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Manchester-by-the-Sea, Massachusetts Boat Rentals

24 listings
Water Ski/Tubing/Wakeboard with Driver/Instructor
Powerboats in Gloucester · 5 guests

Water Ski/Tubing/Wakeboard with Driver/Instructor

New
$145hour
Large Group Experience : Private Events  in Gloucester, Massachusetts
Events in Gloucester · 46 guests

Large Group Experience : Private Events in Gloucester, Massachusetts

New
$499-$699hour
Sail with us aboard ARTEMIS in Gloucester MA and New England
Sailing in Gloucester · 6 guests

Sail with us aboard ARTEMIS in Gloucester MA and New England

5.0
$250hour
Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!
Sailing in Gloucester · 6 guests

Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!

New
$175-$225hour
Authentic 122ft Schooner Adventure - A National Historic Landmark!
Sailing in Gloucester · 60 guests

Authentic 122ft Schooner Adventure - A National Historic Landmark!

New
$1,150-$1,200hour
Enjoy Fishing In Gloucester, Massachusetts With Captain Dana
Fishing in Gloucester · 4 guests

Enjoy Fishing In Gloucester, Massachusetts With Captain Dana

4.9
$119hour
Private Charters on Classic 80' Schooner yacht in Salem, Massachusetts
Sailing in Salem · 6 guests

Private Charters on Classic 80' Schooner yacht in Salem, Massachusetts

5.0
$498-$550hour
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$150hour
Robalo R222 Center Console Rental in Newburyport, MA
Powerboats in Newburyport · 5 guests

Robalo R222 Center Console Rental in Newburyport, MA

New
$100hour
Shark Fishing in Newburyport, Massachusetts
Fishing in Newburyport · 6 guests

Shark Fishing in Newburyport, Massachusetts

New
$124-$133hour
Mainship 40ft Yacht with Captain in Newburyport
Events in Newburyport · 12 guests

Mainship 40ft Yacht with Captain in Newburyport

5.0
$300hour
⭐️⭐️⭐️⭐️⭐️Jump on Board the Just Hangin’.
Tours in Winthrop · 8 guests

⭐️⭐️⭐️⭐️⭐️Jump on Board the Just Hangin’.

4.7
$300hour
34 ft Sea ray Sun-dancer Yacht in Boston for rent
Events in Winthrop · 8 guests

34 ft Sea ray Sun-dancer Yacht in Boston for rent

New
$325hour
A Real Vibe On Boston Harbor! Rent the Regal Commodore 2760 Motor Yacht!
Events in Winthrop · 6 guests

A Real Vibe On Boston Harbor! Rent the Regal Commodore 2760 Motor Yacht!

5.0
Superowner
$325hour
48 ft Motor Yacht Elixir
Events in Winthrop · 6 guests

48 ft Motor Yacht Elixir

4.9
Superowner
$375hour
Book the Classic Bertram 26 Open Sport Motor Yacht in Boston, Massachusetts
Powerboats in Boston · 6 guests

Book the Classic Bertram 26 Open Sport Motor Yacht in Boston, Massachusetts

5.0
$150hour
40ft Pursuit Express Motor Yacht in Boston
Events in Boston · 6 guests

40ft Pursuit Express Motor Yacht in Boston

New
$300hour
38' Power downeast cruiser in Hull
Events in Hull · 6 guests

38' Power downeast cruiser in Hull

New
$180hour
Luxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in Boston
Sailing in Boston · 6 guests

Luxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in Boston

New
$500hour
Luxury Yacht Boston Harbor Sunset Cruise and Boat Tours
Events in Boston · 6 guests

Luxury Yacht Boston Harbor Sunset Cruise and Boat Tours

5.0
$225hour
Cycleboat Boston BYOB Public Cruises & Private Charters Boston, Massachusetts
Powerboats in Boston · 26 guests

Cycleboat Boston BYOB Public Cruises & Private Charters Boston, Massachusetts

5.0
$69person
25' Sport Boat Charter in Boston with Captain
Powerboats in Boston · 7 guests

25' Sport Boat Charter in Boston with Captain

5.0
$200hour
Cruise or Fish Boston Harbor & it's surrounding area with Boston's Best Captain
Powerboats in Boston · 6 guests

Cruise or Fish Boston Harbor & it's surrounding area with Boston's Best Captain

New
$85-$250hour
A stunning 2000 Regal Commodore 2760 Motor Yacht for any occasion ready to rent in Boston, Massachussets
Events in Boston · 6 guests

A stunning 2000 Regal Commodore 2760 Motor Yacht for any occasion ready to rent in Boston, Massachussets

5.0
Superowner
$325hour

Manchester-by-the-Sea Reviews

  1. David
    David
    Sail with us aboard ARTEMIS in Gloucester MA and New England

    Rick and Deb create an unmatched experience. Once someone experiences 64’ and multiple sails propelling one through the water…. The comforts, viewing and lounging locations onboard…and the company/conversation with the captain/first mate (Rick and Deb). Anyone will consider this one of the greatest values and investments in experience they have made in a long time. Highly recommend.

