Sidecar Winery Tours — High-End Incentive Travel

Transform top-performer recognition into unforgettable luxury winery experiences with Sidecar Winery Tours — High-End Incentive Travel. Calusa Marketing designs premium, transferable travel rewards that motivate sales teams, retain VIP customers, and celebrate exceptional performance. From week-long vineyard tours in Napa to custom dream experiences, every itinerary, booking, ticket, transfer, and guest detail is handled with white glove care.

Luxury winery tour incentive travel experience

Our Sidecar Winery Tours Services

Premium incentive travel solutions that reward performance with luxury experiences, seamless logistics, and measurable business impact.

Luxury Travel Rewards

Reward top performers with luxury winery tours, fine dining, golf, sports, or international travel experiences designed to motivate action and create lasting emotional impact.

Winery Experiences

Create premium vineyard experiences such as Napa wine tours, private tastings, curated dining, transportation, lodging, and guest coordination for exceptional incentive recipients.

Group Incentive Travel

Plan executive retreats, President’s Club trips, customer loyalty travel, and recognition events for groups ranging from small leadership teams to large audiences.

Dream Experiences

Choose from 200+ pre-packaged travel experiences starting at $500, with premium options up to $25,000 for two adults.

Sales Incentive Trips

Use aspirational travel to increase sales contest participation, reward high performers, retain valuable accounts, and make top-tier incentives feel truly exclusive.

Travel Fulfillment

Calusa Marketing handles bookings, confirmations, airline, transportation, event tickets, guest coordination, questions, and customer service from award through redemption.

Luxury winery incentive travel planning session

Our High-End Travel Reward Process

Define Goals and Reward Strategy

We begin by identifying your target audience, performance goals, budget, and desired behavior. Whether the program supports sales growth, VIP retention, or President’s Club recognition, Calusa Marketing designs the travel reward around measurable business outcomes.

Curate the Experience Options

Manage Every Travel Detail

Support Guests Through Fulfillment

Trusted By Leaders

Success Stories

Companies trust Calusa Marketing to motivate performance, increase loyalty, and simplify complex incentive fulfillment.

"Great business to partner with! I love awarding my clients for their commitment to buying thru us!"

Stephani Raabe
Stephani Raabe

"We absolutely love working with Calusa Marketing! They took a previously troublesome process of gift card fulfillment and made it "trouble free" for us and our Denver Post subscribers. The staff is very friendly and very responsive to any request. They handle all customer service issues with no further complaints..."

Steve Johansson

"My husband and I recently won a trip to Paris. We were extremely hesitant to book the entire trip with Calusa Marketing but have to say I am SO glad we did. Neither one of us truly knew what we were doing and they made our trip so amazing. They..."

Lindsay Blaylock
Lindsay Blaylock

"Great business to partner with! I love awarding my clients for their commitment to buying thru us!"

Stephani Raabe
Stephani Raabe

"We absolutely love working with Calusa Marketing! They took a previously troublesome process of gift card fulfillment and made it "trouble free" for us and our Denver Post subscribers. The staff is very friendly and very responsive to any request. They handle all customer service issues with no further complaints..."

Steve Johansson

"My husband and I recently won a trip to Paris. We were extremely hesitant to book the entire trip with Calusa Marketing but have to say I am SO glad we did. Neither one of us truly knew what we were doing and they made our trip so amazing. They..."

Lindsay Blaylock
Lindsay Blaylock

"Great business to partner with! I love awarding my clients for their commitment to buying thru us!"

Stephani Raabe
Stephani Raabe

"We absolutely love working with Calusa Marketing! They took a previously troublesome process of gift card fulfillment and made it "trouble free" for us and our Denver Post subscribers. The staff is very friendly and very responsive to any request. They handle all customer service issues with no further complaints..."

Steve Johansson

"My husband and I recently won a trip to Paris. We were extremely hesitant to book the entire trip with Calusa Marketing but have to say I am SO glad we did. Neither one of us truly knew what we were doing and they made our trip so amazing. They..."

Lindsay Blaylock
Lindsay Blaylock
The Calusa Difference

Why Choose Calusa Marketing?

Calusa Marketing turns premium travel rewards into practical, results-driven incentive programs.

White Glove

Calusa Marketing handles bookings, confirmations, travel details, and support so clients avoid operational strain.

Deep Expertise

Over 75 years combined experience shapes incentive programs that motivate performance and fit budgets.

Buying Power

Strong travel buying power helps secure memorable experiences while saving clients time and money.

Proven Trust

A 99% client retention rate reflects consistent service, accountability, and results-focused program execution.

