10 Tips to Help You Plan Your Dream Trip

Written By: The Planet D

Planning travel can be overwhelming. It can be difficult deciding on what destination you want to go to, what activities you want to do and what budget you want to spend.

It’s hard enough planning a trip, let alone planning your dream trip.

But we’ve put together a list of questions to ask yourselves before you decide to book your flight or buy a package.

If you follow these steps, you’ll have the tools to create the vacation of a lifetime without breaking the bank.

Tips to Help You Plan Your Dream Trip

1. Where do you want to go?

plan your dream trip relaxing Cancun
Relax and enjoy your vacation

We have been to110 countries and we still have a hard time choosing our destination.

It’s a big world and whenever we plan our vacations, we can feel overwhelmed deciding on what destination to choose.

What do you want to do?

So instead of just picking a country out of a hat, we think about what we want to do.

  • Do we want our trip to be an adventure?
  • Do we want warmth and sunshine?
  • Do we want a beach to walk on?
  • Do we want to be in the mountains?
  • Are we looking for cultural experiences?
  • Do we want to relax?

When you know what you want to do, it’s easier to narrow down a destination.

New Zealand or Iceland is great for adventure.

The Caribbean and Mexico are super for fun in the sun.

The Mediterranean is a wonderful place to relax while immersing in the culture.

2. What is your budget? 

plan your dream trip Thailand boats

Location plays a huge part in deciding your budget and choosing a destination.

Southeast Asia is probably the most affordable destination on the planet.

South and Central America are more reasonable than North America.

Package tours to the Caribbean and Mexico can save you a lot of money.

Read Our Tips on How to Save Money For Travel Can help you find more money for your next trip.

Eastern Europe is cheaper than western Europe and the Eastern countries of Europe are less traveled and can feel like you are going off the beaten path.

If we want a luxury escape, we can stay in 5-star hotels in Southeast Asia or Central America, but there is no way we can afford five-star in Europe or the US.

3. How Far Will Your Dollar Stretch?

euros in a piggy bank

We also think about currency exchange.

For Canadians, the United States can be an expensive vacation, but for people making purchases on the Euro or British Pound, it can be a bargain.

We look up the exchange of the country to see how far our Canadian dollar will go.

How far will your dollar stretch? The British Pound is worth a lot more than the Mexican Peso, for example.

We’ve splurged on what felt like an ultra-luxury vacation in Mexico (for our Canadian budget) but when we talk to someone from Britain, it’s quite affordable to them.

4. What Type of Accommodation do you Prefer?

apartment in rome

Accommodation plays a huge role in budgeting your trip. Our Apartment in Rome was spacious and cheaper than a luxury hotel

Depending on the trip we take, we sometimes want a luxury 5-star hotel, but other times a budget hotel will do just fine?

If we are staying in a place for an extended period of time, we will want to look at apartment rentals and AirBnBs.

When staying in an apartment and cooking meals at home we can save our budget for adventures like climbing mountains or going kayaking.

Think of all these questions to help decide how much your budget will get you.

5. Do I have Any Travel Rewards Points? 

plan your dream vacation AmEx
Amex Rewards work for us!

You’ll see this in a lot of “How to Plan Your Travel” posts, And with good reason!

Avid travelers recommend rewards credit cards because they work!

If you know you are going to be traveling a year from now, sign up for a credit card that offers rewards.

Put your everyday purchases on that card to rack up the points, but make sure to pay it off monthly.

Normally credit card programs have signing bonuses where they’ll offer you enough points for a free domestic flight or several nights in a hotel.

Dave and I have put a two thousand dollars in points towards a luxury vacation with our own private pool en-suite. We couldn’t’ have afforded such a luxury room without them.

We’ve stayed all over the world, using our American Express points.

We always have several hundreds of dollars worth of points to use because we use our card to buy the everyday items that we would already need to purchase like gas, groceries, and day to day items. 

Points can add up quickly.

But remember, don’t overextend yourself. Ever.

