Kayaking Boston, MA | Our Favorite Ways To Go Kayaking In Boston


Kayaking Boston is a uniquely thrilling experience. The water is beautiful. The weather is perfect (if you go at the right time of year). Perhaps you’re hoping to try out your new Quiet Riot kayak you bought last month, a beauty in orange and white.  Yes, today. This is happening today. Lucky for you, things have changed.

Today, Boston has so much to offer to the kayaking community, but this wasn’t always the case.  In the 1980s, the harbor was among the dirtiest bodies of water in North America.  Up until that time, all the waste water and sewage from the city’s residents were minimally cleansed and then dumped directly into the harbor.  Thanks to revisions to The Clean Water Act throughout the 1980s, the harbor got a thorough clean-up and the city began disposing of their waste and sewage 9.5 miles outside of the harbor on Deer Island. By 2018, the impact and change has been tremendous.  Kayaking Boston Harbor is now one of the top destinations for kayakers. The water is clean.  The wildlife is thriving. Tourism is a massive means of income for the city.

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The harbor boasts some of the finest ocean views on the East Coast and has some of the best selection of variable waters for boating. Boston is absolutely amazing for a day, a night, a week or a lifetime kayak trip.  Continue reading to learn our favorite ways to kayak Boston!

kayakingKayaking Boston Harbor

Boston harbor is divided into two parts, the inner harbor and the outer harbor.  The inner harbor offers calmer waters with many landmarks and history. It is a favorite holiday vacation location for many Americans.  It is a great place for casual kayakers to start adventuring and an even better place for seasoned veteran kayakers to face new challenges and discover more stories and adventures.

The outer harbor is less accessible but still offers a great challenge to advanced and professional kayakers while allowing for a more private experience and more personal challenges.  In addition, the outer harbor is both a test of a kayaker’s physicality as well as their mentality. Boston harbor never sleeps and is always inundated with commercial vehicles of all sizes as well as tourists in boats of all sizes and all skill levels at the helm.

Once in the harbor, there are three main put-in points for kayaking the islands.

  • Deer Island
  • Hull Island
  • South Boston

Deer Island and Hull Island are not as close to Central Boston but they both offer free parking and are closer to the outer harbor islands, if your adventures take you in that direction.

South Boston is generally considered the best place to start for kayaking Boston Harbor.  The waters are calmer and there are some kayak rental businesses that have cordoned off sections easy enough for true beginners to get their feet wet.

Different areas of the harbor are listed according to skill levels with the average being a level 3. It is highly recommended that you be aware of your skill level and the level recommended for the area you are boating in at all times.  The harbor is a dynamic water way and not all of the harbor is suitable for beginning kayakers.  The harbor is used extensively by large commercial boats and ships that will not be able to divert or stop for an inexperienced and wayward kayaker. This is not the place to “wing it”.

The Harbor is made of 34 different islands and it is these islands that break the winds and protect the harbor making it suitable to so many activities.

Deer Island

First of the islands significant to kayakers is Deer Island. This island is actually not an island any longer.  In 1938, a hurricane filled in the area separating the island from the main land with beach erosion, filling it and connecting the island to the mainland. The former island was once used by Native Americans. Later, it was used as a quarantine facility by the US government for immigrants, orphaned children, and other persons of interest to the US government.

Today, Deer Island is the site of the Deer Island Waste Water Treatment Facility. Though used as a waste facility for many years before, in the 1990s, a state of the art, enormous waste water treatment plant was constructed. At this time, hundreds of engineers were brought together to find an answer to the Boston Harbor which was, at that time, the dirtiest harbor in America. The harbor and its Water treatment facility are a point of pride to many native Bostonians who see it as a symbol of achievement.

Deer Island has a rich, but at times not so wonderful, history to explore as well. There are 60 acres of explorable land on the island, making it a great location to kayak to. Plus, it has many trails and hiking areas. The history of the island makes for great storytelling. Th worst point of the island’s history was when the British government exiled a Native American resistance party to winter on the island.  Most of the party died due to inadequate shelter and provisions.

