I can’t tell you the number of times I’ve started to plan a trip and wanted to throw in the towel almost immediately. I LOVE to travel and I LOVE to plan travel but it can still be overwhelming at times – especially if you don’t know where to start.
I’ve broken down my best travel planning strategies into nine simple steps to help you plan your next trip without all the stress and worry that actually comes with planning. Imagine if you enjoyed the planning process almost as much as your actual trip. Planning doesn’t have to be hard – I promise!
Even if you’re an experienced planner, I encourage you to read on. Nine steps you say? Yes. Nine Steps. This comprehensive post covers EVERYTHING you need to consider when planning a trip from flights and accommodations to activities and setting an overall budget. And as a bonus – I’ve included a FREE Travel Budget Worksheet so you can stop dreaming and start planning.
Nine Simple Steps to Planning Your Next Trip
Step 1: Consider What Your Trip Will Look Like
Are you really into cruising or are you interested in trying out an all-inclusive resort experience? Do you want to road trip across the United States or fly across the pond to tour quaint English towns? Have you had your heart set on traipsing through Germany like my husband and I? I will talk more about choosing the destination and accommodations in the next steps but here you should consider what you want your trip experience to look like first.
Think about what your trip should look like in terms of your accommodations, your pace of travel, and what you’re looking to gain from the overall experience. Are you looking to stay in a high-end resort where you can go to a single destination to relax and unwind for a week? Do you want a more active experience that will keep you on the move and allow you to see something new every day? Perhaps, you want some combination, such as planning to see five destinations in 10 days, spending a few days at each location.
When it comes to the experience itself, will you be booking guided excursions or tours or do you prefer to explore on your own? Consider what the must-sees are in each location you plan to visit.
Take a minute to answer these questions because it will help you determine what your trip is going to look like and that will play a part in your planning and budgeting.
I’m currently planning a trip to Germany and even though I have been there a handful of times as a kid, my husband has never been there before. Now, I want to experience this destination with him especially because it’s been on his bucket list a few years now.
While we have yet to really iron out a lot of the specifics, we know we want to take a few weeks to road trip through Germany. Our list of towns, sights, and must-sees is long but we both agree we want to go and see as much as we can and take a good amount of time off from our jobs to do so.
While I dream of flying first class and staying in high-end boutique hotels, I know that’s not realistic for our budget. Spending the extra Benjamin’s on a cushy flight isn’t practical because it would take up too much of our budget and take away from the things we want to see and do. Sure, I like being pampered on vacation but maybe that’s best saved for an all-inclusive rather than a road trip through Germany.
Step 2: Pick a Destination
There are many factors to consider when selecting a destination. Perhaps, you have a bucket list of places like myself or maybe a friend shared a travel experience that piqued your interest. Maybe it’s a place you saw on TV.
If you don’t have a specific place in mind and you’re in need of a little inspiration my advice is to check out Pinterest, talk to friends and family about their favorite trips, check out travel bloggers on Instagram, look at a map and Google destinations that catch your eye, check YouTube for reviews and of course, there’s always plenty of travel blogs like this one to read.
Once you have your destination in mind, there are still other factors to consider. What time of year are you planning to travel? Is it the off-season? Is the high season? How does that impact cost? When might flights be more expensive or less available? Are there weather concerns to think about such as taking a cruise during hurricane season? What kind of experience are you looking for? Do you want a warm-weather beach vacation or a cold-weather ski vacation? Cruise or All-inclusive? Road trip through several cities or stay in one city? There are plenty of questions to consider as you select your destination and begin to plan.
Step 3: Set Your Budget
Once you’ve determined what your trip will look like and where you want to go, you can more easily set a budget. Setting a budget is one of the things we’ve always done early on in our planning process.
Your budget needs to include all aspects of your trip such as your transportation (flights, car rental, taxi, etc.), lodging, activities and entertainment, food, travel insurance, gratuities (if traveling on a cruise or to an all-inclusive) and any additional expenses.
