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Top 10 Best USA Sailing Trips

Found 442 Sailing Trips activities in USA. Sort by Popularity.
 

Miami Millionaires Sightseeing Cruise

(4.3 of 1,699 reviews)

Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmerizing beauty of Biscayne Bay, while getting an exclusive glimpse into the luxurious lifestyle of Miami's elite, with a bilingual com... More

Free Cancellation
Start From $18.00
 
Miami Millionaires Sightseeing Cruise

Miami Millionaires Sightseeing Cruise

  • USA
  • Exellent1,699 reviews4.3

Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmeriz....

    Free Cancellation
    Start From $18.00
 
 

Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings

(4.6 of 1,327 reviews)

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More

Free Cancellation
Start From $53.31
 
Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings

Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings

  • USA
  • Superb1,327 reviews4.6

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....

    Free Cancellation
    Start From $53.31
 
 

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

(4.9 of 4,509 reviews)

The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great way to have fun in the sun and enjoy the best of what Panama City Beach has to offer! Cruise over to Shell Island where you and the... More

Free Cancellation
Start From $57.59
 
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Tim....

  • USA
  • Superb4,509 reviews4.9

The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great w....

    Free Cancellation
    Start From $57.59
 
 

Key West Signature Sunset Sail with Live Music, Open Bar & Food

(4.5 of 358 reviews)

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More

Free Cancellation
Start From $72.00
 
Key West Signature Sunset Sail with Live Music, Open Bar & Food

Key West Signature Sunset Sail with Live Music, Open Bar & Food

  • USA
  • Exellent358 reviews4.5

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....

    Free Cancellation
    Start From $72.00
 
 
-10% San Francisco Bay Cruise

San Francisco Bay Cruise

(4.4 of 330 reviews)

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour excursion heads underneath the Golden Gate Bridge, around Alcatraz Island, past Angel Island State Park, and alongside the cit... More

Special Offer
Free Cancellation
Start From $35.10
(Saving 10% ) $39.00
 
-10% San Francisco Bay Cruise

San Francisco Bay Cruise

  • USA
  • Exellent330 reviews4.4

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hou....

    Special Offer
    Free Cancellation
    Start From $35.10
    (Saving 10% ) $39.00
 
 

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

(4.7 of 3,669 reviews)

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern sailing catamarans while sipping sparkling wine or your favorite cocktail and fea... More

Free Cancellation
Start From $79.00
 
Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

  • USA
  • Superb3,669 reviews4.7

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....

    Free Cancellation
    Start From $79.00
 
 

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

(4.7 of 1,556 reviews)

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look for dolphins, whales, and other marine critters as you sip a drink, snap som... More

Free Cancellation
Start From $222.86
 
Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

  • USA
  • Superb1,556 reviews4.7

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....

    Free Cancellation
    Start From $222.86
 
 

Kona Signature Catamaran Sunset Sail

(4.8 of 250 reviews)

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean and coastline as the sky transforms with vibrant hues of orange, pink and gold. Relax on d... More

Free Cancellation
Start From $109.00
 
Kona Signature Catamaran Sunset Sail

Kona Signature Catamaran Sunset Sail

  • USA
  • Superb250 reviews4.8

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloh....

    Free Cancellation
    Start From $109.00
 
 

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

(4.5 of 653 reviews)

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall Ship for a unique sailing experience. There is no better way to witness all o... More

Free Cancellation
Start From $48.00
 
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor Likely to Sell Out

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....

  • USA
  • Exellent653 reviews4.5

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....

    Free Cancellation
    Start From $48.00
 
 

Turtles & Tacos Luxury Catamaran Snorkel

(4.7 of 115 reviews)

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and snorkel alongside Hawaiian green sea turtles and colorful tropical fish at ... More

Free Cancellation
Start From $199.00
 
Turtles & Tacos Luxury Catamaran Snorkel Likely to Sell Out

Turtles & Tacos Luxury Catamaran Snorkel

  • USA
  • Superb115 reviews4.7

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....

    Free Cancellation
    Start From $199.00
 
 

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

(4.6 of 22 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
 
Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar Likely to Sell Out

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

  • USA
  • Superb22 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
 
 

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,551 reviews)

The water is clean, clear, and safe following the recent storms! Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from Waikiki. ... More

Free Cancellation
Start From $49.95
 
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Likely to Sell Out

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • USA
  • Superb1,551 reviews4.9

The water is clean, clear, and safe following the recent storms! Experience one Viator's 2025 Top 2....

    Free Cancellation
    Start From $49.95
 
 

Key West Reef Morning Snorkeling with Breakfast and Mimosas

(4.5 of 613 reviews)

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More

Free Cancellation
Start From $35.00
 
Key West Reef Morning Snorkeling with Breakfast and Mimosas Likely to Sell Out

Key West Reef Morning Snorkeling with Breakfast and Mimosas

  • USA
  • Exellent613 reviews4.5

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....

    Free Cancellation
    Start From $35.00
 
 

Kauai: Leila Na Pali Sunset Dinner Sail

(4.7 of 540 reviews)

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will s... More

Free Cancellation
Start From $263.82
 
Kauai: Leila Na Pali Sunset Dinner Sail Likely to Sell Out

Kauai: Leila Na Pali Sunset Dinner Sail

  • USA
  • Superb540 reviews4.7

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....

    Free Cancellation
    Start From $263.82
 
 

Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure

(4.7 of 1,397 reviews)

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join us for a **2-hour snorkeling adventure** at **Turtle Canyon**, one of Oahu’s top snorkeling spots! Cruise along the stunning **W... More

Special Offer
Free Cancellation
Start From $68.60
(Saving 15% ) $80.71
 
-15% Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure Likely to Sell Out

Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure

  • USA
  • Superb1,397 reviews4.7

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join ....

    Special Offer
    Free Cancellation
    Start From $68.60
    (Saving 15% ) $80.71
 
 

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

(4.9 of 1,930 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 $45.00
 
Dolphin Sunset Cruise in Panama City Beach on the Likely to Sell Out

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

  • USA
  • Superb1,930 reviews4.9

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

    Free Cancellation
    Start From $45.00
 
 

Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail

(4.9 of 2,266 reviews)

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with premium drinks, indescribable views, and music. As we sail alongside Oa... More

Free Cancellation
Start From $89.99
 
Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail Likely to Sell Out

Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail

  • USA
  • Superb2,266 reviews4.9

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....

    Free Cancellation
    Start From $89.99
 
 

Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

(4.7 of 547 reviews)

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the ocean, with the iconic Waikiki coastline as your backdrop. As the sun begins to se... More

Free Cancellation
Start From $56.00
 
Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure Likely to Sell Out

Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

  • USA
  • Superb547 reviews4.7

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....

    Free Cancellation
    Start From $56.00
 
 

Buccaneer Pirate Cruise in Destin

(4.9 of 110 reviews)

Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family! Enjoy a fun cruise with interactive pirate-themed activities, entertainment, and treasure hunts. Take in the beauty of the Emeral... More

Free Cancellation
Start From $55.00
 
Buccaneer Pirate Cruise in Destin Likely to Sell Out

Buccaneer Pirate Cruise in Destin

  • USA
  • Superb110 reviews4.9

Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family!....

    Free Cancellation
    Start From $55.00
 
 

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,681 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 Likely to Sell Out

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

  • USA
  • Superb1,681 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
 
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