Cape Ann Cruises 

 63 Rogers Street, Gloucester, MA 01930, United States

Cape Ann Cruises 

Gloucester, MA, United States
53 feet
46

Step aboard Cape Ann Cruises—a beautifully restored 1967 Royal Lowell-designed Phil Fessenden Custom Headboat, now modernized in 2023 for comfort, charm, and performance. Departing from Gloucester, this spacious vessel welcomes up to 46 guests, making it perfect for unforgettable group outings, celebrations, or relaxed coastal explorations.

Powered by twin 318 HP GM diesel inboards, she cruises smoothly at 14 knots. Onboard, you’ll find all the essentials for an enjoyable experience: an audio system, fishfinder, inside/outside speakers, refrigerator, and ice box.

Led by seasoned local Captain Jeff Brown, you can choose from a variety of experiences—island hopping, dolphin watching, sightseeing, or lively booze cruises. With comfortable amenities like a flybridge, kitchen, sundecks (bow and aft), and an onboard restroom, you're set for a relaxing and memorable time.

Optional add-ons include drinks, lunch, and snacks, and the vibe onboard is welcoming and flexible: alcohol, red wine, smoking, swimming, and children are all allowed.

Safety is a top priority. The vessel is equipped with life jackets, GPS, sonar, radar, VHF radio, autopilot, depth finder, chart plotter, and more.

Whether you're planning a fun-filled party cruise or a scenic coastal day with friends and family, book your adventure today and cruise Cape Ann in classic New England style!

Step aboard Cape Ann Cruises—a beautifully restored 1967 Royal Lowell-designed Phil Fessenden Custom Headboat, now modernized in 2023 for comfort, charm, and performance. Departing from Gloucester, this spacious vessel welcomes up to 46 guests, making it perfect for unforgettable group outings, celebrations, or relaxed coastal explorations.

Powered by twin 318 HP GM diesel inboards, she cruises smoothly at 14 knots. Onboard, you’ll find all the essentials for an enjoyable experience: an audio system, fishfinder, inside/outside speakers, refrigerator, and ice box.

Led by seasoned local Captain Jeff Brown, you can choose from a variety of experiences—island hopping, dolphin watching, sightseeing, or lively booze cruises. With comfortable amenities like a flybridge, kitchen, sundecks (bow and aft), and an onboard restroom, you're set for a relaxing and memorable time.

Optional add-ons include drinks, lunch, and snacks, and the vibe onboard is welcoming and flexible: alcohol, red wine, smoking, swimming, and children are all allowed.

Safety is a top priority. The vessel is equipped with life jackets, GPS, sonar, radar, VHF radio, autopilot, depth finder, chart plotter, and more.

Whether you're planning a fun-filled party cruise or a scenic coastal day with friends and family, book your adventure today and cruise Cape Ann in classic New England style!

