Boating & Watersports

Don’t visit Cape Cod without getting on the water! Whether you’re all about fishing or looking to relax with a glass of champagne, Chatham Bars Inn has a boating experience for you. Our private fleet offers charters, cruises, fishing trips and even kid-friendly tours that get the whole family involved.

Boating is available from April through October. Space is limited and many of these experiences sell out quickly, so make sure to reserve as far in advance as possible by calling 800.527.4884.

If you need to change or cancel your reservation, we do require notice 24 hours in advance.

Charters and Cruises

Nantucket Cruise

We’ll whisk you away to Nantucket Island in just over an hour. Walk the charming cobblestone streets, visit quaint shops and galleries, and dine at one of grey lady’s many seaside restaurants.

Martha’s Vineyard Cruise

The natural beauty of Martha’s Vineyard’s pristine beaches, clay cliffs, historical and cultural attractions, exquisite dining and one-of-a-kind boutiques provide for a perfect day trip.

Champagne Bay Cruise

Experience the beauty and calm waters of Pleasant Bay. Sit back and sip bubbly aboard Shooting Star, our 38’ Shelter Island Runabout as we explore the bay including Strong Island, Eastward Ho, and The North Cut. Champagne and soft drinks provided. Additional snacks and beverages available.

Evening Harbor

Sit back and reflect on the day’s events while taking an early evening cruise along the picturesque Chatham coastline.

Pirate Cruise - Kid Friendly!

Join the Captain and crew on “Bargh Tender” as they hunt down The Black Stargh and it’s dirty, rotten Captain! Young pirates prepare for battle with tattoos and face paint and don their pirate gear. They unroll the ole treasure map and cast off in search of the stolen treasure!

Fishing Trips

Lobstering - temporarily unavailable

Experience the daily routine of a lobsterman as you participate in the excitement of hauling, emptying and baiting the traps on Lob Star.

Inshore Fishing

We will fish the rips and waters surrounding Chatham in search of striped bass, bluefish, bonito, and false albacore. All tackle is provided. The captain will gladly clean your catch and deliver it to the resort kitchen for our chef’s to prepare for a nominal fee.

Offshore Fishing

Chatham is home to some of the most fertile waters on the East Coast. Head offshore in pursuit of blue water species such as Bluefin tuna. StarStruck is fully equipped with top-of-the-line electronics and the finest fishing tackle. Our knowledgeable captains will provide you with a memorable fishing experience that is second to none.

Sailing Trips - Temporarily Unavailable

Evening Sail - temporarily unavailable

Enjoy a relaxing evening sail while the sun sets to the west. The sweeping vistas of Chatham’s coastline, historical landmarks like the Chatham Lighthouse and the barrier beach provide the perfect backdrop for your sail.

Youth Sailing Instruction - temporarily unavailable

Our instructors provide children with basic sailing instruction in a safe and fun environment. The goal is for each child to develop skills while building knowledge and confidence. Children will learn basic boat handling, terminology, rigging and sail trim. Participants must be 7 years of age or older.

Wildlife Adventures

Shark Expeditions

Our shark shadow and shark beacon expeditions aren’t just your best chance to see great whites near Cape Cod - they’re once-in-a-lifetime experiences that you can’t find anywhere else in the world. Learn more about our shark expeditions and reserve today!

Whale Watching Tours

You’ll set out on the Shooting Star, our 38-foot Shelter Island Runabout originally designed by Billy Joel. Our captains will take you the waters east of Chatham, where whales gather from April to October to feed and raise their young. Primarily, our tours spot humpback whales, though it’s not uncommon for guests to also see pilot whales, minke whales, whale sharks and giant mola mola as well. Learn more about our whale watching tours and reserve today!

Morning Seal Cruises

Pleasant Bay is home to hundreds of gray & harbor seals. This tour is an opportunity to see them up close and learn about their eating and migratory habits. You may see them on the sandbars at low tide basking in the sun or frolicking in the water at high tide. This cruise also includes passing the Chatham Lighthouse and the Municipal Fish Pier.


Kayak Rentals

Single and tandem kayaks available. All rentals include proper instruction and safety information, and life vests. Participants must be 6 years of age or older, and those under 18 years of age must be accompanied by a parent or guardian.

Hobie Catamaran Rentals - temporarily unavailable

These fast and fun Hobie Cats make for excellent sailing in Chatham Harbor. Available for sailing lessons and rentals.

Our Fleet

Shooting Star

Type: 38’ Shelter Island Runabout

Capacity: 6 Passengers

The traditional beauty of the 38’ Shelter Island Runabout and her incredible performance can quickly whisk you away to Nantucket, Martha’s Vineyard or to some of the most spectacular whale watching spots in New England. Cruise in speed, comfort and style.


Type: 34’ Regulator Center Console

Capacity: 6 Passengers

This is the ultimate sport fishing machine. StarStruck will take up to six guests to the fishing grounds comfortably, safely, and quickly. The waters off of Chatham boast some of the finest striper and tuna fishing on the east coast and, whether you prefer offshore big game or inshore light tackle fishing, StarStruck’s state-of-the-art equipment and experienced captains will help you land “the big one”!

Lob Star

Type: 21’ Parker Center Console

Capacity: 6 Passengers

Experience the daily routine of a lobsterman as you participate in the excitement of hauling, emptying and baiting the traps on Lob Star. Get an up-close and personal view of the other marine life that finds its way into the traps including crabs, sea stars, moon snails and other shellfish.

Stars & Stripes

Type: 26’ Latitude Tandorne

Capacity: 6 Passengers

Trimmed inside and out with satin-varnished mahogany and teak decking, the Tadornes are attractive boats that are fast under sail. Her cockpit is wide and spacious making Stars & Stripes ideal for a classic sailing excursion, a family sailing lesson or a relaxing sail.

Bar Tender

Type: 29’ Custom Launch

Capacity: 18 Passengers

Built in Chatham and trimmed with teak decks and beautifully varnished mahogany, Bar Tender has a remarkably shallow draft that affords easy access to the beach and remote areas of Pleasant Bay.

Complimentary Shuttle Service: Daily to North Beach Island is available exclusively to guests of Chatham Bars Inn. In addition to a variety of scheduled cruises, Bar Tender may also be reserved for private charters and cocktail cruises for parties of up to 18 passengers.

Private Charters

All of our boats are available for private charters, including, but not limited to wedding photo shoots, bachelor and bachelorette cruises, birthday parties and more! Call 1.800.527.4884 to book.

Remember - space is limited! Reserve as far in advance as possible by calling today.

View our Boating & Watersports brochure for more info on everything from fishing to charters to kids' programs and more!

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