How to Start Planning Your Next Vacation Now

Every trip starts with the same question—Where should we go? It begins with conversations like: Should we book something tropical or with a cooler climate? Car, airplane, or boat? Is this a solo or companion trip? Am I craving a vacation or an exploration? (Check out the blog post “Three Reasons You Need More Than a Vacation” for more on this.) These are just some of the questions to ask before planning your next vacation. 

This blog post is focused on how to plan for time away from home in a way that increases anticipation, narrows down those “I forgot that at home” realizations, and focuses on all the packing list must-haves for whichever destination you choose this year. 

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Three Steps Closer to Your Next Vacation

Repeat after me: Planning is fun. Trips are affordable. Preparing is easy. 

I’ll prove it—here are three ways to start planning your next trip today. 

1. Revisit those questions surrounding Where are we going? And spend time visualizing the kind of experience you want to create. I like to do this by taking a long walk without music or audio books to distract my attention. Then I free write some of the memories I would like to collect on this adventure. I think about past vacations and what I did and didn’t like about the time away.  
2. After asking these questions (from the first paragraph), it’s time to put those thoughts and ideas into a Word Doc or into the Note App. I alternate between both but have found that the trips with other people are easier to plan when using the Note App, because we can both add ideas, photos, and links quickly throughout the day. 
3. Make a Pinterest travel-focused board with destination-inspiration that you add to throughout the year. That way, when it’s time to book the next vacation, you already have ideas for where to go. This can be very specific. I like to even include the kind of meals I want to have, outfits to bring, and activities/excursions to book. I have LOTS of travel inspiration boards HERE. 🙂

Growing up, Dad would always hold family meetings to talk about the details of where we were going, what to pack, and what to expect upon arrival. I most enjoyed the anticipation leading up to our Disney World trips. Even as children, my parents would include us in the planning process—letting us have a say about restaurants, daily itinerary, and lodging. By talking to us about the details of trip-building, my brothers and I now know how to plan a trip anywhere around the world—and have. I am using all these planning steps as I prepare for a trip to Iceland at the end of May with my brother, Cage. Here’s what my Pinterest board is looking like so far: 

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Planning Your Next Vacation

I like to think of planning for trips in five categories. After spending time making a Pinterest board of “this would be fun” photos and thinking through the kind of memories you want to design, it’s time to starting thinking about transportation, lodging, food, activities, and cultural must-dos. Here are some efficient tools for planning in each category.  

1. Transportation: Plane travel: I start by searching on Google Flights and looking at roundtrips into major airports. Flights are almost always cheapest from the USA to Europe when flying from NYC to London, Amsterdam, Barcelona, or Paris. 
2. Lodging: Air B&B, Hostels, and Hotels are my three go-to lodging options. I stick to mostly hotels in the US and hostels when I’m in Europe. HostelWorld.com is a good site for finding and comparing hostel prices. And if you find yourself traveling often domestically, a travel credit card where you can earn points at hotels might be worth looking into. I currently love my Delta Gold card. I have found Air B&B to be the best option for renting spaces for larger groups. There are lots of unique house and apartment options all over the world.  
3. Food and Beverage: Instagram is a great place to look for local food spots. I find these by either searching the name of the restaurant or by searching the location and looking under the tagged posts. Also, if you are a foodie like me, chances are that you also watch Food Network or the Cooking Channel. These shows often have the-best-of in large cities and I have eaten at some great places recommended on these shows. 
4. Activities: When it comes to filling the day with happenings, I like to focus on movement, being outdoors, and participating in activities that are unique to my travel destination. This might include a sunrise/sunset hike, a trip to the closest beach, attending a sporting event, collecting food from the market for a picnic lunch, and so much more. 
5. Culture: The key to fully enjoying a place and feeling present there, is to experience its authentic culture. While many locals in tourist towns like to keep to themselves, it’s always a treat when you find where the local families eat for dinner, shop, or spend their free time. My Yaya is the queen of what I like to call traveling like a local. When we were in Barcelona, she asked the bus driver where to eat for dinner, and after following his suggestion, we ended up in a square full of children playing soccer, while the parents watched from surrounding restaurant outdoor seating areas. 

