FREQUENTLY
ASKED
QUESTIONS

In a nutshell, just $99 per travel day planned. Your custom trip is planned on your custom budget. Get links to individual items with individual pricing, so you choose where to spend your vacation dollars​. Pay for only what you want planned. 1 planned day =12 hours of detailed planning by Jess for $99. Jess recommends at least 50% of your travel days to be planned by her with a minimum 3 days planned. "Days planned" can be full days or half days. Think the day you arrive and day you depart as half days. "Free days" are exactly that.....free! Think of these as your resort day, beach day, or day you wander aimlessly. Jess's formula for the perfect combo of excitement and relaxation= 75% days planned by her + 25% free days. Also offered is a lower cost Old School Travel Agent plan for a $199 flat fee. With this choice Jess will provide you with some options of pre-designed packages you could purchase. Remember those old brochures at a Travel Agency office? Yeah, those. Still great, just not custom. If you're ready to rock, click here to pay.

Because Google can’t read your mind. Sure, you could spend 20 hours researching and still end up booking the same tourist trap five million influencers already posted about. At Jess.Travel, we offer custom travel planning that’s based on you — your preferences, your budget, your vibe. You’re not paying for a middleman. You’re paying for someone who’s done the research, skipped the fluff, and built a stress-free, tailor-made itinerary you’ll actually enjoy. And yes, that includes restaurant reservations, transfers, and excursions.

Traditional travel agents work on commission. That means they usually book you with suppliers they have deals with; whether or not those options are actually the best for you. Jess.Travel is a paid, flat-rate travel planning service that doesn’t depend on kickbacks. We’ll book whatever fits you best, whether that’s a boutique hotel, a private boat tour, or a weird roadside museum no one talks about. It’s personal, not packaged.

Jess.Travel was founded by me, Jess Dorsey, a certified Nurse Anesthetist (CRNA), mother, and natural organizer who started booking custom travel experiences for friends and family before turning it into a business.

Travel agents often work for free and have connections and partnerships with various hotels, tours, and cruises. You'll have to work with those they work with, and their motivation is to make the most money they can off of your trip. Jess charges by the day, and will happily book anything for you regardless of if there's a kickback.

We work with busy professionals, families, honeymooners, burnt-out moms, unconventional couples, big groups, and people who just want someone else to do the damn planning. Most of our clients are travelers who want more than a copy-paste itinerary, they want something built around how they actually live and travel. If you value smart structure with room for spontaneity, you're in the right place.

I used to accept just a small deposit, but too many people took advantage and ran away with my itineraries without making the final payment. Now (and you can blame them for it) I require full payment to start.

You probably could find a bunch of it online—but you'd have to sift through outdated blogs, fake reviews, and sponsored lists that all say the same five things. What we offer is context. We know what’s worth your time, how long to spend in each place, when to go, and how to structure your trip around who you are. It's curated, not copied and pasted.

Fill out the Free Inquiry form and speak with me. After that, I'll shoot you an invoice.

Trip planning and booking, soup to nuts. Destination Research. Lodging suggestions and booking. Restaurant suggestions and reserving. Excursion suggestions and booking. Transportation suggestions and booking. Itinerary creation and delivery via PDF and app.

Yes! Each trip is completely tailored to you and your travel companion's needs/wants. We consider your tastes, preferences, dietary restrictions and more. It's as personal as it gets.

Got decision fatigue? Opt to add a Jess Pitch Meeting, where I pitch 3 great overall itinerary choices (can be similar or different locations), and a phone call to collaborate....for just $198 additional. But when we speak in our initial Free Inquiry, I'll throw out some opinions that might just solve it right then and there.

Absolutely! We'll be in constant contact, making sure everything is to your liking.

You will be notified as soon as Jess is informed of the change, and refunded by that company. If you like, Jess will attempt to make other arrangements for you. However, Jess is not responsible for any cancelations by hotels, airlines, tour excursions etc.. It's pretty understandable; Jess books these things for you, she doesn't run their companies. More info here in our terms and conditions. We always recommend purchasing insurance. If you want a 24/7 concierge while you're traveling, let us know. We offer it as an add-on if it's available.

We can and we do. It’s part of our early intake process. You tell us what matters—whether it's needing step-free accommodations, avoiding sensory-heavy environments, or finding gluten-free food that doesn’t suck—and we plan accordingly. I even had a gluten free donut once that was solid.

Certainly, just disclose them during the initial consultation to make sure they get worked in.

That's fine. Just tell us which days you want planned. We'll work within your parameters.

We're on your timetable. You'll set the date for delivery, and Jess will hit it, exactly.

Yes. Romantic or raunchy. Who am I to judge?

Yes. Jess can organize business air bookings for a fee, as well as hotels, cruises, transfers, and excursions. Got an eccentric boss? Outsource the workload to Jess.

Yes. As a licensed agent, I can score you some solid hotel deals, but if Airbnb or VRBO makes more sense, we can recommend them to you.

Yes—repeat and referral clients make up most of our business. We don’t run a massive ad campaign because we don’t need to. People come back when they realize how stress-free the planning process can be when someone actually listens to what they want.

We will do a flight consultation, but normally you the customer will book your own flights. I rarely book flights, but when I do there's an additional fee of $25 per person. Normally, you start the process with me as soon as you're committed to flights.

Yes! Come sail away with me! Well, not me, you, but you get it.

All of them as far as I know. If you want to go to North Korea, then maybe not. I like a challenge though.

Yes. The trip will be on your app, but the itinerary can and should be printed just in case.

Yes, but it depends on the service level you choose. We’re not a 24/7 concierge (unless you add that on), but we are available if something goes sideways. If your tour cancels or your transfer ghosted you, we’ll help you pivot. Plus, your entire trip plan is delivered as a mobile-friendly itinerary and printable PDF, with direct links to bookings and contact info. Think of it like having a travel brain in your pocket without having to text us every five minutes. Unless you want to, in which case... let’s talk concierge upgrade.

Yes. Head here or email jess@jess.travel and tell me how many days you'd like to purchase. We'll send you a gift card.

Maybe. Maybe not. Maybe go pitch yourself.

Yes. We are a travel host agency as well. If you'd like to explore a high-paying, side-hustle opportunity, head here for more info.