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Top 10 Best USA Sailing Trips

Found 452 Sailing Trips activities in USA. Sort by Popularity. - Page 16
 

Oyster Bay Two Hour Sailing Experience

(5 of 2 reviews)

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and the impressive estates that line the bay. WINDSWEPT is metic... More

Free Cancellation
Private Tour
Start From $625.00
 
Oyster Bay Two Hour Sailing Experience

Oyster Bay Two Hour Sailing Experience

  • USA
  • Superb2 reviews5

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oys....

    Free Cancellation
    Private Tour
    Start From $625.00
 
 

San Diego Sailing Private Activity

(5 of 1 review)

We are a hands on sailing adventure we encourage our guests to participate. Guests who chose to relax and enjoy the scenery and vibe are welcome to do so, you may bring beer or wine or other snacks no red wine please.... More

Free Cancellation
Private Tour
Start From $189.00
 
San Diego Sailing Private Activity

San Diego Sailing Private Activity

  • USA
  • Superb1 review5

We are a hands on sailing adventure we encourage our guests to participate. Guests who chose to rela....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Key West Sunset Sail Aboard Legendary Schooner Appledore

(5 of 361 reviews)

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comf... More

Free Cancellation
Private Tour
Start From $89.00
 
Key West Sunset Sail Aboard Legendary Schooner Appledore

Key West Sunset Sail Aboard Legendary Schooner Appledore

  • USA
  • Superb361 reviews5

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Skagway Trail and Sail

(4.8 of 8 reviews)

This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike Electric Bicycles where you will join us for a self-guided ride to some of Skagway's best sites! You will visit a waterfall, scenic... More

Free Cancellation
Private Tour
Start From $299.00
 
Skagway Trail and Sail

Skagway Trail and Sail

  • USA
  • Superb8 reviews4.8

This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike E....

    Free Cancellation
    Private Tour
    Start From $299.00
 
 

Key West Sail and Snorkel Day Trip from Fort Lauderdale

(3.1 of 16 reviews)

Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it out for the first time! This day trip from Fort Lauderdale promises thrilling experiences and breathtaking sights both above and ... More

Free Cancellation
Private Tour
Start From $149.00
 
Key West Sail and Snorkel Day Trip from Fort Lauderdale Likely to Sell Out

Key West Sail and Snorkel Day Trip from Fort Lauderdale

  • USA
  • Good16 reviews3.1

Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Exciting Public Afternoon Sail in Hilton Head

(3.1 of 16 reviews)

Looking for a more personal sailing experience without booking an entire private charter? The Afternoon Public Sail is the perfect balance. With a maximum of just six guests onboard, you’ll enjoy an intimate, relaxed atmosphere.... More

Free Cancellation
Private Tour
Start From $119.00
 
Exciting Public Afternoon Sail in Hilton Head Likely to Sell Out

Exciting Public Afternoon Sail in Hilton Head

  • USA
  • Good16 reviews3.1

Looking for a more personal sailing experience without booking an entire private charter? The Aftern....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

2hr. PRIVATE Sailing Experience on San Francisco Bay (6 Guests)

(3.1 of 16 reviews)

This is a "Private Charter" Sailing Experience on San Francisco Bay for up to 6 guests, with a USCG licensed captain and crew where you'll sail past the Golden Gate Bridge, Alcatraz and Angel Islands and across the San Francisco w... More

Free Cancellation
Private Tour
Start From $795.00
 
2hr. PRIVATE Sailing Experience on San Francisco Bay (6 Guests) Likely to Sell Out

2hr. PRIVATE Sailing Experience on San Francisco Bay (6 Guests)

  • USA
  • Good16 reviews3.1

This is a "Private Charter" Sailing Experience on San Francisco Bay for up to 6 guests, with a USCG ....

    Free Cancellation
    Private Tour
    Start From $795.00
 
 

Private Morning Sail, Dolphin and History Tour on Mystique

(5 of 85 reviews)

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. For over 12 years, our sailing yachts are the highest quality and operated by two professional ... More

Free Cancellation
Private Tour
Start From $525.00
 
Private Morning Sail, Dolphin and History Tour on Mystique Likely to Sell Out

Private Morning Sail, Dolphin and History Tour on Mystique

  • USA
  • Superb85 reviews5

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

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

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

(5 of 34 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
  • Superb34 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
 
 

2 Hour Chesapeake Day Sail on Catamaran Epiphany

(5 of 9 reviews)

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel offers cushioned seating and panoramic views of the Chesapeake Bay. Glide... More

Free Cancellation
Private Tour
Start From $245.00
 
2 Hour Chesapeake Day Sail on Catamaran Epiphany Likely to Sell Out

2 Hour Chesapeake Day Sail on Catamaran Epiphany

  • USA
  • Superb9 reviews5

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. ....

