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Jess Custom Travel Planner FAQ


  • How much does it cost?
    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! 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.
  • Who is behind Jess.Travel?
    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.
  • What's the difference between Jess and a regular travel agent?
    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.
  • How much do I pay to start?
    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. Click here to pay.
  • What's the first step?
    Just determine your travel dates and fill out the questionairre. Pay your total via this link.
  • What's included?
    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.
  • Is it really custom?
    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.
  • Can I give input into my trip?
    Absolutely! We'll be in constant contact, making sure everything is to your liking.
  • What if I don't even know where I want to go?
    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.
  • 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.
  • What if I'm disabled/have a large group/have kids/eldery travelers/vegan/etc.?
    Just let me know. I've planned trips for large groups with all sorts of crazy logistics. That's my job.
  • If I already have some plans made is that ok?
    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.
  • Do you do bachelor/bachelorette parties/honeymoons etc?
    Yes. Romantic or raunchy. Who am I to judge?
  • Do you do business travel bookings?
    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. 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.
  • 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 of $25 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.
  • What destinations do you cover?
    All of them as far as I know. If you want to go to North Korea, then maybe not. I like a challenge though.
  • 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 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 part-time, high-paying, side-hustle opportunity, head here for more info.
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