On the water · SAILING & TALL SHIP CRUISES

15 Tall Ship Cruises Worth Flying For

22 tours  ·  from $35 a head

Under canvas a harbour goes quiet, which is the whole reason to pay for it. The 15 below cover the schooners of New England, the sailing dinners out of Auckland and the day sails, with prices and season notes.

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor - Fort Sumter, the Battery, and Charleston’s waterfront
Charleston Harbor Cruises, Harbour Cruises, Sailing & Tall Ship Cruises, Sailing Cruises in the USA, Sightseeing Boat Tours, Sightseeing Boat Tours in the USA, Tour Reviews, USA Harbor Cruises, Whale & Dolphin Harbour Cruises, Whale and Dolphin Cruises in the USA

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

1.Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

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

Board the 84-foot Schooner Pride at Aquarium Wharf for a 90-minute, mostly quiet sail around Charleston Harbor. The crew raises the sails by hand, points out Fort Sumter, Patriots Point, USS Yorktown, the Battery, and the Ravenel Bridge, and may let you help with the lines. Bring snacks, buy drinks on board, and watch for dolphins.

“The crew is pleasant and outgoing. It was really a nice experience especially for my wife who is not a friend of water.”

Check availability →Read our full review

Classic Tall Ship Cruise in Boston Harbor - Raising the sails with Captain Fredo, Jess, and Max
Boston Harbor Cruises, Harbour Cruises, Sailing & Tall Ship Cruises, Sailing Cruises in the USA, Tour Reviews, USA Harbor Cruises

Classic Tall Ship Cruise in Boston Harbor

2.Classic Tall Ship Cruise in Boston Harbor

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

Board the Liberty Star at Marina Overlook for a relaxed 90-minute sail around Boston Harbor. Captain Fredo and crew members Jess and Max may invite you to help raise the sails, while you enjoy skyline views, snacks, drinks, and fresh air. The route depends on wind and conditions, so this is a sailing experience, not a guaranteed trip to the harbor islands.

“Just loved the sailboat — not your usual tourist attraction, but definitely something worth doing! Pure zen time: peaceful, beautiful, unforgettable.”

Check availability →Read our full review

Auckland Harbour Sailboat Cruise Including Three Course Dinner - Auckland Harbour Bridge and the city’s working waterfront
Auckland Harbour Cruises, Harbour Cruises, Harbour Dinner Cruises, New Zealand Harbour Cruises, Sailing & Tall Ship Cruises, Tour Reviews

Auckland Harbour Sailboat Cruise Including Three Course Dinner

3.Auckland Harbour Sailboat Cruise Including Three Course Dinner

★★★★★★★★★★4.5 · 476 reviews · from $105

Board a 50-foot sailing yacht at Viaduct Harbour for a 2.5-hour evening cruise with a welcome drink, live commentary, and three-course dinner. You’ll pass the Sky Tower, Harbour Bridge, Ferry Building, and Mt. Eden, with chances to help hoist the sails or try the wheel. Jackets and blankets are provided.

“The sailing and crew were great the food was tasty, but dinner was not very hot and serving size was small. It was a wonderful evening.”

Check availability →Read our full review

Seattle Sailing Harbor Tour - Elliott Bay and the Seattle skyline
Harbour Cruises, Sailing & Tall Ship Cruises, Sailing Cruises in the USA, Seattle Harbor Cruises, Tour Reviews, Tours, USA Harbor Cruises

Seattle Sailing Harbor Tour

4.Seattle Sailing Harbor Tour

★★★★★★★★★★4.5 · 473 reviews · 2 hours (approx.) · from $39

Spend about two hours sailing from Pier 66 Bell Harbor Marina aboard a historic tall ship. The crew may invite you to help raise the sails, while the captain shares the water with you from a comfortable, relaxed setting. Buy drinks and snacks onboard, watch for Mount Rainier and the Olympic Mountains, and return to the same downtown pier.

