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Cape Cod
Offsite

At A Glance

50
Attendees
Activities
Company Meeting

Program Introduction

The client hosts an annual offsite meeting, alternating between Europe and North America. Since last year’s event was held in London, this year’s focus was on North American destinations. The group is known for being active and adventurous, so remote locations that offer outdoor experiences were prioritized. However, proximity to a major international airport was essential, as attendees travel in from around the world. Chatham Bars Inn in Cape Cod, Massachusetts, offered the perfect blend – secluded and charming, yet only a two-hour drive from Boston Logan International Airport.

Program
Itinerary

Execution

Logistics & Events

Arrivals

Cain Travel managed global flight bookings to ensure attendees arrived efficiently in Boston. Upon arrival, participants could choose between rental cars or private transfers to Cape Cod. Rental cars were secured through National, ensuring reliable service for those comfortable navigating on their own. This option gave attendees the freedom to explore the Cape. For those preferring not to drive, private transfers were arranged through Cain’s trusted transportation partners. 

Activities

To reflect Cape Cod’s charm, the Cain team curated a variety of quintessential local experiences. Activities included lobstering, sailing, fishing, and a historical tour – many of them water-based to highlight the region’s coastal culture. During registration, attendees were asked to select their top two preferences from a list of options. While severe weather forced some activities to be altered or moved indoors, the Cain team swiftly adapted, ensuring the experience remained enjoyable. The lobstering excursion stood out as a crowd favorite, offering participants a glimpse into the daily life of a lobsterman, with the added bonus of enjoying freshly caught lobster for dinner. 

Meeting

The offsite’s core purpose was to facilitate collaboration through in-person meetings and breakout sessions. Cain supported all logistical elements, from room setup and facilitation to coordinating breakfast and lunch buffets. These meetings provided a valuable opportunity for employees to work together in a dynamic, face-to-face setting. 

Case Study – Cape Cod Offsite – 2025

Dine Around

On select evenings, attendees received a per diem and were encouraged to explore downtown Chatham on their own. This flexible approach allowed them to experience local dining and the charm of the town independently. 

Case Study – Cape Cod Offsite – 2025

Welcome Dinner

A scenic dinner was hosted at The Chatham Inn, featuring a room with floor-to-ceiling windows overlooking the ocean. A guitarist set a relaxed mood with live music. Guests enjoyed a classic cookout with burgers, hot dogs, and traditional sides, followed by a cozy bonfire where they could roast marshmallows and socialize. 

Case Study – Cape Cod Offsite – 2025

Farewell Dinner

Originally planned as an outdoor farewell dinner, inclement weather prompted a quick change of venue, so the Cain team seamlessly transitioned the event indoors. Guests enjoyed a Cape Cod-inspired buffet featuring whole lobsters and freshly shucked oysters, a fitting culinary send-off that embraced the local culture and cuisine. 

Outcome

The offsite at Chatham Bars Inn was a resounding success, balancing professional collaboration with authentic regional experiences. Despite unexpected weather challenges, Cain’s proactive coordination ensured all activities, logistics, and events ran smoothly. Attendees left feeling energized and connected, having explored the beauty and charm of Cape Cod while engaging in meaningful face-to-face interactions with colleagues. The event reinforced the value of thoughtful planning and highlighted the importance of blending work with enriching, memorable experiences.