Where to Start: the 10 Best Sailing Trips Worldwide

1.Historical San Juan Bay Sunset Sailing Tour

★★★★★★★★★★4.5 · 710 reviews · from $115Our pick

You’ll sail San Juan Bay for about two hours aboard a 30-foot J30 racer-cruiser with a captain such as Ivan, Joe, or Carlos. Expect views of El Morro, harbor traffic, local history, sunset photos, and complimentary beer, sangria, rum and Coke, soft drinks, and water.

“What an incredible experience! The sunset sail was intimate, relaxing, and absolutely beautiful. Our captain was interesting, knowledgeable, and genuinely funny—he brought so much personality to the trip and made the whole experiRead more”

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2.Lisbon Sunset Sailing with Portuguese Wine and History

★★★★★★★★★★5.0 · 668 reviews · 2 hours (approx.) · from $54Top rated

Join Pedro, David, or another two-person crew for a relaxed two-hour shared sail from Doca de Santo Amaro. With no more than 14 people aboard, you’ll hear Lisbon history, pass Belém Tower and Commerce Square, and sip included Vinho Verde as the sun drops over the Tagus.

“David was the best possible tour guide! Knowledgeable and personable, he provided great commentary and a fun experience. The ship was comfortable and the wine was good! Highly recommend this experience to any and all travelers!!!”

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3.Lisbon: Sunset Sailing with Portuguese Wine and History

★★★★★★★★★★5.0 · 270 reviews · 2 hours · from $49

Join Pedro, David, or another friendly two-person crew for a relaxed two-hour sunset sail from Doca de Santo Amaro. You will pass Belém Tower, the Discoveries Monument, Cristo Rei, Commerce Square, and the 25 de Abril Bridge while hearing stories of Lisbon and enjoying vinho verde.

“Was really nice evening experience! To see Lisbon from the river it was an excellent choice☺️ the guides were perfect,thank you Caroline and Pedro!☺️”

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4.Nydri: Sailing Through History. Daily Cruise with Beach BBQ

★★★★★★★★★★4.9 · 253 reviews · 8 hours · from $88

Sail from Nydri aboard the family-run Odysseia, a replica ancient Greek warship. Swim in Papanikolis Cave, tour Spartochori and its 300-year-old church, snorkel at Klimaki, and enjoy a local pork or vegetarian BBQ with wine and soft drinks.

“This was by far the best boat tour we've done, and we've made quite a few. You could tell from the start that it is a family business and that they pour their heart and soul in this. Most boat tours don't give you so much time to enjoy the island and the beaches. The trip was awesome and the crew was super friendly. Everything was really fun and overall an extraordinary experience.”

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5.Camden: Historic Schooner Day Sailing Trip

★★★★★★★★★★4.7 · 181 reviews · 2 hours · from $59

Join the 49-passenger schooner Appledore II for a two-hour sailing from Camden Harbor into Penobscot Bay. You can help hoist the sails, take the wheel, hear local and ship history from the English-speaking crew, and buy drinks onboard. Bring layers: the bay feels cooler than shore.

“Great ! Best thing we've done in a long time, we loved it.”

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6.Salem: Historic Schooner Sailing Cruise

★★★★★★★★★★4.9 · 84 reviews · from $39

Spend 100 minutes aboard the gaff-rigged schooner Fame from Pickering Wharf Marina. Help raise the sails, take the tiller, hear Captain Mike and the crew explain Salem Sound’s privateering past, and enjoy beer, wine, rum punch, soft drinks, or snacks from the licensed bar.

“Amazing! The Captain & Crew were wonderful. The boat was beautiful and the weather was just fantastic. I highly recommend this!”

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7.Evening Champagne Cruise on Historic 1935 Motor Yacht.

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

Meet at Te Anau’s historic wharf for a 90-minute evening cruise aboard Faith, a 1935 Scottish motor yacht. Captain Adam and the crew share the boat’s story, serve unlimited drinks and canapés, invite you to help steer or sail, then pause in a quiet cove before gliding back across Lake Te Anau.

“A wonderful way to conclude our trip in Te Anau. Beautiful boat and the friendliest staff. They went out of their way to make this excursion one of our favourite parts of our holiday.”

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8.Chicago River Architecture Tour Aboard a Historic Yacht

★★★★★★★★★★5.0 · 45 reviews · from $49

Spend about 90 minutes on Chicago’s river aboard a historic wooden yacht. A captain handles the route while a guide explains roughly 50 buildings, from the Wrigley Building to the Michigan Avenue Bridge. Expect soda, coffee, snacks, and a steady stream of architecture and city history.

“The tour guide was terrific - super informative, fun to listen to, and maintained control of the crowd so that folks could actually hear him. He also invited and answered random questions. The boat ride was smooth and beautiful. I’m so glad we opted for a smaller vessel so we could hear and see everything. This tour was my and my 16-year old son’s (!!) favorite!”

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9.Lisbon Sunset Sailing – Small Group (max 10) Wine & History

★★★★★★★★★★4.8 · 41 reviews · 2 hours · from $29Best value

Spend two hours aboard the Mabi IV with Lisbon-born skipper Rui Domingos, hearing local stories as you sail past the 25th of April Bridge, Belém Tower, MAAT, and Praça do Comércio. Two glasses of Portuguese wine, blankets, and a maximum of 10 people keep the evening personal and calm.

“Ne pas vouloir me prendre pour 5 minutes de retard….160 euros”

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10.Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique

★★★★★★★★★★5.0 · 32 reviews · 2 to 4 hours (approx.)

Spend two to four hours aboard the 43-foot Mystique with a private group of up to six. Captain Scott, Sam, Rob, Sophia, Adam, Darby, Dustin, or another crew member may guide you past the Battery, Ravenel Bridge, Yorktown, and Fort Sumter, with dolphins possible.

“Rob and Sophia were great! Very informative and helpful. Sophia was very attentive and catered to our every whim. Book your trip now”

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