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Top 10 Best USA Sailing Trips

Found 450 Sailing Trips activities in USA. Sort by Popularity. - Page 6
 

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

(4.8 of 217 reviews)

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More

Free Cancellation
Start From $200.00
 
Molokini Snorkel and Performance Sail: Mā’alaea Harbor

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

  • USA
  • Superb217 reviews4.8

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....

    Free Cancellation
    Start From $200.00
 
 

Spectacular Sunset Sail on San Diego Bay

(5 of 29 reviews)

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group, local captain sharing hidden stories, hands-on sailing, wildlife encounters, and unforgettable vistas of San Diego Bay. Participate or sit back and en... More

Free Cancellation
Start From $120.00
 
Spectacular Sunset Sail on San Diego Bay

Spectacular Sunset Sail on San Diego Bay

  • USA
  • Superb29 reviews5

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group, local captain sharin....

    Free Cancellation
    Start From $120.00
 
 

Daytime Sailing Along San Diego's Skyline

(4.9 of 149 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

Free Cancellation
Start From $79.00
 
Daytime Sailing Along San Diego's Skyline Likely to Sell Out

Daytime Sailing Along San Diego's Skyline

  • USA
  • Superb149 reviews4.9

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

    Free Cancellation
    Start From $79.00
 
 

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

(4.5 of 41 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

Free Cancellation
Start From $109.95
 
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch Likely to Sell Out

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

  • USA
  • Exellent41 reviews4.5

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

    Free Cancellation
    Start From $109.95
 
 

New York City Sailboat Day Cruise to the Statue of Liberty

(4.9 of 160 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

Free Cancellation
Start From $60.08
 
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
  • Superb160 reviews4.9

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

    Free Cancellation
    Start From $60.08
 
 

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

(5 of 93 reviews)

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More

Free Cancellation
Start From $149.00
 
2hr. INTERACTIVE Sailing Experience on San Francisco Bay Likely to Sell Out

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

  • USA
  • Superb93 reviews5

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....

    Free Cancellation
    Start From $149.00
 
 

1-Hour Interactive Pirate Cruise (arrive 30 minutes early)

(4.9 of 1,516 reviews)

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along Florida’s Intracoastal Waterway that’s fun for the whole family! T... More

Free Cancellation
Start From $35.00
 
1-Hour Interactive Pirate Cruise (arrive 30 minutes early) Likely to Sell Out

1-Hour Interactive Pirate Cruise (arrive 30 minutes early)

  • USA
  • Superb1,516 reviews4.9

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure ....

    Free Cancellation
    Start From $35.00
 
 

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

(4.8 of 21 reviews)

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air! Fun for all ... More

Free Cancellation
Start From $91.23
 
Sail on Tall Ship Windy, join us for our Likely to Sell Out

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

  • USA
  • Superb21 reviews4.8

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This ....

    Free Cancellation
    Start From $91.23
 
 

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

(4.9 of 108 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pal... More

Free Cancellation
Start From $59.95
 
Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise Likely to Sell Out

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

  • USA
  • Superb108 reviews4.9

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....

    Free Cancellation
    Start From $59.95
 
 

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

(4.9 of 461 reviews)

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay for over 15 years, just for the fun of it. We started this eco-tour in 2018 to share the ama... More

Free Cancellation
Start From $129.00
 
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling Likely to Sell Out

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

  • USA
  • Superb461 reviews4.9

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....

    Free Cancellation
    Start From $129.00
 
 

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

(4.9 of 988 reviews)

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Incl... More

Free Cancellation
Start From $108.91
 
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses Likely to Sell Out

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

  • USA
  • Superb988 reviews4.9

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....

    Free Cancellation
    Start From $108.91
 
 

Sailing on Historic Schooner Yacht in Salem, MA

(4.9 of 174 reviews)

Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience the majesty aboard John G. Alden's personal schooner yacht Malabar X. Winner of the 1930 and 1932 Newport to Bermuda race and open... More

Free Cancellation
Start From $55.00
 
Sailing on Historic Schooner Yacht in Salem, MA Likely to Sell Out

Sailing on Historic Schooner Yacht in Salem, MA

  • USA
  • Superb174 reviews4.9

Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience ....

    Free Cancellation
    Start From $55.00
 
 

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

(4.9 of 58 reviews)

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay and National Seashore. Or explore the Condor: walk around, do the Titanic po... More

Free Cancellation
Start From $99.00
 
Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise Likely to Sell Out

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

  • USA
  • Superb58 reviews4.9

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chil....

    Free Cancellation
    Start From $99.00
 
 

Seattle’s Original Sailing Cruise (Est. 1984) – 70ft Boat - BYOB

(4.9 of 182 reviews)

This is a boat ride like nothing else in Seattle! Our 70ft custom built sailboats were created to race around the world, and now are perfectly at home on Puget Sound. Sit back and relax as our trained crew hoist the sails and turn... More

Free Cancellation
Start From $60.00
 
Seattle’s Original Sailing Cruise (Est. 1984) – 70ft Boat - BYOB Likely to Sell Out

Seattle’s Original Sailing Cruise (Est. 1984) – 70ft Boat - B....

  • USA
  • Superb182 reviews4.9

This is a boat ride like nothing else in Seattle! Our 70ft custom built sailboats were created to ra....

    Free Cancellation
    Start From $60.00
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 860 reviews)

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays!  Upon arriving, receive an in... More

Free Cancellation
Start From $154.51
 
Sunset and Manta Ray Snorkel Adventure Likely to Sell Out

Sunset and Manta Ray Snorkel Adventure

  • USA
  • Superb860 reviews4.9

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....

    Free Cancellation
    Start From $154.51
 
 

Windjammer Classic Sunset Sail from Camden, Maine

(4.9 of 425 reviews)

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More

Free Cancellation
Start From $64.95
 
Windjammer Classic Sunset Sail from Camden, Maine Likely to Sell Out

Windjammer Classic Sunset Sail from Camden, Maine

  • USA
  • Superb425 reviews4.9

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....

    Free Cancellation
    Start From $64.95
 
 

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

(4.8 of 58 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

Free Cancellation
Start From $90.01
 
Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu Likely to Sell Out

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

  • USA
  • Superb58 reviews4.8

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

    Free Cancellation
    Start From $90.01
 
 

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

(5 of 48 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 for over 12 years, our sailing yachts are the highest quality and op... More

Free Cancellation
Private Tour
Start From $599.00
 
Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique Likely to Sell Out

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

  • USA
  • Superb48 reviews5

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

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

Private Sailing Charter with Captain, BYOB

(5 of 77 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 Likely to Sell Out

Private Sailing Charter with Captain, BYOB

  • USA
  • Superb77 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
 
 

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

(5 of 6 reviews)

Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and unforgettable views in one trip. We reach Turtle Canyon quickly, giving you more time in the water to s... More

Free Cancellation
Private Tour
Start From $130.00
 
Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise Likely to Sell Out

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

  • USA
  • Superb6 reviews5

Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining a....

    Free Cancellation
    Private Tour
    Start From $130.00
 
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