You may have to do some preliminary research to get an idea of what you can reasonably expect to spend in each category. It’s important to consider how much you will realistically spend on each category of your trip to best understand what the numbers look like for your type of vacation and destination. I have to know what the numbers look like before I start booking things.
Here’s an example of my cruise vacation budget:
7-Day Cruise For Two – Budget $3,500.00 – $4,000.00
My budget for a 7-day cruise for two where we fly to the port is typically around $3,500.00 – $4,000.00. Since the fare includes food, lodging, and a lot of on-board entertainment it’s proven to be a very economical way for us to travel.
Of course, you can take a cruise vacation for more or less than my proposed budget, and a variety of factors such as stateroom type, dates traveled, and the cruise line can impact your budge. For the purposes of this post, I’m sharing my typical cruise vacation budget.
So how did I come up with these numbers, exactly? Well, the flights take up a decent chunk of my budget right off the bat. Then, we typically book on Carnival Cruise Line, in either an ocean view or balcony stateroom. We most often cruise in early Spring (March/April) or late summer (August/September). Late summer is hurricane season but check out this post where I share why it’s still one of my favorite times to cruise.
In addition to my stateroom type, dates traveled and cruise line, I also like to fly in the day before we are scheduled to board the ship so we aren’t rushed or stressed. This means extra money in a one-night accommodation but it’s something I’ve chosen to build into my budget. Then there is travel insurance, gratuities, and of course plenty of fun money for excursions built into my budget, too.
The numbers break down like this:
$1,500.00 – cruise fare for two
$800.00 – round trip flights for two
$200.00 – accommodations for one night
$600.00 – excursions or port day activities
(3 stops/$600.00 = $200.00 a day/ $100.00 per person)
$400.00 – onboard spending/ souvenirs *
($50.00 a day)
$150.00 – travel insurance
$200.00 – gratuities**
——————– $3,850.00
We set a maximum budget of $4,000.00 for a 7-day cruise vacation but as you can see, I still have a little wiggle room and I know what to reasonably expect budget-wise. I can always make adjustments or re-prioritize things (such as booking an ocean view cabin instead of splurging on a balcony cabin or driving to a port instead of flying) if I need to cut my costs down without sacrificing my overall vacation experience.
*I know plenty of people who don’t spend anything extra on the ship. We typically give ourselves $50.00 a day in case we want a cocktail or two on the ship or buy a souvenir at a port stop.
**Gratuities are typically automatically charged on the first or second day of your cruise. It’s a set rate (rate varies depending on the cruise line) and recommended tipping value for staff.
Step 4: Book Your Flight
Once I’ve determined my destination and how much of my budget I have for flights, I immediately begin “stalking” them. I lovingly say “stalking” because I’ve always made it a practice to check airfare pricing before I buy my ticket. In fact, I used to check in on pricing on multiple airline websites a few times a week. I did it the old school way and when I found a deal, I booked my ticket.
Skyscanner helps me find the best flight times, and pricing for my travel dates and destinations. Set up price alerts and compare a variety of airlines. The site will even suggest the best times to travel to certain destinations based on ticket pricing so you can fly for less with Skyscanner.
In addition to Skyscanner, it’s worth mentioning that Southwest Airlines has a low fare calendar tool that’s super helpful. This is especially great if your travel dates are somewhat flexible and if they fly to your destination.
How Far in Advance Should You Book?
Finding the best deal and maximum savings is a crucial part of my travel practices but what does that mean for your booking timeline? Well, how far in advance to book depends on a few things.
Are you traveling during peak season or a holiday? If so, you’ll want to secure your flight as soon as possible. If you’re traveling during the off-season, you’ll have a little more time to finalize your plans. It also depends on if you’re traveling domestic (within the US) or international.
My recommendation is to book 1-4 months out for domestic. I’ve found the sweet spot to be around 3-4 months out from my home town to many destinations.
