TALL SHIP AND SCHOONER SAILING

Tall Ships and Schooners: the 15 Best Sails in the World

91 sailings  ·  from $6 a head

Square rig and gaff schooners are the only boats here that put a rope in your hands. These 15 are compared on the age of the hull, how long the sail runs and how much of it is under canvas rather than engine.

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres - The marina meeting point and boarding routine
Key West Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tall Ship and Schooner Sailing, Tall Ship Sailing in Key West, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours

Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

1.Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

★★★★★★★★★★5.0 · 804 reviews · 2 hours (approx.) · from $122Our pick

Board America 2.0 at Key West Bight Marina for a two-hour sunset sail past Fort Zachary, Sunset Pier, and Sand Key Lighthouse. Captain Janet, Captain Rae, Captain Dan, and their crews have been praised for friendly service, clear sailing explanations, and hands-on moments such as raising the sails. Beer, wine, Champagne, soda, and plated hors d’oeuvres are included.

“This was our first time sailing on a schooner and it was amazing. Our captain Dan and his crew were all so nice and welcoming. We had such a wonderful evening. We will definitely be back aboard the America 2.0 next year.”

Check availability →Read our full review

Toronto Tall Ship Boat Cruise - Raising the sails with the crew
Canada Sailing Tours, Sailing Tours, Tall Ship and Schooner Sailing, Tour Reviews

Toronto Tall Ship Boat Cruise

2.Toronto Tall Ship Boat Cruise

★★★★★★★★★★4.5 · 676 reviews · 2 hours (approx.) · from $38

Set sail from downtown Toronto aboard the three-masted Tall Ship Kajama, a 1930s schooner. You can help raise the sails, hear sea shanties, watch the crew fire a cannon, and see the Toronto Islands and skyline from Lake Ontario. Food and drinks are available for purchase, but narration about the city is limited.

“Staff was friendly and it was a great experience. Just the right amount of time on the water. Would book it again.”

Check availability →Read our full review

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger - Key details before you book
Sailing Tours, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

3.Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

★★★★★★★★★★5.0 · 668 reviews · 1 hour 30 minutes (approx.) · from $47

Meet the crew at Harbour Town and set sail aboard the Black Dagger for a 90-minute pirate show made for families. Kids receive pirate names, face paint, temporary tattoos, costume gear, and lessons from characters such as Scurvy and Captain Kaitlyn. They follow a treasure map, battle Stinky Pete with water cannons, and take home a share of the loot.

“We loved it all! It was very interactive, and the kids had a great time! Ever did a great job, thank you guys!”

Check availability →Read our full review

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor - What the non-narrated format really means
Bay, Harbour and Coastal Sailing, Charleston Sailing Tours, Coastal Sailing Tours in the USA, Sailing Tours, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

4.Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

★★★★★★★★★★4.5 · 620 reviews · 1 hour 30 minutes (approx.) · from $45

Spend 90 minutes aboard the 84-foot Schooner Pride, a real sailing ship that uses wind power when conditions allow. The crew raises the sails, answers questions, and may let you help with the lines. Look for dolphins, Fort Sumter, the USS Yorktown, the Battery, and the Ravenel Bridge. Snacks are welcome, but drinks must be purchased on board.

“It was so fun! They really give you the experience you signed up for. We saw dolphins and they provided drinks and a few snacks as well.”

Check availability →Read our full review

Classic Tall Ship Cruise in Boston Harbor - Boarding at Marina Overlook
Bay, Harbour and Coastal Sailing, Boston Sailing Tours, Coastal Sailing Tours in the USA, Sailing Tours, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours

Classic Tall Ship Cruise in Boston Harbor

5.Classic Tall Ship Cruise in Boston Harbor

★★★★★★★★★★4.5 · 615 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $35

Board Liberty Fleet of Tall Ships at Marina Overlook for a 90-minute sail aboard the Liberty Star. Captain Fredo and crew may invite you to help raise the sails while sharing harbor commentary. Bring a bagged lunch, buy drinks onboard, and enjoy skyline and Constitution views from the water.

