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Top 10 Best USA Sailing Trips

Found 429 Sailing Trips activities in USA. Sort by Popularity. - Page 14
 

Private Sailboat Charter on San Francisco Bay

(5 of 8 reviews)

Sunny winter days can be the Best on San Francisco Bay! No Fog, gentle breeze and sunshine! 3 hour PRIVATE Charter with a unique experience aboard Carmelita, our beautiful and pristine Catalina 42 sailboat. We provide our clients ... More

Free Cancellation
Private Tour
Start From $995.00
 
Private Sailboat Charter on San Francisco Bay

Private Sailboat Charter on San Francisco Bay

  • USA
  • Superb8 reviews5

Sunny winter days can be the Best on San Francisco Bay! No Fog, gentle breeze and sunshine! 3 hour P....

    Free Cancellation
    Private Tour
    Start From $995.00
 
 

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

(4.8 of 14 reviews)

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More

Free Cancellation
Private Tour
Start From $1,150.00
 
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

  • USA
  • Superb14 reviews4.8

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....

    Free Cancellation
    Private Tour
    Start From $1,150.00
 
 

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

(5 of 32 reviews)

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor since 2012, our sailing yachts are the highest quality and operated ... More

Free Cancellation
Private Tour
Start From $525.00
 
Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique

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

  • USA
  • Superb32 reviews5

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

New York City Live Jazz Sail

(4.9 of 14 reviews)

Step aboard 105-foot Schooner America 2.0, a modern tribute to the first boat that won the America's Cup in 1851, for a 2-hour sail around New York Harbor. Sit back and relax while enjoying live Jazz music played throughout this s... More

Free Cancellation
Private Tour
Start From $131.72
 
New York City Live Jazz Sail Likely to Sell Out

New York City Live Jazz Sail

  • USA
  • Superb14 reviews4.9

Step aboard 105-foot Schooner America 2.0, a modern tribute to the first boat that won the America's....

    Free Cancellation
    Private Tour
    Start From $131.72
 
 

New York Harbor Wine and Jazz Sail aboard Clipper City

(4.4 of 21 reviews)

Sail toward the sun setting behind the Statue of Liberty and return with the Manhattan skyline glittering before you—a view that captures New York at its very best. More than a cruise, this is an homage to the owner’s New York... More

Free Cancellation
Private Tour
Start From $140.08
 
New York Harbor Wine and Jazz Sail aboard Clipper City Likely to Sell Out

New York Harbor Wine and Jazz Sail aboard Clipper City

  • USA
  • Exellent21 reviews4.4

Sail toward the sun setting behind the Statue of Liberty and return with the Manhattan skyline glitt....

    Free Cancellation
    Private Tour
    Start From $140.08
 
 

Schooner Eastwind Sunset Sail to see the Maine Coastline

(4.7 of 61 reviews)

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More

Free Cancellation
Private Tour
Start From $59.95
 
Schooner Eastwind Sunset Sail to see the Maine Coastline Likely to Sell Out

Schooner Eastwind Sunset Sail to see the Maine Coastline

  • USA
  • Superb61 reviews4.7

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Key West: Sunset Sail + Reef Snorkel & Sandbar

(5 of 29 reviews)

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • Guided Snorkeling Your mate hops in the water with you and points out animals and shows yo... More

Free Cancellation
Private Tour
Start From $143.05
 
Key West: Sunset Sail + Reef Snorkel & Sandbar Likely to Sell Out

Key West: Sunset Sail + Reef Snorkel & Sandbar

  • USA
  • Superb29 reviews5

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. Wh....

    Free Cancellation
    Private Tour
    Start From $143.05
 
 

New York City Skyline Lights Sail

(4.7 of 13 reviews)

Experience New York City from the water on classic Schooner Adirondack. Gaze at the city lights from the water and enjoy a peaceful setting as you escape the city and take to a quiet harbor at night. Key points about this activ... More

Free Cancellation
Private Tour
Start From $67.01
 
New York City Skyline Lights Sail Likely to Sell Out

New York City Skyline Lights Sail

  • USA
  • Superb13 reviews4.7

Experience New York City from the water on classic Schooner Adirondack. Gaze at the city lights fro....

    Free Cancellation
    Private Tour
    Start From $67.01
 
 

Captain Steve's Sailing Experience on Long Island

(5 of 10 reviews)

Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best enjoyed from the water. With Captain Steve's Sailing Experience, you can experience the beauty of the area from a unique perspecti... More

Free Cancellation
Private Tour
Start From $475.00
 
Captain Steve's Sailing Experience on Long Island Likely to Sell Out

Captain Steve's Sailing Experience on Long Island

  • USA
  • Superb10 reviews5

Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best ....

    Free Cancellation
    Private Tour
    Start From $475.00
 
 

San Diego Half-Day Marine Wildlife Tour with Lunch

(4.8 of 27 reviews)

Experience an exciting adventure while sailing along the San Diego coastline. Venture off into the Pacific Ocean and catch a chance to see local marine wildlife in its natural habitat, including sea lions, pelicans, and migrator... More

Free Cancellation
Private Tour
Start From $196.00
 
San Diego Half-Day Marine Wildlife Tour with Lunch Likely to Sell Out

San Diego Half-Day Marine Wildlife Tour with Lunch

  • USA
  • Superb27 reviews4.8

Experience an exciting adventure while sailing along the San Diego coastline. Venture off into the P....

