COASTAL SAILING TOURS IN THE USA

15 Coastal Sailing Tours in the USA, Best Day First

63 sailings  ·  from $35 a head

This is the shortlist you would send a friend: 15 coastal sailing tours in the USA worth the money, each with its price, its verdict from the people who sailed it, and the one thing to know before you commit.

Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail - What the Moana Catamaran feels like underway
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Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

1.Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

★★★★★★★★★★5.0 · 2,205 reviews · 2 hours (approx.) · from $89Our pick

Board the Hawaii-built Moana Catamaran at Kewalo Basin Harbor for a two-hour sunset sail along Waikiki and past Diamond Head. Your captain and crew serve a complimentary first drink from the premium bar, with more available for $8. Look for dolphins, and humpback whales from November through May. Shoes are collected before boarding.

“A really wonderful expierence, we did the VIP which we liked to board early and get the free drinks included. Lovely hosts and weather was amazing!”

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Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure - Reaching the Captain Cook Monument
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Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

2.Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

★★★★★★★★★★5.0 · 695 reviews · 4 hours (approx.) · from $189

Set sail from Kailua-Kona aboard a 50-foot catamaran with a friendly crew such as Captain Dan and Captain Jacques. Enjoy Kona coffee and pastries, snorkel for about an hour at Kealakekua Bay, then build a deli lunch before sailing home. Instruction, gear, flotation noodles, drinks, and reef guidance are included.

“Amazing snorkeling trip. Friendly and helpful crew, amazing boat and snorkeling gear and the fish and coral are incredible!”

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San Francisco Bay Sailing Cruise - Alcatraz from the water
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San Francisco Bay Sailing Cruise

3.San Francisco Bay Sailing Cruise

★★★★★★★★★★5.0 · 629 reviews · 1 hour 30 minutes (approx.) · from $72

Set out from Pier 39 on Adventure Cat, a 55- or 65-foot catamaran carrying up to 42 people. You’ll sail past Alcatraz, under the Golden Gate Bridge, and toward Sausalito, with covered seating, trampoline nets, onboard drinks, and multilingual audio guides. Crew members have included Captain Mike, Wolfgang, Chad, and Lisa.

“The sailing catamaran was amazing! We scored with the best weather and minimal passengers onboard. The best staff and service 10/10 🙌🏻”

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Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor - What the non-narrated format really means
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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.”

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Classic Tall Ship Cruise in Boston Harbor - Boarding at Marina Overlook
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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.”

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Sightseeing Day Sail around Boston Harbor - Fan Pier, Moakley Courthouse, and Harpoon Brewery
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Sightseeing Day Sail around Boston Harbor

6.Sightseeing Day Sail around Boston Harbor

★★★★★★★★★★5.0 · 541 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $66

Sail Boston Harbor aboard Schooner Adirondack III or IV for 1.5 or 2 hours. You’ll pass the Seaport District, Fan Pier, Castle Island, Fort Independence, Spectacle Island, and Long Island. The crew answers questions, drinks are sold by card, and the boat often sails under wind power rather than engine power.

“We learned some history and some local spots from the water. We also got some tips for restaurants and activities in the area. Good experience and beautiful views from the boat”

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Kauai’s Na Pali Coast Snorkel and Sail Tour - Leaving Port Allen on the Leila catamaran
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Kauai’s Na Pali Coast Snorkel and Sail Tour

7.Kauai’s Na Pali Coast Snorkel and Sail Tour

★★★★★★★★★★5.0 · 541 reviews · 6 hours (approx.) · from $292

Join Holo Holo Charters at Port Allen for a roughly six-hour catamaran trip along Kauai’s Na Pali Coast. You’ll get breakfast, lunch, snorkel gear, instruction, and drinks, with crews led by captains such as Kelly, Jess, and Mike. Expect sea turtles, dolphins, seasonal whales, reef snorkeling, and no shore landings.

“Amazing experience! The views, the food, the captain and the crew could not have been any better. What an incredible day!”

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Seattle Sailing Harbor Tour - Mount Rainier, the Olympics, and the Cascades
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Seattle Sailing Harbor Tour

8.Seattle Sailing Harbor Tour

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

Spend about two hours aboard Seattle’s historic tall ship, sailing from Pier 66 into Elliott Bay. Expect Space Needle and skyline views, possible Mount Rainier and mountain-range views, onboard restrooms, drinks for purchase, and a chance to help raise the sails.

“It was really something different. Wish we could have music or some kind of singing.. it was just a little boring.”

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Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling - Crossing Biscayne Bay under sail
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Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

9.Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

★★★★★★★★★★5.0 · 441 reviews · 3 hours 30 minutes (approx.) · from $129

Spend about 3.5 hours sailing Biscayne Bay aboard a wind-powered Hobie catamaran with captains such as David, JP, James, or JD. Stop at sandbars, snorkel, walk among mangroves or islets, and watch for dolphins, manatees, turtles, rays, and starfish. The small boats hold up to five people each.

“Friendly captain who was relaxed and never in a rush. Communicated clearly the day before and day of our sailing. Got to snorkel with a sea turtle, see a nurse shark, and enjoy the beautiful views.”

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Sunset Sailing Cruise on a Tall Ship in Boston Harbor - Two hours of sailing, not a landmark lecture
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Sunset Sailing Cruise on a Tall Ship in Boston Harbor

10.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.”