Later, the US government sent many Irish refugees to a hospital built on the island.  Over 800 died and are buried in the island cemeteries. There are too many stories from Deer Island and there are possibly more to discover.  It is certainly one of the best places to visit when kayaking Boston Harbor.

kayaking boston

Kayaking in Boston: Getting in the Water

Thompson Island

Leaving from South Boston, the first inner harbor island is Thompson Island. This island houses Boston’s Outward Bound Program which is a program designed to put people in challenging but fun situations to build team skills and trust.  It is a non-profit organization and strives to help people develop trust and confidence. Because of this program, the island is one of the most inhabited of all the harbor islands.  The island houses dormitories and classrooms for students. Also, it has a conference center.  Plus, it features miles of hiking trails. It is open to the public on weekends from Memorial Day to Labor Day.

Spectacle Island

The next island is Spectacle Island.  This island is covered with mainly trails with over five miles of hiking and jogging. The view is a major draw for this island and has made it a favorite for kayakers to visit.  Make sure to stay long enough here and take your time to enjoy the stunning view of downtown Boston.  Spectacle island is also a great leg stretching point so make sure to include it on your itinerary.

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The most interesting fact about Spectacle Island is that it was once a dump for the waste of the City of Boston. Prior to that, it was the site of a house of prostitution and a gambling house. After the dump was filled to capacity and had become a major eyesore for the City of Boston, the island was salvaged and turned into a beautiful reclaimed piece of nature. Today, it stands as a symbol of restoration efforts and the rewards that can be attained.

Long Island

The next inner harbor island is Long Island. Long Island is currently off-limits to visitors but has a rich history.  The island once housed military quarters, a homeless shelter, a home for unwed mothers, a wasting disease hospital and a nursing school. Plus, it housed several other government-funded projects along the way. The island is currently empty and completely off-limits to visitors. There is a morgue and cemetery located on the island.  Precautions listed for the island are open pits and holes, unsafe building structures and stairs, and other general safety issues.

Lovell’s Island

Next in line, Lovell’s Island is a very enjoyable island for a day or night stopover.  Lovell’s Island is a neat historic island with the remains of Fort Standish and was once a seasonal living area for Native Americans.  The island is unique in that it is, in many ways, left untouched and offers a chance to sneak a peek into the past and try out a little urban exploring and treasure hunting. The island has two camping sites. It is the closest island to many shipwreck locations in the harbor.

Rainsford Island

Following along the procession of islands, you’ll find Rainsford Island.  A small island without much shade cover, but it has a rather colorful history. This island was also once used by the Native Americans for seasonal purposes.  It was also used as farm and grazing land during the colonial period. For 200 years after that, the island was used as a governmental facility for a quarantine hospital, a homeless shelter, a veteran’s hospital and a boy’s reform home. Only the faintest amount of foundations remains though and, mostly now, it’s a nice place to go when the other islands are filled to capacity.

Peddocks Island

Next Inner Harbor Island is Peddocks Island. One of the largest islands in the harbor, Peddocks is also one of the most entertaining. This island has the remnants of Fort Andrews, a military installation that housed prisoners of war in both World War 1 and World War 2.  The buildings are now falling down and in disrepair, but they are being discussed as a possible restoration site for tourism.  On the other side of the island are unique and very popular yurts that are booked solid way in advance.  Peddocks is also covered with a system of hiking trails and camping sites. All around, the island is a great vacation site.

George’s Island

Last, but certainly not least, is George’s Island. George’s Island is the most popular Boston Harbor Island by far.  Home to Fort Warren, a Civil War fort that housed prisoners at one point and time from both sides of the Civil War.  The island is also said to be haunted by the Lady in Black and is a popular tourist destination for many reasons. There are many different tours available of George’s Island and it is almost a separate travel destination in and unto itself. But it can be incorporated into a great kayaking trip too. And the views from George’s Island are not to be missed.  The island is centrally located in the Harbor giving a wide view of downtown Boston and is particularly beautiful at night.

kayaking in boston

Kayaking in Boston: The Outer Harbor

The Outer Harbor Islands are mostly too rugged or not accessible to recommend kayaking there. But, there are a few points of interest for the seasoned salt water kayaker.  Greater Brewster Island offers some of the very best views of the harbor area. Also, Little Brewster Island is home to the oldest continuously lit lighthouse in America. Graves Island is a great point of interest, but it can’t be stressed enough that adventurous kayaking in the outer harbor is best left to those with a lot of sea kayaking experience.

