“The Nashville Itinerary was a lifesaver! Every detail was planned out - from the best brunch spots and daytime activities we never would’ve found on our own to where to go out on Broadway - it made the trip seamless and stressfree. We got to enjoy everything the city has to offer without worrying about the planning. We will definitely book with The Itinerary Issue again!” - Crystal
“Our Jersey Shore girls’ trip for LDW was unforgettable thanks to The Itinerary Issue. They gave us the perfect mix of beach time, fun restaurants and nightlife options. We could just show up, relax and enjoy the long weekend without having to do all the planning ourselves.” - Alizendie
“This Newport weekend gave us the most special mother-daughter getaway. From the mansion tours to the best little cafes, everything was thoughtfully planned just for us. We truly make memories that we’ll treasure forever” - Laura
“We booked a weekend in Sleepy Hollow and the itinerary made the whole experience perfect. It included all the must see spooky sights, plus some exciting hidden gems. It turned a short trip into something so memorable. Without The Itinerary Issue, we never could have planned a trip like this” - Elise
Please reach us at danielleoconnor10@gmail.com if you cannot find an answer to your question.
At The Itinerary Issue, we take the stress and second-guessing out of trip planning. Instead of spending hours scrolling TikToks and review sites trying to piece together a plan, we give you a curated itinerary that’s tailored to your style, budget and must-sees. We focus on the little details - like timing, flow and hidden gems - so your trip feels seamless instead of overwhelming.
Unlike doing it on your own, our itineraries save you time, keep you from missing out on local favorites and make your trip more organized and enjoyable.
Our process is simple and stress-free! We will have you fill out a short questionnaire on our website about your travel style, interests and must-have group preferences. From there, we create a personalized itinerary that covers everything from dining and activities to timing and local tips, designed to flow seamlessly from start to finish. You’ll receive your full itinerary digitally, with all the details laid out so all you have to do is pack your bags and enjoy the trip.
We recommend reaching out at least 2 weeks before your trip so we have plenty of time to carefully curate and perfect your itinerary. The more notice you can give us, the better - we love being able to dive deep into research, snag hidden gems and ensure everything flows seamlessly.
For last-minute requests, we’ll always do our best to accommodate, but advance planning helps us deliver the most thoughtful, stress-free experience possible.
Depending on the length of your trip, our typical turn-around time is usually between 1-2 weeks!
- Fully personalized & detailed Day-by-Day Plan - all the key moments mapped out
- Restaurant & Bar Recommendations - from local favorites to hidden gems
- Shopping & Boutique Finds
- Day Time Activities & Experiences
- Outfit Inspiration - Style Ideas and Outfit Links for your planned activities and nights out
- Insider Tips & Tricks - shortcuts, must-knows and additional information
- Extra Travel Resources - location links and helpful contacts
- Seamless Trip Flow - thoughtful planning so your days feel balanced and perfectly fit what you’re looking for
- Additional locations if the ones provided are not to your liking
We plan every type of trip including your typical getaway weekend, bachelorette/bachelor trips, birthday trips, romantic getaways and everything in between!
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