    Free Cancellation
    Private Tour
    Start From $196.00
 
 

Guided Seattle Sailing Adventure from Bainbridge Island

(5 of 82 reviews)

Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning waterfront homes, and maybe even spot whales. Or we could see a nuclear submarine, inbound container ships, or century-old schooners... More

Free Cancellation
Private Tour
Start From $295.00
 
Guided Seattle Sailing Adventure from Bainbridge Island Likely to Sell Out

Guided Seattle Sailing Adventure from Bainbridge Island

  • USA
  • Superb82 reviews5

Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning wa....

    Free Cancellation
    Private Tour
    Start From $295.00
 
 

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

(5 of 121 reviews)

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the North side of the island. During the day, this is generally filled with exciting winds for gre... More

Free Cancellation
Private Tour
Start From $485.00
 
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail Likely to Sell Out

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

  • USA
  • Superb121 reviews5

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind....

    Free Cancellation
    Private Tour
    Start From $485.00
 
 

Private Classic Sailboat Tour in New York City

(5 of 1 review)

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a unique and immersive experience on the Hudson River. You'll enjoy stunning views of iconic landmarks like the Statue of Liberty, E... More

Free Cancellation
Private Tour
Start From $800.00
 
Private Classic Sailboat Tour in New York City Likely to Sell Out

Private Classic Sailboat Tour in New York City

  • USA
  • Superb1 review5

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a ....

    Free Cancellation
    Private Tour
    Start From $800.00
 
 

New York City Skyline Night Sailboat Tour

(5 of 13 reviews)

Step aboard a beautiful sailboat, Schooner America 2.0, for a relaxing city lights tour around New York. See the New York City skyline, the Statue of Liberty and Ellis Island lit up at night. Sit back and relax while enjoying a pe... More

Free Cancellation
Private Tour
Start From $67.01
 
New York City Skyline Night Sailboat Tour Likely to Sell Out

New York City Skyline Night Sailboat Tour

  • USA
  • Superb13 reviews5

Step aboard a beautiful sailboat, Schooner America 2.0, for a relaxing city lights tour around New Y....

    Free Cancellation
    Private Tour
    Start From $67.01
 
 

Polynesian Canoe Morning Sail

(5 of 18 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Free Cancellation
Private Tour
Start From $200.00
 
Polynesian Canoe Morning Sail Likely to Sell Out

Polynesian Canoe Morning Sail

  • USA
  • Superb18 reviews5

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Free Cancellation
    Private Tour
    Start From $200.00
 
 

Brunch Cruise with Buffet in Washington

(4 of 10 reviews)

Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer three public sailing tours daily from Seattle’s downtown waterfront. Our beautiful sailing ship, the Bay Lady, evokes the romanc... More

Free Cancellation
Private Tour
Start From $98.21
 
Brunch Cruise with Buffet in Washington Likely to Sell Out

Brunch Cruise with Buffet in Washington

  • USA
  • Very Good10 reviews4

Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer ....

    Free Cancellation
    Private Tour
    Start From $98.21
 
 

1 Hour Private Charter in New York Harbor for up to 6 people

(4.9 of 52 reviews)

This is a private tour which means it is just you and your party on board. You will be sailing on our beautiful classic sailboat named Tara. Tara is a classic sailboat and one of a kind in NYC. You will sail past Elis Island and t... More

Free Cancellation
Private Tour
Start From $375.00
 
1 Hour Private Charter in New York Harbor for up to 6 people Likely to Sell Out

1 Hour Private Charter in New York Harbor for up to 6 people

  • USA
  • Superb52 reviews4.9

This is a private tour which means it is just you and your party on board. You will be sailing on ou....

    Free Cancellation
    Private Tour
    Start From $375.00
 
 

Monterey Private 3 - 4 Hour Whale Watching Cruise

(5 of 2 reviews)

Enjoy a 3 - 4 hour sailing cruise on the Monterey Bay. This Marine Mammal and Wildlife Safari is a private guided tour and can accommodate up to 6 people. Whale sightings are NOT guaranteed. However, this tour is designed to give... More

Free Cancellation
Private Tour
Start From $950.00
 
Monterey Private 3 - 4 Hour Whale Watching Cruise Likely to Sell Out

Monterey Private 3 - 4 Hour Whale Watching Cruise

  • USA
  • Superb2 reviews5

Enjoy a 3 - 4 hour sailing cruise on the Monterey Bay. This Marine Mammal and Wildlife Safari is a p....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Private Oahu Sunset Charter with Tasting and Drinks

(5 of 48 reviews)

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people while enjoying the West Oahu Sunset on this 2.5-hour experience. There’s more than enoug... More

Free Cancellation
Private Tour
Start From $1,413.61
 
Private Oahu Sunset Charter with Tasting and Drinks Likely to Sell Out

Private Oahu Sunset Charter with Tasting and Drinks

  • USA
  • Superb48 reviews5

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world....

    Free Cancellation
    Private Tour
    Start From $1,413.61
 
 

Private Sailing Tour of Bodega Bay

(4.8 of 86 reviews)

This is a unique experience because you get to sail a 33' boat with a licensed captain. You can be involved as much or as little as you want... More

Free Cancellation
Private Tour
Start From $122.50
 
Private Sailing Tour of Bodega Bay Likely to Sell Out

Private Sailing Tour of Bodega Bay

  • USA
  • Superb86 reviews4.8

This is a unique experience because you get to sail a 33' boat with a licensed captain. You can be i....

    Free Cancellation
    Private Tour
    Start From $122.50
 
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