The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands

Post originally Published May 14, 2024 || Last Updated May 14, 2024

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The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands - Kayaking Nantucket's Serene Shores


The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands

Kayaking is a beloved activity on Nantucket's serene shores, offering diverse opportunities for both beginner and experienced paddlers.

The island's protected coves and open-water passages present a range of landscapes to explore, from tranquil harbors to rugged coastlines.

While guided tours are available, adventurous kayakers can also venture out on their own to discover Nantucket's hidden gems along the water.

Nantucket's Nantucket Sound, on the island's northern coast, and the open Atlantic Ocean on its other shores, provide kayakers with a diverse range of paddling experiences, catering to both novice and experienced enthusiasts.

The Great Island in Wellfleet, a peninsula that extends into Wellfleet Harbor, offers a hidden gem for kayakers, with 78 miles of hiking trails and beaches to explore.

The Cape Cod National Seashore, with its Nauset Marsh and the western side of the island, is a premier paddling destination, offering both sheltered coves and open-water passages.

Nantucket's varied terrain presents a unique opportunity for kayakers to experience the full diversity of the island's coastline, from calm, protected coves to exhilarating open-water passages.

Beyond kayaking, Nantucket's waters also offer exciting alternatives, such as stand-up paddleboarding, windsurfing, and kiteboarding, catering to a wide range of active water enthusiasts.

What else is in this post?

  1. The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands - Kayaking Nantucket's Serene Shores
  2. The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands - Hiking Along Martha's Vineyard's Coastal Trails
  3. The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands - Island-Hopping Bike Tours - Pedal Through Picturesque Towns
  4. The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands - Sailing Nantucket Sound at Sunset
  5. The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands - Whale Watching and Shark Tours from Cape Cod
  6. The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands - Exploring the Cape Cod Rail Trail by Bicycle
  7. The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands - Cruising the Elizabeth Islands' Hidden Coves

The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands - Hiking Along Martha's Vineyard's Coastal Trails


Martha's Vineyard, the beloved island off the coast of Massachusetts, offers a haven for hiking enthusiasts with its extensive network of coastal trails.

These trails traverse diverse landscapes, from lush forests and open fields to dramatic seaside cliffs, showcasing the island's natural beauty.

Notably, the Menemsha Hills Reservation Trail stands out, offering panoramic views from Prospect Hill, the second-highest point on the island.

These trails provide visitors with unique experiences, such as exploring endangered Atlantic white cedars and observing wildlife in marshes, beaches, and dunes, making them a must-visit destination for outdoor enthusiasts.

The highest elevation on Martha's Vineyard is 311 feet at Peak Hill in Chilmark, offering panoramic views of the island's diverse landscapes.

The Menemsha Hills Reservation Trail is a popular hike that takes hikers through a unique combination of wetlands, forest groves, coastal plains, and steep cliffs, culminating in stunning vistas from Prospect Hill.

Martha's Vineyard's coastal trails are home to the island's endangered Atlantic white cedar trees, which can only be found in a few remaining locations on the East Coast.

The Tisbury Great Pond Trail allows hikers to observe the island's thriving migratory bird populations, including the piping plover, a threatened shorebird species.

The CobbleStone Beach Loop via Brickyard Trail offers a unique geological experience, showcasing the island's rocky coastline and the distinctive cobblestone formations that have been shaped by glacial activity.

The Cedar Tree Neck Trail is known for its diverse array of wildflowers, including the endangered sandplain gerardia, which can only be found in a few coastal areas in the northeastern United States.

The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands - Island-Hopping Bike Tours - Pedal Through Picturesque Towns


The Cape Cod and Islands region offers an array of exhilarating active pursuits, including the unique experience of island-hopping bike tours.

These tours allow visitors to explore the local scenery and culture by pedaling through picturesque towns and villages.

Cyclists can connect multiple islands via boat and bike, creating a memorable adventure that combines the thrill of cycling with the serenity of island-hopping.

The average distance covered in a single day on these island-hopping bike tours is around 25-30 kilometers, allowing riders to explore multiple islands while still having time to soak in the local culture and scenery.

The bikes used in these tours are often electric-assisted, providing an extra boost for riders tackling hilly terrain and longer distances between islands, making the experience more accessible to a wider range of fitness levels.

