Where to Book: the 6 Best Historical Harbour Cruises Worldwide

1.Sailing on Historic Schooner Yacht in Salem, MA

★★★★★★★★★★5.0 · 172 reviews · 2 hours (approx.) Our pick

Set sail from 10 Blaney Street in Salem aboard the classic schooner Malabar for about two hours. You’ll cruise Salem Sound, Marblehead, and nearby islands while the crew explains the vessel and may invite you to help raise the four sails. Captain Seth and crew members such as Kos and Kate bring the boat’s story to life. Drinks are available for purchase onboard.

“Very nice and relaxing experience! The crew were very helpful and welcoming! A very romantic setting for couples as well.”

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2.Scenic Cruise & Guided Walk on Historic Motor Yacht Lake Te Anau

★★★★★★★★★★5.0 · 165 reviews · from $102 a seat

Spend about three hours on Lake Te Anau aboard the historic motor yacht Faith, with live commentary, afternoon tea, and a guided walk to a clear forest lake. The small group, usually capped at 16, keeps the outing personal. Crew members such as Adam, Megan, Paul, and Jackie share the boat’s story and Fiordland’s natural details, though the exact crew may vary.

“The day was perfect - clear and sunny skies, the water was fairly smooth, the boat ride was relaxing and a little breezy! Paul and Jackie were a blast! Jackie’s commentary along the hike was great! Funny and she pointed out fun tips of plantsRead more”

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3.Scenic Cruise & Guided walk on Historic Motor Yacht Lake Te Anau

★★★★★★★★★★5.0 · 76 reviews · from $102 a seat

Set out from Te Anau on the restored historic yacht Faith with a crew that may include Adam, Jackie, or George. Cruise into the South Fiord, walk 15 minutes to a Hidden Lake, enjoy tea and snacks, then sail back when the wind allows. The half-day trip carries no more than 16 people.

“Captain Adam and First Mate Jackie were wonderful! They were so welcoming and told us to pretend their boat was ours for the journey. My husband and brother-on-law poked around the vessel and helped raise and lower the sails. All oRead more”

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4.Evening Champagne Cruise on Historic 1935 Motor Yacht.

★★★★★★★★★★4.9 · 48 reviews · 1h 30m · from $86 a seat

Board Faith, a lovingly preserved 1935 Scottish motor yacht, at Te Anau’s historic wharf. Captain Adam and the crew guide you across Lake Te Anau for 90 minutes, with unlimited drinks, canapés, boat stories, a sheltered cove stop, and the chance to help steer or handle the sails.

“A fabulous evening in stunning scenery with a lovely host.”

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5.Chicago River Architecture Tour Aboard a Historic Yacht

★★★★★★★★★★5.0 · 45 reviews · from $49 a seat Best value

Board a historic wooden yacht at 465 N McClurg Ct for a 90-minute Chicago River architecture cruise. Your captain handles the route while a guide explains roughly 50 skyscrapers, bridges, and landmarks, including the Wrigley Building and Michigan Avenue Bridge. Soda, coffee, and snacks are included, with alcoholic drinks available to buy.

“Your guide was amazing! She was very knowledgeable! Great experience! Learned a lot! Five stars! Thank you!”

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6.Yacht Sailing Tour With Portuguese Wine and History

★★★★★★★★★★5.0 · 4 reviews · 2 hours · whole boat $235, up to 6

Spend two hours on a private 12-meter sailboat from Doca de Santo Amaro to Belém and back. Your two-person crew speaks English, Portuguese, Spanish, and French, sharing Lisbon history, sailing tips, and a glass of wine. You will see the bridge, Christ the King, Praça do Comércio, MAAT, and Belém Tower from the river.

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