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Top 10 Best USA Sailing Trips

Found 426 Sailing Trips activities in USA. Sort by Popularity. - Page 2
 

Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

(4.6 of 88 reviews)

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience offers breathtaking views of the sunset complemented by deligh... More

Free Cancellation
Start From $141.98
 
Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

  • USA
  • Superb88 reviews4.6

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....

    Free Cancellation
    Start From $141.98
 
 

Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full Open Bar

(5 of 88 reviews)

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based on weather, tides, and ocean conditions. • Explore Lana... More

Free Cancellation
Start From $242.60
 
Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full Open Bar

Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full Open Bar

  • USA
  • Superb88 reviews5

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where ....

    Free Cancellation
    Start From $242.60
 
 

Lahaina Maui Sunset Sail on 'Alihilani

(4.9 of 214 reviews)

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for a luxurious experience, allowing for incredible views of Maui and the inter islands from the... More

Free Cancellation
Start From $126.82
 
Lahaina Maui Sunset Sail on 'Alihilani

Lahaina Maui Sunset Sail on 'Alihilani

  • USA
  • Superb214 reviews4.9

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....

    Free Cancellation
    Start From $126.82
 
 

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,786 reviews)

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island relaxation in one extraordinary outing. Swim among sea turtles and tropical fi... More

Free Cancellation
Start From $89.56
 
Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

  • USA
  • Superb1,786 reviews4.8

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This pop....

    Free Cancellation
    Start From $89.56
 
 

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

(4.9 of 1,014 reviews)

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985... More

Free Cancellation
Start From $49.99
 
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

  • USA
  • Superb1,014 reviews4.9

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....

    Free Cancellation
    Start From $49.99
 
 

Sunset Windjammer Cruise Along the Coast of Portland Maine

(4.7 of 218 reviews)

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. (NOTE: This is NOT a narrated tour, bu... More

Free Cancellation
Start From $77.00
 
Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

  • USA
  • Superb218 reviews4.7

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to exper....

    Free Cancellation
    Start From $77.00
 
 

Waikiki 2 hour Turtle Canyon Snorkeling Adventure

(4.7 of 1,518 reviews)

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard the either 55-ft open-style catamaran or 50-ft double-decker power catamaran and ... More

Free Cancellation
Start From $80.71
 
Waikiki 2 hour Turtle Canyon Snorkeling Adventure

Waikiki 2 hour Turtle Canyon Snorkeling Adventure

  • USA
  • Superb1,518 reviews4.7

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cr....

    Free Cancellation
    Start From $80.71
 
 

Key West Afternoon Reef Snorkeling with Open Bar

(4.5 of 491 reviews)

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More

Free Cancellation
Start From $59.07
 
Key West Afternoon Reef Snorkeling with Open Bar

Key West Afternoon Reef Snorkeling with Open Bar

  • USA
  • Exellent491 reviews4.5

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....

    Free Cancellation
    Start From $59.07
 
 

Afternoon Windjammer Cruise Along the Coast of Portland Maine

(4.7 of 301 reviews)

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds (NOTE: This is NOT a narrated tour,... More

Free Cancellation
Start From $69.00
 
Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

  • USA
  • Superb301 reviews4.7

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to e....

    Free Cancellation
    Start From $69.00
 
 

Deluxe Sunset & Day Sail Small Group

(5 of 368 reviews)

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as the sky transforms into a masterpiece of color. Keep an eye out for playfu... More

Free Cancellation
Start From $119.00
 
Deluxe Sunset & Day Sail Small Group

Deluxe Sunset & Day Sail Small Group

  • USA
  • Superb368 reviews5

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....

    Free Cancellation
    Start From $119.00
 
 

Happy Hour Sunset Sail on Maui's Luxury Catamaran

(4.8 of 101 reviews)

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted drinks, vibrant music, and a relaxed-yet-refined vibe that turns every pour ... More

Free Cancellation
Start From $169.00
 
Happy Hour Sunset Sail on Maui's Luxury Catamaran

Happy Hour Sunset Sail on Maui's Luxury Catamaran

  • USA
  • Superb101 reviews4.8

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....

