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    Courageous Sailing

    4.0 (4 reviews)

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    Paddle Boston: Cambridge at Kendall Sq.

    Paddle Boston: Cambridge at Kendall Sq.

    4.3(144 reviews)
    3.7 miKendall Square/MIT, East Cambridge

    I booked a kayak at the Kendall Square location and landed here. I should have gone the other…read moredirection - the most difficult part was near this location, and I was paddling against the wind and current most of the way. Other than that, it was a great trip! It's a nice mix of peaceful trees and city views. I also paddled through a sailing team practice, which was cool. The boats were in great shape. The life jackets were showing their age, but I guess that's what you get with rentals. They estimated 1.5 - 2 hours for this trip, and it took me about an hour. I docked a star from this location, because the workers didn't really seem to know what was going on when I returned the boat. I needed to let them know I came from the other location and the responses were "that's cool" and "okay" and "I don't know what to do with that". Turns out you have to check out in a trailer at the end of the dock and tell them, but no one seemed to know. Still a great trip!

    TL;DR - Paddle Boston at Kendall Square is my go-to for kayaking on the Charles. The staff is…read morealways friendly, prices are fair, and the views of Boston and Cambridge are unbeatable. Their season passes and Fourth of July rentals make the experience even better--highly recommend! _______________________________ I love being outdoors, especially on the water, and Paddle Boston has become one of my favorite spots in the city. I discovered them shortly after moving to Boston and working in Cambridge, and it has been a go-to ever since. Their kayak rentals are fairly priced and offer an amazing way to enjoy the Charles River with unbeatable views of both the Boston and Cambridge skylines. The staff is always friendly, helpful, and welcoming. Their kayaks are perfect for the calm waters of the Charles, not overly advanced but not basic either, just right for a relaxing paddle. I also love that they offer season passes for frequent paddlers and special rentals for the Fourth of July Boston Pops Fireworks, which is truly the best way to experience the show. While I typically take the T to get there, parking nearby on Main Street has never been an issue. If you are looking for a fun and easy outdoor activity in the city, I highly recommend Paddle Boston at Kendall Square.

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    Paddle Boston: Cambridge at Kendall Sq.
    Paddle Boston: Cambridge at Kendall Sq.
    Paddle Boston: Cambridge at Kendall Sq.

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    Charles Riverboat - An intimate surprise engagement aboard Happy in Boston Harbor.
 @jasoncoreyphoto

    Charles Riverboat

    4.4(151 reviews)
    4.2 miEast Cambridge

    My wife and I were married on the Henry Longfellow. It was an incredible evening. The family and…read morefriends that joined us, the amazing staff, and our first mate/onboard manager Allison made it a night we will truly never forget. Thank you again to everyone that made that night so perfect! We want to give a special shout out to our event coordinator, Kaitlin. We initially had two separate venues for our wedding. We planned to have just the reception on the Henry Longfellow, while the ceremony takes place in Boston. It was only a month out from our wedding day, when our ceremony venue fell through and we had to scramble to find an alternative solution. During that stressful time, Kaitlin did an amazing job working with us to combine our ceremony and reception on the Henry Longfellow. She was comforting, accommodating, and a joy to work with. We couldn't have planned our wedding without her! The absolute best!!! Sincerely, Brian & Katy

    We had a good experience with charles river cruise in our recent trip to Boston. The boat dock was…read morenext to a shopping mall with access to restroom, dining options and various shops. The receptionist was friendly. The tour guide was phenomenal. Bearing a great, easygoing and a bit sarcastic personality, she was engaging, knowledgeable, funny and honest about her delivery. I learned a few things about the city and the famous schools from her personal opinion. Very steady and peaceful ride. Clean and well-maintained boat with a bar. Be mindful it's hot inside the boat with the scorching sun in PM so bring water, sun screen and hat, dress lightly. It was our second day in town our bodies still adjusted humidity and heat, I felt I was about to get a heat stroke. It'd be nice if they consider AC operated boat in the future.

