Tips on How to Plan the Ultimate Trip in 5 Steps

Planning a trip can sometimes be a little stressful and overwhelming.  The key is staying organized and really honing in on what this vacation is about and what you’re hoping to gain from it. This too, can help you decide where in the world you want to go. I want this to serve as a step-by-step guide for you when planning your trips so you don’t have to worry so much about “what’s next” or how should I go about this. I will lay it all out for you. 🙂

Step 1) Pick a Destination 

What are you hoping to achieve on your trip? Time away from technology and a chance to recharge in the wild? A sunny vacation among the sands of a beautiful beach? Or a longing to explore a new city and play tourist? Once you’ve decided what your body and mind needs – you can go from there! Here’s a list of example destinations:

Mountain Adventures:

Salida, Colorado
Sedona, Arizona
Grand Canyon
National Parks in Utah
Appalachian Trail
Banff and Lake Louise, Alberta, Edmonton, Canada
Telluride, Colorado
Big Bear, California
Swiss Alps
Breckenridge or Aspen, Colorado
Queenstown, New Zealand

Countryside Retreats:

Hudson Valley, New York
Rhinebeck, New York
Fredericksburg, Texas
English countryside
Sicily & Tuscany, Italy
Greenville, Maine
Marfa, Texas
Stowe, Vermont
Napa Valley, California

Salt & Sea Vacation:

San Diego, California
Pensacola, Florida
Key West, Florida
Jersey Shore, New Jersey
Bar Harbor, Maine
Santa Barbara, California
Costa Rica
Carribbean Islands
Malibu, California
Santorini, Greece
Nice, France
Sydney, Australia
Cape Town, South Africa
Cozumel, Mexico

City Exploration:

Chicago, Illinois
Austin, Texas
New York City
San Francisco, California
New Orleans, Louisiana
London, England
Dublin, Ireland
Rome, Italy
Toronto/Montreal, Canada
Paris, France
Tokyo, Japan
Hong Kong, China
Berlin, Germany
Buenos Aires, Argentina
Madrid, Spain

Desert Oasis:

Palm Springs, California
Wadi Bani Khalid, Oman
Cairo, Egypt
Siwa Oasis, Egypt
Huacachina Oasis, Peru
Ein Gedi, Israel
Tuscon, Arizona

Personally, we like to plan trips around the season and, a lot of the times, sports games! My boyfriend and I are currently attempting to visit all of the nation’s baseball ballparks together and so far have made it to see Diamondbacks, Angels, Astros, Cubs, and White Sox , but we have a long way to go! This winter, we’re actually heading to South Bend, Indiana and Chicago for the 2019 NHL Winter Classic! Any Hockey fans in the house?

Once you’ve decided why you’re in need to travel and you’ve chosen where you want to go – next step is finding accommodation!

Step 2) Find Accommodation

This can also play into WHY you’re in need of this trip. If you’re looking for a beach vacation where you can sip on a margarita and turn your cell phone off, maybe look into an all-inclusive resort.

We typically use Airbnb when booking travel stays because we love the affordability and the convenience. Also, many hosts go above and beyond to ensure every guest has an amazing stay, so they can serve as great city guides! We’ve stayed in a number of different housings through Airbnb, from a small airplane to a farmhouse in a vast field. Airbnb can be perfect for those looking for a quiet cottage retreat, or a condo in the middle of a big city! Definitely look here first when searching for a place to stay.

Another good thing about Airbnb is you can book “experiences,” too. Experiences are a way to try tours or fun activities guided by locals in the area.

I also recommend though I don’t use it as much, but it’s great for when you want to sleep in an actual hotel. compiles a list of hotels from all over the city with comparatively cheaper prices.

If  you’re feeling really risky, you can use the app Hotel Tonight, which provides last minute discounts on hotels! We have only used this once on a road trip from Florida back to Texas, but we stayed in what is now one of my favorite hotels ever for such a low price!

An important thing to note is location. What are you going to be doing during your stay? When we stayed in Chicago last Spring, we stayed in a little brownstone apartment that was only a few blocks from the train, walking distance to Wrigleyville, and near so many restaurants and bars! We absolutely loved the location and it was perfect for all of the activities we did while we were there.

Step 3) How to Get There

How far away is your destination? Can you road trip? Do you have to fly?

Road trips will often take longer, but driving there can be half the fun!

When booking flights, I always use Skyscanner initially. This is how I research various flights and dates.

Once I’ve solidified the days of our outgoing and return flights, I will plug them into the app Hopper. This will help me monitor the flight prices: Should I book now? Are they projected to decrease in the next few months?

Then, I’ll use all of this information to eventually know when to book my flight, what airline, and what days.

I always book on either Skyscanner, or using the flight information I will book directly  with the airline. I never book through Hopper because they add an extra charge.

Once our flight is booked, we can officially say we’re going on vacation!

Step 4) Building an Itinerary

This will also stem from why you’re planning this trip. If it’s to go backpacking through the Appalachian trail, then you’re pretty much set on what you’re going to be doing, unless you’re roadtripping and want to add in extra stops along the way.

I usually will start out by making a list of A) Things to do recreationally B) Restaurants and bars. Be sure to include what part of town each activity or place is in.

I never like to make a strict itinerary; I always leave room for spontaneity. But we usually have an idea of which part of town we want to be in each day, and then we look at our list to see what’s in that area.

If you’re hiking/backpacking, or roadtripping, make a map or route to incorporate sites you want to see.

Step 5)  What to Pack

Your flight and stay is booked, you have an idea of what you want to do, and now all you have to do is get yourself ready.

This is mostly self-explanatory. Monitor the weather, know what attire to bring, and know whether or not you need to leave room in your suitcase for shopping.

Try to think ahead – what could you need? This might result in overpacking, depending on how much you think of, but you can always try to distribute among your group to help maximize space. Though I like to pack lightly, sometimes I thank myself for having packed those extra items that I’m unsure of.

Sometimes I will bring traveling size shampoo and conditioner, it just depends on where we are staying. I’ll bring lotion if I am going somewhere cold, along with lavender oil cream(it’s SO good for your skin). I’ll pack an umbrella or rain jacket if the weather looks like it’ll be rainy, or multiple pairs of sunglasses if it’s going to be sunny. You get the idea.

For the flight, I like to bring a book, along with earphones, my Ipad, a blanket, and some snacks. I love NatureBox snacks because they’re healthy, light, and so freaking tasty, not to mention their packaging is perfect for on-the-go.


Once everything is in place, you can sit back and not relax because you’re SO EXCITED you’re going on vacation!!!

Even for my expert trip planners, I hope this helped you in any way! If there’s any other tips or questions you have, feel free to comment below!



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