Captain Paul's Harbor Charters 

5.0/5 (1 review)
 Little Mystic Channel, Boston, MA 02129, United States

Captain Paul's Harbor Charters 

Boston, MA, United States
30 feet
6
5.0/5 (1 review)

Experience Boston Harbor from the water aboard a classic 1999 Mainship Pilot Downeast Trawler, a comfortable vessel perfectly suited for sightseeing, historic harbor tours, lighthouse adventures, and unforgettable sunsets. Accommodating up to six guests, the boat is powered by a reliable 320 HP Yanmar diesel engine with a cruising speed of up to 14 knots.

USCG-certified Captain Paul Regan specializes in Harbor Tours with historic narration upon request, Lighthouse Tours, Sunset Cruises, and Valet Services, creating a relaxed and personalized experience for every group.

Enjoy plenty of space to take in the scenery from the aft and bow sundecks, along with a cabin, head (toilet), refrigerator, ice box, audio system, and indoor and outdoor speakers. Optional drinks, lunch, and snacks are available to make your day on the water even more convenient.

Safety is a top priority, with GPS, chart plotter, radar, depth finder, VHF radio, anchor, and life jackets onboard. Children are welcome, and alcohol is permitted; children 12 and under must wear a life jacket at all times.

Whether you're discovering Boston's maritime history, visiting iconic lighthouses, or watching the sun set over the harbor, Captain Paul's Harbor Charters offers a memorable way to experience the city from the water.

Book your Boston Harbor adventure today!

Experience Boston Harbor from the water aboard a classic 1999 Mainship Pilot Downeast Trawler, a comfortable vessel perfectly suited for sightseeing, historic harbor tours, lighthouse adventures, and unforgettable sunsets. Accommodating up to six guests, the boat is powered by a reliable 320 HP Yanmar diesel engine with a cruising speed of up to 14 knots.

USCG-certified Captain Paul Regan specializes in Harbor Tours with historic narration upon request, Lighthouse Tours, Sunset Cruises, and Valet Services, creating a relaxed and personalized experience for every group.

Enjoy plenty of space to take in the scenery from the aft and bow sundecks, along with a cabin, head (toilet), refrigerator, ice box, audio system, and indoor and outdoor speakers. Optional drinks, lunch, and snacks are available to make your day on the water even more convenient.

Safety is a top priority, with GPS, chart plotter, radar, depth finder, VHF radio, anchor, and life jackets onboard. Children are welcome, and alcohol is permitted; children 12 and under must wear a life jacket at all times.

Whether you're discovering Boston's maritime history, visiting iconic lighthouses, or watching the sun set over the harbor, Captain Paul's Harbor Charters offers a memorable way to experience the city from the water.

Book your Boston Harbor adventure today!

Paul Regan
Captain
Paul Regan
ID & credentials verified
responds within an hour

Trip availability and prices

Trip Date:
Group Size:
Select date to see availability
September 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
1 Hour – Harbor Tour
FREE Cancellation 3 days notice
1 hour trip starts at 1:00 PM
Seasonal trip
Jun 1 - Sep 30
US $300
Private tour: up to 6 people
2 Hour – Island Tour
In high demand Last booked: 6 days ago
FREE Cancellation 3 days notice
2 hour trip starts at 1:00 PM
US $400
Private tour: up to 6 people
3 Hour – Lighthouse Tour
FREE Cancellation 3 days notice
3 hour trip starts at 12:00 PM
Seasonal trip
Jun 1 - Sep 30
US $600
Private tour: up to 6 people

Customer reviews

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Rating

5.0
(1 review)
5.0
Boat & equipment
5.0
Captain & crew
5.0
Experience

All reviews (1)

Showing 11 of 1 review
Brittany Cremmen
Brittany Cremmen
us
Massachusetts, US
Member since 2026
5.0
Verified
New
Can’t wait for next time!
2 Hour – Island Tour on September 12, 20266 adults

We had the best time on our harbor cruise with Captain Paul and Alex! They were friendly, fun and very accommodating. They shared some fun facts along the ride but also let us do our thing, including control the music. Would 100% recommend them to anyone and look forward to the next occassion I have to book a trip.