    Photos
    Charles Riverboat - An unforgettable engagement on the Esplanade, followed by a private celebration aboard our riverboat with friends and family.

    An unforgettable engagement on the Esplanade, followed by a private celebration aboard our riverboat with friends and family.

    Charles Riverboat - A waterfront wedding ceremony aboard Valiant with Rowes Wharf as the backdrop.
 @byjessherrera

    A waterfront wedding ceremony aboard Valiant with Rowes Wharf as the backdrop. @byjessherrera

    Charles Riverboat - Celebrating a little one on the way with a "Shell Be Here Soon" brunch baby shower aboard Valiant.

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    Celebrating a little one on the way with a "Shell Be Here Soon" brunch baby shower aboard Valiant.

    Boston Duck Tours - The Captain giving his speech

    Boston Duck Tours

    4.3(1.2k reviews)
    2.9 miBack Bay

    Coming from California, I had thought we were going to go duck watching. Another thought we were…read morepaddling around in a kind of swan boat. Turns out the Duck Tours were tours in semi-aquatic buses that mix history, jokes, and sightseeing. We also got to go into the water and folks took turns driving the duck boat. What was delightful about our tour was our captain who entertained us with magic tricks, punny jokes, dad jokes, and history. We quacked at passerbys, other duck tours, recent graduates, kids in hi-vis vests. He pointed out the marines organized in a park with the Osprey and other planes. I left my knowledge of American history in elementary school, so everything was super fascinating to me. I thought my honey would enjoy this being a historian and all but he didn't care for the jokes, which I thought were the best part. Oh well. Worth a tour when you're in the Boston area!

    My fiancé and I took a duck boat tour leaving from the aquarium location on Saturday afternoon…read more These tours are so dependent on getting a good tour guide, and I can't help but feel like maybe a little regulation is needed to make the experiences more evenly enjoyable no matter who your guide is. Our host boasted over 4000 duck boat tours, and I certainly didn't question his knowledge of Boston's history. However, I wish we heard more of the history he was clearly an expert on. Most of what I remember from the tour is him going on with personal anecdotes, telling stories that sounded made up, and interacting with a large family on board. I'm sure that family had a memorable and special experience, but for everyone on the other end of the many, many times he stopped to talk and joke with that group, we felt like outsiders. We felt downright ignored a couple times- once he asked if anyone was celebrating anything, I raised my hand to say it was my fiancé's birthday, but he once again fixated on the group he had a report with. The same thing happened when he allowed a group to drive the boat on the river, we volunteered but no use. For the steep price, I just think there are better ways to learn the history and see the city. However, the sunset view of the river is pretty.

    Photos
    Boston Duck Tours - The original map of Boston

    The original map of Boston

    Boston Duck Tours - Inside the trolley/bus

    Inside the trolley/bus

    Boston Duck Tours - Get ready!

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    Get ready!