“We had such an amazing time. The crew was very friendly and took care of us throughout the sailing adventure. I also enjoyed the great wines being served, being able to help with the sails and of course - the views were stunning.”

Check availability →Read our full review

Auckland: Harbour Sailing Cruise with 3-Course Dinner - Sailing Waitematā Harbour on a 50-foot yacht
Auckland Harbour Cruises, Harbour Cruises, Harbour Dinner Cruises, New Zealand Harbour Cruises, Sailing & Tall Ship Cruises, Tour Reviews

Auckland: Harbour Sailing Cruise with 3-Course Dinner

5.Harbour Sailing Cruise with 3-Course Dinner

★★★★★★★★★★4.5 · 319 reviews · 2h 30m · from $95

Join Explore Group New Zealand at Viaduct Harbour for a 2.5-hour evening sail aboard a 50-foot yacht. Enjoy a welcome drink, local commentary, and a three-course meal from The Lula Inn. You may help the crew or try the wheel, while jackets and blankets keep you comfortable when Auckland’s weather turns cool.

“A nice and windy evening, so lots of great sailing. Food was tasty.”

Check availability →Read our full review

Auckland Harbour 1.5-Hour Sailing Cruise - Passing the Sky Tower and Auckland skyline
Auckland Harbour Cruises, Harbour Cruises, New Zealand Harbour Cruises, Sailing & Tall Ship Cruises, Tour Reviews

Auckland Harbour 1.5-Hour Sailing Cruise

6.Auckland Harbour 1.5-Hour Sailing Cruise

★★★★★★★★★★4.7 · 301 reviews · 1h 30m · from $65

Meet the Explore Group crew at Viaduct Harbour for a relaxed 90-minute sail on a 50-foot yacht. You’ll pass the Sky Tower, Harbour Bridge, Westhaven Marina, Devonport, and Auckland’s skyline. The crew may let you steer or help with the sails, with coffee, tea, hot chocolate, and a cookie included.

“Fabulous sail. Several passengers had a go at the helm including my husband. It was a bucket list present for his 80 bday and couldnt have been a better gift. Thank you so much Captain and crew for a fantastic sail.”

Check availability →Read our full review

Boston: Tall Ship Harbor Sail - Boston skyline views from the deck
Boston Harbor Cruises, Harbour Cruises, Sailing & Tall Ship Cruises, Sailing Cruises in the USA, Tour Reviews, USA Harbor Cruises

Boston: Tall Ship Harbor Sail

7.Tall Ship Harbor Sail

★★★★★★★★★★4.6 · 261 reviews · 1h 30m · from $35

Leave Fan Pier Marina aboard a classic Liberty Fleet schooner and spend 90 minutes under sail in Boston Harbor. Expect skyline views, harbor traffic, open water, and a friendly crew who may let you help raise the sails. Drinks are sold onboard, but narration is informal rather than scheduled.

“This was such a fun afternoon activity! We had a long layover in Boston so wanted to get out of the airport and do something fun to kill some time. We’ve been to Boston before and done one of the other Harbor Cruises but this was even more fun! The whole crew is so personable and makes the entire ride interactive. They let anyone who wishes to help with raising and lowering the sails. They chat with everyone but also tell little stories and tell you various facts about the boat you’re on and other Boston fun facts. The whole experience was so much fun. We will definitely save this…”

Check availability →Read our full review

Charleston: Schooner Sailing Harbor Tour & Dolphin Watch - The pleasure of a quiet harbor sail
Charleston Harbor Cruises, Harbour Cruises, Sailing & Tall Ship Cruises, Sailing Cruises in the USA, Tour Reviews, Tours, USA Harbor Cruises, Whale & Dolphin Harbour Cruises, Whale and Dolphin Cruises in the USA

Charleston: Schooner Sailing Harbor Tour & Dolphin Watch

8.Schooner Sailing Harbor Tour & Dolphin Watch

★★★★★★★★★★4.6 · 255 reviews · from $48

Join the captain and crew aboard the three-masted Schooner Pride at Aquarium Wharf for a 1.5-hour Charleston Harbor sail. You can help raise sails reaching 84 feet, pass Fort Sumter and Castle Pinckney, and watch for dolphins. This is mainly a peaceful boat ride, not a fully narrated history tour. Drinks are sold on board.