Jeff Brown
Captain
Jeff Brown
responds within an hour

Trip availability and prices

Trip Date:
Group Size:
Select date to see availability
September 2026
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Number of days
1
Group Size
2 adults • 0 children
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2 Hour – Weekday Experience (8AM)
FREE Cancellation 30 days notice
2 hour trip starts at 8:00 AM
Seasonal trip
(Mon, Tue, Wed, Thu)
+2
US $1,400
Private tour: up to 46 people
2 Hour – Weekend Cruise (7AM)
FREE Cancellation 30 days notice
2 hour trip starts at 7:00 AM
Seasonal trip
(Fri, Sat, Sun)
+2
US $1,800
Private tour: up to 46 people
2 Hour – Weekend Cruise (11AM)
FREE Cancellation 30 days notice
2 hour trip starts at 11:00 AM
Seasonal trip
(Fri, Sat, Sun)
+2
US $1,800
Private tour: up to 46 people
2 Hour – Weekend Cruise (3PM)
FREE Cancellation 30 days notice
2 hour trip starts at 3:00 PM
Seasonal trip
(Fri, Sat, Sun)
+2
US $1,800
Private tour: up to 46 people
3 Hour – Weekday Experience (8AM)
FREE Cancellation 30 days notice
3 hour trip starts at 8:00 AM
Seasonal trip
(Mon, Tue, Wed, Thu)
+2
US $2,100
Private tour: up to 46 people
3 Hour – Weekend Cruise (7AM)
FREE Cancellation 30 days notice
3 hour trip starts at 7:00 AM
Seasonal trip
(Fri, Sat, Sun)
+2
US $2,700
Private tour: up to 46 people
4 Hour – Weekday Experience (8AM)
FREE Cancellation 30 days notice
4 hour trip starts at 8:00 AM
Seasonal trip
(Mon, Tue, Wed, Thu)
+2
US $2,800
Private tour: up to 46 people
4 Hour – Weekend Cruise (7AM)
FREE Cancellation 30 days notice
4 hour trip starts at 7:00 AM
Seasonal trip
(Fri, Sat, Sun)
+2
US $3,200
Private tour: up to 46 people
5 Hour – Weekend Cruise (7AM)
FREE Cancellation 30 days notice
5 hour trip starts at 7:00 AM
Seasonal trip
(Fri, Sat, Sun)
+2
US $3,700
Private tour: up to 46 people
6 Hour – Weekend Cruise (7AM)
FREE Cancellation 30 days notice
6 hour trip starts at 7:00 AM
Seasonal trip
(Fri, Sat, Sun)
+2
US $4,200
Private tour: up to 46 people
6 Hour – Weekday Experience (8AM)
FREE Cancellation 30 days notice
6 hour trip starts at 8:00 AM
Seasonal trip
(Mon, Tue, Wed, Thu)
+2
US $4,200
Private tour: up to 46 people
8 Hour – Weekend Cruise (7AM)
FREE Cancellation 30 days notice
8 hour trip starts at 7:00 AM
Seasonal trip
(Fri, Sat, Sun)
+2
US $5,000
Private tour: up to 46 people
8 Hour – Weekday Experience (8AM)
FREE Cancellation 30 days notice
8 hour trip starts at 8:00 AM
Seasonal trip
(Mon, Tue, Wed, Thu)
+2
US $5,600
Private tour: up to 46 people
10 Hour – Weekend Cruise (7AM)
FREE Cancellation 30 days notice
10 hour trip starts at 7:00 AM
Seasonal trip
(Fri, Sat, Sun)
+2
US $5,800
Private tour: up to 46 people
12 Hour – Weekend Cruise (7AM)
FREE Cancellation 30 days notice
12 hour trip starts at 7:00 AM
Seasonal trip
(Fri, Sat, Sun)
+2
US $6,600
Private tour: up to 46 people
10 Hour – Weekday Experience (8AM)
FREE Cancellation 30 days notice
10 hour trip starts at 8:00 AM
Seasonal trip
(Mon, Tue, Wed, Thu)
+2
US $7,000
Private tour: up to 46 people
12 Hour – Weekday Experience (8AM)
FREE Cancellation 30 days notice
12 hour trip starts at 8:00 AM
Seasonal trip
(Mon, Tue, Wed, Thu)
+2
US $8,400
Private tour: up to 46 people
There are 4 people looking at this charter.

Customer reviews

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FAQs about Cape Ann Cruises

Cape Ann Cruises offers the following trips to customers:
  • US $1,400 per group - 2 Hour – Weekday Experience (8AM) (2 hours)
  • US $1,800 per group - 2 Hour – Weekend Cruise (11AM) (2 hours)
  • US $1,800 per group - 2 Hour – Weekend Cruise (3PM) (2 hours)
  • US $1,800 per group - 2 Hour – Weekend Cruise (7AM) (2 hours)
  • US $2,100 per group - 3 Hour – Weekday Experience (8AM) (3 hours)
  • US $2,700 per group - 3 Hour – Weekend Cruise (7AM) (3 hours)
  • US $2,800 per group - 4 Hour – Weekday Experience (8AM) (4 hours)
  • US $3,200 per group - 4 Hour – Weekend Cruise (7AM) (4 hours)
  • US $3,700 per group - 5 Hour – Weekend Cruise (7AM) (5 hours)
  • US $4,200 per group - 6 Hour – Weekday Experience (8AM) (6 hours)
  • US $4,200 per group - 6 Hour – Weekend Cruise (7AM) (6 hours)
  • US $5,000 per group - 8 Hour – Weekend Cruise (7AM) (8 hours)
  • US $5,600 per group - 8 Hour – Weekday Experience (8AM) (8 hours)
  • US $5,800 per group - 10 Hour – Weekend Cruise (7AM) (10 hours)
  • US $6,600 per group - 12 Hour – Weekend Cruise (7AM) (12 hours)
  • US $7,000 per group - 10 Hour – Weekday Experience (8AM) (10 hours)
  • US $8,400 per group - 12 Hour – Weekday Experience (8AM) (12 hours)
When you book a trip with Cape Ann Cruises, you can expect the following amenities onboard:
  • GPS
  • VHF Radio
  • Radar
  • Chart Plotter
  • Depth Finder
  • Sonar
  • Bow Thruster
  • Autopilot
  • Anchor
  • Wheel Steering
  • Life Jackets
  • Flybridge
  • Kitchen
  • Bow Sundeck
  • Aft Sundeck
  • Audio System
  • Inside Speakers
  • Outside Speakers
  • Refrigerator
  • Ice Box
  • Fishfinder
Trips booked with Cape Ann Cruises include:
  • Fishing Equipment
  • Catch cleaning & filleting
  • Snacks
  • Drinks
  • Lunch
Cape Ann Cruises offers the following activities:
  • Boat & Yacht Tours
  • Island Hopping
  • Booze Cruises
  • Whale & Dolphin Watching
  • Eco-Tours

