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FREQUENTLY
ASKED
QUESTIONS
TLDR: Jess.Travel is a paid, personalized travel planning service that builds custom itineraries for families, couples, solo travelers, and groups. We charge $99 per travel day for personalized trip planning. We may earn supplier commissions on certain bookings, but those commissions never determine what we recommend. Our recommendations are based on what fits your trip, budget, and preferences best. Whether you need help planning a honeymoon, group vacation, family trip, or business travel, we handle the details so you don’t have to. You’ll get a fully researched and bookable plan delivered via app and PDF — structured, flexible, and made just for you.
Why should I pay for a travel planner instead of booking everything myself?
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.
How is Jess.Travel different from traditional travel agents or tour companies?
Many traditional travel agencies rely primarily on supplier commissions. Jess.Travel uses a fee-based planning model, so we’re paid for the work of researching and designing your trip regardless of which suppliers make the most sense. We may earn a commission when an appropriate supplier offers one, but that never determines what we recommend.
Who is behind Jess.Travel?
Are you feeling relaxed? Maybe that’s the anesthesia, or maybe it’s me, Jess. I’m a mild-mannered (CRNA) anesthesia nurse by day, but by night I’m a travel-planning superhero fighting the cookie-cutter trips and tired tourist traps of the travel world.
Is Jess different from a regular travel agent?
Yes. Many traditional travel agents are compensated mainly through supplier commissions. Jess.Travel charges a planning fee, which means we can recommend the hotel, tour, cruise, rental, or other option that makes the most sense for your trip whether it pays us a commission or not. When an appropriate supplier does pay a commission, we may earn it, but your trip comes first.
What kinds of travelers use Jess.Travel the most?
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.
What's the upfront cost to start?
I used to accept a small deposit, but too many people took advantage and ran away with my itineraries without making the final payment. So now (and you can blame them for it) I require full payment to start.
How do I know you're not just booking the same stuff I could find on Google or Expedia?
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.
What's the first step?
Fill out the Free Inquiry form and speak with me. After that, if you're down with the Jessness, I'll shoot you an invoice.
What exactly does Jess.Travel include when planning a trip?
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.
How personalized is the travel planning service from Jess.Travel?
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.
I have a budget, a general timeframe, and a few ideas—but no clue where I actually want to go. Can you help narrow it down?
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.
Can I give input into my trip?
Absolutely! We'll be in constant contact, making sure everything is to your liking.
What if a tour or flight gets canceled?
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.
What if I'm disabled/have a large group/have kids/eldery travelers/vegan/etc.?
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.
Can Jess.Travel still help if I’ve already booked part of my trip?
Certainly, just disclose them during the initial consultation to make sure they get worked in.
What if I only need you to plan part of my trip?
That's fine. Just tell us which days you want planned. We'll work within your parameters.
When do I get the itinerary?
We're on your timetable. You'll set the date for delivery, and Jess will hit it, exactly.
Does Jess do bachelor/bachelorette parties, honeymoons, and large group travel?
Yes. Romantic or raunchy. Who am I to judge?
Does Jess.Travel plan business travel?
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.
Do you book hotels?
Yes. Hotels, villas, castles, treehouses...nuclear bunker-turned-Bnb, as a licensed agent, I can score you some solid hotel deals, but if Airbnb or VRBO makes more sense, we will recommend them to you as well.
Do you have any actual data on how many clients come back or refer others?
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.
Do you book flights?
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 per person. Normally, you start the process with me as soon as you're committed to flights.
Can you book cruises or large groups?
Yes! Come sail away with me! Well, not me, you, but you get it.
I am a Virgin Voyages specialist, but I've got the details on them all.
Can I view my trip offline?
Yes. The trip will be on your app, but the itinerary can and should be printed just in case.
Can I give the gift of Jess.Travel Planning?
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.
Are you hiring?
Maybe. Maybe not. Maybe go pitch yourself.
I want to become a travel planner, can Jess help?
Yes. We are a travel host agency as well. If you'd like to explore a high-paying, side-hustle opportunity, head below for more info.
www.jess.travel/agency
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