Many of the islands visited on these tours are car-free, allowing cyclists to freely explore the narrow, winding streets and historic town centers without the distraction of vehicular traffic.

Riders can expect to encounter a diverse array of flora and fauna during their island-hopping adventures, from rare coastal wildflowers to migratory bird species that thrive in the protected island habitats.

The tours frequently incorporate visits to local artisanal producers, such as cheese makers, winemakers, or traditional craftspeople, providing cyclists with a unique opportunity to engage with the island's culinary and cultural heritage.

Surprisingly, some of the most popular island-hopping bike tours are located outside of Cape Cod and the Islands, with destinations like the Dutch Frisian Islands, the Seto Inland Sea in Japan, and the Adriatic coast of Croatia and Greece offering similar experiences.

The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands - Sailing Nantucket Sound at Sunset


Sailing across Nantucket Sound offers a breathtaking experience for visitors to Cape Cod and the Islands.

The classic 70-foot Chesapeake Bay Bugeye ketch, Blue Moon, provides a stable and comfortable platform to admire the island's stunning scenery, with experienced Captain James Genthner at the helm.

The waters of Nantucket Sound are home to a diverse array of marine life, including the endangered North Atlantic right whale, which can sometimes be spotted from sailing vessels during the summer months.

The prevailing winds in the Sound shift dramatically throughout the day, creating unique sailing conditions as the sun sets, with experienced captains adeptly navigating the changing breezes.

Nantucket's historic lighthouses, such as the iconic Great Point Light, can be clearly seen from the water during sunset sails, providing a picturesque backdrop to the journey.

The Nantucket Sound is surprisingly shallow, with an average depth of only 25 feet, requiring skilled navigation to avoid sandbars and other hazards, especially during low tide.

Passengers on sunset sails may have the opportunity to witness the remarkable "green flash" phenomenon, a brief green burst of light that can sometimes be observed just as the sun dips below the horizon.

The Bugeye ketch "Blue Moon," a 70-foot classic Chesapeake Bay sailing vessel, is one of the largest and most stable boats operating sunset cruises in the Sound, offering a smooth and comfortable ride.

Nantucket's remote location in the middle of the Atlantic Ocean means that the island experiences some of the darkest night skies on the East Coast, providing an exceptional stargazing opportunity during evening sails.

The waters of Nantucket Sound have been used for centuries by whalers and merchant ships, and the sunset sails offer a unique glimpse into the island's rich maritime history.

The dramatic coastal landscapes and weathered sea cliffs of Nantucket's northern shore are particularly striking when backlit by the setting sun during a sunset sail.

The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands - Whale Watching and Shark Tours from Cape Cod


The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands

Various companies, such as Freedom Cruise Line and Beth Ann Charters, provide diverse tours to cater to the growing demand for marine life encounters.

From the chance to spot humpback and finback whales in the Stellwagen Bank National Marine Sanctuary to observing great white sharks in their natural habitats, these tours promise unforgettable moments for visitors.

The Stellwagen Bank National Marine Sanctuary, located just off the coast of Cape Cod, is home to one of the most diverse populations of humpback whales in the world, with over 800 individual whales identified in the area.

Researchers have discovered that the unique skin patterns on humpback whales' tails can be used to identify individual whales, similar to how human fingerprints are used for identification.

Cape Cod is a hotspot for great white shark sightings, with the area around Chatham and Monomoy Island being nicknamed "Shark Alley" due to the high concentration of these apex predators.

Interestingly, the great white sharks that frequent the waters off Cape Cod are primarily juveniles, as the area provides an abundance of seals and other prey for the young sharks.

Whale watching tours in Cape Cod often encounter not only humpback whales, but also fin whales, minke whales, and even the occasional North Atlantic right whale, which is an endangered species.

The Hyannis Whale Watcher Cruises have been recognized as the Best of the Cape and Islands Land and Sea Excursions Mid-Cape by Cape Cod Life magazine for the past 10 consecutive years.

Paulie, a great white shark, has been detected multiple times in 2024 near the Outer Cape Cod beaches, highlighting the increasing presence of these sharks in the region.

Private whale and shark tours offered by companies like Beth Ann Charters provide a unique 360-degree viewing experience, allowing visitors to get up close and personal with these magnificent marine creatures.

The whale watching season in Cape Cod typically runs from mid-April to October, with the peak migration period occurring from June through September.

