Corporate Outings
Looking for a memorable way to bring your team together? Our private corporate boat charters in Portland, Maine offer a relaxed, scenic setting for team outings, client entertainment, and company celebrations.
Private Boat Charters for Teams, Clients & Company Celebrations
Step aboard our comfortable cocktail cruiser and enjoy Portland from the water while your group connects, unwinds, and celebrates in true Maine style. Book your corporate or team outing today or reach out with questions—we’re happy to help you plan the perfect day on Casco Bay.
What to Expect Onboard
Your group will cruise aboard our spacious cocktail cruiser, the Calista Ann, designed for comfort, conversation, and casual sightseeing.
- Open layout perfect for mingling
- Professional captain and crew
- Private restroom available onboard
- BYOB and food (cooler and ice provided!)
- Free Starlink WiFi
If you’re planning around a meeting schedule, conference, or off-site agenda, we’ll help you choose the right timing and length for your charter.
Private Charter Details
With a private charter, your group enjoys the boat exclusively—no shared tours, no interruptions, just your people and the open water.
- Location: Downtown Portland, Maine
- Duration: Flexible charters, from 2 hours up to 8+ hours available to fit your cruise schedule
- Group Size: Maximum of 12 guests, ideal for small to mid-size teams
- Season: May through October (weather permitting)
- Experience: Fully private boat charter with licensed captain
Why Teams Love Chartering with Sail Portland Maine
Swap conference rooms and crowded restaurants for fresh air, coastal views, and an experience your team will love.
- Private, stress-free experience
- Scenic backdrop for meaningful connection
- No planning headaches or rigid schedules
- Easy add-on to conferences or retreats in Portland
- A memorable alternative to traditional venues
Many companies tell us this ends up being the highlight of their time in Maine!
Book Your Cruise in Portland, Maine
Make the most out of the summer season with the best sunset cruise Portland, Maine has to offer. Whether you're visiting from out of town, planning a unique, intimate event, or simply spending time with loved ones, let us provide you with the best possible chartered boat experience.