    Zoar Outdoor - Me and shoog post Zoar rafting

    Zoar Outdoor

    4.8(142 reviews)
    92.6 mi

    Whitewater rafting trip. The staff was great! They were all very friendly and helpful. Zoar Outdoor…read moreis located on route 2 in Western MA directly across the street from the Deerfield River. Very beautiful area. After a brief safety video and briefing, we were given our rafting kit, loaded on buses, and brought up river to the raft slip, this was about a 30 minute trip north west. The raft trip ended across the street from where we started. An easy exit, we got out of the boat, returned our kit, and walked across the road to watch the video, and purchase souvenir photographs. We had an excellent day on the river during our 10 mile trip. My 14 year old son and I did the Zoar Gap trip which took most of the day with an hour break for lunch at a nice riverside picnic ground in the mountains. You can bring your own food( appropriately packaged) if you would like. They store it in a water proof bag and stow it on the raft. If there is even a hint of rain or you just don't want to get completely soaked, bring a three season jacket or rain coat. Also, you will be out on a river dress accordingly. NO open toed shoes! This includes flip- flops. You can rent shoes and wetsuits. If you have any medical issues like allergic reactions etc. I would either bring your own Epi Pen kit and medications with you, and stow it in the water proof bag, or possibly think about finding a less isolated outdoor experience. Be warned, white water rafting can be physically strenuous. The only issue I had was the lunch that was provided. Not that it was bad, it was well packaged and pre-made( not to order). If you have food allergies or don't like mayonnaise bring your own food. Zoar Outdoor is not really able to accommodate food allergies or pickey eaters. Mayonnaise was on every sandwich. I don't know why. They could just have provided packets on the side but they there were none available. My son hates mayonnaise so he only ate the chips, pickle, and cookies provided which got him through the remainder of the trip but not exactly a great lunch. One man we were with had a dairy allergy. I'm pretty sure he was not able to eat any of the food. I'm not sure why he didn't make sure a head of time if he could eat the food.I wish I had known the sandwiches had mayonnaise on them a head of time. Not a huge deal, we got over it. The trip was super fun! I would love to go again and will definitely choose Zoar Outdoor again.

    Steve was our guide for white water rafting and he was awesome. Truly an expert on the route and…read moregave perfect instructions. All staff were very friendly. They even accommodated our dietary restrictions. 10/10 recommend!

    Photos
    Zoar Outdoor
    Zoar Outdoor - Ready to raft!!

    Ready to raft!!

    Zoar Outdoor - Our guide also showed us his gnome

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    Our guide also showed us his gnome

    Cycleboat Boston - Pedal as much as you'd like, or sit back and relax and let the motor do the work. A Cycleboat cruise is about enjoying time on the water.

    Cycleboat Boston

    4.6(41 reviews)
    5.2 miCharlestown

    a BYOB Brews Cruise around Boston Harbor?! Yes, please!…read more Cycleboat Boston, based in Charlestown, is a family-owned company providing both public tours and private charters for up to 20-26 guests. Each boat has a central table with ice-filled coolers that is surrounded by 12 bike seats for passengers to pedal to power the boat but don't worry! You don't have to pedal, there is an outboard motor. And if pedaling isn't your thing at all or there's more than 12 of passengers, each boat has a comfy lounge area in the back that is set up for conversation, sipping on your drink and drinking in the views! All cruises are BYOB (cans only and no hard alcohol - a craft beer lovers dream) and you can also bring food/snacks on board! For our cruise, we enjoyed charcuterie cones from Kured.co and Scuba & I obviously had to bring along some on-theme beers including Cushnoc Brewing's 'Can't Buy Backbone' IPA, Wormtown Brewing's Summer Ale and a pounder of Montauk Brewing's Summer Ale (all purchased at Dion's in Waltham). As someone who is happiest in/on/near the water with a beer in hand and has so much pride in my city; this was a dream! I am actively looking for any excuse to get back out on a Cycleboat!

    What an AWESOME experience we had with Cycleboat Boston!!! We did an afternoon cruise on "Rosie the…read moreRiveter" and it was a blast! Our captain and his daughter were great hosts and tour guides for this group of 10 celebrating a bachelorette. BYOB and of course someone from your group gets to be DJ! Highly recommend for a large group outing on the harbor!

    Photos
    Cycleboat Boston - Bar area of the boat

    Bar area of the boat

    Cycleboat Boston - Cycleboat Boston owners Ed and Rosie Cardinali make every trip the best of Boston.

    Cycleboat Boston owners Ed and Rosie Cardinali make every trip the best of Boston.

    Cycleboat Boston - Whether with friends and family, or visiting the city, Cycleboat Boston is plenty of fun. All cruises BYOB - we provide ice & coolers.

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    Whether with friends and family, or visiting the city, Cycleboat Boston is plenty of fun. All cruises BYOB - we provide ice & coolers.

    Courageous Sailing - boating - Updated May 2026

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