some businesses will be gearing up for the high season or closing down the season and will be likely to have great offers.

Finally there is:

  • Low Season or Off-Season: is the least popular time of the year to visit. Mainly because you run the risk of inclement weather affecting the things you can do, but you find cheap hotels and flights.

Insider Tip: In my opinion, the shoulder season is the best time to travel. Mainly because you can avoid the crowds, and you can also get great prices on hotels, flights, and restaurants.

Do a quick search to find out the weather forecast, compare hotel and flight prices to help you decide on the best dates.

You are well on your way to planning your trip, the time you are investing is well worth it because you are taking care of all the details. Next, it is time look for flights.

4. Book Your Flights

How to plan a trip? Buy Flights

After you have decided on the dates, it is time to book your flights and make the trip definite. This is a big step!

How to book your flights?

  • Book with your favorite airline, that you know you love and gives you rewards points, free checked luggage, and lounge access. Perhaps you can even snag an upgrade too! 
  • Use a search engine like Skyscanner that does all the research for you and compares thousands of flights giving you the results on one page. You can filter the page and sort to find the best flight. It even has a “month view” that allows to quickly check prices for each day of the month.
  • Search using The Flight Deal, you can book last minute flights and also book flights far in advance. If you have the flexibility on dates this can be a great tool to plan your trip and find the best airfare. Who doesn’t love a good value?
  • Insider Tip: book your flights well in advance. Which includes booking your domestic flights and also your international flights further in advance. Booking in advance is important because the closer in that you book a flight you run the risk of higher airfare and fewer flight options available. Consider nearby airports around you to compare airfare and schedules.

After booking your flights the following step is to look for accommodations.

5. Confirm Your Accommodations

Book accommodations

My favorite part of planning a trip and hopefully yours too. This is why: the accommodations you choose are a huge component of your travel experience. Now, more than ever before, you have accommodation options to fit every need and travel style. So get excited!

What are the best accommodations for you?

  • Are you looking for a luxury hotel, a boutique lifestyle hotel, or do you prefer an apartment or a villa in a local neighborhood?
  • Do you need all the amenities and service of a hotel or are you looking to trade those amenities to find accommodations that offer features that are more important to you?
  • Consider the location that makes the most sense based on the activities you will be doing. Does it make sense to stay in the most popular area at heart of it all, do you prefer a quiet neighborhood or are you looking for a completely secluded area that offers a retreat from the hustle and bustle?

With so many options to choose from, your accommodations should offer you an experience in of its own. It has become the standard now, to offer an experience not just four walls and a bed.

 To book accommodations

  • Book directly with the Hotel, if you know the hotel you want to stay at, you can search the hotel’s website and see the best offers available.
  • Search using a site like to search hundreds of hotels and get results using only one site. You can sort by star rating, location, price, and read the reviews. Do you want a free cancellation policy? offers free cancellation policy on select bookings.
  • Use Airbnb to book some of the most amazing and unique accommodations in your destination. Accommodations that are: authentically local, from the design and decoration to the people that own and operate them.

Airbnb’s are some of the greatest hidden gems that a destination has to offer. Traveling around the world, I have found Airbnb’s that have had the best location, ambiance, and views to rival the most popular options in town. Sometimes you even get to meet the locals who own the Airbnb whom then become a valuable resource to find out the best things to do in town. Not only do they know the destination inside and out, but they also know what to do, when to go, and most importantly, what to avoid. Leave it to the locals to know the best! 

Always read the reviews before you book accommodations. See what past guests say about the place, location, service, cleanliness, safety, etc.

Book directly with the hotel:

Insider Tip: If you need to book a hotel, contact the hotel directly. It pays off to take the time to call or email the hotel directly–you will be surprised what this can do for you. Ask what their offers are, then if you found something better online, see that they match it. It is better to book directly with the hotel and establish a relationship with the staff because they will make your stay more enjoyable than if they never heard from you. Then you are not just a number (a reservation) you are someone they know and are eager to welcome as their guest. So then it makes sense to always share your preferences with the reservations agent when making a reservation.

This is a top-secret! With your preferences, a hotel can then make sure to have the room set with personalized touches to make your stay more enjoyable. Preferences are things like whether you like foam pillows vs down pillows. Also things like letting them know if you have any allergies to fabrics or cleaning products. Moreover, tell them if you are traveling with kids because they can prepare the room in a way that makes it more comfortable for the entire family. Especially, tell them if you are celebrating a special occasion. Finally, some of the best hotels have entire departments dedicated to personalizing your stay-take advantage of it to enhance your experience.

Once you have found the ideal accommodations the next step is to decide what activities you want to do during your visit.

6. Plan Your Activities

How to plan a trip? Plan acyivities

To plan the activities focus on your top interests. Ask yourself: what are the must-do items that will make the trip feel like it was well worth the effort, time and resources?

