Things to do in Chatham, Massachusetts (MA): The Best Tours

July 12, 2021 Janette Largent

This pleasant, walkable town right at the elbow of Cape Cod is a classic New England vacation spot. Bringing kids? Check out calm beaches like Cockle Cove Beach and Harding’s Beach. If you’re looking for stunning scenery, however, try Chatham Lighthouse Beach. Its tides can be strong (heed the posted warnings), but it’s one of the most beautiful beaches on the Cape.
Restaurants in Chatham

1. Monomoy Sportfishing

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5.0 based on 38 reviews

Monomoy Sportfishing

Customized Fishing Charters, Eco-Tours, Great White Shark Tours, Whale Watching, Harbor & Seal Tours in Chatham, Massachusetts with USCG Master Captain

2. Capeshores Charters

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5.0 based on 76 reviews

Capeshores Charters

Offering light tackle sport fishing charters twice daily since 1997 for striped bass, bluefin tuna and other fishes from the Chatham Municipal Fish pier located at Shore Road and Barcliffe Avenue extension. Free parking, bathrooms and safe walkways and ramps to the dock are located at the Pier for your convenience. Reserve your dates as early as possible as we do book up during our busy June through September season.

3. Chatham Boat Tours

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5.0 based on 81 reviews

Chatham Boat Tours

Let us customize a cruise for you. Celebrate a Special Occasion or Relax and Enjoy our beautiful unspoiled Chatham Islands and Barrier Beaches. • Come see the seals, birds, wildlife, and the 3 Chatham lighthouses from the boat. • Watch or help us check our lobster pots. • Want to see shellfish harvested? • Capture the beauty with your awesome photos and videos. • Customize a sunset cruise

4. Stick'n Rudder Aero Tours

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5.0 based on 278 reviews

Stick'n Rudder Aero Tours

Stick'n Rudder Aero Tours offers sightseeing rides and flight instruction around the gorgeous lower cape area with tours ranging from a quick jaunt around Chatham to longer tours to Provincetown and back. Call us at 508-945-2363 for more information!

5. Chatham Sport Fishing

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5.0 based on 40 reviews

Chatham Sport Fishing

Chatham Sport Fishing is one of the only charters on the Cape that offers charters of less than 4 hours. Trips of 2, 3 and 4 hours are family-friendly. After years of taking our own children out fishing, we've recognized the need for a shorter charter for the young ones or those who just wish to try fishing the Cape without a 4 hour commitment. We specialize in striped bass and blues fishing.

6. Sea Charters Sportfishing

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5.0 based on 1 reviews

Sea Charters Sportfishing

Fishing charters provided for up to 6 people aboard a 34 ft Venture Center Console with twin outboard engines. Fishing the waters off Chatham providing an incredible experience of sightseeing, exciting fishing for striped bass, bluefish, fluke, sea bass and tuna, shark and cod.

7. Monomoy Fishing Charters

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5.0 based on 4 reviews

Monomoy Fishing Charters

Captain Greg, one of the best fishing guides on Cape Cod, has been in Chatham waters and fishing the backside for over 30 years. We specializes in light tackle, spin fishing and fly fishing for bass, tuna & blues. Fishing tactics include live baiting, fly casting, casting popping plugs, soft plastics & metal jigs with spinning rods. We supply all the tackle necessary to hook these powerful fish.

8. Outermost Harbor Marine

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5.0 based on 3 reviews

Outermost Harbor Marine

Voted best marina in Chatham three years running Outermost Harbor Marine is located on the “elbow” of Cape Cod, offering a rare and exciting perspective on the natural beauty of Cape Cod.OHM now offers a number of exciting excursions. From beach shuttles to beautiful south beach, to birding and wildlife/seal tours on monomoy, to kayak&paddle board rentals, to fishing charters, OHM has it all!

9. Got Stryper Charters

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5.0 based on 33 reviews

Got Stryper Charters

Light tackle and fly fishing cape cod and the islands . From novice to expert we try to show you a great time.

10. Chatham Sailboat Rentals

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5.0 based on 18 reviews

Chatham Sailboat Rentals

Sailboat rentals, kayaks, stand-up paddle boards, lessons and tours in Chatham, Massachusetts, on the kid-friendly Ridgevale Beach. Family owned & operated for over 50 years in conjunction with the Ridgevale Beach Snack Bar, Chatham Sailboat Rentals offers water activities for all skill and age levels to be enjoyed on Buck's Creek and Nantucket Sound.

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