Watersports and Sightseeing

Experience Luxurious Cape Cod Living

Chatham, located on the southeastern edge of Cape Cod, is a picturesque town that is known forits sandy beaches that are ideal for swimming, sunbathing, or taking a leisurely stroll.

Watersports

Kayaking and stand-up paddle boarding are a great way to spend a few hours exploring the water in Chatham and other areas like the salt marshes. Cape Cod is a popular destination for kayaking and paddle boarding because of the sheer diversity of its water bodies. Some rental companies are:

Adventure Chatham – Private lessons available for individuals or groups of friends and family

Chatham Kayak Company – Guided Tours on Oyster River

North Chatham Outfitters – Kayaks and Paddle Boards

You can fish for everything from striped bass to bluefish to blue-fin tuna. The Atlantic Ocean, just to the east of Chatham and the island of Monomoy, continues to be one of the most scenic and productive spots on the East Coast.

Fish Chatham Charter – specializes in full-day trips for Bluefin Tuna.

Outermost Harbor Fishing Charters – 33’ Grady White Canyon Center Console & 26’ Regulator Classic Center Console.

Monomoy Fishing Charters – specializes in fishing for striped bass, bluefish and tuna.

Zen Charters – 2014 Grady White 271 Canyon that can accommodate up to six people on an Ecotour or a fishing charter.

Kiteboarding (kitesurfing) and windsurfing are wonderful ways to experience the water and get exercise at the same time. Kiteboarding has been growing in popularity, since unlike windsurfing or sailing, it requires less wind to get its wings up in the sky. However, when kite surfing in Chatham, remember to be on the lookout for seals.

Fun Seekers – Located in Wellfleet, and offers surf school, SUP, windsurfing and kiteboarding lessons.

Inland Sea – Located close to West Dennis Beach and offers rentals, sales, tours.

Sailing around Cape Cod is one of the best ways to get to know the area and have fun while doing it. You can see animals, the amazing coastline, as well as beautiful homes while enjoying the breeze as you relax on a sailboat. There are many options to choose from, including trips that last a couple of hours to day charters to an overnight stay on the sailboat.

Cape Sail – For charters or lessons on the 39 Southern Cross, they leave from the dock at Stage Harbor Marine in Chatham, and for lessons on the 16ft Day Sailor, they meet across the street from 699 Run Hill Rd, Brewster.

Chatham Sail – is located on Ridgevale Beach. It offers waterfront sailing, kayaking and stand-up paddle boarding as well as expert-led tours and lessons.

Sightseeing Excursions

Martha’s Vineyard is a lovely island seven miles off the Southern coast of Cape Cod. It has boutique shops, great dining, gorgeous beaches, colorful gingerbread cottages, five lighthouses and farmers markets. You can go inside four of the five lighthouses and they are a great way to see fantastic views of island. Martha’s Vineyard Museum manages two of the lighthouses – the Edgartown Lighthouse and East Chop Lighthouses. The picturesque Edgartown lighthouse is located on the beach, just minutes from the center of town.

The island is nine miles wide and 26 miles long at its furthest points. It has six towns (“down island” and “up island”). The three “down island” towns are Edgartown, Oak Bluffs and Vineyard Haven. They bustle with great shopping, dining, and other attractions. They have seasonal or year-round ferry service and are typically the most frequently visited. The ”up island” towns of West Tisbury, Chilmark and Aquinnah tend to be more rural. Chilmark is home to the small fishing village of Menemsha, where Jaws was filmed. West Tisbury has a weekly Farmer’s Market and Agricultural Fair, and the Gay Head Cliffs are in Aquinnah.

Peak tourist season is July and August, with August being the busiest. July Fourth and Labor Day have the biggest weekend crowds. June and September are also popular months for visitors.

Cars are allowed on the island, and bringing your car is an option, but it comes at a high cost and with limited parking options. It is usually cheaper to rent a car, moped or bike. Biking is one of the most fun (and affordable) ways to get around the vineyard. You can catch a ferry to Martha’s Vineyard from Hyannis Port via Hy-Line Cruises Ferry (about 35-minute drive depending on traffic).