6. Are my Travel Dates Flexible?

how to travel for cheap flights with skkyscanner

Is your dream trip a spur of the moment vacation where you’ll be looking for last-minute deals?

It’s possible to get great discounts if you can book at the last minute.

If you have flexible dates, you can save a bundle as well!

We use Skyscanner to search for flights and look 3-5 days on either side of our desired date.

We have saved thousands of dollars on a flight (for two people) just by moving our travel dates by a day or two.

We’ve also found business class tickets for the same (or cheaper) flight on a different date than flying coach.

7. Am I willing to Visit During Shoulder Season?

planning your dream vacation Bahamas off season
The Bahamas in August is more affordable than March

If you have flexibility in your dates, you can go anywhere.

But if you have fixed travel dates because of work, look for the destinations that are in the offseason that fit into your schedule.

Shoulder seasons are different for each part of the world.

The high season in Peru is very different from the high season in the Bahamas.

Can you travel during the shoulder season when everyone else is at work?

You can save a lot of money during the off-season and the crowds are far less.

It’s worth looking into the time of year you are traveling and then deciding on a destination that is currently just coming out of, or just about to enter the high season.

8. Should I travel on a Group Trip?

plan your dream trip group travel
Is group travel or independent travel right for you?

Do you want to travel with a group on a tour or do you want to plan your own itinerary?

There is nothing wrong with either way. You just need to make a choice.

Many people choose group trips to ease the stress of planning and having to make bus, train, or transfer plans. 

When you go with a group, all you have to do is select the tour and book your ticket.

This is an excellent choice for busy professionals that only have a week or two of vacation time a year.

When you have limited time, you don’t have a lot of room for error, so it is a good idea to leave the planning up to the travel professionals.

9. Should I Travel Independently?

rally car breakdowns dave

Independent travel can also be far more affordable than a prepaid package tour, but it can also take a lot more time to plan.

It’s important to think about how much time you have before your vacation to plan your travels and how much time you have during your vacation.

Independent travel tends to be slower and there is more room for error, so you may find yourself lost or changing plans along the way.

10. Do I Have all the Right Documents?

how to plan your dream trip travel documents
Keep documentation handy

Before you travel, make sure you look to see if you need visas.

Is your passport up to date? Many countries won’t let you enter if your passport expires within 6 months.

If you are renting a car, do you need an international driver’s license or will your home country’s license suffice?

After you’ve done everything. Make backup copies of all your documents and store them on email or in the cloud.

All of these tips will get you started on the right foot when you are planning out where you want to take your next vacation.

More Travel Planning Resources:

What’s your best tip for planning your travels?

Travel Planning Resources

Looking to book your next trip? Why not use these resources that are tried and tested by yours truly.

Flights: Start planning your trip by finding the best flight deals on Skyscanner

Book your Hotel: Find the best prices on hotels with these two providers. If you are located in Europe use Booking.com and if you are anywhere else use TripAdvisor

Find Apartment Rentals: You will find the cheapest prices on apartment rentals with VRBO

Travel Insurance: Don't leave home without it. Here is what we recommend:

  • Allianz - Occasional Travelers.
  • Medjet - Global air medical transport and travel security.

Need more help planning your trip? Make sure to check out our Resources Page where we highlight all the great companies that we trust when we are traveling.

About The Planet D

Dave Bouskill and Debra Corbeil are the owners and founders of The Planet D. After traveling to 115 countries, on all 7 continents over the past 13 years they have become one of the foremost experts in travel. Being recognized as top travel bloggers and influencers by the likes of Forbes Magazine, the Society of American Travel Writers and USA Today has allowed them to become leaders in their field.

Leave a Comment

28 thoughts on “10 Tips to Help You Plan Your Dream Trip”

  1. Thanks for the reminder about getting all the right documents. I am trying to plan an anniversary trip. I think it would be lovely to stay in a nice hotel.

