Begin With Discovery
We learn how you usually travel, what you want to preserve, and where this trip should take a new direction.
About We Book Travel
Travel Planning That Starts With You
Thoughtful advice. Honest guidance. A trip built around how you want to travel.
We do not begin with a promotion or a predetermined itinerary. We begin with a conversation about what would make your trip feel meaningful, comfortable, and unmistakably yours.
More Than a Booking Service
We Book Travel was founded in 2017 to give travelers something increasingly difficult to find: personal guidance from an advisor who takes the time to understand the trip behind the booking.
Since then, we have helped clients plan thousands of vacations across ocean and river cruises, guided tours, resorts, and customized journeys.
Our role is not to tell you what you should want. It is to ask better questions, explain the real tradeoffs, and help you shape a trip that fits your priorities, pace, budget, and definition of success.
Our Philosophy
Good travel planning is not about finding the most options. It is about identifying the right options and understanding why they fit.
Recommend for Fit
We compare the experience, inclusions, pace, and tradeoffs so each recommendation has a reason behind it.
Stay With You
You work directly with an advisor who knows your plans and remains available before, during, and after your trip.
A Planning Process Built Around Real Conversation
01
Discover
We explore your travel history, interests, priorities, pace, and what absolutely cannot go wrong.
02
Compare
We show what your ideal experience requires and what can be achieved within the budget you have allocated.
03
Refine
Together, we adjust the details until the trip reflects the right balance of comfort, activity, independence, and value.
04
Support
We organize the moving parts, prepare you for travel, and remain a real point of contact throughout the journey.
What We Help You Plan
Different travel styles create different experiences. Our job is to help you choose the one that best matches this trip.
Meet Your Travel Advisors
Experience matters, but so does fit. Learn more about the people who will help shape your journey.
Owner & Travel Advisor
Jesse Morris
Jesse brings firsthand cruise and destination experience, thousands of planned vacations, and a belief that informed guidance should make complex choices feel clear.
Meet Jesse → Travel Advisor
Jimmy Maass
Jimmy plans family, group, luxury, and solo travel with a personal approach that keeps clients connected to a real advisor from the first conversation onward.
Meet Jimmy → Personal Recommendations
Built around your priorities, not a generic ranking.
Firsthand Perspective
Real travel experience helps turn marketing claims into useful context.
Honest Comparison
We explain the tradeoffs so you can make an informed decision.
Questions Before We Begin?
A few quick answers about working with We Book Travel.
Do I need to live in Virginia to work with you?
No. We work with travelers throughout the United States and Canada by phone, email, and online appointments via Zoom.
Do you charge a planning fee?
In most cases, there is no planning fee. Certain trips may involve unique circumstances that require one. If that applies to your plans, we will explain the fee in full and receive your approval before any work begins.
Can you help if I already have a cruise line, tour, or resort in mind?
Absolutely. Bring us what you have found and we can help evaluate whether it fits the experience you want.
Can you help me if I have already booked my trip?
In some cases, yes. Depending on how your trip was booked and how long ago the reservation was made, it may still be eligible for transfer to our agency so we can help manage it. A short call or email will help us determine whether a transfer is possible and guide you through the process.
What happens after I contact you?
We begin with a conversation about your plans and priorities, then agree on the best next step for research and recommendations.
Ready to Start the Conversation?
Tell us what you are considering. We will help you decide what comes next.
Schedule Online via Zoom
Choose a time that works and we will save it on the calendar.
Schedule now →About We Book Travel, LLC: Your Experts in Travel
Meet
Our Team
.
Meet Jesse Morris
Travel has always been more than a hobby for me. It is a passion that has allowed me to experience different cultures, meet incredible people, and gain a deeper appreciation for the world around us.
As the owner of We Book Travel LLC, I have helped clients plan more than 3,000 vacations since founding the agency in 2017. My focus is helping travelers create memorable experiences through premium, upper-premium, and luxury travel experiences including ocean cruises, river cruises, all-inclusive resorts, guided tours, and custom itineraries.
What makes my approach different is that I believe recommendations should come from real-world experience whenever possible. I have personally traveled on more than 90 cruises and have visited destinations throughout North America, Europe, the Caribbean, French Polynesia, and beyond. These experiences allow me to provide practical advice and first-hand insights that go beyond what can be found in a brochure or online review.
In addition to serving clients, I remain actively involved in the travel industry through education and leadership roles. I am a Certified Travel Industry Executive (CTIE), a Featured Educator for The Travel Institute, a presenter at CruiseWorld, and serve on the Advisory Board for Global Travel Marketplace. I am also a Brand Ambassador for Travel Professional NEWS.
Whether you are planning a luxury cruise, a river cruise through Europe, a guided tour, a family vacation, or a once-in-a-lifetime bucket-list adventure, my goal is to help simplify the planning process while ensuring every detail is carefully considered.
I believe travel is one of the most valuable investments we can make in ourselves and the people we care about. The memories created often last far longer than the trip itself, and I consider it a privilege to help clients create those memories every day.
Jimmy Maass is your dedicated Travel Advisor specializing in family, luxury, and solo travel. He is an expert in crafting memorable group vacations, including trips for extended families, friends, and those who share a common interest. With expertise across land packages, private guided tours, ocean cruising, and intimate river cruising, Jimmy meticulously crafts personalized vacations for almost any budget. His mission is to deliver an extremely positive experience backed by genuine, one-on-one customer service. You will always connect with him directly via text, phone, or email, guaranteeing that the person you call is familiar with you and your travel dreams—never a call center.
Meet Jimmy Maass
Jimmy Bio
Connect
With Us!
Using
a Travel Advisor
Check out the information below to learn more about our services, and give us a call today to begin planning your trip!