How to Successfully Book a Mystery Trip

Dreaming BIG

This fall, I embarked on a two-week long “surprise journey” to Europe with Jubel. (read more about that not-so-positive experience here).

I wanted to explore some European beauty products and treatments, and a mystery tour where I could organically uncover them (instead of planning every detail months in advance) was just the ticket. Plus, I love surprises! This new type of holiday is gaining popularity rapidly, and companies like Jubel (global), Pack Up + Go (3-day weekends in the continental U.S), and Magical Mystery Tours (also global) are there to help you along the way. Why so popular you ask? People just love the idea of showing up at the airport with little more than a passport and just flying somewhere spontaneously, and this allows you to do it with a helping hand. Also, it can be super simple and stress-free to let someone handle all the details when done correctly (and with my tips below!). And did I mention the crazy-cool Instastories you can share? 

I can be quite a control freak when traveling (I have to get the perfect flight, on the perfect date and time, all for the lowest price possible. Talk about a challenge!), and having (and paying) someone at Jubel plan this for us was WAY out of my comfort zone, but totally possible to overcome! With that, I wanted to write some very important tips for you in case you are thinking of taking a surprise holiday of your own...


Planning for the Un-planner

Since your travel company is choosing your destination(s) for you, you'll still want to ask your travel agent to pre-plan your top 1-2 must-see things for you. The last thing you want is to land and realize that you should have booked tickets to the Blue Lagoon weeks ago and that it is totally sold out! 

If you have NO IDEA where in the world/U.S. you are going: Tell your TA (travel agent) the type of things you like to do or see. For example, my guilty pleasure is going for a massage and pedicure at the best local spa in town. They can book those appointments for you, or at least have a list of a few top choices for you to check out on your own to save precious vacation time. 

If you have some idea of where you are going: Give your TA a list of the top 2 things you must do or see for every single possible location they could be sending you. I know, I know -  this sounds like a heck of a lot of work (we gave Jubel a list of twelve possible destinations!) - but it will be soooo worth it and save a ton of potential heartbreak down the road if you miss out. Plus since you're not booking your own trip, you now have time to do it! 


Your Destination(s)

What a “destination” is to you may not be a “destination” to your tour company, especially if you’re embarking on a trip to takes you to more than one place. Be very clear about your destination expectations! Ask exactly what that means to them (I found out after we confirmed and paid with Jubel that a destination to them can be a town, state, or country... very different things! If you are going to two different destinations, do they mean two different cities (Los Angeles and San Diego?) or to two different areas (Upstate New York and Manhattan?) or two completely different countries (Iceland and France)? This will make a big difference in transportation fees, and your expectations. 



Ask your TA for a few menus of various local restaurants. They can blur out the name and other identifying details, of course. This will help you plan if you have any gluten or food allergies. It also allow you to plan for how much money you’ll want to bring - when we arrived in Iceland, I was completely floored at how expensive everything was, and I live in Manhattan! 


Tours and Excursions

Be sure to ask your TA what type of tours and excursions are available (meaning private vs. group) and which they’ll be booking or reserving for you (if any) - AND the individual price breakdown of each. The price quote for a single private tour in Iceland was nearly $2,000 US for three people and we weren't offered any cheaper group options! The difference can be hundreds (or thousands) of dollars, so please ask as many questions as you can first. Remember, it's your trip, your memories, and your money.



In different parts of the world, budget, mid-range, and luxe hotels all mean very different things in regards not only to hotel room size but most importantly, the price. A “luxe” hotel in Bangkok could easily be half of the price of a “budget" hotel in New York City. When talking accommodations with your TA, give them a price range or specific black-and-white specs (like "no stairs" or “no shared bathroom”!) instead of a hotel category. It’ll help both of you to stay on the same page - and prevent you from spending way more money on accommodations that you otherwise would have! 


Itemized Pricing List

This could be the most important tip of all: Get a detailed, itemized price list before making any payments. You’ll want to be sure how much of your budget is being spent where (hotels, transfers, etc) and where to adjust if need be. And remember - there is no such thing as a silly question! :)

And lastly - take tons of pics and tell me if my tips helped you! Comment below and tag me in your Instas so I can follow your mystery journeys. Thanks for reading!