“I enjoyed it. even go to help pull up the main sail!! Would love to do it again, actually go to get involved and do some of the tasks.”

Check availability →Read our full review

Schooner Fame Sailing Tour - What happens after you meet at Pickering Wharf
Sailing Tours, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, Tours, USA Sailing Tours

Schooner Fame Sailing Tour

6.Schooner Fame Sailing Tour

★★★★★★★★★★5.0 · 571 reviews · 1 hour 40 minutes (approx.) · from $50

Spend about 1 hour 40 minutes sailing Salem Sound aboard the replica privateer schooner Fame. From Pickering Wharf Marina, you can help raise the sails, steer, fold the flag, and hear stories about Salem’s privateers, pirates, and merchant ships. Captain Mike and the crew keep the trip friendly and hands-on. Drinks, snacks, blankets, and a cannon firing may add to the fun.

“It was a great experience. The captain and crew asked for volunteers to hoist the sails, steer the ship and at the end, fold the flag. It does get cold in the evening, so a sweatshirt is advisable, however they do provide blankets.”

Check availability →Read our full review

Sydney Harbour Tall Ship Twilight Dinner Cruise - Starting at Campbells Cove in The Rocks
Australia Sailing Tours, Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in Australia, Dining Experiences, Dinner and Evening Sailing Cruises, Sailing Tours, Sydney Sailing Tours, Tall Ship and Schooner Sailing, Tour Reviews

Sydney Harbour Tall Ship Twilight Dinner Cruise

7.Sydney Harbour Tall Ship Twilight Dinner Cruise

★★★★★★★★★★4.5 · 451 reviews · from $63

Meet at Campbells Cove in The Rocks for a twilight dinner cruise aboard a restored tall ship, sometimes the 104-year-old Southern Swan. Enjoy dinner, live commentary from hosts such as Howard or Ruth, and views of the Opera House, Harbour Bridge, Fort Denison, Taronga Zoo, Luna Park, and more. Mast climbing costs extra.

“Sitting out on the deck of a three mastered tool ship nibbling canapés and sipping bubbles. There is no better way to experience Sydney Harbour and it’s very best.!”

Check availability →Read our full review

Dublin: Jeanie Johnston Tall Ship Irish Famine History Tour - Starting above deck with the masts and Docklands views
Historical Tours, Sailing Tours, Tall Ship and Schooner Sailing, Tour Reviews, Tours

Dublin: Jeanie Johnston Tall Ship Irish Famine History Tour

8.Dublin: Jeanie Johnston Tall Ship Irish Famine History Tour

★★★★★★★★★★4.8 · 431 reviews · from $16Best value

Board the Jeanie Johnston at Dublin’s Custom House Quay for a 50-minute English-language tour. Guides such as Steve, Claire, Eoin, and Katrina explain the famine, the ship’s voyages, and the personal stories of passengers and crew. You’ll see the upper deck, then cramped below-deck quarters. Comfortable shoes are essential.

“Steve was friendly, very informative and entertaining. In all of my visits to Dublin I’ve never managed to make time to see the Jeanie Johnston and I’m so glad I did. I learned a lot about the famine and an important part of Irish history and enjoyed exploring the ship. Thank you, Steve!”

Check availability →Read our full review

Sunset Sailing Cruise on a Tall Ship in Boston Harbor - Two hours of sailing, not a landmark lecture
Bay, Harbour and Coastal Sailing, Boston Sailing Tours, Coastal Sailing Tours in the USA, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

9.Sunset Sailing Cruise on a Tall Ship in Boston Harbor

★★★★★★★★★★4.5 · 414 reviews · 2 hours (approx.) · from $68

Board at Fan Pier Marina for a two-hour sunset sail aboard a classic Boston tall ship, often the Liberty Star. Expect skyline and harbor views, a relaxed crew, drinks and snacks for purchase, and possibly a chance to help with the sails. Capt. Fredo, Jess, and Max have worked some recent departures.

“The crew was fantastic. The views were amazing and drinks were good. Everyone onboard was having a great time. If you have never been on a tall ship this is a nice experience.”

