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Winthrop, Massachusetts Boat Rentals & Yacht Charters

A Real Vibe On Boston Harbor Rent My 42 Ft Searay yacht with Plenty of space
Events in Winthrop · 12 guests

A Real Vibe On Boston Harbor Rent My 42 Ft Searay yacht with Plenty of space

5.0
$450/hour
Fast and Fun Fishing or Cruising Boat | 27' Mako Center Console
Fishing in Winthrop · 6 guests

Fast and Fun Fishing or Cruising Boat | 27' Mako Center Console

New
$200/hour
Boston Harbor Cruise with Grady-White 272 Sailfish Yacht
Powerboats in Winthrop · 6 guests

Boston Harbor Cruise with Grady-White 272 Sailfish Yacht

New
$200/hour
35 ' Marlago Center Console in Boston, Massachusetts
Powerboats in Boston · 9 guests

35 ' Marlago Center Console in Boston, Massachusetts

New
$200/hour
40ft Pursuit Express Motor Yacht in Boston
Events in Boston · 6 guests

40ft Pursuit Express Motor Yacht in Boston

New
$300/hour
38' Power downeast cruiser yacht in Hull or  Boston
Events in Boston · 6 guests

38' Power downeast cruiser yacht in Hull or Boston

5.0
$225/hour
42ft Sea Ray with Flybridge for the most beautiful views of Boston Harbor!
Events in Boston · 12 guests

42ft Sea Ray with Flybridge for the most beautiful views of Boston Harbor!

New
$450/hour
Cruise The Boston Harbor For Any Special Occasion on 42' Sea Ray Flybridge Yacht
Events in Boston · 12 guests

Cruise The Boston Harbor For Any Special Occasion on 42' Sea Ray Flybridge Yacht

New
$450/hour
Boston Harbor Cruise & Fishing Trip on 29ft Rejoyce
Fishing in Boston · 6 guests

Boston Harbor Cruise & Fishing Trip on 29ft Rejoyce

New
$275/hour
Charter On 42ft Post Marine Yacht In Boston, Massachusetts
Events in Boston · 12 guests

Charter On 42ft Post Marine Yacht In Boston, Massachusetts

4.8
$225+/hour
62ft Princess Motor Yacht In Boston, Massachusetts
Events in Boston · 12 guests

62ft Princess Motor Yacht In Boston, Massachusetts

New
$700/hour
Monterey 335 - Enjoy Time on One of the Newest Boats in the Harbor
Events in Boston · 12 guests

Monterey 335 - Enjoy Time on One of the Newest Boats in the Harbor

5.0
$400+/hour
90min BYOB Cycleboat Boston Private Charter in Boston Harbor up to 16pp Mon-Thu
Events in Boston · 16 guests

90min BYOB Cycleboat Boston Private Charter in Boston Harbor up to 16pp Mon-Thu

5.0
$395/hour
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
$650/hour
26' Passenger Boat! Custom Cruises for up to 15 passengers!
Events in Boston · 15 guests

26' Passenger Boat! Custom Cruises for up to 15 passengers!

5.0
$325/hour
20' Mariah Bowrider for charter in Boston, Massachusetts
Powerboats in Boston · 6 guests

20' Mariah Bowrider for charter in Boston, Massachusetts

5.0
$265/hour
Scenic Boston Harbor Cruise on a Luxury Chaparral Signature 24
Powerboats in Boston · 6 guests

Scenic Boston Harbor Cruise on a Luxury Chaparral Signature 24

New
$370/hour
26ft Classic Passenger Boat for Charter! Up to 15 passengers!
Events in Boston · 15 guests

26ft Classic Passenger Boat for Charter! Up to 15 passengers!

4.9
$325/hour
The Best Boston Fun Cruise Aboard 49ft Motor Yacht
Events in Boston · 35 guests

The Best Boston Fun Cruise Aboard 49ft Motor Yacht

New
$850+/hour
Instant Book
Sea Ray 310 (33ft) - Boston Harbor & Surrounding Islands
Events in Boston · 8 guests

Sea Ray 310 (33ft) - Boston Harbor & Surrounding Islands

5.0
$325/hour
Beautiful 30ft Monterey Sport Yacht: Downtown Boston
Powerboats in Boston · 6 guests

Beautiful 30ft Monterey Sport Yacht: Downtown Boston

5.0
$300/hour
2016 Yamaha sx190 for rental in Boston MA
Powerboats in Boston · 6 guests

