About Your Guide

Steve Robinson

Outfitter

Captain Steve is a lifelong sailor with a deep background in both competitive and offshore sailing. With experience ranging from long-distance boat deliveries to high-level racing and instruction, he brings a well-rounded and confident approach to every trip.

After years of teaching and coaching, he transitioned full-time to life on the water, combining his passion for sailing with a focus on creating memorable experiences for his guests. He’s a certified sailing instructor and holds a USCG Master license with a sailing endorsement.

Known for his calm, knowledgeable style, Captain Steve enjoys sharing his love of the water—whether that means guiding a relaxing cruise or helping guests get hands-on and learn the ropes.

About Your Guide

Steve Robinson

Outfitter

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Sailing The Harbor/Bay

NEW New Bedford, MA 1 - 6 People 2 - 4 Hours From $440

About Your Trip

Type

Boat Cruise

Skill Levels

Beginner, Intermediate, Advanced

Weather

You won’t lose your deposit if the trip is canceled due to weather

About Your Trip

Get out on the water for a classic New England sailing experience, combining steady coastal winds, open water, and incredible views. These private sailing charters offer a perfect mix of relaxation and hands-on adventure.

Departing from New Bedford Harbor, you’ll sail past working waterfronts and historic vessels before heading into the open waters of Buzzards Bay. With consistent breezes and wide-open space, it’s an ideal setting for smooth, enjoyable sailing.

The Experience

This trip can be as laid-back or interactive as you’d like. Sit back and take in the scenery, or step in and learn the basics of sailing along the way.

You may spot seabirds, seals, or even dolphins as you move along the coastline, with views stretching out toward the Elizabeth Islands and surrounding waters. Sunset sails are especially popular, offering incredible lighting and a calm, memorable finish to the day.

Good to Know

Trips range from 2 hours to full-day charters and are fully customizable based on weather and your preferences. You’re welcome to bring snacks and beverages, with beer and wine allowed in moderation.

Water and seltzer are provided, and restroom facilities are available onboard.

Amenities

Type

Boat Cruise

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Boat Restroom

This boat has a restroom.

Weather

You won’t lose your deposit if the trip is canceled due to weather

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 10 days before the trip.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

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About Your Boat

Boat Type: Sailboat
Boat Manufacturer: Pearson
Year Built: 1979
Boat Length: 35'

About Your Boat

Boat Type: Sailboat
Boat Manufacturer: Pearson
Year Built: 1979
Boat Length: 35'
Boat Restroom: Yes
Engine Manufacturer: Westebeke
Additional Amenities: GPS, VHF Radio, Chart Plotter, Depth Finder, Anchor, Wheel Steering, Life Jackets, Ice Box