If you’re traveling internationally, you may need to book a little further out, closer to the 3-6-month range. However, it just depends on your destination. I’ve found deals on flights to the Caribbean with only 3-months advance but when I took at European destinations, I know I need to book at least 6 months out.
As mentioned above, I’m planning a trip to Germany for the Summer of 2021. I plan to start looking at airfare for this trip about seven months out. Because I like to watch prices and shop around, I always give myself a little extra time and I’ll likely buy my tickets no later than five months out.
Booking flights is one of my favorite steps to planning because once you lock down your flights, it sets things in motion and makes the trip “real”.
Step 5: Book Your Accommodations
In order to decide where to stay, you need to consider the environment in which you would like to stay. Do you prefer high-end boutique hotels, moderately priced hotel chains, private apartments/ condos or are you more of a budget traveler looking for a hostel? Maybe it’s a combination of all.
When I travel within the U.S., I’m always looking for a hotel that will be comfortable and meet my budget. I tend to gravitate to specific hotel brands where I’ve had the best experiences first but will only book them if it works within my budget. I’ve booked condos and houses and stayed at independent accommodations such as a Bed and Breakfasts as well.
When I travel internationally, I’m more open to booking outside of the chain hotels, especially if I’m traveling in the countryside or outside of a major city where chains are less likely to be an option.
For me, the cost is one of the most important determining factors of where I will stay because staying within the budget I set is how I’m able to travel often. Plus, I know I’ll always find an option that’s both comfortable and budget-friendly in every destination.
Step 6: Plan and Book Your Activities
So you’ve chosen your destination, booked your flights and accommodations, and now it’s time to think about what you’re actually going to do, where do you want to eat, what do you want to see. This is my FAVORITE part of planning.
My husband will tell you there’s never a shortage of places to see or eat on my list and thankfully he’s all for it as he’s become very accustomed to a long to-do list. When we visit a new place, I’m all about researching the heck out of it. I’ll make sure to book the shows, the tours, the excursions, etc. early. I want to see EVERYTHING that I can and I want to make sure I don’t miss anything.
When we spent four days this past fall in New Orleans, I had a full itinerary for us from the moment we checked in. I wanted to get out and explore ASAP. I was also looking forward to stuffing my face with as much seafood as I could get my hands on and I also needed to make sure I ate my weight in beignets. You know… priorities.
I tend to spend a good amount of time planning excursions when we cruise. As we’ve traveled more on our own, I’ve gotten away from booking directly through the cruise line. I can usually find the same excursion on my own at a better price and I like to book directly with locals. I read lots of reviews of course and once I have a comfort level, I’m all in. There have also been times when we don’t set anything in stone, I’ll say take me to a beach and from there we just spend the day exploring.
Booking an all-inclusive was great because there wasn’t really any additional research needed. We planned to show up, unpack, enjoy the resort, and figured we’d book a few things once we got there. Outside of lounging by the pool, we chose to book a massage on the beach and do an ATV tour. It was a pretty low-key vacation that required really no additional planning for activities.
Again, depending on the type of vacation your planning, the activities and excursion will vary but you should still spend time figuring it out as part of your planning process.
Step 6: Buy Travel Insurance
Once you’ve started to book things and you’ve put money down on your trip, I highly recommend that you purchase travel insurance for every international trip.
Travel insurance protects against illness, accidents, emergencies, and even death. It also protects against things like trip interruption, offers rental car coverage and covers things like lost luggage. Yes, it’s an additional cost to your trip but it also gives you peace of mind when traveling abroad. My go-to for travel insurance is RoamRight travel insurance.
You’ll want to buy your insurance as soon as possible because it will give you the most amount of coverage. Most insurance carriers will include a pre-existing condition clause in the coverage if you purchase your policy within 14 days of your initial deposit or payment.
