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Top 10 Best USA Sailing Trips

Found 426 Sailing Trips activities in USA. Sort by Popularity. - Page 15
 

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

(5 of 34 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 $575.00
 
Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique

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

  • USA
  • Superb34 reviews5

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

    Free Cancellation
    Private Tour
    Start From $575.00
 
 

Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering

(5 of 41 reviews)

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, kn... More

Free Cancellation
Private Tour
Start From $599.00
 
Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering

Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering

  • USA
  • Superb41 reviews5

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht ....

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

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 Statue of Liberty Sailing Tour

(5 of 14 reviews)

Experience a luxury sailing adventure! Enjoy a spacious deck lounge, sun pad, cabin lounge with table seating for six, Bluetooth sound system, luxury wraps, lavatory, and curated amenities. Fully staffed by USCG licensed captain a... More

Free Cancellation
Private Tour
Start From $800.00
 
Private Statue of Liberty Sailing Tour

Private Statue of Liberty Sailing Tour

  • USA
  • Superb14 reviews5

Experience a luxury sailing adventure! Enjoy a spacious deck lounge, sun pad, cabin lounge with tabl....

    Free Cancellation
    Private Tour
    Start From $800.00
 
 

Key West's Locals' Top Sandbar and Sailing Experience

(4.3 of 16 reviews)

Join us on Sebago's newest trip, designed to allow guests to experience the waters around Key West as so many locals do, visiting little known, breathtakingly beautiful spots with small groups of friends while enjoying great food ... More

Free Cancellation
Private Tour
Start From $193.45
 
Key West's Locals' Top Sandbar and Sailing Experience

Key West's Locals' Top Sandbar and Sailing Experience

  • USA
  • Exellent16 reviews4.3

Join us on Sebago's newest trip, designed to allow guests to experience the waters around Key West a....

    Free Cancellation
    Private Tour
    Start From $193.45
 
 

Captain Steve's Sailing Experience on Long Island

(5 of 11 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 $550.00
 
Captain Steve's Sailing Experience on Long Island

Captain Steve's Sailing Experience on Long Island

  • USA
  • Superb11 reviews5

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

    Free Cancellation
    Private Tour
    Start From $550.00
 
 

Private Oahu Sunset Charter with Tasting and Drinks

(5 of 55 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

Private Oahu Sunset Charter with Tasting and Drinks

  • USA
  • Superb55 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
 
 

Baltimore Inner Harbor Sail on Summer Wind

(4.6 of 125 reviews)

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling city from the water. Explore the Inner Harbor and the joy of sailing on t... More

Free Cancellation
Private Tour
Start From $65.00
 
Baltimore Inner Harbor Sail on Summer Wind Likely to Sell Out

Baltimore Inner Harbor Sail on Summer Wind

  • USA
  • Superb125 reviews4.6

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authe....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Private Charleston Harbor Catamaran Sail

(5 of 29 reviews)

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a panoramic view with large sliding glass doors between the saloon and the rear deck space, with... More

Free Cancellation
Private Tour
Start From $950.00
 
Private Charleston Harbor Catamaran Sail Likely to Sell Out

Private Charleston Harbor Catamaran Sail

  • USA
  • Superb29 reviews5

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing cata....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Guided Seattle Sailing Adventure from Bainbridge Island

(5 of 85 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 $360.00
 
Guided Seattle Sailing Adventure from Bainbridge Island Likely to Sell Out

Guided Seattle Sailing Adventure from Bainbridge Island

  • USA
  • Superb85 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 $360.00
 
 

Key West Dolphin Watch and Sunset Sail on Catamaran

(4.7 of 43 reviews)

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of wind. This tour is perfect for all ages and offers a wide-open, unobs... More

Free Cancellation
Private Tour
Start From $117.17
 
Key West Dolphin Watch and Sunset Sail on Catamaran Likely to Sell Out

Key West Dolphin Watch and Sunset Sail on Catamaran

  • USA
  • Superb43 reviews4.7

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the ligh....

    Free Cancellation
    Private Tour
    Start From $117.17
 
 

Deluxe private Sunset & Day Sail

(5 of 3 reviews)

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks, and into the heart of coastal paradise. Feel the wind in your... More

Free Cancellation
Private Tour
Start From $714.00
 
Deluxe private Sunset & Day Sail Likely to Sell Out

Deluxe private Sunset & Day Sail

  • USA
  • Superb3 reviews5

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling ....

    Free Cancellation
    Private Tour
    Start From $714.00
 
 

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

Free Cancellation
Private Tour
Start From $1,200.00
 
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....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

Wrightsville Beach Day Sail Private Catamaran Charter

(5 of 1 review)

On this 4hr private charter, you will work with your captain to plan your perfect itinerary of islands and local spots. Upon anchoring, the crew will dinghy you around wherever you'd like to go! The boat is fully equipped with ai... More

Free Cancellation
Private Tour
Start From $1,200.00
 
Wrightsville Beach Day Sail Private Catamaran Charter Likely to Sell Out

Wrightsville Beach Day Sail Private Catamaran Charter

  • USA
  • Superb1 review5

On this 4hr private charter, you will work with your captain to plan your perfect itinerary of islan....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

(5 of 125 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
  • Superb125 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
 
 

Baltimore Inner Harbor Sail on the Unforgettable

(4.8 of 25 reviews)

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling city from the water. Explore the Inner Harbor and the joy of sailing on t... More

Free Cancellation
Private Tour
Start From $65.00
 
Baltimore Inner Harbor Sail on the Unforgettable Likely to Sell Out

Baltimore Inner Harbor Sail on the Unforgettable

  • USA
  • Superb25 reviews4.8

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authe....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound

(5 of 36 reviews)

Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these waters back in 1792. From Seattle’s Shilshole Bay Marina we sail west across Puget Sound toward the magnificent Olympic Mountains. A... More

Free Cancellation
Private Tour
Start From $125.00
 
Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound Likely to Sell Out

Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound

  • USA
  • Superb36 reviews5

Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these wate....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Key West Private Charter: Sandbar and Snorkeling

(5 of 20 reviews)

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a formal, guided eco-tour, this trip offers a more laid-back vibe, allowing you t... More

Free Cancellation
Private Tour
Start From $950.00
 
Key West Private Charter: Sandbar and Snorkeling Likely to Sell Out

Key West Private Charter: Sandbar and Snorkeling

  • USA
  • Superb20 reviews5

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who wa....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

BYOB Friday Night Fireworks Cruise

(4.3 of 6 reviews)

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More

Free Cancellation
Private Tour
Start From $138.95
 
BYOB Friday Night Fireworks Cruise Likely to Sell Out

BYOB Friday Night Fireworks Cruise

  • USA
  • Exellent6 reviews4.3

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....

    Free Cancellation
    Private Tour
    Start From $138.95
 
 

Lahaina Maui Whale Watch Motors Off Sailing in Humpback Sanctuary

(4.9 of 38 reviews)

Experience Maui’s magnificent humpback whales on a 2-hour whale watch aboard a sailing catamaran in the ʻAuʻau Channel, home to one of Hawaii’s greatest concentrations of humpbacks. Morning conditions often bring smooth sea... More

Free Cancellation
Private Tour
Start From $110.28
 
Lahaina Maui Whale Watch Motors Off Sailing in Humpback Sanctuary Likely to Sell Out

Lahaina Maui Whale Watch Motors Off Sailing in Humpback Sanctuary

  • USA
  • Superb38 reviews4.9

Experience Maui’s magnificent humpback whales on a 2-hour whale watch aboard a sailing catamaran i....

    Free Cancellation
    Private Tour
    Start From $110.28
 
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