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1.5-Hour San Francisco Bay Sailing Tour - Alcatraz and Angel Island from the water
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1.5-Hour San Francisco Bay Sailing Tour

11.1.5-Hour San Francisco Bay Sailing Tour

★★★★★★★★★★5.0 · 393 reviews · 1 hour 30 minutes (approx.) · from $99

Join the San Francisco Sailing Company for a 90-minute cruise from Pier 39 on a teak-decked, double-masted sailboat carrying up to 18 people. Captain Michael, Dave, or another crew member may steer the route, with two included drinks and views of Alcatraz, Angel Island, the Bay Bridge, Sausalito, and the Golden Gate Bridge.

“Very engaging team on the sailboat, very friendly - great time, highly recommend!! Good tour, great recommendations, a lot of fun!”

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2-Hour Sunset Sail on the San Francisco Bay - Alcatraz and Angel Island from the water
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2-Hour Sunset Sail on the San Francisco Bay

12.2-Hour Sunset Sail on the San Francisco Bay

★★★★★★★★★★5.0 · 392 reviews · 2 hours (approx.) · from $129

Meet the captain and first mate at Pier 39, then board the Privateer for a two-hour sunset sail. You’ll pass Alcatraz and Angel Island, cruise near Sausalito, and go beneath the Golden Gate Bridge when conditions allow. Two drinks are included, with beer, wine, soda, and water available. The boat carries up to 18 travelers.

“It was a great experience, better than we expected! The crew is very knowledgeable of what they’re doing, so just relax and enjoy your time out in the water with no worries.”

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San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included - The Maritime Museum and Star of India
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San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

13.San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

★★★★★★★★★★5.0 · 331 reviews · 2 hours 30 minutes (approx.) · from $115

Join Captain Phillip aboard Liberty, a hand-restored reproduction of a 1904 sailboat, for a 2.5-hour evening cruise on San Diego Bay. The small group, usually limited to six people, keeps the outing personal. You can help with the sailing, watch for sea lions and dolphins, and enjoy beer, white wine, soft drinks, water, and light snacks.

“The boat is very nice but definitely just fits 6 plus Captain Philip. It does get chilly on the water as the sun is starting to set but we came prepared so we were quite comfortable. There was plenty of refreshments on the boat and everything was clean and shiny. I think the Captain knows a lot about the area and could share a lot of info about what you're seeing but he pretty much read his audience and did tell us about a lot of things and was very knowledgeable and always answered our questions but as we were girlfriends (plus my lucky husband) of close to 60 years…”

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Boston: Harbor Champagne Sunset Sail from Rowes Wharf - The first views: Fish Pier and Fan Pier
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Boston: Harbor Champagne Sunset Sail from Rowes Wharf

14.Harbor Champagne Sunset Sail from Rowes Wharf

★★★★★★★★★★4.8 · 299 reviews · 2 hours · from $82

Spend two hours sailing Boston Harbor aboard Schooner Adirondack III or IV from Rowes Wharf. You’ll see the Fish Pier, Castle Island, Charleston Navy Yard, and the skyline while crew members such as Steve or Therese may share local stories. Bring a picnic, buy drinks by credit card, and dress warmly for the cool water.

“The sailboat cruise was a lot of fun. The captain and staff were personable and engaged with the guests. Chocolate cookies are good! The weather was colder than expected, and souvenir blankets were available for purchase, which was great, too.”

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Boston: Tall Ship Harbor Sail - Raising the sails and settling into harbor time
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Boston: Tall Ship Harbor Sail

15.Tall Ship Harbor Sail

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

Step aboard a classic Liberty Fleet schooner at Fan Pier Marina for a 90-minute Boston Harbor sail. You can help raise the sails, ask the captain about landmarks, and buy Boston-brewed beer, wine, or cocktails onboard. Expect a relaxed outing with skyline views, but no formal narration and possible motor use when the wind is light.

“Lots of fun for my family celebrating my husband's 75th birthday.”

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Newest in Coastal Sailing Tours in the USA

★ 5.0Oyster Bay Two Hour Sailing ExperienceFrom $595 whole boat, up to 62 reviews
★ 5.0Coast of Ka’anapali Beach Sunset Dinner SailFrom $158121 reviews
★ 5.0Private 90-Minute Harbor Sailing Charter in Key West18 reviews
★ 5.0Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht FateFrom $599 whole boat, up to 642 reviews
★ 5.0Private Sailboat Charter on San Francisco BayFrom $995 whole boat, up to 68 reviews
★ 5.0Boston Harbor Sunset Sail TourFrom $82132 reviews
★ 4.7Tall Ship Harbor CruiseFrom $7386 reviews
★ 4.7Elliott Bay Sailing CruiseFrom $6040 reviews
★ 5.0Sunset Sail to see the Maine CoastlineFrom $594 reviews
★ 4.7Schooner Apple Jack Sunset Sailing CruiseFrom $5945 reviews
★ 5.0(2hr) SUNSET Sailing Experience on SF BayFrom $14913 reviews
★ 5.0San Diego Bay Sailing TourFrom $650 whole boat, up to 62 reviews
★ 5.0San Diego Bay: 2.5 hour Pure Catamaran Sailing CruiseFrom $11916 reviews
★ 4.6Portland: Schooner Tall Ship Cruise on Casco BayFrom $111104 reviews
★ 4.8Monterey Bay: Sunset Catamaran Sailing CruiseFrom $9531 reviews

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