Your operator

Jeff Brown
Jeff Brown
Jeff Brown

Gloucester, Massachusetts, United States

Response time within an hour
Member since April 2025

Meet Capt. Jeff Brown, a seasoned mariner based in Gloucester, MA, who runs unforgettable adventures aboard a classic Royal Lowell-designed Phil Fessenden Custom Headboat. With years of local experience, Capt. Jeff specializes in scenic boat tours, lively booze cruises, island hopping, and dolphin watching along the beautiful New England coast. His passion for the water and deep knowledge of the area ensure every trip is both relaxing and memorable.

Response time within an hour
Member since April 2025

Meet Capt. Jeff Brown, a seasoned mariner based in Gloucester, MA, who runs unforgettable adventures aboard a classic Royal Lowell-designed Phil Fessenden Custom Headboat. With years of local experience, Capt. Jeff specializes in scenic boat tours, lively booze cruises, island hopping, and dolphin watching along the beautiful New England coast. His passion for the water and deep knowledge of the area ensure every trip is both relaxing and memorable.

What the boat is like

Boat category
Headboats
Boat type
Headboat
Boat manufacturer
Royal Lowell Designed Phil Fessenden
Boat Model
Custom
Year built
1967
Restored in
2023
Boat length
53 ft
Capacity
46 persons
Engine model
GM
Max crusing speed
14 knots
Powered by
2 x 318HP
Engine Type
Inboard
Fuel Type
Diesel
Number of toilets
1 toilet
Boat category
Headboats
Boat type
Headboat
Boat manufacturer
Royal Lowell Designed Phil Fessenden
Boat Model
Custom
Year built
1967
Restored in
2023
Boat length
53 ft
Capacity
46 persons

Which kind of activities are offered

Boat & Yacht Tours
Island Hopping
Booze Cruises
Whale & Dolphin Watching
Eco-Tours

Which amenities are available onboard

GPS
VHF Radio
Radar
Chart Plotter
Depth Finder
Sonar
Bow Thruster
Autopilot
Anchor
Wheel Steering
Life Jackets
Flybridge
Kitchen
Bow Sundeck
Aft Sundeck
Audio System
Inside Speakers
Outside Speakers
Refrigerator
Ice Box
Fishfinder

What's included in the trip price

Fishing Equipment
Catch cleaning & filleting
Snacks
Drinks
Lunch

What’s allowed on the boat

Child Friendly
Alcohol
Shoes
Swimming
Red Wine

What additional terms you should be aware of

Security deposit of US $500 per tour is required

A refundable deposit of US $500 per tour is required at boat pick-up and will be returned to you when the boat is returned without damage. Security deposit is to be paid directly to the charter operator.


Fuel is included

Fuel is included in the price of the rental.

How cancellations work

Free cancellation up to 30 days prior to trip

You can cancel or modify your booking up to 30 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.

More details

How you can pay

Reserve with a 10% booking deposit, pay the captain the rest

When the captain confirms your trip, BoatBooker charges your credit card a 10% booking deposit to guarantee your reservation.

The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:

 Cash

 Visa

 Mastercard

 American Express

When paying the remaining balance with a credit card, an additional 2% charge will apply.

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