Check availability →Read our full review

Sydney Harbour: Tall Ship Afternoon Cruise - The Opera House and Fort Denison from the Water
Australia Sailing Tours, Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in Australia, Sailing Tours, Sydney Sailing Tours, Tall Ship and Schooner Sailing, Tour Reviews

Sydney Harbour: Tall Ship Afternoon Cruise

10.Tall Ship Afternoon Cruise

★★★★★★★★★★4.6 · 412 reviews · 1h 30m · from $48

Spend 90 minutes aboard an 1850s-style wooden tall ship with an English-speaking crew. Help raise the sails, try the helm, hear Sydney stories from guides such as Ruth and Jim, and pass the Opera House, Fort Denison, and Harbour Bridge. Snacks and drinks are available onboard, but mast climbing costs extra.

“We really enjoyed the cruise. The kids had great fun helping with the sails and looking round the ship.”

Check availability →Read our full review

Bay of Islands Tall Ship Sailing on R. Tucker Thompson Including BBQ Lunch - Morning tea and the easy rhythm of the first hours
Bay, Harbour and Coastal Sailing, BBQ, Coastal Sailing Tours in New Zealand, Island Hopping Sailing Trips, Island Hopping Sailing Trips in New Zealand, Lunch Experiences, New Zealand Sailing Tours, Sailing Tours, Sailing Tours with Lunch and BBQ, Tall Ship and Schooner Sailing, Tour Reviews

Bay of Islands Tall Ship Sailing on R. Tucker Thompson Including BBQ Lunch

11.Bay of Islands Tall Ship Sailing on R. Tucker Thompson Including BBQ Lunch

★★★★★★★★★★5.0 · 361 reviews · from $111

Spend 5.5 hours aboard the R. Tucker Thompson, a working replica schooner sailing from Russell through the Bay of Islands. Help with the ropes, steer the ship, climb the rigging, swim or walk on an island, and enjoy scones, tea, and a chicken BBQ lunch. Captain Magnus and the crew keep the day friendly and active.

“This was an amazing day out. The crew are very welcoming and inclusive. We were all encouraged to participate.”

Check availability →Read our full review

Sailing day trip on Tall Ship Andrea Jensen with Lunch and Wine - Capo Caccia and the Coral Riviera
1-Day Tours, Alghero Sailing Tours, Italy Sailing Tours, Lunch Experiences, Sailing Tours, Sailing Tours with Lunch and BBQ, Sailing Tours with Lunch in Italy, Tall Ship and Schooner Sailing, Tour Reviews, Wine Tours

Sailing day trip on Tall Ship Andrea Jensen with Lunch and Wine

12.Sailing day trip on Tall Ship Andrea Jensen with Lunch and Wine

★★★★★★★★★★5.0 · 360 reviews · 7 hours (approx.) · from $169

Spend about seven hours aboard the 86-year-old wooden tall ship Andrea Jensen, sailing from Alghero with Colin and Rachel. See Capo Caccia’s cliffs, stop in a clear bay for swimming and snorkeling, and enjoy a freshly prepared two-course lunch with wine, beer, soft drinks, and water. The group is limited to 12 people.

“A wonderful day trip on a beautiful boat, with some freshly prepared lunch and opportunities to snorkel and enjoy the water - would highly recommend!”

Check availability →Read our full review

New York City: Sunset Sail Aboard a Schooner - Boarding at Pier 62 in Chelsea
New York City Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours

New York City: Sunset Sail Aboard a Schooner

13.New York City: Sunset Sail Aboard a Schooner

★★★★★★★★★★4.9 · 344 reviews · 2 hours · from $101

Spend two hours aboard the 105-foot Schooner America, sailing from Chelsea Piers past Ellis Island and the Statue of Liberty. You get one beer, wine, or Champagne if you are 21 or older, plus a polished crew and wide harbor views. Captain Shannon and crew members Colin and Grant have earned special praise, though you should bring a warm layer.

“The trip was great, but there was no champagne. No issue for me, as I prefer wine, but it should still be changed in the description.”

