Sailing The Harbor/Bay

NEW New Bedford, MA 1 - 6 People 2 - 4 Hours From $440 Trip #12819
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin

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.

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...

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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Pricing Matrix

2 hours 3 hours 4 hours
1 Person
$440.00
$689.00
$848.00
2 People
$440.00
$689.00
$848.00
3 People
$440.00
$689.00
$848.00
4 People
$440.00
$689.00
$848.00
5 People
$440.00
$689.00
$848.00
6 People
$440.00
$689.00
$848.00
Pay 15% of the price as a deposit today, with the balance due on the day of the trip.

About Your Guide

Steve R.

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...

About Your Guide

Steve R.

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.
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Start Location & Lodging Options

New Bedford, Massachusetts

About Your Boat

Boat photo for Sailing The Harbor/Bay
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
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Trip Details & 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.

Everything Else to Know

Everything is included, but we also recommend bringing sunglasses, sunscreen, weather-appropriate clothing, and anything else you might want on the trip.
This trip is managed by an outfitter. Steve will be your point of contact and you will go out with one of their guides.
We use a cashless autopay system. We'll send you a boarding pass, and on the day of the trip, your guide will scan your boarding pass to automatically transfer the remaining balance. The only cash needed is to tip your guide (we recommend 20%).
Cancel for free up to 10 days before the trip and receive credit back to your account. Cancelling within 10 of the trip will forfeit your deposit to the guide. Day-of cancellations and no-shows will be charged the full balance of the trip to their card.
In the event of inclement weather you'll be covered by out 100% Weather Guarantee and will not lose your deposit.

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First Time Booking with Us?

Captain Experiences is home to thousands of quality, vetted fishing, hunting, and other outdoor sports guides across the US and beyond. Our mission is to Unlock the Outdoors by making it quick and easy to book the trip of a lifetime every time with our Damn Good Guides.
We vet our guides and only partner with the best of the best. Our guides do their very best to keep you safe, show you a great time, and send you home with a memorable experience shared with family and friends.
Once you've paid your deposit at checkout, we'll send you a QR Code boarding pass. Just show your guide your boarding pass on the day of the trip, they'll scan it, the remaining balance will transfer automatically, and you'll be all set to get out there. Just make sure you bring a cash tip for the guide!
In the event of inclement weather, our guides will check the conditions and make the final call on whether its safe to go on the trip. If they decide the trip needs to be postponed, we'll work closely with you to reschedule or provide a credit for the full deposit, which can be applied to any of our trips in the US and beyond.
Each trip's price is determined by the guide and reflects all associated costs. A significant factor in pricing is often the type of boat and the corresponding fuel expenses. Additional costs may include leases, marina or slip fees, and the expenses involved in providing and maintaining the necessary gear for your trip.
After booking your trip, we'll connect you directly with your guide to discuss additional details. In the meantime, our team is here to answer any questions via email, text, or phone.
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