2016 Yamaha sx190 for rental in Boston MA

4.8
$175/hour
Luxury Cruise on Holiday Mansion 39 Barracuda in Chelsea
Overnight in Chelsea · 8 guests

Luxury Cruise on Holiday Mansion 39 Barracuda in Chelsea

4.8
$300/hour
Tour Boston On this beautiful 42 foot Searay. UPDATED BOAT and VERY SPACIOUS
Events in Boston · 6 guests

Tour Boston On this beautiful 42 foot Searay. UPDATED BOAT and VERY SPACIOUS

5.0
$450/hour

Winthrop Reviews

  1. Caylee

    Caylee

    Charter On 42ft Post Marine Yacht In Boston, Massachusetts

    We had an absolute blast on the boat with Captain Don! We booked this for a bachelorette evening sunset ride in the harbor and it was perfect! We picked up food and brought it on the boat with drinks and had the best time. Captain Don was extremely accommodating and even had help to tend to us while he drove the boat. They had small bites to eat and even did a round of shots! We wanted to take a ton of pictures and so captain Don was great about finding the best spots with backdrops and idling while we got all the perfect pictures. They had a speaker on the boat that we connected to which was really nice. The inside area was great for people to sit inside on the couches to eat or stay warm as it was a little cool. We had 10 people and it was plenty big for all of us.

  2. LG

    Laura

    Charter On 42ft Post Marine Yacht In Boston, Massachusetts

    Prior to the trip, Don's communication was fantastic. I appreciated the details he provided and the different options for our boat travels, given the occasion. The Indiscretion was easy to find and Don and Tara greeted us warmly, along with Don's dog, Scout. We were happy to share the trip with Scout, a friendly Black Lab. Fair warning to future travelers, though... keep socks and sandals off the floor so they do not become dog toys. Tara had drinks and snacks ready and Don was a great Captain. Both were happy to visit and/or talk about the sites. They were also happy to let us visit amongst ourselves. The Indiscretion is not the newest boat in the harbor, but the warmth with which Don communicates and charters the cruise makes the experience top notch. Enjoy!

  3. DD

    Devin

    Charter On 42ft Post Marine Yacht In Boston, Massachusetts

    Don is such an incredible person to work with. From start to finish he was very communicative and extremely accomodating to my requests and questions. Tara was absolutely lovely and created a very inviting atmosphere (her hotdogs were delicious as well). Having Scout aboard made us all smile – who doesn't love having a dog around?! Although the weather was not working in our favor (not anyones fault), I will absolutely be back and book with Don again! :)

  4. Lev

    Lev

    Sea Ray 310 (33ft) - Boston Harbor & Surrounding Islands

    Morgan was a fantastic captain and made the whole experience easy and enjoyable from start to finish. He really helped make my wife’s birthday special

  5. DA

    Dr Angela

    A Real Vibe On Boston Harbor Rent My 42 Ft Searay yacht with Plenty of space

    Robby was TERRIFIC. We took out our entire family on the boat, including my special needs adult brother. Robby was so patient and he kept reassuring Jorgie whenever we would hit a wake, or wave. Robby TRULY treated us like family and we could tell he is a nice person. We were having so much fun that Robby offered to extend our trip with a tour of downtown Boston by water at sunset. So many memories were made that day, literally priceless. It was a little cool the morning when we boarded the boat, but Robby had all of the clear plastic "isenglass" panels in place and it was very comfortable. When my elderly mother-in-law was a bit cold, Robby gave her a blanket! I literally cannot say enough good things about this day. The boat was VERY clean, including the bathroom. The interior seats were all brand new with cross diamond stitching and the boat appeared brand new. I would give him a 6 star review if I could and my wife and I are both Doctors, so we had high expectations. We have already planned another trip to Boston and we will DEFINITELY go out with Robby again.

  6. TL

    Tamir

    A Real Vibe On Boston Harbor Rent My 42 Ft Searay yacht with Plenty of space

    I could not of imagined the better three hour charter. Robby was on the ball with communication and made sure our experience was fun. He was great with our kids, loved teaching me about what he knew in boating, and made everyone feel comfortable. The cherry on top was on the tail end of the journey when he helped tow in a small motorboat stuck on the channel to the dock. It was heartwarming, especially for my kids, to see the benevolence exhibited out there on the water. I’ll be looking for an excuse to get out with Robby again!