01
Two hours · From $450
Sunset Cruise
Golden hour on the Sound, with the skyline behind you and a drink in hand.
Stamford, Connecticut · Long Island Sound
Leave the shore.
Find the moment.
Private, captained experiences for sunsets, celebrations, watersports and strategy sessions—designed around your people and your day.
Now booking2026 season
Scroll to explore
01 / THE EXPERIENCE
Your time, differently
The finest hours happen on a boat.
There is a different quality to conversation on the water. The city falls away. Time opens up. Whether you are marking a milestone, chasing the sunset, or thinking through what comes next—we create the space for it.
Choose your escape
Four ways
to get out there.
Every charter is private, captained, and shaped around your group. Pick a starting point—we will tailor the rest.
02
Custom occasion
Celebrations
Birthdays, proposals, bachelor and bachelorette parties. Your crew, our deck.
03
Half-day · From $850
Watersports
Tubing and towables for the whole crew, with a captain who knows the calm coves.
04
Facilitated offsite
Leadership & Team Building
Step away from the conference room. We run the session so your team can focus on the thinking.
The unusual offering
Boardroom
on the Bay.
Private technology and AI strategy sessions, run from the water. For founders and teams who think more clearly away from the office—with the Sound, your roadmap, and an advisor who has built and shipped real products.
AI roadmap & build vs. buyArchitecture & team strategyHalf-day · NDA-friendly
Facilitated add-on+$800on a half-day charter
02 / TRIPS & PRICING
Simple by design
Captain included.
No hidden current.
Choose a format. We tailor the route, timing and amenities to your group. Final quotes reflect your date, duration and requests.
Sunset Cruise
from$450
- Up to 6 guests
- Golden-hour route + skyline
- Bring drinks & snacks
Half-Day Charter
from$850
- Cruise, celebration or watersports
- Route built around your group
- Gear & cooler space included
Boardroom on the Bay
+$800half-day · +$1,500 full day
- Private AI & tech strategy
- Pre-call to set the agenda
- Written next steps
On the water
A different
point of view.
Stamford Harbor → Long Island Sound
May through October
Request a date
Tell us when.
We handle the boat.
Share a few details. We will reply within one business day with availability and a quote. No payment until your date is confirmed.
Good to know
Questions,
answered.
Are your charters captained?+
Yes. Every trip is privately captained by a licensed skipper. You and your guests simply arrive; we handle navigation, safety and the route.
Where do we depart?+
From the Harbor Point marina district in Stamford's South End. Your exact slip and parking details arrive once your date is confirmed.
How many guests can come?+
Up to 6 guests, per Coast Guard limits for the vessel. For larger gatherings, ask us about coordinated options.
What if the weather turns?+
Safety is the captain's call. If conditions are not right, we reschedule or refund weather cancellations in full. No fine print.
What is Boardroom on the Bay?+
A private technology and AI strategy session on the water. We set the agenda beforehand and provide written next steps after.
How do I book and pay?+
Request your date. We confirm availability, send a quote and deposit link, then collect the balance on the day of your trip.