TRAVEL SHOULD BE FUN.

Let us take the stress out of trip planning for you.

Whether you’re looking for recommendations of coffee shops in a certain area, or needing a fully planned trip from start to finish, we’ve got you covered.

We (Kailey and Will) have bonded over a passion for travel since the day we met. So naturally, we’ve traveled as much as possible and are always itching for our next trip.

We’ve also discovered along the way that the planning of these trips is something we absolutely love to do. But we know that isn’t the case for everyone.

We get an absolute kick out of digging to find that hole-in-the-wall restaurant where you’ll have the best meal of your life, that little-traveled hiking trail with breathtaking views, and the underrated travel destinations you won’t see on every influencer’s social media page.

Have you ever run into any of these issues when planning a trip?

If so, that’s where we come in!

“I know where I want to go, but I have no idea where to start planning the actual trip.”

“I want to get out of my comfort zone, but the thought of a new place scares me. How do I navigate that?”

“I want to travel but don’t know how to make it work within my budget.”

“I want to visit this place, but want to avoid touristy areas. How do I find the hidden gems?”

“I want to plan an amazing trip, but I get overwhelmed by the amount of information out there.”

“I know I want to travel somewhere warm, but have no idea how to pick a location.”

Why should I hire you to plan my trip?

Whether you’re interested in having us plan and book your entire trip, or simply give you some ideas for what to do once you reach your destination, we make the process so much easier for you.

We’ve spent years planning trips and traveling as much as possible, and while we personally love the process, we know that it’s not everyone’s cup of tea.

There’s also sooooo much information about travel out there, and with the increase in AI-created content (which sometimes even recommends places that don’t exist!), it can feel impossible to narrow down your trip or find a destination or trip itinerary that actually suits you.

When you let us plan a trip for you, you get a trip that’s actually made for you. So if you hate crowds, we aren’t going to recommend a trip to Disney World. If you aren’t a foodie, we won’t recommend you check out that overhyped restaurant where the meals are $100/each.

Each piece of our itineraries, from the coffee shops we suggest to the lodging we recommend will be specific to you and your party’s likes and preferences.

Lastly, and maybe most importantly, we go beyond what you get from other travel advisors or online travel guides. We don’t just tell you fun things you can do on your trips. WE want to truly make your trip simpler, less stressful, and waaaay more enjoyable. You can probably tell that by what all we include with our itineraries (see below FAQ about what’s included!)

What makes you different than other travel advisors & online trip planners?

Simply put, we go above and beyond what other travel advisors do. Our priority is not booking you the trip that will earn us the most commission or to quickly get you in and out and onto the next client. We actually genuinely care about you and your travel experience.

Our mission with our entire business, right from the beginning, was to help others travel easier, explore more, and reconnect with the world around them. We bring that mission into our travel planning business.

We also provide things that other travel advisors don’t- from extra travel guides included with all itineraries (see the ‘What’s included’ tab) to personal touches customized to you and your travel party.

With us, you can feel confident that we’re doing the work to save you the stress (and save you money) all while customizing everything just for you!

Step 1: Fill out an inquiry form for free

This form just has a few questions about where you are in the trip planning process, when your trip is (if you know already), and about you! This step is completely free!

You can fill out that inquiry form here → GET YOUR FREE INQUIRY

Step 2: We send next steps & a questionnaire for you to fill out

Once we get your inquiry form and confirm we’re able to take on your trip, we will send you an email with a little more information about the service(s) you requested along with a questionnaire for you to fill out.

This questionnaire has all kinds of questions about your upcoming trip, how you and your party like to travel, and so much more. This helps us get to know you and your travel preferences better and this is what we use to find activities and recommendations we know you’ll love.

We will also let you know in this email how much your requested services will cost.

After you fill out the inquiry form, we aim to respond back to you within 48 hours.

Step 3: We agree on a service & collect a deposit

Once we agree to work together, we will collect a deposit from you for a portion of the cost of service. This protects us in the situation that someone would not pay for the product(s) that we spent weeks working on.

Step 4: We get to work planning

Using your questionnaire answers and our extensive knowledge of travel, we get to work crafting the best trip for you. Depending on what services you hired us for, this might look like scoping out the best hikes in the area, finding unique hotel stays you’ll love, or even planning out the entire trip, start to finish, with details we know you’ll enjoy.

Depending on the service(s) you booked, the service period may look different. For basic itineraries, we give a time frame of 2 weeks, but for more in-depth services that require much more work from us, this can be slightly longer. We will let you know up front how long you can expect the process to take.

If we have any additional questions for you that weren’t answered on the questionnaire, we will reach out to you at this point.

Step 5: You get the final product

(for basic itineraries)
If you requested a simple itinerary/recommendations packet for your trip, you will receive it during this step and we will collect payment for the remainder of the service costs (minus your deposit).