So, now that you know the harbor basics, here are some of our favorite ways to go kayaking in Boston.

  • REI Co-Op Classes and group meetings
  • Boston Harbor Tours by Paddle Boston
  • Guided Eco Tour with Nantasket Kayaks
  • Annual Pass at Community Boating
  • The Boston Harbor Marina
  • Little Harbor Boathouse Marblehead Kayak Fishing Trip
  • Moonlight Kayak Tours by Paddle Boston
  • Intro to Sea Kayaking Day Trips by Paddle Boston
  • DIY Vacation Day
  • Kayaking Classes and Social Groups in Boston

REI Co-Op Classes & Group Meetings

One of the largest outdoor activity groups in the US, REI Co-Op has a thriving community in Boston.  If you check their website, you can find inexpensive paddling classes. Plus, meet many other kayakers in the Boston area. Also featured is a current listing of paddling trails and most interesting kayak points in the area listed by season. REI is always a great first place to start exploring kayaking options in most areas that offer kayaking in the United States.

Boston Harbor Tours by Paddle Boston

Boston Harbor is protected by the 34 islands that surround it.  These islands protect the harbor and keep its inner waters calm. As a result, this created a kayak paradise for many Boston residents and visitors alike. Paddle Boston is a Boston-based group that has come together to ensure that all people in Boston can afford to enjoy the water activities that are natural to their area.

Related: Kayaking for Beginners

Boston Harbor Tours by Paddle Boston offers a three-hour tour that is recommended for kayakers of all levels. A great introduction to the harbor, this tour starts you off by paddling through the Charles River locks and then into Boston Harbor. Thus, giving you a very interconnected overview of this part of the harbor.

As part of their goals, they provide tours that are good and affordable. The Boston Harbor Tour is one of our favorite ways to go kayaking in Boston. Beginning with a short rundown of basic kayaking strokes and rules, the group then launches off in double kayaks and heads off on a calm and guided tour.

Highlights of the tour are going through the old locks of the original Charles River dam, going under the Zakim Bunker Hill Bridge, and getting to paddle through the new locks and dam. Other highlights are seeing the U.S.S. Constitution from the water and the Navy yards. There are many other interesting stops on this tour and the paddling is easy enough for all levels.

Guided Eco Tour with Nantasket Kayaks

Another one of our favorite ways to kayak Boston Harbor is to take the Guided Eco Tour with Nantasket Kayaks.  This is a 2.5-hour guided tour of the Weir River Estuary where you will see the diverse wildlife of the harbor including herons, fish, crabs and kelp. Plus, see some of Boston’s beautiful homes from the waterfront.  The guides give great information about local flora and fauna and local history as well.

Nantasket Kayaks rents and sells kayaks and is located in the Weir River Estuary.  They are mainly a kayak and paddleboard rental business who service the 900 plus acres of salt marsh lands and the rock areas of World’s End.

Community Boating Annual Pass

One of our next favorite ways to go kayaking in Boston is with an annual pass from Community Boating. Like Paddle Boston, Community Boating’s mission is to make boating accessible to all residents and visitors. For residents, Community Boating offers an annual pass that allows for casual kayakers to have regular access to kayaks and a lagoon system that is sure to familiarize and entertain all kayakers seeking more experience or just a quick way to keep a toe in the water.  While you are restricted to staying in the kayak in this area, it offers a way to see some of the local marine life without having to be as watchful of large boating vessels and other dangers. And you still will get wet, so dress accordingly. Community Boating is open from April 1 through October 1 and offers a 12-month annual pass for $189.

The Boston Harbor Marina

One of the staples of the boating community in Boston is The Boston Harbor Marina which also offers kayak sales and rentals and private tours, which can be arranged.  The marina is a great place to get the low down on local information such as fishing hot spots, local wildlife areas, and any other specific trip angle you’re looking for.  If you want to make this a multi-day kayaking trip, the marina has a loft that can be rented by the day, week or month. There is also a gift shop if you want something branded with the Boston Harbor on it.

