Nantucket, with its rich maritime history, natural beauty, and coastal vistas, offers a variety of adventures for families seeking memorable experiences on the water. Whether you’re casting lines for the day’s catch, learning to hoist the sails aboard historic vessels, or relaxing as you enjoy unparalleled views of our island from the water, here are four different outings that promise fun and learning for all ages.
Start early with the thrill of a charter fishing trip aboard the Herbert T. Children eagerly grasp their rods, eyes sparkling with excitement as they envision the treasures that lie beneath the waves. Captain Fred Tonkin will share his knowledge and passion plus some fun fish tales, making each trip a lesson in the joys of fishing. Every tug on the line from a Nantucket blue will be met with cheers of triumph.
Captain Fred has more than 40 years experience sport fishing, and he knows the best spots and methods. He enjoys taking families out and introducing all ages to fishing, offering valuable tips for first-timers and trading stories with anglers. Children can reel in blues under his expert guidance, and the excitement peaks at the dock when Captain Fred cleans the catch, for a dinner fresh from the sea.
Herbert T charters are available at 7 am, 10 am, 1 pm, and 4 pm. All gear and bait are included.
If yours is a family of experienced fishermen, Captain Fred can take you out on a private charter where he finds the sauce every time. Five-hour trips on the Herbert T are designed for anglers specifically looking to target striped bass. Ask him about opportunities to bottom fish for fluke and sea bass for a portion of the trip.
You’ll find the Herbert T on Straight Wharf at Slip 14: stop by to book a charter or call 508-228-6655 (daytime) or 508-257-4176 (evenings).
One slip over on Straight Wharf, you’ll find Endeavor, the longest operating sailing charter on Nantucket. Captain Jim Genthner welcomes all ages aboard this Friendship Sloop that he built when they join him on a leisurely sail past Brant Point Lighthouse, through the jetties, and into Nantucket Sound. During the 90-minute day sail, kids can lend a hand raising sails and feel the exhilaration of the wind through their hair.
During the sail, Captain Jim will regale passengers with Nantucket’s exciting maritime history and point out sights along the waterfront. He can trade sailing stories and share his knowledge of traditional boat building.
The 90-minute sail aboard Endeavor departs at 10 am, 1:30 pm, and 3:30 pm. They also offer a sunset cruise. Singles, couples, and small families are welcome to join these public sails: it’s a fun way to meet and engage with fellow travelers.
Captain Jim also offers private charters aboard Endeavor, which is Coast Guard certified to carry 14 passengers. Private sails are a great choice for multigenerational trips and are a great way to share the wonder of sailing with your children and grandchildren. Private charters are fun and memorable for celebrations (yes, you can bring aboard beverages and snacks), bachelor and bachelorette parties, family reunions, and proposals—there have even been weddings on Endeavor.
To book a public sail or charter, call 508-228-5585, visit endeavorsailing.com, or stop by Slip #1015 on Straight Wharf, across from the Hyline ticket office.
Nantucket by Water is another beloved local enterprise. Their array of tours and eco-tours caters to diverse tastes and a range of ages, delighting passengers from youngsters to grandparents. They have several one-hour cruises, including an Ice Cream Cruise, where you enjoy an indulgent treat as you glide around the harbor, past luxurious yachts and waterfront estates. On the Whaling History Cruise, passengers learn about Nantucket’s storied past with engaging narratives on whaling history while seeing historic landmarks. There’s also a Kids’ Fishing Trip with a hands-on introduction to catch-and-release fishing.
Their longer 90-minute adventures include a Shanty Singers Cruise featuring local musicians; a Sip & Fish Cruise with fun for both kids and parents; a BYOB Cocktail Cruise for ages 21+ with breathtaking views and on-board music; and a Sunset Cruise. Nantucket by Water also offers a 2-hour Oyster Farm Cruise to 5th Bend Oyster Farm, during which you will learn how oyster farming in Nantucket waters is done and how it is beneficial to our island.
Private charters are also available, and the crew of Nantucket by Water is happy to help you design a custom experience on The Wampum for small groups of up to 11, or on The Minke for larger groups of up to 23 passengers.
To explore options and book your cruise, stop by Slip 1011 on Straight Wharf, visit nantucketbywater.com, or call 508-228-7037
For a true taste of history, step back in time aboard the majestic Tall Ship Lynx: a true interpretation of a privateer from the War of 1812. This adventure isn’t just about sailing; it’s an immersive educational experience where families actively participate in sail training aboard a wooden sailing ship.
Captain Donald Peacock and his engaging and experienced crew tell tales of the sea, encourage passengers to help hoist the sails, show how to steer the ship, ring the bell, and explain how they navigate the seas as sailors did centuries ago. You might even hear a sea shanty or two, all while experiencing first-hand Nantucket’s maritime heritage.
Day Sails depart at 1 pm, and Sunset Sails depart at 5 pm. Private charters aboard Lynx for a three-hour sunset sail are available for up to 40 passengers. Book your adventure at tallshiplynx.org
The Lynx is proud to partner with the Egan Maritime Institute of Nantucket to offer a combined curriculum called “Sea of Opportunities.” In addition to unique educational opportunities for students, this partnership also offers special public programs such as Sea Songs aboard the Tall Ship Lynx (July 26), Youth Adventure Sails (July 31 and August 21), and Tall Ship Lynx Sunset Sail & Shipwreck Stories (August 6). The partner sails can be booked at eganmaritime.org/tall-ship-lynx
Each of these adventures on the water offers a distinct flavor of Nantucket’s maritime charm, whether you’re angling for fish, reliving history on the Tall Ship Lynx, or sailing and cruising with loved ones. Be sure to book in advance and prepare for memorable views and unforgettable island adventures on the water, where learning and leisure blend seamlessly on the shimmering seas.