How to Plan a Big Trip

Caila Quinn the bachelor Travel Hoxton Hotel Tonight Travel App robe Travel tips blog post

So, you’ve decided you’re going on a big trip - yay!

Whether you dream of exploring the safari’s of South Africa, letting wild monkeys climb you like a tree in Indonesia, or want to backpack your way via Eurorail trains, it can be intimidating to book a big trip. There are many moving pieces you need to consider, so once you’ve decided on your destination I’m excited to share this post on…


1. Book flights – 1 year to 6 months before

To me, booking flights is the catalyst of any long trip. We can talk and daydream all we want, but once you book it makes it official!

It’s challenging to find dates that works for everyone in a group traveling together, so continuing to look for the perfect time for everyone could take forever and keep you from actually going. Whether with friends or a partner, I’ve learned the best way to go on a trip is get everyone together on the phone & book spontaneously. Doing this holds us accountable and gives us that, “Wow this is actually happening!”  feeling.

2. Create a Google Doc and Spreadsheet itinerary – 4 months before

Google Doc 

Google docs are a great way to make sure everyone is a part of the planning process. You can share with everyone in your group and they can add details & edit at their convenience!

Under each city, start by making 4 lists for people to contribute to: Restaurants, Sights, Activities to Book, and Hotels. Sometimes it’s helpful to put an estimated amount of time next to each activity as well (1 - 2 hrs) just to help when it comes to planning (1/2 day).

Caila quinn the bachelor Travel Tips planning a long trip excel asia document

 Google Spreadsheet

Making spreadsheet takes your organization to the next level by planning a long trip day by day, even hour by hour. Map out where the sites are you want to visit and try to cluster them by location so you can plan out seeing them in an order that makes the most of your time. Keep in mind this is a working document until takeoff! Plans will change and that’s OK. The purpose of the itinerary is to optimize your time and not take away from it. If you take anything away from this article, remember…

the best traveler is a chill traveler.

TRAVEL TIP When planning sightseeing, schedule the most popular sights in the mornings/ during the first half of your day. This way, there are fewer people when you visit and if it’s summer the temperature isn’t as hot. Then, in the afternoon you can relax a bit more and do the less physically strenuous activities like seeing a show or enjoying some afternoon tea. You’ll also feel more rested for the next activity-packed morning the following day.

3.   Book Hotels – 3 months before

Completing this step always helps me breathe a sigh of relief. If nothing else, at least you know you have some place to stay when you arrive at your final destination! My favorite site to use is for reliable and trendy travel options. I also look for ideas from other bloggers because they usually have useful insight about the hotel and pictures to help me make an informed decision. Remember – location, location, location! Look for a hotel that is centrally located so you can easily get to other areas of the city.

4. Research and Reservations – 6 weeks before

Now we’re getting to the fun part. Utilize Pinterest, Instagram, and other platforms to get some inspiration for what you want to do. The earlier you’re able to book activities or make reservations - the better. Some restaurants require reservations to be made a month before desired time and you don’t want to miss out. For example, Nick and I were really looking forward to going to the Pokemon Café in Tokyo for our upcoming Asia trip. We checked their website three weeks before the date we were hoping to reserve and all of the reservations were taken!!! SO TRAGIC!

Additionally, tickets to shows and entrance for popular museums are usually cheaper when bought online and in advance. Having a ticket already cuts waiting time down so you don’t have to waste hours standing in line. Some great sites I love to use for booking are and If you’re interested in booking a photographer for some nice vacation pictures, has amazing options around the world so you can find a photographer no matter where your travels take you.

p.s. Remember to continuously add the reservations into your spreadsheet to make sure not to double book yourself. To make things especially easy, I create a key for my excel sheet (shown above). Yellow signifies for travel (flights, trains, etc.), green indicates all booked activities that we can’t miss and have already paid for, and orange stands for the activities we want to do but aren’t a priority.

5. Finalize the itinerary - 4 weeks before

It’s really important for big trips to get together with or FaceTime the whole group to talk everything through. This way, you can make sure everyone is on the same page with the plans and feels like they have a say in the trip. Most likely, everyone has at least one activity they’re most looking forward to and will make sure to voice their preference.

When we went to Iceland for our girls trip, one friend really wanted to go horseback riding while another felt strongly about snorkeling in glacial waters. While neither of these things was a priority for me personally, after talking through our plans it was then important to me that we did these activities, because it was important to them. In return, they were conscious about allowing me to take pictures at each location, something that I shared was a priority.

After being finalized, I always put the itinerary into an email format and send it to myself & those I’m traveling with (pictured below). Just in case I need to pull it up via email or want to forward it along during my travels.

Caila Quinn the bachelor Travel Guide planning itinerary for a long trip to asia

6. Print everything - 1 week before

This might sound old school, but print a paper copy of your itinerary, all your tickets, reservations, and address. In many cities, it may be hard to find WiFi to access your spreadsheet and see what’s next on the agenda. You put all this time and effort into creating it, make sure you’re able to use it! Also, if you’re not able to find the address of a restaurant, you may miss your reservation time.  

I suggest printing copies for every travel companion in the group. This way, everyone knows what the plan is and can help with getting to the next destination. Though you might love them dearly, we all know traveling with someone constantly asking, “what now?”, can definitely get frustrating!

I know this might seem like a daunting list of steps. Take it from me, the more you prepare beforehand, the more stress-free you’ll be. Traveling far and for an extended period of time is a big investment of time and money, these steps help make sure you’re traveling efficiently so you can fully enjoy your well-deserved vacay. Even if you’re not always organized doesn’t mean you can’t be for this trip!


Love reading about travel tips?

Learn from my mistakes and make sure you avoid any unforeseen travel woes by reading my blog post on the Top 10 Travel Secrets People Assume You Know, But Never Actually Tell You.