    Free Cancellation
    Start From $169.00
 
 

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

(4.7 of 625 reviews)

-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boarding — no harbor shuttle, no bus, no wasted time -Spacious 45-foot catamaran with near 360 degree view -Families welcome: Keiki ra... More

Free Cancellation
Start From $84.77
 
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

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

  • USA
  • Superb625 reviews4.7

-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boardi....

    Free Cancellation
    Start From $84.77
 
 

Sailing on Historic Schooner Yacht in Salem, MA

(4.9 of 308 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 $58.44
 
Sailing on Historic Schooner Yacht in Salem, MA

Sailing on Historic Schooner Yacht in Salem, MA

  • USA
  • Superb308 reviews4.9

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

    Free Cancellation
    Start From $58.44
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 862 reviews)

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More

Free Cancellation
Start From $213.41
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • USA
  • Superb862 reviews4.7

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....

    Free Cancellation
    Start From $213.41
 
 

Dolphin Sunset Cruise in Panama City Beach on the "Island Time"

(4.9 of 2,135 reviews)

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in Panama City Beach, FL. Enjoy a rum punch while cruising along the beautiful Gulf Coa... More

Free Cancellation
Start From $41.73
 
Dolphin Sunset Cruise in Panama City Beach on the

Dolphin Sunset Cruise in Panama City Beach on the "Island Time"

  • USA
  • Superb2,135 reviews4.9

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....

    Free Cancellation
    Start From $41.73
 
 

Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing

(4.9 of 45 reviews)

Experience a romantic Maui evening aboard Paragon, Sail Maui's flagship 47-foot performance sailing catamaran. Settle in together and experience the peace and serenity of sailing the beautiful ʻAuʻau Channel, surrounded by the s... More

Free Cancellation
Start From $126.82
 
Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing

Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing

  • USA
  • Superb45 reviews4.9

Experience a romantic Maui evening aboard Paragon, Sail Maui's flagship 47-foot performance sailing ....

    Free Cancellation
    Start From $126.82
 
 

Sunset Sail Along the San Diego Skyline

(4.9 of 659 reviews)

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water.  Our San Diego Bay Sunset Sailing Cruises provide an up-close and personal view o... More

Free Cancellation
Start From $99.00
 
Sunset Sail Along the San Diego Skyline Likely to Sell Out

Sunset Sail Along the San Diego Skyline

  • USA
  • Superb659 reviews4.9

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....

    Free Cancellation
    Start From $99.00
 
 

St. Augustine Live Music Sail with Drinks & Sunset Option

(4.7 of 419 reviews)

Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience! Opt for a two-hour live music sunset sail with all sails raised, or unwind on a 90-minute After Dark Live Music Cruise (no sailin... More

Free Cancellation
Start From $66.49
 
St. Augustine Live Music Sail with Drinks & Sunset Option Likely to Sell Out

St. Augustine Live Music Sail with Drinks & Sunset Option

  • USA
  • Superb419 reviews4.7

Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience!....

    Free Cancellation
    Start From $66.49
 
 

2-Hour Sunset Sail on the San Francisco Bay

(4.7 of 435 reviews)

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous traditional vessel to take in the sights at the most bewitching time of d... More

Free Cancellation
Start From $129.00
 
2-Hour Sunset Sail on the San Francisco Bay Likely to Sell Out

2-Hour Sunset Sail on the San Francisco Bay

  • USA
  • Superb435 reviews4.7

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....

    Free Cancellation
    Start From $129.00
 
 

Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

(4.9 of 40 reviews)

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More

Free Cancellation
Start From $203.16
 
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali Likely to Sell Out

Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

  • USA
  • Superb40 reviews4.9

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....

    Free Cancellation
    Start From $203.16
 
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