Focus on your top interests to choose activities:

  • Start building an itinerary of what each day will look like. This ensures that you don’t miss out on doing the things that are high on your priority list. The itinerary outlines what each day will look like.
  • Chose 3 main activities to do per day, it allows you to plan them well and gives you the flexibility to add more as you go. For example, one main activity for the morning, another one for the afternoon and lastly anotherone for the evening. It avoids exhaustion which can be counterproductive. In my humble opinion, it’s all about quality vs quantity.
  • Are there any day trips to nearby points of interest worth including? See which activities you need to book in advance and confirm them. Find out how long each activity will take and transfer times to and from

Leave time throughout the day for yourself to unwind:

Unwind and enjoy the destination (and by this, I don’t mean at the end of the day when one would sit in the hotel room to rest after the long day). You will find that if you take the time throughout the day to sit back and relax for a few minutes, take in the views, sip on your favorite brew and take in the essence of the place, you will have a much better experience and memory of your time there.

Insider Tip: experience the destination in the early morning, the appeal is that almost no one is around. There is something else about strolling around in the early morning, could be the fresh morning air, the luxury of being the only one around and having the place to yourself, or the beauty of the soft morning sun reflected around the buildings giving light to the day ahead.

You are making excellent progress, the bulk of the planning is done. Congratulations! Now, we continue consider transportation options.

7. Local Transportation

How to plan a trip? Research transportation

Find out what are the suggested ways to get around at your destination. Is it best to use a taxi, Uber, Lift? Some cities offer excellent public transportation, subways, bus, ferries, etc. Find out if those are convenient and reliable for you to use.

Are you visiting several cities during your trip? Then, how will you get from one city to the next? Do you need to book flights, train tickets?

Take the time to think about transportation before you get there. It will save you time during your trip. It will make transportation arrangements easier in a city that you are just getting to know.

You are almost done, just a couple more things to consider if you are traveling internationally.

8. Are you traveling abroad?

Get your passport

Are your documents ready for an international trip? Check your passport validity and check visa requirements for the country you are visiting.

Get your travel documents in order

Have you checked your passport? The passport has to be valid more than 6 months from the dates of your trip. See if you need to get it renewed and complete the process on time for your trip.

Check to see if your destination requires a visa. If it does, find out if you can get it on arrival, or if you have to have it beforehand. Find out if you can do the process online or if you have to go to the embassy or consulate. Finding out the visa requirements is imperative–avoid getting caught off guard and have a visa issue ruin your trip. Getting a visa can be a process that requires time, make sure to plan ahead.

Find out the vaccine requirements, some countries require specific vaccines to protect you against diseases common in the area. Follow up with your doctor if you need to get any suggested immunizations.

How will you access your money abroad?

  • If you are planning to use your credit card or ATM card–find out what their international fees are. These add up quickly, and there are ways to avoid them. Find out what your options are for the bank to waive the international fees.
  • Or sign up for a card that waives international fees and ATM fees.
  • Do you know what the local currency is?
  • What is the exchange rate? Many things will be quoted in the local currency and you will have to convert to your currency. Find out the exchange rate to calculate how much things will cost you.

9. Travel Insurance

How to plan a trip? Buy travel inurance

Traveling abroad and buying travel insurance go hand in hand. So it makes sense to buy travel insurance because it protects you in the event of an unforeseen event. More importantly, if something happens, you will have a team to help you out in a foreign country where you might not know what to do. Leave it to the experts and get peace of mind.

Now its time to think about what to pack.

10. Pack Your Suitcase

How to plan a trip? Pack

To make sure you don’t forget anything follow the suggestions below:

  • Check the weather forecast over your dates. Is it expected to be sunny, windy, is there a chance of rain or snow?
  • Consider the activities you are planning to do, will you be doing a lot of walking, attending formal dinners, participating in outdoor activities, etc. This will help you decide what you need to pack for every activity.
  • Curate your wardrobe, consider a capsule wardrobe to pack smartly.

Insider tip: Trade large suitcases for a carry-on.  

Switching to a carry-on will change your life!

With proper planning, a capsule wardrobe will give you the best outfits that can fit in one carry-on. Smart packing!

This will not only save you from having to pull along a huge suitcase all over town. It will save you precious time at the airports too. Who likes waiting for luggage, and need I mention the possibility of lost luggage? Oh, yes, best to carry-on.

Does it seem like a mission impossible? Believe me, it can be done. Between you and me, in my early travel days, I used to over-pack. Now, I have been known to travel for 2 weeks to Europe for vacation and to attend an over the top luxurious wedding in Paris– packing only a carry-on for the entire trip. I had the perfect outfits for each occasion and it all fit in one carry-on. At the end of the day, you know what works best for you and what will make you feel more comfortable, follow your instinct.

Congratulations! You have learned how to plan a trip and by following the 10 step guide you are now an expert at planning a trip. Most importantly, you have planned your trip taking the time to think about every detail to make it an unforgettable experience. I hope that you have found this 10 step guide helpful in planning your trip. You are now on your way to planning the trip you have been dreaming about.

Happy Travels!


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