Nantucket is a magical place that is both charming and relaxing. Nantucket served as the whaling capital of the world for nearly a century and has three lighthouses. It is a destination with tons of things to do, whether you prefer walking along the beach at sunset, biking along the bike trails, grabbing a latte in the morning, or feasting on seafood. Nantucket is well known for its seafood, particularly fried clams, oysters, and lobster. It has over 80 miles of gorgeous coastline and looks like a postcard that came to life. The most popular places for tourists to visit are its historic downtown and Siasconset, which are on the east side of the island. Traffic, especially during the summer, tends to be terrible. Save yourself the aggravation and rent (or bring) a bike instead. Exploring the island by bike is a popular pastime. There are three main bike trails on the island, with one each located in Madaket, Surfside, and Sconset.

Summer is the high season in Nantucket, and the best weather is typically from Memorial Day to Labor Day. Early May and late September are also a good time to go since you will miss the summer crowds. Nantucket hosts a series of events and festivals year-round, among them are the Nantucket Daffodil Festival (April), Nantucket Wine Festival (May), and Nantucket Book Festival (June).

Nantucket Island is 30 miles off the coast of Cape Cod and is only accessible ferry. The closest ferry is the Freedom Cruise Line which leaves from Harwich Port (about a 10-minute drive from Chatham)

Provincetown is a picturesque coastal resort town with a year-round population of close to 3,000, but during the summer it grows to as many as 60,000. It is known as a fun destination with plenty of cool activities. The main thoroughfare is Commercial Street, and it is loaded with boutiques, galleries, and restaurants. It is a LGBT-friendly destination that has some of the best beaches in Cape Cod. It is about 35 miles from Chatham to Provincetown by car, following the MA 28 route, which is about a 50-minute drive depending on traffic.

The waters off Cape Cod are full of life, and it is a terrific place to see whales and dolphins. Chatham is centrally located between Barnstable Harbor and Provincetown Harbor, where many dolphin and whale watching cruises originate. Charter companies typically offer excursions from mid-April through late October, when the whales migrate to the waters near Chatham. The best whale watching is usually in June, July, August, and September.

Seal cruises are another fun experience, allowing you to get up close to these playful mammals. Whichever excursion you choose, you can be sure you will have a memorable experience. During the summer months, traffic can be very heavy heading toward Provincetown, so if you choose to go whale watching from Provincetown rather than Barnstable, be sure to factor traffic conditions into your plans!

Hyannis Whale Watcher Cruises – Their ship named Whale Watcher, is high-speed and was designed specifically for whale watching. It is 130 feet long and has interior cabins, a galley with plenty to choose from, and outdoor decks for close-up viewing. Don’t be fooled by the company’s name, they sail from Barnstable Harbor – not Hyannis Harbor.

Whale Watch Dolphin Fleet of Provincetown – They have several ships which are fully equipped with walkout platforms on the bow, viewing decks, and cabins equipped with heat and air conditioning. Their focus is education and their trips, guided by naturalists, last three to four hours.

SeaSalt Charters– Their boats have a maximum capacity of six people, so if you prefer a private tour with a small group this is a good option. They offer shared or private whales watches – so if you are single or a couple, you can share the expense with another group or choose to charter the boat privately.

Sealwatch – They offer fun seal tours in Pleasant Bay, between North Beach, Chatham Light and the break. Tours typically last one and a half hours and the boat can hold up to 29 people. They do not set a schedule until July.

Cape Cod has several wineries that offer informative tours and typically follow the wine-making process, starting with the harvest, then grape selection, fermentation, aging and bottling. Remember to wear comfortable shoes since you will be walking all around the vineyard as you learn about the growing process. Consider it the perfect opportunity to spend some quality time with friends or family. You can explore the winery at your own pace and have a glass of wine after you are done! Please note that Covid may have impacted tour and tasting schedules.

Vineyards & Wineries

Truro Vineyards, founded in 1992, offers private tastings and tours for groups of 10 or more. The tours give a brief history of the vineyard as well as a walk through the vineyard, ending in the barrel room. The tasting ends with a sampling of 5 vintages and a small cheese platter. Be sure to check tour times and availability in advance.

Cape Cod Winery – The Cape Cod Winery is in East Falmouth. They offer nine different varieties of wine. Tastings here are by appointment only on weekdays and run on a seasonal schedule.

First Crush Winery – First Crush Winery is located in Harwich. It is run as a cooperative and has 600+ members. Tours and tastings start at $10 per person to taste six of their wines. Private tours are also available.