Now that the planning is underway, let’s talk clothes and packing essentials.

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Packing Like a Pro

I normally only bring a carry-on backpack on trips whether it is domestic or abroad. Here’s why: 

• If you change plans more than once, you run the risk of losing your luggage. I eliminate this risk by only bringing a backpack. 
• If you check luggage, you’ll always having to wait for it in the airport after landing. And, it may not arrive when you do.
• I like to be mobile right when I land in case there is an activity I want to do right away, or the hotel/hostel check-in isn’t for a few more hours.
• You can always buy things at your destination if you forgot it (except for your passport and travel documents—focus on remembering those). This helped soothe a lot of anxiety for me when I packed for my first solo trip to Europe.

Remember, you don’t need as much as you think and with a little extra preparation, you’ll have just the right size backpack to be mobile, enough space left over to bring a few souvenirs home, and no possibility of losing luggage in transit. 

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Pack This, Not That

You’re right to be wondering: Okay, but what are the most important things to bring if I’m only going to have a carry-on amount of space? 

Carry-on Backpack & Daytime Pack

You know when you buy something and wish you had purchased three more of the same? That’s how I feel about this backpack from Made By Design. Before traveling to Europe with my brother in 2019, I searched for months to find the ideal traveler’s pack. Some of my must-haves: a neutral color, adjustable straps, a padded sleeve for my laptop, a few compartments separated by zippers, so my dry clothes stay dry among all those hygiene products, and most importantly, discount airline approved size. After much online searching–I found this gray backpack at Target and bought one for me, and for Cage. It was a bonus that we would be trekking through Europe with matching backpacks– how cute. And you know he especially loved it! 

I can confirm that this backpack is, along with these look-likes below, suitable for all over the world. Mine has been to Austria, France, Spain, United Kingdom, Italy, Belize, and The Netherlands. 

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Clothes for Layering

• Rain jacket: for scheduled rain and unexpected storms
• Lightweight (but warm) hoodie: for layering and using it as a neck pillow on the plane 
• Fitted long sleeve: as a versatile option to go with all the bottoms suggested below
• Tank tops: for layering–I swear by these from Zara. They come in eight colors but the tan, black, white and orange are my go-tos right now. 
• Black yoga pants: for active and airport days
• Comfortable jeans: I look for a denim option with some stretch. Currently loving a light-washed, square-pocket pair I found at H&M
• Underwear: the no-show neutral pack below is great 
• Feetures socks: for moisture wicking and a fast dry if you need to wash them in the sink between wears
• Volcom Flip flops: It’s best to choose a pair that dry quickly—in case you have a community shower at a hostel. Overall, good to pack one sneaker alternative. 
• Hoka One One: I purchased these tennis shoes for the first time when I started training for a marathon and have been wearing them since. I love the Cliffton 7/8 and the Bondis best. 

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In addition, I pack accessories for a pop of color. These items take up little room and make each outfit feel more elegant and fun. My top three accessories: 

1. A scarf: One of my favorite accessories for travel is a thrifted pastel from Amsterdam. Traveling with only a backpack means everything must have multiple functions. This scarf doubles as a belt, hair embellishment, dressy neck piece, creative way to attach a water bottle to a day purse, tube-top for dinner, and beach cover up. 
2. Scrunchies & hair claws. I clip my extra claw clips to the side of my backpack, so they don’t break in transit. 
3. Earrings and rings to layer and mix-up throughout the trip. I don’t bring my nicest pieces because as a female traveler, I don’t like to draw too much attention by wearing expensive items. 

Overall, I keep my packing simple and light, knowing I will pick up a few special items along the way.

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Conclusion

Overall—don’t wait to start checking those places off your bucket list. Life is so much sweeter when there are memories to recall, pictures from faraway places in photo albums, and an expanded perspective from years of experiencing the many joys of travel.

xxx

Allie M