Meet The Calusa Team

Meet the experts behind premium incentive travel fulfillment.

Portrait of Mike Giroud, President of Calusa Marketing

Mike Giroud

President

Mike Giroud serves as President of Calusa Marketing, the St. Petersburg, FL-based incentive marketing firm he has helped grow since its founding in 2015. With deep roots in loyalty and engagement program strategy, Mike provides executive leadership across all facets of the business, from platform development to client relationships. Under his direction, Calusa Marketing has grown to manage over 1,000 programs serving more than 500,000 members while maintaining a 99% client retention rate. Mike is committed to delivering results-driven incentive solutions that help clients generate leads, inspire sales teams, and improve retention — all backed by decades of combined industry experience and a culture built on integrity, accountability, and perseverance.

Portrait of Alex Philips, EVP of Sales at Calusa Marketing

Alex Philips

EVP, Sales

Alex Philips is the Executive Vice President of Sales at Calusa Marketing, where he leads the company's national sales strategy and client acquisition efforts across a broad range of industries. With extensive experience in loyalty and incentive marketing, Alex works closely with prospects and existing clients to design programs that drive measurable results — from increased customer spend to improved employee retention. He brings a consultative approach to every engagement, ensuring that each program is tailored to the client's specific goals and budget. Alex is a key driver behind Calusa Marketing's impressive growth and its reputation for delivering high-impact incentive solutions with white glove service.

Portrait of Jon Riggleman, EVP at Calusa Marketing

Jon Riggleman

EVP

Jon Riggleman serves as Executive Vice President at Calusa Marketing, playing a pivotal role in the company's strategic direction and operational excellence. With a career steeped in loyalty, engagement, and incentive program management, Jon brings a wealth of knowledge that contributes to Calusa Marketing's over 75 years of combined team experience. He works across departments to ensure that client programs are executed with precision, accountability, and measurable outcomes. Jon is deeply committed to the company's core values and is instrumental in maintaining the high standards of service that have earned Calusa Marketing a 99% client retention rate and a reputation as a trusted partner across multiple industries.

Portrait of Evan Blake, VP of Technology at Calusa Marketing

Evan Blake

VP, Technology

Evan Blake is the Vice President of Technology at Calusa Marketing, overseeing the development and management of the company's cloud-based SaaS reward platforms. Evan ensures that Calusa Marketing's technology solutions remain cutting-edge, user-friendly, and seamlessly deployable — requiring no integration and no app download for clients or their customers. His technical expertise enables rapid program configuration and easy ongoing management, giving clients a competitive edge in their loyalty and incentive initiatives. Evan is passionate about leveraging technology to reduce operational burden while maximizing program effectiveness, and his work is central to Calusa Marketing's ability to serve over 1,000 programs across diverse industries nationwide.

Portrait of Tom Rocca, VP and Advisory Board Member at Calusa Marketing

Tom Rocca

VP / Advisory Board

Tom Rocca serves as Vice President and a member of the Advisory Board at Calusa Marketing, bringing decades of strategic insight and industry expertise to the organization. In his dual role, Tom both contributes to day-to-day leadership and provides high-level guidance that shapes the company's long-term vision. His experience across loyalty, incentive marketing, and reward fulfillment is a cornerstone of Calusa Marketing's 75+ years of combined team knowledge. Tom is a trusted voice in shaping client program strategies that deliver lasting results, and his commitment to excellence and integrity reflects the values that have made Calusa Marketing a recognized leader in incentive and engagement solutions.

Portrait of Alex Brown, Sales Director at Calusa Marketing

Alex Brown

Sales Director

Alex Brown is a Sales Director at Calusa Marketing, responsible for identifying and developing new business opportunities while building lasting relationships with clients across a variety of industries. Alex brings a client-first mindset to every conversation, taking the time to understand each organization's unique challenges and goals before recommending an incentive program solution. With expertise spanning loyalty programs, digital punch cards, gift card solutions, and travel incentives, Alex helps clients unlock new revenue streams and motivate both their employees and customers. His dedication to delivering results and his collaborative approach make him a valued partner for businesses seeking to grow through strategic incentive marketing.

Portrait of Thomas Ris, Sales Director at Calusa Marketing

Thomas Ris

Sales Director

Thomas Ris is a Sales Director at Calusa Marketing, where he works with clients across multiple sectors to design and implement incentive programs that drive meaningful business outcomes. Thomas brings a data-driven approach to sales, aligning program structures with each client's specific performance goals to ensure measurable ROI. Whether working with HVAC distributors, media companies, or retail organizations, he takes pride in crafting solutions that are fast to deploy, cost-effective, and easy to manage. Thomas embodies Calusa Marketing's commitment to diligence and perseverance, consistently going above and beyond to ensure that every client program is set up for long-term success.