(for travel you’d like us to book)
If you chose a service where we book anything for you (lodging, experiences, rental car, etc.), we will send you a few recommendations to pick from at this point. Once you pick, we will then book everything and provide you with a final copy of your itinerary using your final choices. We will never book anything for you without your approval.

The basics of what you’ll get

Depending on what service(s) you book, your final packet might look a simple list of recommendations for things to do/eat/see once you reach your destination, or it could look like a fully mapped-out itinerary from the moment you leave home to the moment you come back.

No matter what package, you’ll receive detailed recommendations from us that are customized to you and your travel party. We try to provide as much deatil as possible to make it easy for you to understand & use our suggestions.

Bonuses included with every service

No matter what type of service you get, you can expect the following at no extra cost to you:

– How to take amazing travel photos guide
– How to pack like a pro guide
– Packing checklist for your destination
– How to be a good steward of the planet while traveling guide
– Information about travel insurance

Additional bonuses you might see

With each individual trip, we might include additional tips & tricks specific to your destination, activities, or travel preferences. For example, if you’re going on a road trip and will be doing some hiking, we would include:

– How to save money on road trips guide
– The best road trip meals & snacks guide
– Hiking gear checklist
– A list of the most useful phone apps for road trips & outdoor adventures
– Road trip packing checklist
– Road trip prep guide

What types of travel do you prefer to plan?

While we love most types of travel and have experience with quite a bit of it, we absolutely LOVE road trips and outdoorsy adventures, especially to national parks.

We are nature lovers to our cores and we are passionate about heping others get outside and see the beauty of the natural world. If you want some help planning a national parks trip or a road trip, PLEASE reach out, we would love to help!

How long does the process take?

We aim to get your itineraries to you as quickly as possible so you can get ready for your trip with plenty of time to spare. With that said, this process does take time, especially because we’re customizing each itinerary rather than creating boilerplate guides.

While we’re creating your itinerary, we’re researching everything about the area you’re going to, finding the hidden gems in each spot, figuring out the places off the beaten path worth visiting, and checking every single box before sending you the guide. We’re not heading the ChatGPT and asking it to create us an itinerary- we’re actually doing every single part of it ourselves so that we can create the best possible trip for you.

For simple trip itinerary-only services, we aim to complete these within 2 weeks. For more in-depth services, this may take a little longer, though we still aim to get them done as quickly as possible. We will give you a heads up on how long we expect your itinerary to take before you pay for any services with us.

Please check out ‘The Process’ tab for more information!

How far ahead of my trip should I reach out?

As soon as possible! Even if you don’t know where you’re going yet or even the exact dates of your trip, we can help!

Depending on the services you choose to hire us for, we will spend at least 2 weeks getting everything ready for you. Some services may take a little longer. For example, if you know where you want to go, what your dates are, and you already have lodging booked, then planning your itinerary will be much simpler than helping someone plan a trip from scratch.

Here’s why else you should reach out sooner rather than later:

– We run this business on our own (just the two of us), so if we get fully booked up, we may have to turn away certain trips. Giving us more advance-notice of your trip means we can reduce the chance of having to turn down working with you when we get too many requests!

– Accommodation prices can vary (and often be cheaper when booked further in advance). So whether you’re having us book your accommodations, or booking them yourself from our recommendations, getting that taken care of ahead of time can save you money!

– It gives us more time to get you extra perks. Part of our process, depending on what services you book, is reaching out to companies directly to get you extra travel perks (VIP experiences, room upgrades, welcome amenities, discounts, and more). We wish that we could rely on these companies to respond to us immediately, but that just isn’t the case. So giving us a little more time to plan your trip may mean a little more wiggle room for us to get perks for you!

Will you only recommend things that earn you a commission?

Absolutely not. While we do earn some commissions from certain bookings as certified travel advisors, that is not the main priority of our business.

We will NEVER suggest something to you unless we truly think you will enjoy it, commission or not. For example:

Option A is something we think you will truly enjoy, but we won’t earn a commission from it.
Option B is something we aren’t sure you would enjoy but we do earn a commission from.

100% of the time, we will recommend Option A. Our first priority is always to make sure you have the best trip possible, and that comes before a commission for us.

Can you book my travel for me?

Mostly, yes. We are certified travel advisors, which gives us access to book a variety of things, from lodging to cruises, experiences, and even rental cars.

However, there are certain things we may not be able to book due to third-party restrictions. In these rare cases, we will try to make it as easy as possible for you to book on your own!

Do I have to do everything you recommend?

Of course not. While we aim to create itineraries you’ll be excited to use, it’s totally up to you what you do with it.

Once we hand off the itinerary to you, you can use it or delete them email and pretend we never sent it- your choice! But we do promise our recommendations will be worth it!