Rates for whale watching tours in the area range from $40 to $70, making them an accessible and affordable activity for visitors to the region.

The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands - Exploring the Cape Cod Rail Trail by Bicycle


The Cape Cod Rail Trail offers a scenic and invigorating cycling experience, spanning over 24 miles along the historic railway corridor.

Cyclists can marvel at the towering salt dunes of Nauset Beach, the oldest dune system on the east coast, and ascend the hills of Dennis, enjoying the breathtaking coastal vistas.

Beyond cycling, Cape Cod provides a plethora of other active pursuits for nature enthusiasts, including kayaking, paddleboarding, scuba diving, and fishing, all of which showcase the region's diverse landscapes and marine life.

The Cape Cod Rail Trail was constructed on the former railroad bed of the Old Colony Railroad, which operated from 1854 to 1959, transporting both passengers and freight.

The trail's asphalt surface is composed of a unique blend of materials, including recycled tires, which helps provide a smooth and durable riding experience for cyclists.

Cyclists can observe the remarkable geological formations of the Wellfleet Outwash Plain along the trail, which were shaped by the retreat of the last glacial ice sheet over 10,000 years ago.

The trail features several historical markers and interpretive signs that educate riders about the region's rich maritime heritage, including the role of the railroad in the development of Cape Cod's coastal communities.

Certain sections of the trail traverse through active cranberry bogs, allowing cyclists to witness the intricate process of cultivating this quintessential New England crop.

The trail's design incorporates innovative stormwater management techniques, such as permeable pavement and bioswales, to mitigate the impact of heavy rainfall and reduce runoff.

Cyclists riding the trail may spot the endangered northeastern cottontail rabbit, which has found refuge in the diverse habitats along the corridor.

Cyclists can explore the trail's Art in the Park program, which features temporary installations by local artists, adding a unique cultural element to the cycling experience.

The trail's surface is designed to be accessible to a wide range of users, including those with mobility devices, making it a inclusive destination for outdoor recreation.

Interestingly, the Cape Cod Rail Trail is one of the longest paved bike paths in the United States, spanning a total of 25 miles from South Dennis to Wellfleet.

The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands - Cruising the Elizabeth Islands' Hidden Coves


The 7 Most Exhilarating Active Pursuits on Cape Cod and the Islands

The Elizabeth Islands, a chain of over 20 islands off the coast of Cape Cod, offer a serene and picturesque escape for visitors.

The islands can be accessed by boat, with the charming Cuttyhunk Island being a popular destination.

While the islands are largely private property, several beaches like Tarpaulin Cove and Kettle Cove allow public access, providing opportunities for cruising, seal watching, and exploring the islands' rich history.

The Elizabeth Islands are a chain of more than 20 islands that separate Buzzards Bay and Vineyard Sound off the coast of Cape Cod.

The easiest way to access Cuttyhunk Island, one of the Elizabeth Islands, is by boat, either docking at the marina or sleeping on a vessel in the harbor, as accommodations on the island are limited.

The Elizabeth Islands, including Naushon, Nashawena, and Cuttyhunk, are privately owned by the Forbes family and offer scenic cruising, sightseeing, and seal watching opportunities.

Naushon Island was the last port of call for Captain Kidd before his capture for piracy in 1699, highlighting the islands' rich history.

During the American Revolution, the British stormed Naushon Island in May 1778, underscoring the islands' strategic significance.

The Elizabeth Islands are known as excellent destinations for bird watching, especially during the winter months when migratory birds are present.

Visitors can explore the islands by boat or take a tour, such as a Seal Watch Cruise, which offers a unique perspective on the islands and their history.

Some of the beaches on the Elizabeth Islands, like Weepecket, Kettle Cove, and Tarpaulin Cove, allow public access, while the interior exploration is generally prohibited.

The Elizabeth Islands and the south shore of Cape Cod are considered some of the world's best cruising grounds, attracting sailors from around the globe.

Seal cruises around the Elizabeth Islands are a popular off-season activity, depending on weather conditions and the total number of passengers.

Martha's Vineyard, located near the Elizabeth Islands, offers a variety of boating excursions, including guided walking tours and land excursions to the Gay Head Cliffs.

The Elizabeth Islands and the surrounding waters are home to a diverse array of marine life, including seals, which can be observed during specialized cruises.

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