Portrait of Brigitt Barclay de Tolly, Sales Director at Calusa Marketing

Brigitt Barclay de Tolly

Sales Director

Brigitt Barclay de Tolly is a Sales Director at Calusa Marketing, bringing a dynamic and personalized approach to helping clients build and execute impactful incentive and loyalty programs. She specializes in understanding the nuanced needs of businesses across diverse industries, from vacation ownership and timeshare companies to blood donation centers and call center operations. Brigitt is known for her consultative style and her ability to match clients with the right combination of platform tools, reward offerings, and fulfillment services. Her commitment to customer satisfaction and her passion for driving results make her a trusted advisor and a key contributor to Calusa Marketing's exceptional 99% client retention rate.

Portrait of Caitlin Knight, Director of Fulfillment at Calusa Marketing

Caitlin Knight

Director, Fulfillment

Caitlin Knight serves as Director of Fulfillment at Calusa Marketing, overseeing the end-to-end delivery of rewards, travel incentives, and gift card programs for clients and their program members. Caitlin ensures that every incentive is fulfilled accurately, promptly, and with the high standard of care that Calusa Marketing is known for. She manages travel bookings, confirmations, and fulfillment logistics, allowing clients to focus on their core business while Calusa handles the operational details. Caitlin's meticulous attention to detail and her dedication to delivering a seamless experience for program members are central to the company's ability to reduce client operational burden and maintain its reputation for white glove service.

Portrait of Jeanna Ortiz, Customer Service Specialist at Calusa Marketing

Jeanna Ortiz

Customer Service

Jeanna Ortiz is a Customer Service specialist at Calusa Marketing, serving as a frontline representative for the company's commitment to exceptional support available seven days a week. Jeanna assists program members and clients with inquiries related to rewards, travel incentives, digital punch cards, and gift card programs, ensuring every interaction is handled with professionalism, warmth, and efficiency. Her dedication to resolving issues quickly and thoroughly reflects Calusa Marketing's core value of integrity — putting customer satisfaction at the center of everything the company does. Jeanna plays a vital role in sustaining the trust and loyalty of the more than 500,000 program members Calusa Marketing proudly serves.

Portrait of Kali Velazquez, Billing Specialist at Calusa Marketing

Kali Velazquez

Billing Specialist

Kali Velazquez is a Billing Specialist at Calusa Marketing, responsible for managing invoicing, payment processing, and financial accuracy across the company's portfolio of over 1,000 client programs. Kali brings precision and reliability to her role, ensuring that billing operations run smoothly and that clients have a clear, transparent view of their program costs. Her attention to detail and commitment to accuracy support Calusa Marketing's promise of being a true partner — one that clients can trust not only for results but for straightforward and professional financial management. Kali's work behind the scenes is essential to the seamless experience that has helped Calusa Marketing achieve its outstanding client retention record.

Frequently Asked Questions

What is Sidecar Winery Tours — High-End Incentive Travel?

Sidecar Winery Tours — High-End Incentive Travel is a premium reward solution for companies that want to motivate top performers, VIP customers, or sales teams with memorable vineyard and luxury travel experiences. Calusa Marketing can provide pre-packaged high-end trips or arrange custom experiences, including winery tours, dining, transportation, flights, guest coordination, and customer service.

How much do high-end incentive travel experiences cost?

Can winery tours be customized for our incentive program?

Who should use luxury winery tours as an incentive?

What logistics does Calusa Marketing handle?

Are high-end incentive travel rewards transferable?

Can this be used for groups or only individuals?

How do we get started with an incentive travel program?

Have More Travel Reward Questions?

Get clear answers before planning your next reward experience.

Certified & Trusted

Awards and Recognition

Incentive Marketing Association member badge

IMA Membership

Professional association for incentive marketing excellence.

ARDA member recognition badge

ARDA Membership

Recognized connection to vacation ownership expertise.

HARDI member recognition badge

HARDI Membership

Trusted across distribution-focused incentive programs.

Design a Travel Reward They’ll Remember

Tell us your audience, budget, timeline, and reward goals. Our team will recommend a high-end incentive travel structure, handle the logistics, and help you deliver a memorable experience without adding operational burden.

Contact Us Today

For immediate assistance, feel free to give us a direct call at (727) 999-3122. You can also send us a quick email at sales@calusamarketing.com.