Prepared for Anything: My Travels Taught Me About Planning and Flexibility

When I first started traveling, I thought I could simply pack my bags and head out on a whim. I used to book flights just a couple of weeks before my departure date, sometimes even less. What I didn’t know at the time was that booking last minute meant higher prices, fewer choices for accommodations and rental cars, and often missing out on popular activities. Over the years, I’ve learned that preparing in advance not only saves you money but also leads to a smoother, more enjoyable experience.

Early Bird Gets the Worm

I can’t stress this enough: booking early is one of the best decisions you can make when planning a trip. Now I aim to book my flights as early as possible, typically nine months in advance. Why? Well, most airlines, like American Airlines and Delta, allow you to book that far in advance, which opens up the best flight options—particularly when it comes to seating and flight times. Nobody wants to land at 6 AM, only to lug their bags around for hours until check-in time at 3 PM. Booking early means you can choose better flight times, ensuring you don’t waste your precious vacation hours waiting around. Plus, when you book ahead, you’re able to secure better seats—no more settling for the middle seat in the back of the plane.

And if you’re like me, you don’t want to leave your paradise at 6 or 7 AM on your last day, missing out on the chance to enjoy your final morning or take in one last activity near the airport. But did you know that most hotels will store your bags for you, or you can leave them in the trunk of your rental car while you continue exploring? A little extra flexibility can make all the difference. One little-known trick I’ve learned is that after booking a flight if you keep an eye on the prices over the next month or so, you can sometimes call the airline and request a refund for the difference if the cost of your flight drops. I did this when I traveled to France—I called a few times and ended up with enough extra money refunded to book an entirely new trip for me and my boyfriend! That’s a win in my book.

The Magic of Booking Accommodations Early

Booking early isn’t just limited to flights. Accommodations are just as important. If you’re someone who likes to stay in the best Airbnb or boutique hotels, you need to book early to get the first choice. When you wait until the last minute, you often find that the best places with your perfect criteria are already taken, leaving you scrambling for a place that meets the minimum standards. I’ve learned this the hard way, and I don’t recommend waiting. If you book ahead, you can ensure your ideal stay without compromising.

For me, it’s about having everything lined up so I’m not stressed when I arrive at my destination. If I plan, I can focus on the exciting parts of my trip, like sightseeing and enjoying local culture. My goal is to avoid last-minute stress and ensure that everything from the home situation to pets and work schedules are all in place before I leave. It’s much more enjoyable to travel when you’ve thought of everything and know that things are taken care of back home.

Planning Your To-Do List: Restaurants, Activities, and More

When it comes to activities, my travel group and I always create a detailed to-do list of things we’d like to experience. We rank everything from “Must-see” to “Maybe if we have extra time.” It’s a great way to organize the things you don’t want to miss while also allowing room for flexibility if you end up discovering something new along the way.

Mapping things out is essential, too. We often make a physical map of the locations we plan to visit and draw dots for restaurants, activities, and the main city spots we plan on exploring. Knowing the distances between locations helps you make the most of your time and energy. It also helps when it comes to getting around. The last thing I want is to waste time driving across the city when I could have been visiting a new spot just around the corner!

For restaurants, we tend to use resources like TikTok, Instagram, and TripAdvisor to find the best-reviewed spots. I love trying new foods and local specialties instead of settling for the familiar. I’ve found that when you follow recommendations from these platforms, you’re more likely to discover hidden gems and unique dining experiences. There’s nothing worse than going to a place just for the food to be subpar or the atmosphere flat. I love a good meal with a beautiful view and an excellent ambiance to match, and planning ensures you’re always eating at the best spots.

But when it comes to popular destinations, don’t forget to book your activities in advance. Nothing is worse than arriving at places like the Louvre or the Eiffel Tower only to find out that all the time slots for the day are booked up, and you can’t get in during the days you need. While this may not be necessary for every single tourist spot, for places like New York, Paris, or Italy, where there are certain landmarks that everyone wants to visit, it’s crucial to check out their availability and book early. This includes booking things like train tickets and rental cars as well.

I had an experience last summer where we booked our train tickets three months in advance, which I believe is the max allowed in Europe. Unfortunately, our friend didn’t book early enough and had to buy a last-minute flight to catch up with us. While it didn’t break the bank, the extra cost and the fact that he had to travel separately from the group definitely changed the vibe of the trip. Moral of the story: Book your activities early to avoid missing out!

Make Restaurant Reservations and Be Respectful

When traveling, I’ve also learned that it’s essential to reserve restaurants in advance, especially for popular spots. It’s always a good idea to book ahead, but don’t forget that canceling in advance is just as important if your plans change. A table held up for hours because someone didn’t show or cancel properly can cause a ripple effect on the restaurant’s flow for the night. Treat others how you’d want to be treated—if you make a reservation, show up or cancel early. We all know life happens, and plans change, but make sure to let the restaurant know as soon as possible so they can offer the table to someone else. Services like OpenTable are perfect for booking reservations, and they make it easy to cancel as well.

Packing for Every Occasion

Being prepared doesn’t stop at booking in advance—it extends to packing as well. Over the years, I’ve learned to create a dedicated travel bag for different types of trips. Whether it’s a beach vacation, a hiking getaway, or a skiing retreat, I always have a plastic tote that can be pulled from when packing the essentials for each occasion. This means I can easily grab the right items for whatever I need. Here are just a few of my travel essentials:

• Beach Vacation: Automatic tube inflator, goggles with defogger, backup phone charger, sunscreen, quick-dry towel, waterproof speaker, flattening cooler, and sun hat.
• Ski Trip: Ski buff, extra gloves for different temperatures, hand warmers, ski hat with built-in earphones, and walkie-talkies for skiing with friends.
• Lake Vacation: Sunblock, sunglasses, inflatable tube, waterproof backpack, and extra chargers.

The more you travel, the more you realize how important it is to pack the right gear for your specific destination. I also keep extra cords, chargers, lighters, and pens in my bag as I’ve learned that these are things you often can’t find when you need them the most.

Understand Your Destination: Research and Local Insights

Before any trip, I always study the weather for both daytime and nighttime temperatures. You don’t want to be stuck in an unfamiliar place without knowing how to dress for the local climate. Plus, being prepared for rainy weather or sudden temperature changes can make all the difference between an uncomfortable trip and one where you feel perfectly at ease.

I also recommend researching the city layout or country you’re visiting. Spend about 15 to 30 minutes reviewing a map to understand the general location of the cities, towns, and major attractions you’ll be visiting. You can even sketch it out on paper or use your phone’s map to get a sense of the distances and best routes.

Don’t forget to ask locals for recommendations. Sometimes, the best spots aren’t listed on tourist websites or apps, so having a conversation with someone who knows the area can lead you to some amazing hidden gems.

I hope these tips will help you plan your next trip with confidence and ease. Traveling is about being prepared, but also staying flexible enough to enjoy the journey.

With love,
Tiffany