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Top 10 Best USA Sailing Trips

Found 447 Sailing Trips activities in USA. Sort by Popularity. - Page 6
 

Waikiki Sunset Cruise from Oahu

(4.7 of 74 reviews)

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point to observe marine life such as dolphins, whales, sea... More

Free Cancellation
Start From $45.00
 
Waikiki Sunset Cruise from Oahu

Waikiki Sunset Cruise from Oahu

  • USA
  • Superb74 reviews4.7

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks an....

    Free Cancellation
    Start From $45.00
 
 

Private Sailing Charter with Captain, BYOB

(5 of 91 reviews)

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's scenic Harbor. The golden hour of sunset is our prime booking time, offering... More

Free Cancellation
Private Tour
Start From $500.00
 
Private Sailing Charter with Captain, BYOB

Private Sailing Charter with Captain, BYOB

  • USA
  • Superb91 reviews5

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6....

    Free Cancellation
    Private Tour
    Start From $500.00
 
 
-10% Kona Tradewind Catamaran Day Sail

Kona Tradewind Catamaran Day Sail

(4.8 of 50 reviews)

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails as you glide across the water, taking in panoramic views of volcanic cliffs, sparklin... More

Special Offer
Free Cancellation
Private Tour
Start From $80.10
(Saving 10% ) $89.00
 
-10% Kona Tradewind Catamaran Day Sail

Kona Tradewind Catamaran Day Sail

  • USA
  • Superb50 reviews4.8

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing ca....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $80.10
    (Saving 10% ) $89.00
 
 
-inf% Escape from the Rock! Cruise around Alcatraz

Escape from the Rock! Cruise around Alcatraz

(4.2 of 162 reviews)

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and past Angel Island State Park before circling Alcatraz Island for an in-depth view of the prison. Take in the sights and sounds of ... More

Special Offer
Free Cancellation
Private Tour
Start From $39.00
(Saving inf% ) $0.00
 
-inf% Escape from the Rock! Cruise around Alcatraz

Escape from the Rock! Cruise around Alcatraz

  • USA
  • Exellent162 reviews4.2

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $39.00
    (Saving inf% ) $0.00
 
 
-inf% Spectacular Sunset Sail on San Diego Bay

Spectacular Sunset Sail on San Diego Bay

(5 of 38 reviews)

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group limited to six people, local captain sharing stories, hands-on sailing, and unforgettable vistas of San Diego. Watch for playful sea lions, dolphins, a... More

Special Offer
Free Cancellation
Private Tour
Start From $10.56
(Saving inf% ) $0.00
 
-inf% Spectacular Sunset Sail on San Diego Bay

Spectacular Sunset Sail on San Diego Bay

  • USA
  • Superb38 reviews5

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group limited to six people....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $10.56
    (Saving inf% ) $0.00
 
 
-inf% Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

(4.9 of 211 reviews)

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Special Offer
Free Cancellation
Private Tour
Start From $79.00
(Saving inf% ) $0.00
 
-inf% Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

  • USA
  • Superb211 reviews4.9

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $79.00
    (Saving inf% ) $0.00
 
 
-inf% Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

(5 of 43 reviews)

Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time, then climb aboard a luxurious, 28-foot powerboat cruiser and enjoy a relaxing and comfortable journey around lower Manhattan. En... More

Special Offer
Free Cancellation
Private Tour
Start From $350.00
(Saving inf% ) $0.00
 
-inf% Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

  • USA
  • Superb43 reviews5

Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $350.00
    (Saving inf% ) $0.00
 
 
-15% Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

(4.3 of 49 reviews)

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise lets you see whales (December through March), fish, even green s... More

Special Offer
Free Cancellation
Private Tour
Start From $93.45
(Saving 15% ) $109.95
 
-15% Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

  • USA
  • Exellent49 reviews4.3

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $93.45
    (Saving 15% ) $109.95
 
 
-inf% Key West Sailing & Snorkeling: A Reef Adventure

Key West Sailing & Snorkeling: A Reef Adventure

(4.7 of 248 reviews)

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Special Offer
Free Cancellation
Private Tour
Start From $79.00
(Saving inf% ) $0.00
 
-inf% Key West Sailing & Snorkeling: A Reef Adventure

Key West Sailing & Snorkeling: A Reef Adventure

  • USA
  • Superb248 reviews4.7

Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $79.00
    (Saving inf% ) $0.00
 
 
-inf% Small-Group San Diego Afternoon Sailing Excursion

Small-Group San Diego Afternoon Sailing Excursion

(4.9 of 563 reviews)

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends and fill up the whole boat!). Sit back, relax and enjoy the com... More

Special Offer
Free Cancellation
Private Tour
Start From $116.00
(Saving inf% ) $0.00
 
-inf% Small-Group San Diego Afternoon Sailing Excursion

Small-Group San Diego Afternoon Sailing Excursion

  • USA
  • Superb563 reviews4.9

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $116.00
    (Saving inf% ) $0.00
 
 
-inf% Classic Key West Schooner Sunset Sail with Full Open Bar

Classic Key West Schooner Sunset Sail with Full Open Bar

(4.9 of 266 reviews)

