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Top 10 Best USA Sailing Trips

Found 418 Sailing Trips activities in USA. Sort by Popularity.
 

Official Miami Millionaires Sightseeing Cruise

(4.3 of 990 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
 
Official Miami Millionaires Sightseeing Cruise

Official Miami Millionaires Sightseeing Cruise

  • USA
  • Exellent990 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
 
 

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

(4.9 of 4,076 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
  • Superb4,076 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
 
 
-9% Waikiki Turtle Snorkeling Boat Tour and Adventure

Waikiki Turtle Snorkeling Boat Tour and Adventure

(4.7 of 1,087 reviews)

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

Special Offer
Free Cancellation
Start From $68.60
(Saving 9% ) $75.00
 
-9% Waikiki Turtle Snorkeling Boat Tour and Adventure

Waikiki Turtle Snorkeling Boat Tour and Adventure

  • USA
  • Superb1,087 reviews4.7

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!** Join us for a **2-ho....

    Special Offer
    Free Cancellation
    Start From $68.60
    (Saving 9% ) $75.00
 
 

2 Hour Sailing Cruise on Lake Tahoe

(4.9 of 793 reviews)

Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing adventure and include complementary local beer and wine, as well as non-alcoholic beverages on all of our daily cruises. Unlike other t... More

Free Cancellation
Start From $140.00
 
2 Hour Sailing Cruise on Lake Tahoe Likely to Sell Out

2 Hour Sailing Cruise on Lake Tahoe

  • USA
  • Superb793 reviews4.9

Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing advent....

    Free Cancellation
    Start From $140.00
 
 

Sunset & Dolphin Catamaran Cruise with Island Time

(4.9 of 1,711 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 $57.59
 
Sunset & Dolphin Catamaran Cruise with Island Time Likely to Sell Out

Sunset & Dolphin Catamaran Cruise with Island Time

  • USA
  • Superb1,711 reviews4.9

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

    Free Cancellation
    Start From $57.59
 
 

Sightseeing Day Sail around Boston Harbor

(4.8 of 458 reviews)

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport district, Castle... More

Special Offer
Free Cancellation
Start From $56.55
(Saving 15% ) $66.54
 
-15% Sightseeing Day Sail around Boston Harbor Likely to Sell Out

Sightseeing Day Sail around Boston Harbor

  • USA
  • Superb458 reviews4.8

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner....

    Special Offer
    Free Cancellation
    Start From $56.55
    (Saving 15% ) $66.54
 
 

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

(4.7 of 3,287 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 Full Bar, Live Music and Hors D'oeuvres Likely to Sell Out

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

  • USA
  • Superb3,287 reviews4.7

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

    Free Cancellation
    Start From $79.00
 
 

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

(4.9 of 2,029 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
 
Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast Likely to Sell Out

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

  • USA
  • Superb2,029 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
 
 

2-Hour Seattle Sailing Harbor Tour

(4.7 of 423 reviews)

Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing tour is family-friendly and is an excellent way to see the Seattle skyline, the beauty of the Puget Sound, even mountain views! We ... More

Free Cancellation
Start From $49.30
 
2-Hour Seattle Sailing Harbor Tour Likely to Sell Out

2-Hour Seattle Sailing Harbor Tour

  • USA
  • Superb423 reviews4.7

Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing t....

    Free Cancellation
    Start From $49.30
 
 

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

(4.1 of 454 reviews)

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises.... More

Free Cancellation
Start From $70.00
 
1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain Likely to Sell Out

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

  • USA
  • Exellent454 reviews4.1

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....

    Free Cancellation
    Start From $70.00
 
 

Evening Colors Sunset Sail Tour in Seattle

(4.8 of 517 reviews)

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hoist the sails, then we will shut the engine down and enjoy the quiet of our beautiful schooner cutting through the tranquil Puget So... More

Free Cancellation
Start From $65.00
 
Evening Colors Sunset Sail Tour in Seattle Likely to Sell Out

Evening Colors Sunset Sail Tour in Seattle

  • USA
  • Superb517 reviews4.8

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hois....

    Free Cancellation
    Start From $65.00
 
 

Leila Na Pali Sunset Dinner Sail

(4.7 of 488 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
 
Leila Na Pali Sunset Dinner Sail Likely to Sell Out

Leila Na Pali Sunset Dinner Sail

  • USA
  • Superb488 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
 
 

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,018 reviews)

2025 VIATOR TOP 20 BEST EXCURSIONS award in the UNITED STATES including the TOP RATED SNORKEL EXCURSION in the US!! Best value in Waikiki! See turtles GUARANTEED or receive a FULL REFUND! Brand new PREMIUM snorkel equipment inclu... More

Free Cancellation
Start From $59.95
 
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Likely to Sell Out

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • USA
  • Superb1,018 reviews4.9

2025 VIATOR TOP 20 BEST EXCURSIONS award in the UNITED STATES including the TOP RATED SNORKEL EXCURS....

    Free Cancellation
    Start From $59.95
 
 

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

(4.8 of 1,518 reviews)

This is the best way to start your day on Oahu! Complimentary cold brew coffee from Honolulu’s local favorite ARVO Café, served with a selection of Anahola Granola bars—Original, Chocolate Chip, Tropical, and Mango & Ginger. ... More

Free Cancellation
Start From $84.77
 
Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran Likely to Sell Out

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

  • USA
  • Superb1,518 reviews4.8

This is the best way to start your day on Oahu! Complimentary cold brew coffee from Honolulu’s loc....

    Free Cancellation
    Start From $84.77
 
 

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

(4.5 of 525 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 $44.00
 
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor Likely to Sell Out

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

  • USA
  • Exellent525 reviews4.5

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

    Free Cancellation
    Start From $44.00
 
 

Deluxe Na Pali Sunset Tour on the Lucky Lady

(4.7 of 1,358 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
 
Deluxe Na Pali Sunset Tour on the Lucky Lady Likely to Sell Out

Deluxe Na Pali Sunset Tour on the Lucky Lady

  • USA
  • Superb1,358 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
 
 

Turtles & Tacos Luxury Catamaran Snorkel

(4.7 of 48 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 $169.00
 
Turtles & Tacos Luxury Catamaran Snorkel Likely to Sell Out

Turtles & Tacos Luxury Catamaran Snorkel

  • USA
  • Superb48 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 $169.00
 
 

Sunset Boat Cruise: Swim and Cruise Waikiki

(4.7 of 468 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 $47.00
 
Sunset Boat Cruise: Swim and Cruise Waikiki Likely to Sell Out

Sunset Boat Cruise: Swim and Cruise Waikiki

  • USA
  • Superb468 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 $47.00
 
 

St. Augustine Live Music Sunset Sail with Drinks Included

(4.7 of 207 reviews)

Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sail! Indulge in complimentary beer, wine, soda, water, margaritas, champagne, and a snack, while enjoying live performances by some ... More

Free Cancellation
Start From $69.17
 
St. Augustine Live Music Sunset Sail with Drinks Included Likely to Sell Out

St. Augustine Live Music Sunset Sail with Drinks Included

  • USA
  • Superb207 reviews4.7

Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sai....

    Free Cancellation
    Start From $69.17
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 800 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 $202.59
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • USA
  • Superb800 reviews4.7

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

    Free Cancellation
    Start From $202.59
 
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