Check availability →Read our full review

Sydney: Tall Ship Harbour Twilight Dinner Cruise - Finding Campbell’s Cove without a scramble
Australia Sailing Tours, Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in Australia, Dining Experiences, Dinner and Evening Sailing Cruises, Sailing Tours, Sydney Sailing Tours, Tall Ship and Schooner Sailing, Tour Reviews

Sydney: Tall Ship Harbour Twilight Dinner Cruise

14.Tall Ship Harbour Twilight Dinner Cruise

★★★★★★★★★★4.4 · 342 reviews · 2 hours · from $77

Join the Southern Swan or Soren Larsen at Campbell’s Cove for a two-hour twilight sail past the Opera House, Harbour Bridge, Fort Denison, and Luna Park. You can help set the sails, steer the ship, or relax with dinner. The English-speaking crew share harbour and ship stories, with drinks and mast climbing sold separately.

“fab trip, great hosts , good food and great that guests could contribute to trip”

Check availability →Read our full review

Key West: Schooner Sunset Sail with Food & Drinks - Checking in behind Schooner Wharf Bar
Food, Food & Drink, Key West Sailing Tours, Sailing Tours, Sailing Tours with an Open Bar, Sailing Tours with an Open Bar in Key West, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tall Ship and Schooner Sailing, Tall Ship Sailing in Key West, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours

Key West: Schooner Sunset Sail with Food & Drinks

15.Schooner Sunset Sail with Food & Drinks

★★★★★★★★★★4.9 · 318 reviews · 2 hours · from $122

Sail for two hours aboard the America 2.0, a polished wooden schooner with teak decks and 3,600 square feet of canvas. Enjoy drinks and a personal hors d’oeuvres plate while the crew sails past Fort Zachary Taylor, Sand Key Reef, Mallory Square, and Sunset Pier. Captain Janet is a favorite on many departures.

“Friendly staff, clean boat, and overall great experience. Would recommend to anyone in the Key West area!”

Check availability →Read our full review

Newest in Tall Ship and Schooner Sailing

★ 5.0Public Schooner Sail in GreenportFrom $1658 reviews
★ 5.0Schooner Appledore Day Sail with Full Bar in Key West89 reviews
★ 5.0Key West Historic Schooner When And If Sunset Cruise114 reviews
★ 5.0Key West Wreckers Race Aboard Schooner America 2.0From $1119 reviews
★ 5.0Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak93 reviews
★ 5.0Key West Night Cruise aboard Schooner America 2.0From $833 reviews
★ 5.0Tour of the island of Procida in a schoonerFrom $8128 reviews
★ 5.0Sail on Tall Ship Windy, join us for our “Chicago Skyline Sail”From $9120 reviews
★ 5.0Chicago’s Fireworks Show aboard Tall Ship Windy!From $11314 reviews
★ 4.0Sailing in Table Bay Cape Town aboard a Classic SchoonerFrom $233 reviews
★ 5.0Day Sails and Sunset tours on Schooner Surprise in Camden MaineFrom $7380 reviews
★ 5.0Bay of Islands Tall Ship Sundowner SailingFrom $61100 reviews
★ 4.8Tall Ship Lunch CruiseFrom $7769 reviews
★ 5.0Sydney Harbor Tall Ship Convicts, Castles & Champagne TourFrom $842 reviews
★ 5.0Sydney Harbor Tall Ship Wine & Canapés Evening CruiseFrom $1053 reviews

Keep browsing

Catamaran Sailing TripsSailing Yacht ChartersPrivate Sailing ChartersNile Felucca Sailing
Scroll to Top

Pick a coast

Sunset, snorkel, or the whole boat.

On deck

Sunset SailsOpen-Bar SailsLunch AboardDinner SailsMusic on Deck

In the water

Snorkel StopsSwim and BeachWhales and DolphinsIsland HoppingHarbour and Coast

The boat

CatamaransYacht ChartersTall ShipsPrivate ChartersNile Feluccas

The Mediterranean

SpainGreeceItalyCroatiaFrance