And if you’re still on the fence about finalizing your activities or hoping to snag a cheaper last-minute non-refundable hotel rate, don’t worry, you can still purchase your insurance.
Since the insurance premium is based on an estimate of what you expect to spend overall, you can refer to your budget to help you here. Just make sure you estimate all expected trip costs (especially those with a non-refundable or upfront cost like flights or vacation packages where you pay in full) to have proper coverage.
Step 7: Check Country Entry Requirements & Understand Cultural Norms
The first thing you will need to travel internationally is a passport. If you don’t have a passport, you’ll need to apply for one and I’ve outlined the process in 5 Simple Steps. New passport applications can require additional documentation or verifications which can slow down the process. Make sure you leave enough lead time before your trip to get your documentation in order. If your passport has recently expired or is about to expire, be sure to plan enough time to get it renewed before your trip as some countries require that you have at least six months remaining on your passport for entry.
In addition to a passport, some countries also require a travel visa and although it’s rare, destinations that are more remote may require specific vaccinations as well. If you’re a U.S. citizen you can find entry requirements to different countries on the U.S. State Department website and if you’re not a U.S. citizen, check with your government or embassy website.
You’ll also want to learn the cultural norms or at least be aware of them before traveling to your destination. Starting with the official language. Find out if English is widely spoken or if you’ll need to learn a few basic phrases and consider a translation helper.
There can also be cultural norms around greetings, food, dress, and public space. Is a kiss on each cheek the standard greeting? Is it considered offensive if you don’t finish your plate? Do you need to cover your arms or legs in public? Is the idea of a personal bubble respected or ignored? All good questions to at least have some idea of the cultural expectations.
Step 8: Organize Your Trip Details
So now you have a whole bunch of stuff booked and now you’ve got to get organized. Make sure you’re documenting EVERYTHING. As you book flights, hotels, and activities you’ll want to easily be able to reference those reservations and their details – including the address to places you plan to stay, see or eat. I also like to keep track of any special instructions I may need while on my trip.
I keep a lot of notes, I like to be prepared and I’m also kind of old school. I like to keep a paper folder with all of our trip details and I pack it in my carry on for easy reference on each of our trips. I keep things organized digitally, too but in case I don’t have an internet connection or can’t get into my email, there’s just something about the physical folder of fun that I can’t let go, at least not yet.
Step 9: Decide What To Pack
Last but not least, packing is also an important part of planning your trip. Even though it’s something you will do when your trip is just a few days away, you should consider the weather and trip duration as part of your packing routine as you may need to buy additional items.
What will the weather be like? Are you going on a beach vacation in the middle of summer? If so, you may need to pack lightweight, breathable clothing, swimwear, sunscreen, and maybe a refillable water bottle or float for the beach. In contrast, if you’re planning a winter ski trip to the Swiss Alps, you’ll want to pack warm layers such as a winter coat, ski gear such as goggles and gloves, maybe some hiking boots, and a scarf.
When we go on a beach vacation or a cruise, I typically pack two outfits a day simply because I have day wear and evening wear. Since we are often out by the pool and out in the sun during the day, we always go back to our room for a shower before dinner.
Your trip duration is also something to take into consideration. For example, on shorter trips, you can easily plan one outfit a day. If your trip is a week or longer, you may want to pack items you can wear a few times and plan mix-and-match outfits to maximize your packing space. If your trip is longer than two weeks, you might want to consider packing clothing for 10-14 days and then pack a small amount of laundry detergent. Personally, I always pack a small amount of laundry detergent in my bag because I inevitably spill things on myself and I like to spot treat or handwash the item so it doesn’t sit until I get home.
So there you have it! These are my tried-and-true steps to planning any trip. Now you know how to plan your dream vacation step by step without getting overwhelmed and without missing anything important. Don’t forget to download my FREE Travel Budget Worksheet so you can stop dreaming and start planning. I promise no matter what you plan and where you go, it will be a trip to love and remember!
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