  2. DB
    David
    Sail with us aboard ARTEMIS in Gloucester MA and New England

    A Memorable Sailboat Adventure: Weathering the Storm with an exceptional Captain. Embarking on a sailboat outing can be an exhilarating experience, and my recent adventure certainly proved to be one for the books. Despite facing harsh weather conditions, the exceptional captain and crew aboard the sailboat managed to turn it into an unforgettable journey. Let me share the highlights of this remarkable trip. From the moment we stepped aboard, it was evident that we were in capable hands. The captain and crew exuded confidence, expertise, and a passion for sailing. Their extensive knowledge of the sea and their professionalism were evident throughout the entire voyage. They skillfully navigated the sailboat through turbulent waters, ensuring our safety remained their utmost priority at all times. The adverse weather conditions presented us with a unique challenge, but it was precisely during these moments that the captain's expertise truly shone. Their ability to handle the sailboat with finesse, adjusting the sails and making necessary adjustments to ensure stability, was nothing short of remarkable. Even amidst the pounding rain and fierce winds, we always felt secure under their capable command. While the tempestuous weather demanded our resilience, the comfort of the sailboat's warm cabin provided a welcome respite. It was here that the crew's attentiveness truly made a difference. They anticipated our needs, promptly offering warm beverages and blankets to keep us comfortable. Their friendly demeanor and willingness to engage in conversation added a delightful personal touch to the entire experience. Now, let's talk about the food. In a word: fantastic! Despite the challenges of preparing a meal aboard a moving sailboat, the crew managed to create a culinary experience that exceeded all expectations. From hearty tea to a delicious charcuterie platter, every bite was a delightful treat for the taste buds. The crew's attention to dietary preferences and dietary restrictions was commendable, ensuring that every guest felt accommodated and satisfied. Though the weather may have posed some difficulties, it ultimately became an unexpected catalyst for camaraderie among the passengers. We bonded over shared experiences and a collective sense of adventure. The captain and crew fostered a warm and inclusive atmosphere, encouraging us to learn about sailing, lending a helping hand, and sharing stories of their own sailing escapades. In summary, despite the challenging weather, my sailboat outing was a resounding success, largely due to the exceptional captain and crew. Their professionalism, expertise, and unwavering dedication to our safety made us feel secure throughout the journey. The outstanding food and the warmth of the cabin were added bonuses that contributed to our overall enjoyment. I highly recommend this sailboat adventure to anyone seeking an unforgettable experience, even in the face of rough seas.

  3. Valerie
    Valerie
    Sail with us aboard ARTEMIS in Gloucester MA and New England

    Deb and Rick were amazing. All the planning went smoothly as well as our sail. They were very accommodating. The lunch provided with our 4 hour sail was delicious and they were able to include a vegan option . I highly recommend to book your next adventure with them . We would definitely do it again .

  4. JB
    Jeff
    Enjoy Fishing In Gloucester, Massachusetts With Captain Dana

    I didn’t know what to expect using an app for a fishing charter, but boy did Captain Dana deliver! Every aspect of the trip was spot on. Captain Dana is a local to Gloucester his entire life and the only thing more impressive than the tidbits of historical information he provided, was the amount of fish he put us on the entire trip. We limited out with plenty of time left to catch and release several more. I’ve been stripper fishing in several of the best locales and our experience with Captain Dana was the best striped bass fishing I’ve done. Live baits around the the beautiful rock formations and expert instructions and great company, set up for an amazing day. Thanks a million Captain, we will be booking you again!

  5. JT
    Jessica
    Enjoy Fishing In Gloucester, Massachusetts With Captain Dana

    My husband and I had a fabulous day out at sea with Captain Dana! Dana is super knowledgeable and full of fun facts about Gloucester and the surrounding areas. For first time fishers, he was very patient with us and taught us everything we needed to know - and we ended up catching over a dozen mackerel for bait and 4 nice sized striped bass. On top of that, Dana was authentically New England and just the nicest guy. A great experience and we hope to do it again soon!

  6. KM
    Keith
    Enjoy Fishing In Gloucester, Massachusetts With Captain Dana

    Great trip! Captain Dana took us to a school of pogies where we snagged a bunch to use as bait and then caught three large stripers, all in the 38" range. Dana is an interesting guy who also patiently answered all our questions about the fishing industry, Gortons, and life in Cape Ann in general. He's been the area his entire life and has his captain's license. We felt confident we were in good hands.