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Ke... More

Special Offer
Free Cancellation
Private Tour
Start From $109.00
(Saving inf% ) $0.00
 
-inf% Classic Key West Schooner Sunset Sail with Full Open Bar

Classic Key West Schooner Sunset Sail with Full Open Bar

  • USA
  • Superb266 reviews4.9

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $109.00
    (Saving inf% ) $0.00
 
 

Daytime Sailing Along San Diego's Skyline

(4.9 of 157 reviews)

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor Sunroad Marina on Harbor Island on San Diego Bay, we often s... More

Special Offer
Free Cancellation
Private Tour
Start From $99.00
(Saving inf% ) $0.00
 
-inf% Daytime Sailing Along San Diego's Skyline Likely to Sell Out

Daytime Sailing Along San Diego's Skyline

  • USA
  • Superb157 reviews4.9

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $99.00
    (Saving inf% ) $0.00
 
 

Portland Tall Ship Cruise on Casco Bay

(4.6 of 242 reviews)

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.... More

Special Offer
Free Cancellation
Private Tour
Start From $101.87
(Saving inf% ) $0.00
 
-inf% Portland Tall Ship Cruise on Casco Bay Likely to Sell Out

Portland Tall Ship Cruise on Casco Bay

  • USA
  • Superb242 reviews4.6

What better way to see the delights of Portland than from the sea in one of the famous schooner tall....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $101.87
    (Saving inf% ) $0.00
 
 

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

(4.8 of 61 reviews)

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, you’ll glide along the coastline and experience an exclusive o... More

Special Offer
Free Cancellation
Private Tour
Start From $90.01
(Saving inf% ) $0.00
 
-inf% Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu Likely to Sell Out

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

  • USA
  • Superb61 reviews4.8

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village di....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $90.01
    (Saving inf% ) $0.00
 
 

Day Sail from Traverse City with Food, Wine, & Cocktails

(4.9 of 185 reviews)

For a full description please visit our website at https://www.winddancertc.com/ where you can learn about the vessel, crew, local history and make your bookings!... More

Special Offer
Free Cancellation
Private Tour
Start From $189.00
(Saving inf% ) $0.00
 
-inf% Day Sail from Traverse City with Food, Wine, & Cocktails Likely to Sell Out

Day Sail from Traverse City with Food, Wine, & Cocktails

  • USA
  • Superb185 reviews4.9

For a full description please visit our website at https://www.winddancertc.com/ where you can learn....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $189.00
    (Saving inf% ) $0.00
 
 

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

(4.6 of 1,335 reviews)

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More

Special Offer
Free Cancellation
Private Tour
Start From $53.31
(Saving inf% ) $0.00
 
-inf% Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu Likely to Sell Out

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

  • USA
  • Superb1,335 reviews4.6

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $53.31
    (Saving inf% ) $0.00
 
 

Luxury Sunset Sail on Serendipity Catamaran in Charleston

(5 of 23 reviews)

Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seabreeze Marina in downtown Charleston. Enjoy stunning waterfront views and local wildlife as the sun dips below the horizon. This up... More

Special Offer
Free Cancellation
Private Tour
Start From $150.00
(Saving inf% ) $0.00
 
-inf% Luxury Sunset Sail on Serendipity Catamaran in Charleston Likely to Sell Out

Luxury Sunset Sail on Serendipity Catamaran in Charleston

  • USA
  • Superb23 reviews5

Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seab....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $150.00
    (Saving inf% ) $0.00
 
 

Beach Island Shelling Cruise to Keewaydin Island Tour

(4.9 of 93 reviews)

Enjoy a family favorite cruise aboard the Sweet Liberty, a 53' sailing catamaran, that can accommodate up to 44 passengers. Cruise along the Gordon River in Naples Bay and head out to Keewaydin Island, a 7-mile barrier island, wit... More

Special Offer
Free Cancellation
Private Tour
Start From $56.00
(Saving inf% ) $0.00
 
-inf% Beach Island Shelling Cruise to Keewaydin Island Tour Likely to Sell Out

Beach Island Shelling Cruise to Keewaydin Island Tour

  • USA
  • Superb93 reviews4.9

Enjoy a family favorite cruise aboard the Sweet Liberty, a 53' sailing catamaran, that can accommoda....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $56.00
    (Saving inf% ) $0.00
 
 

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(5 of 2 reviews)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot ca... More

Special Offer
Free Cancellation
Private Tour
Start From $1,200.00
(Saving inf% ) $0.00
 
-inf% 2 Hour Private Catamaran Charter in Waikiki (7-12 Guests) Likely to Sell Out

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

  • USA
  • Superb2 reviews5

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,200.00
    (Saving inf% ) $0.00
 
 

New York City Sailboat Day Cruise to the Statue of Liberty

(4.9 of 179 reviews)

Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as the crew raises sail and the boat effortlessly glides along the Hudson Rive... More

Special Offer
Free Cancellation
Private Tour
Start From $60.08
(Saving inf% ) $0.00
 
-inf% New York City Sailboat Day Cruise to the Statue of Liberty Likely to Sell Out

New York City Sailboat Day Cruise to the Statue of Liberty

  • USA
  • Superb179 reviews4.9

Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by t....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $60.08
    (Saving inf% ) $0.00
 
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