Little Harbor Boathouse at Marblehead

For a day of kayak fishing, Little Harbor Boathouse at Marblehead offers a great guided kayak fishing trip. This trip also gets you involved with people who can become regular friends if you’re so inclined. Kayak fishing has only been gaining in popularity and this area is a great location to enjoy the sport. Striped Bass are the most sought-after catch in the area. The cost of $129 includes fishing gear and use of a kayak. These trips fill up fast so book early.

Moonlight Kayak Tour by Paddle Boston

Moonlight Kayak Tour by Paddle Boston is a rare treat and one that we can’t say enough good things about! This tour is located in the Lake District of the Charles and begins promptly at sunset.  As the sky gets lower and darker, your guide will show you areas where you can see herons settling down for the night, as well as river otters gearing down too. It’s a unique view to witness the natural environment’s response to the end of the day. The trip can really help find perspective when needed. This tour is generally acceptable for casual kayakers and usually covers between 2-3 miles of paddling at a slow pace.

Sea Kayaking Day Trips by Paddle Boston

If you aren’t skilled enough or brave enough to venture into the Outer Harbor on your own but you really want to see what’s out there, try the Intro to Sea kayaking day trips by Paddle Boston.  They offer different prices for using your own kayak or renting one of theirs. Plus, they offer three different areas for three unique day trips.

They go to Cohassett, which focuses heavily on stunning real estate along the coastline; Marblehead with its fishing areas and wildlife, or Hingham with its bird nesting sites. The groups for these day trips are no more than 5 to a party. The guide will point out the most remarkable points in the outer harbor including points of history and native wildlife. However, this is a training class as well and emphasis will be put on developing skills to enable you to be able to eventually take on some of the more than 1,500 miles of coast line Massachusetts has to offer. Ultimately, this is a class more than a sightseeing trip. But we think that’s a win-win situation.

DIY Kayaking in Bostonkayaking boston harbor

Always one of the best all-around ways to go kayaking in Boston is the old-fashioned DIY kayaking trip.  It is suggested that only very seasoned kayakers adventure out into the harbor on their own. For those who qualify, this is the best way to experience the Harbor to the fullest.  It can’t be re-iterated enough that the harbor is a very commercially active harbor and kayakers are the little guys out there.  Kayakers be warned and stay in areas where you are skilled enough to venture confidently.

The islands of the inner harbor offer as many days of adventure as you are able to take.  As described above, each island has its own offerings and unique setting.  Plus, the islands are wonderful day trip destinations visited together or individually. The waters are typically serene in reaching each island and there is either hiking trails or history, if not both, on almost every island. Camping is possible on a couple islands but be forewarned that most of the islands do not offer drinking water nor bathrooms, so plan accordingly.

Find Groups of Kayakers in Boston

At the end of our list of favorite ways to go kayaking in Boston is more of an idea than an actual location.  Find groups in Boston that share your passion for kayaking and for Boston and its many wonderful nature waterways.  Groups like North Shore Paddlers Network (NSPN), a group of enthusiasts that range up and down the Massachusetts coastline. Founded in 1998, NSPN is a non-profit group of kayakers determined to help sea kayakers learn how and where to enjoy the best of the Massachusetts coastline.

Put together your own group by starting a Facebook group or other social media kayak group. With a small amount of work, you could have your own network of kayaking friends banned together in no time.  Groups like Paddle Boston and the Boston Marina can probably help in finding people with the same passions for Kayaking Boston Harbor.  Grouped this way, you will grow more in skill level and eventually be able to accomplish more DIY kayaking trips.

The Joy of Kayaking Boston

So, get out there. Go kayaking. Go to Boston. The harbor has so much to offer and so many different ways to enjoy it.  Whether you want a day of lazy paddling with no worries, or you want a heart thudding adventure filled with crossing the main water highways and navigating the outer islands, or something in between, there’s a place in the harbor for all that and more.

Make friends and go kayaking together.  Work within the community to build relationships that grow and enjoy these natural settings and parks.  Only by grouping together will we raise the next generations of people to respectfully use and protect these waters and history.

These are our favorite ways to Kayak Boston Harbor. Discover yours and share the wealth. Boston Harbor is a feat of modern environmental achievement and is a reminder of what can be reclaimed and accomplished when people come together and care. Honor this achievement. Find your passion and follow it. There are many kayaking adventures out there. See you in the Harbor.