Trip Planning & Itinerary Packages

Below are the packages we offer

See/Eat/Do

$130+

A simple itinerary with recommendations for what to do, eat, and see on your trip

Learn more

This is for you if: You already know where you’re going & where you’ll be staying, but want some recommendations for what to do when you get there. We provide you with a PDF of activity/experience recommendations/tips for your trip. Super simple!

See/Eat/Do/Stay

$200+

Itinerary + recommendations on what to see/eat/do, plus lodging suggestions

Learn more

This is for you if: You know the destination but want help finding lodging, along with activities/experiences.

We will provide you with a PDF of our recommendations for where to stay, and what to do/eat/see when you reach your destination!

National Parks Trip

$130+

Our favorite type of trip to plan. Let us handle your national parks trip for you!

Learn more

If you want to explore one or more national parks in the US, please reach out! Whether you’re looking for a customized road trip itinerary for a month-long national parks tour, or just a lodging recommendation near a park you’ll be visiting, we can help!

National Parks trips are the bread and butter of our business and what we’re most passionate about.

If you book this service, you will also get a bundle stuffed full of our best national parks travel tips & tricks!

Prices are the same as the other packages listed, depending on where you are in the trip planning process!

Full Planning

$450+

Planned trip, from start to finish, including destination ideas & a full itinerary

Learn more

This is for you if: You haven’t picked your destination yet or done much planning at all. We will help you plan everything from a super cool location to helping you find things to do while you’re there!

With this option, we can simply recommend and let you book, or we can book for you for an additional fee (see below ‘extra fees’ section).

Additional Fees:

Group Trips: For groups larger than 6 people, there will be an additional charge of $40 per planned day

Booking Services: If you’d like us to book any part of your trip for you, there will be an additional charge of $50 per 7 days of travel (1-7 = $50, 8-14 = $100 and so on)

Individual Services & Extras

Below are additional services you can purchase individually or add onto a package!

Trip Planning Workbook

$47

For those who want to plan their own trip (but with a little guidance)

Learn more

This workbook is coming soon!

Want to plan your own trip but don’t know where to start? This trip planning workbook was made for you (literally).

In this workbook we walk you through each step of the trip planning process, from helping you pick a location to helping you figure out your budget, plan your activities, and pack your bags.

This packet is absolutely full of tips and tricks designed to help you plan the best trip ever and enjoy the heck out of it while you’re there.

If you enjoy the travel planning process but like a little more organization and guidance, this is just what you need.

Lodging Recommendations

$25/place

Let us source lodging recs for you at the destination(s) of your choice

Learn more

If you only need help finding unqiue or beautiful lodging options for your trip, this is for you.

Pricing explained: if you’re going on a road trip for 7 days and will be staying at 3 different places throughout your trip, you will get charged $75. $25 x 3 = $75.

Destination Recommendations

$100+

We can provide ideas for trip destinations based on your preferences

Learn more

Only need help figuring out where to go? No problem. We’ll ask you a few questions about your preferences (e.g. weather, time of year, mountains vs beach, outdoors vs city) and recommend a few destinations for you!

Pricing explained: If you are looking for a single destination where you’ll be staying the whole trip, it’s $100 only. If you’re taking a road trip or multi-destination trip, it’s the base price of $100, plus an additional $25 per each additional destination.

So if you want help planning a road trip to 5 different national parks, it’ll be $200 total.
$100 (base fee) + ($25 x 4 extra destinations) = $200

30-Minute Consultation Call

$50

A quick call at the beginning of the process to address any questions/concerns you may have

Learn more

While we try to do as much as possible through email & documents, we understand that some clients may prefer to talk things out. This 30-minute consultation call can be scheduled after the initial inquiry, as sort of a get-to-know-you type meeting where we can learn more about your trip ideas/plans and your travel preferences!

This is completely optional and by no means required for any of our services.

Miscellaneous

$100/hour

For any miscellaneous tasks requested by you that aren’t a part of our regular services

Learn more

If there is anything else related to your trip that you’d like assistance with, let us know! If we agree to take on the projeect, these tasks will be $100 per hour and bille din 15-minute increments.

Not seeing the trip planning service you were hoping to find? Send us an email at trips@kaileyandwill.com and let us know what you’re looking for. We will see if we can help!

Ready to have the trip of your dreams? Let’s get started.

Fill out the free inquiry below and we will be in touch soon!

FREE INQUIRY

Let us take the stress out of trip planning for you.

Have you ever run into any of these issues when planning a trip?

Trip Planning & Itinerary Packages

See/Eat/Do

$130+

See/Eat/Do/Stay

$200+

National Parks Trip

$130+

Full Planning

$450+

Individual Services & Extras

Trip Planning Workbook

$47

Lodging Recommendations

$25/place

Destination Recommendations

$100+

30-Minute Consultation Call

$50

Miscellaneous

$100/hour

Ready to have the trip of your dreams? Let’s get started.

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