    Free Cancellation
    Private Tour
    Start From $245.00
 
 

Private Catamaran: Snorkel, Swim and Dolphin Watching

(5 of 1 review)

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take you to some of the best spots the area has to offer while you are visiting the Emerald Coast.... More

Free Cancellation
Private Tour
Start From $465.00
 
Private Catamaran: Snorkel, Swim and Dolphin Watching Likely to Sell Out

Private Catamaran: Snorkel, Swim and Dolphin Watching

  • USA
  • Superb1 review5

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion....

    Free Cancellation
    Private Tour
    Start From $465.00
 
 

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

(5 of 124 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
  • Superb124 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
 
 

St Augustine Nights of Lights Tour with Live Music and Sunset Opt

(4.6 of 70 reviews)

Fury’s Nights of Lights cruises offer a one-of-a-kind way to experience St. Augustine’s holiday magic from the water, giving guests sweeping, unobstructed views of the illuminated bayfront, the Bridge of Lions, and Castillo de... More

Free Cancellation
Private Tour
Start From $82.69
 
St Augustine Nights of Lights Tour with Live Music and Sunset Opt Likely to Sell Out

St Augustine Nights of Lights Tour with Live Music and Sunset Opt

  • USA
  • Superb70 reviews4.6

Fury’s Nights of Lights cruises offer a one-of-a-kind way to experience St. Augustine’s holiday ....

    Free Cancellation
    Private Tour
    Start From $82.69
 
 

Baltimore Harbor Evening Sail on the Unforgettable

(4.6 of 5 reviews)

Enjoy a beautiful time on the water as you sail through beautiful Baltimore Harbor, take in the gorgeous scenery of the skyline as the city lights up. Treat yourself and a loved one on this elegant sailing experience.  It's BYOB,... More

Free Cancellation
Private Tour
Start From $75.00
 
Baltimore Harbor Evening Sail on the Unforgettable Likely to Sell Out

Baltimore Harbor Evening Sail on the Unforgettable

  • USA
  • Superb5 reviews4.6

Enjoy a beautiful time on the water as you sail through beautiful Baltimore Harbor, take in the gorg....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

(4.9 of 204 reviews)

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat enjoying the fresh air and best that San Diego has to offer. On your adventure yo... More

Free Cancellation
Private Tour
Start From $119.00
 
Luxury Sailing Tour of San Diego's Bay and Coastal Waterways Likely to Sell Out

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

  • USA
  • Superb204 reviews4.9

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Shallow Water Snorkeling and Dolphin Watching in Key West

(4.6 of 472 reviews)

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s weather refunds of course. Premium drinks & snacks included! Enjoy a premium sha... More

Free Cancellation
Private Tour
Start From $108.91
 
Shallow Water Snorkeling and Dolphin Watching in Key West Likely to Sell Out

Shallow Water Snorkeling and Dolphin Watching in Key West

  • USA
  • Superb472 reviews4.6

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 wee....

    Free Cancellation
    Private Tour
    Start From $108.91
 
 

Private Sailing Tour through the Ten Thousands Islands

(4.9 of 156 reviews)

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos where built in the early 80s and are known through out the sailing community as the fastest, driest, beachable catamaran on the ma... More

Free Cancellation
Private Tour
Start From $450.00
 
Private Sailing Tour through the Ten Thousands Islands Likely to Sell Out

Private Sailing Tour through the Ten Thousands Islands

  • USA
  • Superb156 reviews4.9

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos ....

    Free Cancellation
    Private Tour
    Start From $450.00
 
 

Sunset Catamaran Sail in Cocoa Beach

(4.9 of 185 reviews)

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the beauty of Floridaâ... More

Free Cancellation
Private Tour
Start From $56.49
 
Sunset Catamaran Sail in Cocoa Beach Likely to Sell Out

Sunset Catamaran Sail in Cocoa Beach

  • USA
  • Superb185 reviews4.9

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....

    Free Cancellation
    Private Tour
    Start From $56.49
 
 

Key West Historic Schooner When And If Sunset Cruise

(4.8 of 135 reviews)

Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner When And If, commissioned by General George Patton in the late 1930s, and sail into a breathtaking Key West sunset. Raise a champ... More

Free Cancellation
Private Tour
Start From $117.18
 
Key West Historic Schooner When And If Sunset Cruise Likely to Sell Out

Key West Historic Schooner When And If Sunset Cruise

  • USA
  • Superb135 reviews4.8

Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner....

    Free Cancellation
    Private Tour
    Start From $117.18
 
 

Private Key West Sandbar and Paddle by Boat

(4.9 of 39 reviews)

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats and wildlife refuges as well as spot an abundance of marine birds and sea life. Padd... More

Free Cancellation
Private Tour
Start From $600.00
 
Private Key West Sandbar and Paddle by Boat Likely to Sell Out

Private Key West Sandbar and Paddle by Boat

  • USA
  • Superb39 reviews4.9

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may....

    Free Cancellation
    Private Tour
    Start From $600.00
 
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