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Maui
Incentive Trip

At A Glance

95
Attendees
Days
Activities
Curated Gifts

Program Introduction

When Cain Travel’s client approached the Cain Meetings and Events team with the goal of rewarding their top employees with a memorable and motivating incentive trip, the parameters were clear: a beach destination with minimal travel time from San Francisco that remained within the budget. With 108 attendeesincluding employees and their gueststhe program needed to balance luxury, relaxation, and cultural authenticity. 

Program
Itinerary

Execution

Logistics & Events

Sourcing

Hawaii was a preferred destination for beautiful, clear-water beaches and proximity to the West Coast, but initial quotes came in well above the client’s budget. Cain Travel took this challenge head-on, leveraging vendor relationships and expert negotiation skills to secure a stunning property, the Grand Wailea, at a cost-effective rate, making the dream destination feasible. 

Gifting

Cain Travel designed a comprehensive and thoughtful gifting experience to enhance the attendee journey from start to finish. Before the trip, qualifiers received custom luggage tags and a handcrafted wooden pineapple dish to celebrate their achievement and build anticipation. Upon arrival, each guest was given a $150 shopping voucher to use during a private event at the onsite Tommy Bahama store. Throughout the program, nightly room drops added surprise and delight: night one featured a waterproof Aloha pouch with reef-safe sunscreen and travel essentials; night two offered a variety of local Hawaiian snacks, including chocolate, shortbread cookies, gummy bears, and potato chips; and night three concluded with a locally made picture frame showcasing a printed photo of each attendee and their guest taken at the Farewell Luau. 

Activities

Cain Travel emphasized flexibility and cultural engagement by designing a program with diverse activity optionsmany of which were hosted onsite to optimize budget and convenience. These included: a catamaran snorkel tour to Molokini Crater, car rentals for self-guided island exploration, non-certified scuba lessons, golf tee times, a beach day package (chairs, umbrellas, watersports), cultural activations (kukui nut bracelet-making and ukulele lessons), and spa treatments. The Cain team expertly managed all logistics and vendor coordination to deliver a seamless experience. 

Case Study – Maui Incentive Trip – 2025

Welcome Dinner

The program kicked off with a relaxed and casual dinner, beginning with a reception featuring drinks and passed appetizers. The reception was followed by a dine around” style dinner where each restaurant showcased its signature dishes, allowing the attendees the opportunity to try numerous cuisines. Entertainment was provided by a local musical duo performing traditional Hawaiian music, adding an authentic touch to the evening. 

Case Study – Maui Incentive Trip – 2025

Dine Around

Through Cain’s experience, they have found that a three-night program can feel overwhelming when packed with daily activities and group dinners each evening. To provide balance, attendees were given the freedom to enjoy dinner on their own—whether onsite, offsite, or in the comfort of their room. Later that evening, they had the option to reconnect at a casual after-party held at an onsite venue called The Cave, which featured VR pods, classic arcade games, and a dessert reception. This two-hour event offered a relaxed, social atmosphere where guests could unwind, play games, and enjoy drinks and sweet treats at their own pace. 

Case Study – Maui Incentive Trip – 2025

Farewell Luau

As attendees arrived, they were welcomed with a traditional lei greeting by two luau performers. During sunset, couples were photographed together, creating a special moment later commemorated with framed prints delivered during the final room drop. Before the luau show started, the CEO took the stage to share a few words of appreciation and congratulations, then invited everyone up for a group photo. Guests then took their seats for the first course as the luau performance began, continuing through dinner and dessert, and bringing the evening and program to a memorable close. 

Testimonial

“I think they struck the perfect balance – location, setting, time, and expense were all thoughtfully considered for every guest. I was genuinely impressed by the level of detail, precision, and care that went into every aspect of the experience. It felt intentional, well-paced, and truly celebratory. A standout event in every way!”

Anonymous Attendee

Outcome

Cain Travel successfully delivered a memorable and luxurious incentive trip. By strategically choosing the right property, curating engaging activities, and executing thoughtful gifting moments, Cain Travel elevated every aspect of the experience. Whether it’s navigating the budget or coordinating complex itineraries, Cain Travel can bring your incentive programs to life with unmatched expertise and care.