Surprise Trips
A perfectly planned adventure with the destination revealed only when it’s time to go.
You love the idea of traveling… but not the decision fatigue. Surprise Trips are for travelers who want the thrill of the unknown without sacrificing comfort, style, or trust.
Surprise Trips can be booked for yourself, a partner, or as a gift for someone else.
No pressure. No obligation. Just clarity.
Friends
Family
Solo Adventurers
This is For You If You ...
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Want to be surprised but not stressed
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Trust expert planning and thoughtful details
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Love the idea of adventure without endless decisions
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Want a unique experience you’ll never forget
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Are open to new places within your comfort zone
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Want to feel excited instead of overwhelmed
Probably Not the Best Fit If You ...
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Need to control every detail of your trip
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Feel anxious without knowing the destination far in advance
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Are looking for ultra last-minute planning (under 2 weeks)
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Prefer heavily structured tours or guided groups
Adventurous
Comfort-Focused
Somewhere in Between
Surprise Doesn't Mean Random
Every trip is carefully designed around:
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Your travel style (relaxed, adventurous, or balanced)
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Your comfort level & boundaries
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Your budget
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Your timeline & flexibility
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Any “hard no’s” (climate, activities, flight length, etc.)
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All included in your pre-trip survey
You’ll never be sent somewhere that doesn’t align with your preferences.
What You’ll Know Going In (and What You Won’t)
You’ll know:
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Trip length
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Budget range
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General climate & packing guidance
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Activity level
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What kind of trip it is (city, outdoors, international, etc.)
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Transportation dates/ type (flying, driving, etc)
You won’t know:
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The destination
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Specific accommodations (you'll know the accommodation type)
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Daily itinerary details (activities, restaurant reservations)
✨Until its time✨
What to Expect
3. The Reveal (Adventure Time!)
Built by Outdoor Professionals!
After you request to book, you’ll complete a short (10–15 minute) questionnaire covering your travel style, preferences, comfort level, budget, and any non-negotiables.
This step is especially important for Surprise Trips. It ensures the experience feels exciting, not stressful.
1. Tell Us About Your Dream Trip
Questions before you go? Need reassurance along the way? We’re here. You’ll have access to email, text, and call support so you feel confident, prepared, and taken care of from start to finish.
4. Ongoing Support
About one to two weeks before departure, you’ll receive a pre-trip PDF with:
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Travel dates
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Airport & departure times
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Climate info
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Packing list
On the day of departure, the full surprise is revealed. You’ll receive a beautifully designed, downloadable itinerary with everything you need: lodging details, activities, maps, restaurant reservations, and a mini guide to read on the plane or in the car.
We’ll meet for a 30–40 minute virtual call to walk through your survey, align on expectations, and answer any lingering questions.
This conversation helps us fine-tune the trip’s vibe, pace, and boundaries so the surprise feels thoughtful and intentional.
2. Let’s Chat
Surprise doesn’t mean unprepared. You’ll always have what you need, when you need it.
What's Included in Every Surprise Trip
Before Departure, You Will Receive
On the Day of Deparure, You will Recieve
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Day-by-day itinerary (broken into morning, afternoon, and evening)
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Lodging arrangements
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Transportation coordination (flights, rental cars, public transportation etc)
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At least 1 pre-booked activity with a list of activity recommendations
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Local restaurant guide and one dinner reservation
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Google Maps with your trip details + offline use instructions
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GPX files for hikes, bike routes, and other out-of-service adventures (if applicable)
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Access to our traveler support team during your trip (call, text, or email).
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Travel Dates (you are in control of these)
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Airport & departure times OR Day 1 drive time (if it's a road trip or nearby adventure)
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Climate Info
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Packing List
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A hint for where you are going
Roam Ready Itinerary Cover Page
Roam Ready Itinerary Table of Contents
Roam Ready Itinerary back page
Roam Ready Itinerary Cover Page
Roam Ready Transportation Bookings
Roam Ready Accommodation Bookings
Roam Ready Activity and Restaurant Bookings
Roam Ready Transportation Bookings
Pricing & Investment
Surprise Trips are designed entirely around your budget. You tell us what you’re comfortable spending, and we plan the best possible trip within that range. No pressure to stretch beyond it.
How Pricing Works
You provide a total trip budget, whatever you are comfortable with.
Our planning fee is 15% of that budget, with a minimum planning fee of $150.
Our goal is never to “use up” your budget. It’s to create the best possible experience within it. If there’s room left, we’ll use it intentionally (experiences, reservations, gift cards) or discuss options with you.
Example Fee Pricing
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$2,000 trip budget → $300 planning fee → $1700 for flights, lodging, activities, and experiences
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$4,000 trip budget → $600 planning fee → $3400 for flights, lodging, activities, and experiences
When Do I Pay?
After your consultation, we’ll confirm the total budget and exact planning fee. Planning begins once payment is received. No surprises there.
Your Budget Includes:
Full Trip Design, Logistics, and Itinerary Creation
Transportation Coordination and Bookings
Accommodation & Activity Bookings
Our Custom Planning Fee
Support Before and During Your Trip
Dining & Experience Reservations
(For 2 people)
Budgets will vary based on dates, location, and traveler count
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Travelers who live close to big airports will have cheaper flight options
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Some travel locations are more expensive during peak seasons
If you’re unsure where you fall, that’s okay! We can help guide you in our 40 min consultation call or our 15-minute call.
You’re never locked into a budget until after our consultation call.