“The crew was very personable and the ship was perfect. They raised sail as soon as the ship was away from the dock. Well priced and worth it.”

Check availability →Read our full review

Boston: Downtown Harbor Sailing Cruise - Inner Harbor Islands and the Charleston Navy Yard
Boston Harbor Cruises, Harbour Cruises, Sailing & Tall Ship Cruises, Sailing Cruises in the USA, Tour Reviews, USA Harbor Cruises

Boston: Downtown Harbor Sailing Cruise

9.Downtown Harbor Sailing Cruise

★★★★★★★★★★4.8 · 227 reviews · 90 minutes - 2 hours · from $66

Sail Boston Harbor aboard the classic Adirondack III or IV, a pilot schooner that passes the Fish Pier, Castle Island, Moakley Courthouse, Aquarium, and Inner Harbor Islands. Captain Teresa, Captain Adam, and other crew members have earned praise for friendly service and clear answers. Choose a 90-minute or 2-hour cruise, bring a picnic, and pay onboard by credit card.

“Captain Adam took us on a great cruise around the harbor - lots of fun with an upbeat crew and wind in our sails.”

Check availability →Read our full review

Seattle: Tall Sailboat Sunset Harbor Cruise - Raising the sails on the Bay Lady
Harbour Cruises, Sailing & Tall Ship Cruises, Sailing Cruises in the USA, Seattle Harbor Cruises, Sunset Cruises in the USA, Sunset Harbour Cruises, Tour Reviews, USA Harbor Cruises

Seattle: Tall Sailboat Sunset Harbor Cruise

10.Tall Sailboat Sunset Harbor Cruise

★★★★★★★★★★4.8 · 223 reviews · 2 hours · from $79

Spend two hours aboard the schooner Bay Lady, sailing from Pier 66 as the sun drops behind the Olympic Mountains. You can help raise the sails, take a turn at the wheel, and buy beer, wine, cider, champagne, snacks, or soft drinks. Bring warm layers: the boat sails rain or shine, and the evening breeze can feel cold.

“Best experience we have had here. The captain and crew were tremendous.”

Check availability →Read our full review

Luxury Sailing Cruise on Sydney Harbour with Lunch - The Opera House, The Rocks, and Sydney’s Colonial Past
Australia Harbour Cruises, Harbour Cruises, Harbour Lunch & Brunch Cruises, Lunch Cruises in Australia, Lunch Cruises in Sydney, Sailing & Tall Ship Cruises, Sydney Harbour Cruises, Tour Reviews

Luxury Sailing Cruise on Sydney Harbour with Lunch

11.Luxury Sailing Cruise on Sydney Harbour with Lunch

★★★★★★★★★★5.0 · 171 reviews · from $251Top rated

Join Captain David aboard the 40-foot yacht Emma Mei for a five-hour Sydney Harbour cruise. You’ll pass the Opera House, Harbour Bridge, Watsons Bay, and Sydney Heads, then stop at Store Beach for swimming, snorkeling, and a gourmet lunch with Australian beer and wine. The group is limited to eight.

“We had a great time sailing with David! He was knowledgeable the Sydney area and his commentary was informative and entertaining. He served an amazing lunch which far exceeded my expectations! I highly recommend this tour!”

Check availability →Read our full review

JFarwell Adventure Yacht Sailing in the Halifax Harbour - Halifax Harbour from the deck
Canada Harbour Cruises, Catamaran & Yacht Cruises, Halifax Harbour Cruises, Harbour Cruises, Sailing & Tall Ship Cruises, Tour Reviews

JFarwell Adventure Yacht Sailing in the Halifax Harbour

12.JFarwell Adventure Yacht Sailing in the Halifax Harbour

★★★★★★★★★★5.0 · 147 reviews · 1 hour 30 minutes (approx.) · from $82

Spend about 90 minutes sailing Halifax Harbour with J Farwell Sailing Tours. Captains such as Jeff, Ryan, and Frankie invite you to help raise the mainsail and jib, assist with tacks, or take the helm. The yacht carries up to 12 people, with Nova Scotia wine, beer, and spirits available for purchase.

