★★★★★
“He took the time to understand our travel preferences and budget and created an itinerary that was beyond our expectations.”
Sue T.
Google Review
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Meet Your Travel Advisor
Meet Jimmy Maass
Clear answers, responsive support, and thoughtful planning for trips that matter.
Jimmy helps clients make informed choices, get meaningful value from their budget, and travel with confidence from the first conversation through the journey home.
Jimmy Maass
Travel Advisor
The Details Matter Because the Trip Matters
Jimmy understands that a vacation can represent years of planning, saving, and anticipation. Whether the trip is a family getaway or a once-in-a-lifetime journey, he believes every client deserves the same level of attention.
He joined We Book Travel in May 2021 after a career centered on safety, risk management, and public outreach. That background shaped the way he works today: ask careful questions, explain the reasoning behind a recommendation, set clear expectations, and remain accountable.
Most importantly, Jimmy wants clients to feel that they have one responsive person who knows their plans and is prepared to help.
My job is to help you get the most value from your budget while creating a trip you will always remember.Jimmy Maass
Since 2021
Planning travel professionally
11 Countries
Visited firsthand
U.S. & Canada
Serving travelers remotely
Built on Trust
Most clients arrive through personal referrals
What Clients Say About Working With Jimmy
Real experiences from travelers who planned their journeys with Jimmy.
★★★★★
“Jimmy Maas made a dream vacation for my husband and I to Venice. Actually we didn’t imagine how perfect it was.”
Melissa D.
Google Review
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★★★★★
“Spends time when setting up trip, answered our many questions, checks in before the trip, follows up after the trip.”
E.L.
Google Review
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Trips Jimmy Helps Plan
Jimmy works across a wide range of travel styles, then narrows the choices according to the people taking the trip.
Cruises
Ocean and river options matched to the right ship, itinerary, activity level, and onboard atmosphere.
All-Inclusive Resorts
Resort experiences selected for service, dining, setting, room needs, and the way you want to spend your days.
Family & Multi-Generational
Trips designed around different ages, interests, schedules, and the shared moments everyone wants to remember.
Private Guided Travel
Personalized journeys shaped around access, pacing, local insight, and experiences designed for the people taking the trip.
Luxury Travel
Thoughtful choices centered on comfort, attentive service, meaningful experiences, and the details that elevate a journey.
Groups & Celebrations
Coordinated travel for friends, families, and shared occasions without losing sight of each traveler’s needs.
What Working With Jimmy Feels Like
Past travel behavior informs the conversation, but every trip is allowed to become something new.
A future Rhine or Danube journey is high on Jimmy’s own list.
01
He Asks First
Jimmy learns what matters, how you normally travel, what should feel different this time, and what cannot go wrong.
02
He Explains the Why
Recommendations come with context. Jimmy wants you to understand why an option fits and where the tradeoffs sit.
03
He Respects the Budget
Jimmy treats every vacation as a meaningful investment and looks for the strongest experience the available budget can realistically support.
04
He Remains Accessible
Clients can communicate by phone, text, or email and receive a clear response, even when more time is needed to research the answer.
05
He Takes Accountability
If something does not unfold as expected, Jimmy communicates honestly and works to identify the best available solution.
Professional Training & Industry Involvement
Ongoing supplier education gives Jimmy more context for comparing products, inclusions, and the client experience.
Industry Involvement
Jimmy has participated in industry programs that bring advisors closer to the trends and decisions shaping travel.
- CruiseWorld STAR Program participant, twice
- CruiseWorld Advisory Board
Selected Supplier Training
- Royal Caribbean Master of Adventure
- Norwegian Cruise Line Ph.D.
- AmaWaterways Certified Advisor
- Holland America Platinum Advisor
- Princess Commodore
- Virgin Voyages Gold Tier
- ALG Vacations ALGVPro
- Disney College of Knowledge graduate
Training helps Jimmy evaluate the experience more thoughtfully. It does not make every supplier the right choice for every traveler. The recommendation still begins with fit.
A Few Things About Jimmy
The person behind the planning has his own travel favorites, family priorities, and long-term wish list.
Favorite Destinations
The Caribbean and Europe
Favorite Vacation
A cruise
Favorite Ship
Icon of the Seas
Dream Journey
A Rhine or Danube river cruise
Bucket List
China and Japan
Before Travel
Jimmy worked in utility inspection, insurance risk management and outreach, and safety coordination in semiconductor manufacturing. He also served as a volunteer firefighter in his hometown for 16 years.
At Home
Jimmy is the father of two boys and spends much of his free time supporting their soccer and band activities. He also enjoys what he jokingly calls “ragebaiting” his dog.
A Favorite Memory
On his oldest son’s first Walt Disney World trip at age four, Jimmy watched him dance with Belle from Beauty and the Beast. It remains one of his most meaningful travel memories.
Questions About Working With Jimmy?
A few quick answers before the conversation begins.
What kinds of trips does Jimmy plan?
Jimmy plans cruises, all-inclusive resorts, family and multi-generational vacations, groups and celebrations, luxury travel, and private guided journeys. The first conversation determines which travel style best fits your priorities.
Will Jimmy help me work within a specific budget?
Yes. Jimmy will explain what the ideal version of the trip requires, what can realistically be accomplished within your budget, and where adjustments may create the strongest overall experience.
How can I communicate with Jimmy?
Clients can communicate by phone, text, or email. Jimmy is diligent about responding, even when the immediate answer is that he needs additional time to research the question.
Does Jimmy only recommend the cruise lines and resorts he personally prefers?
No. Personal experience adds useful context, but the recommendation is based on your trip. Jimmy compares the experience, inclusions, pacing, service, and tradeoffs before suggesting a direction.
Do I need to live in Virginia to work with Jimmy?
No. We Book Travel works with travelers throughout the United States and Canada by phone, email, text, and online appointments via Zoom.
Ready to Start a Conversation With Jimmy?
Share what you are considering and what would make the trip feel successful. Jimmy will help you identify the right next step.
Schedule Online via Zoom
Choose a time that works and we will save it on the calendar.
Schedule now →