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Family Reunion Ideas – Seven WOW! Tall Ship Sailing Experiences. For more family fun just add water. The best family reunions have at least one shared experience that packs an extra WOW! Sailing aboard a tall ship fits into that category. S/V Denis Sullivan Lake Michigan Family Sailing Adventures

Here’s the scoop. I recently returned from a family vacation part of which included a three-day family reunion gathering. In addition to board games, wine tasting and campfire gatherings, our WOW! experience included a day excursion aboard a pontoon boat on the Mississippi. Awesome in it's own way, it was a memory maker but that is not the point of this post. 

As our Huck Finn inspired Mississippi excursion concluded my niece asked, “So what’s it going to be next year?” Not missing a beat she said, “I’ve got it. Let’s sail on a schooner like the one in Milwaukee.” Sure, why not? Really, what I was thinking to myself was why hadn’t I thought of it?
And so humbled by a 20-something, I have taken the time to research tall ship excursions for families. I have learned that they are indeed popular for family reunions offering most remarkable experiences ideal for those who are looking to share time with three generations. I am jazzed by the possibilities. My list is by no means complete but it does offer a starting point. 

Wisconsin – Sail aboard the S/V Denis Sullivan from Milwaukee. The classic sailing vessels of the Great Lakes offer a countless stories of American spirit and tenacity. A sail on the 19th century schooner S/V Denis Sullivan provides a deck top view of the daily workings of freshwater sailor. For more than a decade it has served as the official flagship for Wisconsin. During the summer months public day sails provide passengers with ways to be as involved in the sailing process as they wish from raising the sails to watching for marine life from the bowsprit. Memory Maker: During Milwaukee’s Summerfest, the schooner sails at sunset just in time to provide passengers with a remarkable view the lake front fireworks. Private Sails: It is possible to charter the crewed vessel and have your own family reunion sail on Lake Michigan. (S/V Denis Sullivan 500 North Harbor Drive Milwaukee, Wisconsin 53204. (414) 765-9966 or

Massachusetts – Sail aboard the Liberty Clipper or the Liberty Star in Boston Harbor. During the summer months tall ship cruises become an important part of Boston’s vacation personality with two schooners lifting sail to passengers living history at its best. Guests are invited to assist the crew in hoisting the sails, coiling the ropes and even taking the helm. Memory Maker: How cool is this? On select days the Liberty Star hosts an interactive “Boston Tea Party” sail experience with costumed actors recreating the historic event. Private Sails: During the summer months the schooners are available in Boston and during the winter months the may be chartered in Caribbean locations including Bahamas and Virgin Islands. (Fleet moored at the New England Aquarium 67 Long Wharf Boston, MA. (617) 742-0333 or Ship Family Sailing in St. Augustine, Florida

Florida – The Freedom sails from St. Augustine.  Sail under the Bridge of Lions and along the Matanzas River to the Atlantic aboard the Freedom, a replica of a 19th century blockade-runner. In addition to three daily sails there is also an interactive sail designed for families which is ideal for three generations. The unique experience includes a chance for passengers to hoist the sails, listen to sea stories, learn nautical trivia, and perhaps spot a few playful dolphins. Memory Maker: On select days throughout the summer, the Freedom partners with Marineland to create a unique dolphin cruise experience. Private Sails: The Freedom has deck space for up to 40 passengers and offers many sailing options for a unique family reunion experience. (Moored at City Municipal Marina St. Augustine, FL 32084. (904) 810-1010 or Sailing Adventures Aboard the Californian in San Diego Bay.

Southern California - Sail aboard the Californian on San Diego Bay. The home of state’s official tall ship, the Californian, is at the Maritime Museum of San Diego. The impressive topsail schooner a replica of the kind used to patrol during the California Gold Rush allows passengers to experience history afloat. Bay sails include stories of sea life and exploration, whaling and sea otter trade.  For those onboard who wish to make their sail more interactive it is possible to work alongside the crew.  Memory Maker: Cover your ears! The four-hour experience ends with a cannon salute. Private Sails: The schooner is also available for charter for four hours or more and has space for 62 onboard. (Maritime Museum of San Diego 1492 North Harbor Drive San Diego, CA 92101. (619) 234-9154 x135 or

Washington - Schooner Zodiac Sails from Bellingham. Plying the waters of Puget Sound and weaving throughout the San Juan Islands, the classic American windjammer Zodiac offers a National Geographic experience for families.  The natural beauty and desolation provide the backdrop for a comfortable sailing adventure. Join a public sail and relax with your family or take part in the sailing activities – hoisting the sails or steering the vessel. Memory Maker: Ride the rails before the sail. Amtrak has direct service between Seattle and Bellingham and the station is just a short walk from the pier. Private Sails: The Zodiac has the capacity for 45 passengers plus crew making it easy to arrange a custom day sail or 26 passengers for an overnight experience. (Schooner Zodiac 1221 Harris Ave PNB 2 Bellingham, WA 98225. (206) 719-7622 or Rover Family Sailing Adventure from Norfolk.

Virginia – American Rover Sails from Norfolk. From mid-April to late Octobers set sail in Hampton Roads Harbor and along the waters of the Elizabeth River under the awesome burnished red sails of the American Rover - a three-masted topsail schooner. Two sails per day offer passengers waterside views of the Navy’s shipyards, cargo bays, private yachts, working tug boats, and the most impressive battleship USS Wisconsin. In addition to narration provided by the captain, passengers are invited to engage with the crew in sailing activities. Memory Maker: To make the sail seem even more real, take a few minutes at the helm of the schooner. Private Sails: Charter the whole schooner and include 120 in your sail. (American Rover 333 Waterside Drive, Norfolk, Virginia 23510. (757) 627-7245 or

South Carolina - Schooner Pride Sails from Charleston. Maritime commerce has always been a rich part of Charleston’s history. Sailing on the 84-foot S/V Pride, a replica of a 19th century Atlantic coastal trading schooner, offers passengers not just a sense of the past but an awesome sea adventure combining waves, wind and sails. Glide by the historic Battery, Ft. Johnston and Ft. Sumter. Sail alongside the famous WWII air craft carrier, USS Yorktown. Memory Maker: Passengers of all ages are invited count seagulls and dolphins and to participate in the sailing of the vessel or just relax and enjoy the perfect balance of wind and sea under sails. Private Sails: The Pride is available for private family reunion gathering complete with beverages and catering options. (The Pride is moored at Aquarium Wharf 360 Concord St. Charleston, SC 2940. Toll-free 1-800-344-4483, (843) 722-1112 or

Content researched and posted by Nancy Nelson-Duac, Curator of the Good Stuff for the Family Travel Files. Images courtesy San Diego Maritime Museum, Discovery World – S/V Denis Sullivan, American Rover, and S/V Freedom. Copyright updated 2017.

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