  2. I loved that you mentioned choosing your location is the very first step to plan your vacation trip. My husband and I are thinking about taking our vacation time together, and we are looking for advice to plan it properly. I will let him read your article to help us plan our dreamed vacation.

  3. Thanks for reminding me that I should learn how to keep a backup copy for all travel-related documents that can be saved either on the email or in the cloud. I’m going overseas for a conference where I’m representing our organization, and I’m sure that I won’t be able to monitor my stuff. With this, I’ll make sure to scan all documents needed for my flight and store all documents in someplace trackable and safely kept.

  4. The flipside to this is that if you don’t plan, you might have a disastrous trip which may lead you to never run out of dinner party conversations! ;P

  5. Thanks for this article. This is helpful especially for the tourist who is willing to travel to multiple places in a small period of time. India is well known for its scenic beauty, its rich heritage, modern art and divine temples. One should definitely consider visiting as many places as possible in India.

  6. You shared this useful & important tips with pictures on planning a trip. It is essential for a plan a trip. I very enjoyed this post. Thanks for sharing it!

  7. Nice tips, very helpful. Thanks for sharing. Especially, the one to have fun. Planning a trip is essential for peace of mind, I love your picture.

  8. Dear Dave & Deb,

    Just when I was planning on surprising my Husband for his birthday in a few months, you guys have saved me from the oblivious demerits of travelling unplanned. These tips are going to be useful! Especially, for a growing mother of a 5yr old… Think I better get started with the necessary requirements to surprise my husband!

  9. I am often too excited to go somewhere that sitting still in front of a guidebook or reading tedious visa material may get overlooked. Like you said, sometimes it’s very inconvenient. Thanks for these great guiding questions!

  10. My suggestion is to seek planning assistance and/or advice from a trusted travel professional- it’s often free and can actually save you time and money. Ask around, the good ones are usually known by word of mouth..

  11. Most of the times we plan our trip, but there are times that we just want to go with the flow and deal with whatever will come our way, but then, mostly it will cost us a lot of money which is not that fun at all;

  12. These are really great suggestions. Planning a trip is essential for peace of mind. The idea of traveling with a group is not something that I have considered before. I may have to look into this. The suggestion for bringing prescription medications is great. Something that I have missed in the past. Learning the local language has always been difficult for me because it would take me a long time to learn a new language; however, these apps that translate can be a help. Just remember to bring one with you.

    • Great recommendation on the apps Bob. I hadn’t thought of them. I am still stuck a bit in my old school way of traveling that it didnt’ cross my mind. I have always travelled and struggled with language, but I forget that there are so many more tools out there to help you communicate. Cheers!

  13. Most of the times we plan our trip, but there are times that we just want to go with the flow and deal with whatever will come our way, but then, mostly it will cost us a lot of money which is not that fun at all haha.

    • Ha, that’s a great point. We have had the same situation many times. One mis step and we’ve taken some wrong turns, had to splurge too much on a hotel or ended up backtracking and spending more on transportation. That can be fun and a great adventure, but I wish we did a teensy bit more planning in the end.

  14. Great points here guy’s.

    I wish that the Australian points market would be better, we are somewhat limited in that compared with the US.

    A tip for you when going on that Cruise, they often have specials on board for the speciality restaurants and the spa’s so it pays to look out for them. We always do that when on board and manage to get a better deal.

    • I have heard that. I hope Australia changes as well. We’re Canadian and I think that America has a much better points system than us too. But we still find points work amazing for us. We paid for most of our Greece travels last year by points and our Airline rewards do wonders for us. We found that we are loyal to just a few programs and our points rack up faster. Thanks for the tips on the restaurants and spas, I’ll look into that. Cheers!

  15. Nice tips, very helpful. Thanks for sharing. Especially, the one to have fun. It is really one of the most important plans of any trip.

    • And it’s something that people forget to think about a lot. Planning travel can be stressful and people forget that it is supposed to be fun.

  16. The flipside to this is that if you don’t plan, you might have a disastrous trip which may lead you to never run out of dinner party conversations! ;P