FAQs about Captain Paul's Harbor Charters

Captain Paul's Harbor Charters offers the following trips to customers:
  • US $300 per group - 1 Hour – Harbor Tour (1 hour)
  • US $400 per group - 2 Hour – Island Tour (2 hours)
  • US $600 per group - 3 Hour – Lighthouse Tour (3 hours)
When you book a trip with Captain Paul's Harbor Charters, you can expect the following amenities onboard:
  • GPS
  • VHF Radio
  • Radar
  • Chart Plotter
  • Depth Finder
  • Bow Thruster
  • Anchor
  • Wheel Steering
  • Life Jackets
  • Bimini
  • Bow Sundeck
  • Aft Sundeck
  • Bathing Platform
  • Audio System
  • Inside Speakers
  • Outside Speakers
  • Refrigerator
  • Ice Box
Trips booked with Captain Paul's Harbor Charters include:
  • Snacks
  • Drinks
  • Lunch
Captain Paul's Harbor Charters offers the following activities:
  • Boat & Yacht Tours
  • Sunset Dinner Cruises
  • Island Hopping
  • Birthday Celebrations
  • Bachelorette & Bachelor Parties

Your operator

Paul Regan
Paul Regan
Paul Regan

Boston, Massachusetts, United States

ID & license verified
1 Customer reviews
Response time within an hour
Member since July 2026

Captain Paul Regan is a USCG-certified captain with a passion for sharing the beauty, history, and character of Boston Harbor from the water. Specializing in harbor tours with historic narration, lighthouse tours, sunset cruises, and valet services, Captain Paul creates relaxed, personalized experiences for guests of all ages. Step aboard and let Captain Paul show you Boston from a whole new perspective!

ID & license verified
1 Customer reviews
Response time within an hour
Member since July 2026

Captain Paul Regan is a USCG-certified captain with a passion for sharing the beauty, history, and character of Boston Harbor from the water. Specializing in harbor tours with historic narration, lighthouse tours, sunset cruises, and valet services, Captain Paul creates relaxed, personalized experiences for guests of all ages. Step aboard and let Captain Paul show you Boston from a whole new perspective!

What the boat is like

Boat category
Cabin cruisers
Boat type
Downeast
Boat manufacturer
Mainship
Boat Model
Pilot
Year built
1999
Boat length
30 ft
Capacity
6 persons
Engine model
Yanmar
Max crusing speed
14 knots
Powered by
1 x 320HP
Engine Type
Inboard
Fuel Type
Diesel
Number of cabins
1 cabin
Number of berths
1 berth
Number of heads
1 head
Number of toilets
1 toilet
Boat category
Cabin cruisers
Boat type
Downeast
Boat manufacturer
Mainship
Boat Model
Pilot
Year built
1999
Boat length
30 ft
Capacity
6 persons

Which kind of activities are offered

Boat & Yacht Tours
Sunset & Dinner Cruise
Island Hopping
Birthday Celebrations
Bachelorette & Bachelor Parties

Which amenities are available onboard

GPS
VHF Radio
Radar
Chart Plotter
Depth Finder
Bow Thruster
Anchor
Wheel Steering
Life Jackets
Bimini
Bow Sundeck
Aft Sundeck
Bathing Platform
Audio System
Inside Speakers
Outside Speakers
Refrigerator
Ice Box

What's included in the trip price

Snacks
BYO or I can provide.
Drinks
BYO or I can provide.
Lunch
BYO or I can provide.

What’s allowed on the boat

Child Friendly
Alcohol
Shoes

What additional terms you should be aware of

Security deposit is not required

A refundable deposit is not required by the charter operator.


Fuel is included

Fuel is included in the price of the rental.

How cancellations work

Free cancellation up to 3 days prior to trip

You can cancel or modify your booking up to 3 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

 PayPal

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Captain Paul's Harbor Charters
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5.0
/5
(1 review)
30 feet
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US $300