Stamford, CT · Long Island Sound

The finest hours happen on a boat.

Privately captained charters for sunsets, fishing, celebrations and watersports. We also run facilitated leadership and strategy sessions on the water. Tell us your date and we'll handle the rest.

Strategy sessions led by industry experts Up to 6 guests Departs Harbor Point
Now booking
2026 season
Stamford, CT · Long Island Sound

The finest hours happen on a boat.

Privately captained charters for sunsets, fishing, celebrations and watersports, plus facilitated leadership and strategy sessions on the water.

What we run

Charters, celebrations, and facilitated sessions on the Sound.

Sunset Cruise

2 hrs

Golden hour on the water with the skyline behind you and a drink in hand.

Celebrations

Custom

Birthdays, proposals, bachelor and bachelorette parties. Your crew, our deck.

Watersports

Half-day

Tubing and towables for the whole crew, with a captain who knows the calm coves.

Leadership & Team Building

Facilitated

Facilitated leadership offsites and team building, 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. Founders and teams think more clearly away from the office, with the Sound, your roadmap, and an advisor who has built and shipped real products.

AI roadmap and build vs. buy Architecture and team strategy Half-day, NDA-friendly
Trips & pricing

Simple rates. Captain always included.

Pick a format and we'll tailor the route, timing and amenities to your group. All trips are privately captained and depart Stamford.

Sunset Cruise

2 hrs
from$450
  • Up to 6 guests
  • Golden-hour route + skyline
  • Bring your own drinks & snacks
Request a date
Most booked

Half-Day Charter

4 hrs
from$850
  • Watersports, celebration or cruise
  • Route built around your group
  • Gear & cooler space included
Request a date

Boardroom on the Bay

Add-on
Facilitated session, added to a charter
+$800on a half-day
+$1,500on a full day
  • Private AI & tech strategy session
  • Pre-call to set the agenda
  • Written follow-up & next steps
Request a date

Rates are indicative. Your captain confirms the final quote based on your date, duration and group size.

Request a date

Tell us your date. We handle the boat.

Send a few details and we'll reply within one business day with availability and a quote. No payment until your date is confirmed.

☎  (203) 828-0852 ✉  [email protected] ⚓  Harbor Point, Stamford CT

By sending, you agree to be contacted about your inquiry. We never share your details.

Request received.

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  1. We confirm availability for your date.
  2. You get a quote and a deposit link to lock it in.
  3. Meet your captain at the dock and we'll handle the rest.
Good to know

Questions, answered.

Yes. Every trip is privately captained by a licensed skipper. You and your guests just show up, and we take care of navigation, safety and the route.

We depart from the Harbor Point marina district in Stamford's South End. Your exact slip and parking details are sent once your date is confirmed.

Up to 6 guests aboard, per Coast Guard limits for the vessel. Planning something bigger? Ask us and we can often coordinate options for larger groups.

Safety is the captain's call. If conditions aren't right, we'll reschedule to another date that works for you, or refund weather cancellations in full. No fine print.

A private technology and AI strategy session held on the water. It's a focused half-day for founders and teams to step back and think, with an advisor who has built and shipped real products. We set an agenda beforehand and send written next steps after.

Send a request above with your date. We confirm availability, send a quote and a deposit link to lock it in, and collect the balance on the dock the day of your trip.