Luxury Travel Advisor | Italy & Cruises

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Jennifer Schaller, Travel Agent in Wheeling, IL

Jennifer Schaller

Wheeling, IL Travel Agent

Jennifer Schaller

Wheeling, IL · 25+ Years of Experience

An independent agent with Travel Leaders Wheeling, IL
5.0
(71)
100% Recommended
Jennifer has been exceptional to work with - she responds very quickly and investigates and makes recommendations for vacation destinations. When we travel, Jennifer always... Read More >
About
Reviews
Certificates & Awards
Travel Stories & Media

Areas of expertise

Destinations:

Italy, Tuscany, Greece, Hawaii, Mexico

Interests:

Luxury, Luxury Cruises, Luxury Hotels, Premier Concierge Services, River Cruises

Suppliers:

Silversea, AmaWaterways, Four Seasons, Auberge Resorts Collection, Aman Resorts

About Me

Tuscan Sun & Vineyards
Tuscan Sun & Vineyards

Meet Jennifer

I’ve spent over three decades in the travel industry, but my passion for luxury experiences began much earlier. Inspired by my aunt, who taught me to savor great food, appreciate beautiful hotels, and embrace the art of travel, I’ve built a career helping others experience the best the world has to offer.

I entered the travel industry in 1991, spending 20 years helping to run a corporate agency before launching Tru Travel. I realized something was missing: genuine care, the kind that makes clients feel truly seen. Luxury leisure travel should be effortless, relaxing, and deeply personal, and that’s exactly what I provide to every client I work with.

Exclusive, personalized experiences

My specialties are luxury cruises and custom Italian itineraries. From a private sunrise Vatican tour with the master key, to a private sail along the Amalfi coast, I help clients uncover the kinds of moments that don’t come with a booking engine. Whether you’re drawn to the intimacy of a Silversea cruise or the rich flavors and rolling vineyards of Tuscany, I’ll design something that feels like it was meant just for you.

By booking with a travel advisor for your dream Italy vacation or luxury cruise, you can expect personalized service, insider perks, and genuine care. I want you to feel the magic of every moment, because travel isn’t just about the destination, it’s about how you feel when you arrive, and the memories you carry long after you return.

The Experience

Working with me begins with a conversation. As a luxury Italy travel advisor and certified luxury cruise specialist, I take the time to understand what inspires you, whether that’s savoring world-class wines, embarking on active excursions, immersing yourself in culture, or simply relaxing at the world’s most luxury resorts. We’ll explore your preferences, priorities, and travel dreams, and I’ll design a journey that is effortlessly luxurious and entirely tailored to you.

Throughout the planning process, I oversee every detail: early check-ins, late checkouts, room upgrades, resort credits, VIP airport assistance, and exclusive dining experiences. I personally coordinate with hotels and cruise partners to ensure you’re treated like a true VIP, recognized, remembered, and genuinely cared for.

Where Luxury Meets La Dolce Vita

Luxury Cruise & Italy Travel Advisor

There’s something magical about being at sea, the gentle rhythm, ever-changing views, and the thrill of waking up somewhere new each day. My passion for luxury cruises began with a Silversea voyage, and I’ve been captivated ever since. I craft personalized sailings with Regent Seven Seas, Explora, Silversea, Seabourn, and private yachts, offering insider access, exclusive perks, and concierge-level service.

Italy is personal to me, inspired by my partner’s Tuscan roots, and I design journeys filled with authentic culture, local cuisine, hidden gems, and effortless elegance. From ocean voyages to Italian escapes, I create luxury travel experiences that are seamless, memorable, and entirely tailored to you.

REVIEWS

Rating: 5.0
71 reviews
100% Recommended
Your trust is our priority. Every review is submitted by verified travelers after they have booked and completed their trips. Learn more about our review guidelines.
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Showing 71 reviews

Honeymoon!
Reviewed By Allie - Barrington, IL | Traveled to Costa Rica ~ Central America
Jennifer has been exceptional to work with - she responds very quickly and investigates and makes recommendations for vacation destinations. When we travel, Jennifer always checks in with us to make sure all is well and if we've had any issues (which adds a nice extra touch). She makes planning our vacations a lot easier because she will literally plan all our activities for us and just let us know when and where to go. Being both very busy, two working parents, when it comes to travel she is my go-to!
I would recommend this agent to my family and friends.
32 of 47 people found this review helpful. Was this review helpful to you?YES|NO
Consistency
Reviewed By Steve - New York City | Traveled to Dallas/Ft. Worth ~ Texas ~ USA
I work with Jenn for both business and personal travel. She's attentive, creative, enthusiastic, and timely. A pleasure frankly. And she gets the service quotient.
I would recommend this agent to my family and friends.
34 of 52 people found this review helpful. Was this review helpful to you?YES|NO
What a fantastic vacation!
Reviewed By Matt - San Antonio, TX | Traveled to Mexico
Jennifer has been terrific to work with. I truly appreciate her providing a variety of options and also her own opinion on properties. It’s comforting to know a professional has seen or collected reviews before making a decision. The prices are great as well. I will continue to book our family vacations with Jennifer in the future.
I would recommend this agent to my family and friends.
31 of 50 people found this review helpful. Was this review helpful to you?YES|NO
My "go to" travel partner!
Reviewed By Kristine Adams - Valparaiso, IN | Traveled to Cabo San Lucas ~ Baja California Sur ~ Mexico
Jennifer is always accessible, on top of things, and willing to go the extra mile for her clients! Luckily we don't have many issues when we travel but when/if we do, she's on it immediately, providing whatever resolution she can. I book all of my trips with her and she's come through every time!
I would recommend this agent to my family and friends.
24 of 37 people found this review helpful. Was this review helpful to you?YES|NO
Honeymoon trip. Jennifer made amazing !
Reviewed By Wedding and Honeymoon National by Jennifer! - San Antonio, Texas | Traveled to Aruba ~ Caribbean
Very pleasant and fun! Excited for our trip and has lots of traveling experience of her own. Was able to recommend events and places to stay and see since she is well traveled.
I would recommend this agent to my family and friends.
27 of 44 people found this review helpful. Was this review helpful to you?YES|NO

Certifications & Awards

The Book with Confidence logo tells you that this Travel Advisor has direct access to comprehensive resources for safe and healthy travel, available at their discretion for sharing with clients.  This includes vetting the details on the health and safety protocols implemented by each travel provider in order to recommend the ideal itinerary for each client’s unique needs.
WBENC

My Travel Stories

Montage Kapalua Bay

Family Time at Montage Kapalua Bay-Maui

An amazing trip to a beautiful resort in Hawaii at the Montage Kapalua Bay in Maui. Spending time with family enjoying the views, food, and experiences such as zip line, sunset cruise, water sports creates beautiful memories that last a lifetime....
Read more