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Pleasant Bay, Nova Scotia Boat Rentals

Page 1 of 124 listings

Custom 49’ Sloop for Sail in Bahamas and Newfoundland
Sailing in Newfoundland and Labrador · 6 guests

Custom 49’ Sloop for Sail in Bahamas and Newfoundland

New
$1,000/day
33ft Flybridge Cruiser with Captain in Halifax
Events in Halifax Regional Municipality · 10 guests

33ft Flybridge Cruiser with Captain in Halifax

5.0
$254/hour
Acadia/Mount Desert Island Sail onboard the classic 46-foot sailing ketch
Sailing in Southwest Harbor · 6 guests

Acadia/Mount Desert Island Sail onboard the classic 46-foot sailing ketch

New
$290/hour
Classic Wooden Lobster Boat in Belfast Maine!!
Events in Belfast · 6 guests

Classic Wooden Lobster Boat in Belfast Maine!!

5.0
$150/hour
Herreshoff 12 1/2 Sailboat Charter
Sailing in North Haven · 3 guests

Herreshoff 12 1/2 Sailboat Charter

New
$50/hour
21' Rigid Inflatable Boat (R.I.B.) - Land anywhere servicing Penobscot Bay
Powerboats in North Haven · 6 guests

21' Rigid Inflatable Boat (R.I.B.) - Land anywhere servicing Penobscot Bay

New
$150/hour
Experience Maine on 65ft Classic Schooner Yacht
Sailing in Rockport · 30 guests

Experience Maine on 65ft Classic Schooner Yacht

5.0
$500/hour
★ 28' Classic Schooner in Rockland, Maine ★
Sailing in Rockland · 4 guests

★ 28' Classic Schooner in Rockland, Maine ★

5.0
$175/hour
★Midcoast Maine aboard the Schooner Yacht Meteor ★
Sailing in Rockland · 4 guests

★Midcoast Maine aboard the Schooner Yacht Meteor ★

5.0
$175/hour
Sail the Maine Archipeligo - Muscongus Bay or the Entire Coast
Sailing in Friendship · 6 guests

Sail the Maine Archipeligo - Muscongus Bay or the Entire Coast

5.0
Snoozed - Active 19 Sep 2025
21' Bass Boat Charter in Nobleboro, Maine
Fishing in Nobleboro · 2 guests

21' Bass Boat Charter in Nobleboro, Maine

New
$50+/hour
Enjoy beautiful Maine at Damariscotta Lake with Mariah SX19 Bowrider!
Powerboats in Nobleboro · 8 guests

Enjoy beautiful Maine at Damariscotta Lake with Mariah SX19 Bowrider!

New
$260+/day
Instant Book
Discover the Damariscotta River with a local captain!
Powerboats in Damariscotta · 6 guests

Discover the Damariscotta River with a local captain!

New
$325/hour
Discover the Damariscotta River where 80% of Maine oysters are farmed
Events in Damariscotta · 49 guests

Discover the Damariscotta River where 80% of Maine oysters are farmed

New
$525/hour
24ft Crestliner Bass Boat Rental in Sidney, Maine
Powerboats in Sidney · 3 guests

24ft Crestliner Bass Boat Rental in Sidney, Maine

New
$81/hour
Sweetwater Pontoon 20ft
Powerboats in Readfield · 10 guests

Sweetwater Pontoon 20ft

5.0
$280+/day
24ft Manitou Pontoon
Powerboats in Readfield · 10 guests

24ft Manitou Pontoon

5.0
$280+/day
22ft Massimo Pontoon Boat with 150hp outboard
Powerboats in Readfield · 10 guests

22ft Massimo Pontoon Boat with 150hp outboard

New
$350/day
Hatteras 50ft Motor Yacht for Cruise or Sightseeing in Boothbay Harbor, Maine
Events in Boothbay Harbor · 6 guests

Hatteras 50ft Motor Yacht for Cruise or Sightseeing in Boothbay Harbor, Maine

New
$350/hour
A memorable journey inside the Saguenay-Fjord- a memorable day on the Fjor
Powerboats in Saguenay · 7 guests

A memorable journey inside the Saguenay-Fjord- a memorable day on the Fjor

New
$164/hour
Cruise Casco Bay aboard the 32ft Flye Point Trawler!
Powerboats in Falmouth · 6 guests

Cruise Casco Bay aboard the 32ft Flye Point Trawler!

5.0
$175+/hour
Instant Book
19’ Classic ski boat - day cruiser 225hp
Powerboats in Maine · 8 guests

19’ Classic ski boat - day cruiser 225hp

5.0
$300/hour
Scenic History & Fishing Charters out of Casco Bay
Tours in South Portland · 6 guests

Scenic History & Fishing Charters out of Casco Bay

5.0
$150+/hour
Day and term sailing charters out New Bedford, Massachusetts and Cape Cod.
Sailing in Portland · 6 guests

Day and term sailing charters out New Bedford, Massachusetts and Cape Cod.

New
$850/day

Pleasant Bay Reviews

  1. Jessica

    Jessica

    33ft Flybridge Cruiser with Captain in Halifax

    Faizan is a wonderful host. He was clear about what we should expect and the boat rules, and also very flexible with our route and itinerary. The boat is well equipped and spacious enough for our group of 7.

  2. MV

    Michael

    ★ 28' Classic Schooner in Rockland, Maine ★

    Great experience. Captain Neal is a wealth of sailing knowledge and a lot of fun. My girls were thrilled for a chance to take the tiller! Would definitely book again.

  3. JA

    Jeremy

    Sail the Maine Archipeligo - Muscongus Bay or the Entire Coast

    Ralph made bareboating a great experience end to end. His Morgan 36-5 Nelson Marek was just right, in working order and easy to sail for just my wife who does not sail and me. The equipment was all good, including a new and simple to use chart plotter mounted right at the helm. Beautiful location, conditions and waters made for great sailing. Convenient getting answers in advance, getting started and finished. All good. Highly recommendation. And there’s a super lobster place right nearby.

  4. Grace

    Grace

    Scenic History & Fishing Charters out of Casco Bay

    Very friendly, the scenic is amazing, definitely recommend

  5. SH

    Sarah

    33ft Flybridge Cruiser with Captain in Halifax

    I rented Faizan’s boat when regular tourist charters were not able to navigate to a certain location where my dad wanted his ashes scattered. He was thoughtful and respectful and navigated our group to the spot over some choppy Atlantic waters. Would recommend Faizan for whatever the occasion.

  6. jj

    jenna

    33ft Flybridge Cruiser with Captain in Halifax

    I chartered a boat with Faizan on Saturday, June 29th, for my boyfriend’s surprise birthday party. Coordinating the surprise required having our friends arrive before us, and Faizan was extremely helpful and accommodating throughout the process. Having never rented a boat with a captain before, I was initially worried about potential scams. Faizan promptly agreed to meet with me beforehand to alleviate my concerns, showing me the boat and providing reassurance. His easygoing, friendly demeanor, and extensive knowledge of boating and boat safety made the experience smooth and enjoyable. We had ten friends on board, and every single one of them expressed their intention to rent with Faizan in the future. I highly recommend Faizan if you want to have a fantastic time on the water with the best captain around!