“There wasn’t much wind for sailing, so we motored around the harbor. But it was a beautiful day and the crew did the best they could under the circumstances.”

Check availability →Read our full review

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor - Helping raise the sails
2-Hour Experiences, Harbour Cruises, Maine Harbor Cruises, Sailing & Tall Ship Cruises, Sailing Cruises in the USA, Tour Reviews, USA Harbor Cruises

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

13.Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

★★★★★★★★★★4.5 · 126 reviews · 2 hours (approx.) · from $54

Spend about two hours sailing from Boothbay Harbor’s historic waterfront aboard the schooner Eastwind. You may help raise the sails, watch for seals and porpoises, and take in islands, lighthouses, and ocean views. Captains and mates such as Sarah, Josh, Luke, Christine, and Mareson are known for friendly, hands-on service. Bring non-alcoholic drinks and snacks, or buy beer, wine, and liquor on board.

“Amazing. Fun. Beautiful views. Great captain and mate. Such a good time with interactive hoisting the sails.”

Check availability →Read our full review

Boston: Sunset Tall Ship Harbor Cruise - Raising the Sails With the Crew
Boston Harbor Cruises, Harbour Cruises, Sailing & Tall Ship Cruises, Sailing Cruises in the USA, Sunset Cruises in the USA, Sunset Harbour Cruises, Tour Reviews, USA Harbor Cruises

Boston: Sunset Tall Ship Harbor Cruise

14.Sunset Tall Ship Harbor Cruise

★★★★★★★★★★4.8 · 115 reviews · 2 hours · from $68

Spend two hours aboard Liberty Fleet’s classic tall ship, sailing from Fan Pier Marina around Boston Harbor at sunset. You can help hoist the sails, ask the English-speaking crew about landmarks, and possibly take the wheel. Drinks, including Boston-brewed beer, are sold onboard, but food is not included.

“We enjoyed this excursion so much. The crew was absolutely phenomenal. Professional while also being really fun, funny, and entertaining. They're characters for sure in the best way. We loved our time on the ship!”

Check availability →Read our full review

Seattle: Tall Ship Harbor Cruise - What the Two Hours Feel Like
Harbour Cruises, Sailing & Tall Ship Cruises, Sailing Cruises in the USA, Seattle Harbor Cruises, Tour Reviews, USA Harbor Cruises

Seattle: Tall Ship Harbor Cruise

15.Tall Ship Harbor Cruise

★★★★★★★★★★4.7 · 86 reviews · from $73

Board the schooner Bay Lady at Pier 66 for a two-hour English-language harbor sail. Crew members Anthony, Madison, and Clark may invite you to raise the sails, steer, or watch a small cannon fire. Expect Seattle skyline views, possible Mount Rainier sightings, marine life, drinks for purchase, and a rain-or-shine outing.

“Loved the cruise I just wish there was more narrated information”

Check availability →Read our full review

New in Sailing & Tall Ship Cruises

★ 5.0Sailing Charter around Vancouver Harbour Private Tour2 reviews

Keep browsing

Catamaran & Yacht CruisesPrivate Harbour ChartersSpeedboat & Jet Boat RidesHarbour Kayak Tours
Scroll to Top

Pick a harbour, pick a boat

Fifty countries, one thing in common: the best view is from the deck.

Big harbours

SydneyThe USABostonSan FranciscoHamburgMalta

On deck

Dinner CruisesLunch & BrunchHarbour LightsSunset SailingsDrinks on Deck

Under sail

Tall ShipsCatamaransPrivate ChartersJet BoatsKayaks

Out of the port

Sightseeing BoatsDolphinsShore ExcursionsHarbour FerriesQuayside Walks