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Top 10 Best USA Sailing Trips

Found 452 Sailing Trips activities in USA. Sort by Popularity. - Page 3
 

Boston Harbor Sunset Sail Tour

(4.8 of 158 reviews)

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. This elegant sailing experience will be aboard either Schooner Adirondack III or Adir... More

Free Cancellation
Start From $82.27
 
Boston Harbor Sunset Sail Tour Likely to Sell Out

Boston Harbor Sunset Sail Tour

  • USA
  • Superb158 reviews4.8

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....

    Free Cancellation
    Start From $82.27
 
 

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

(4.7 of 188 reviews)

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More

Free Cancellation
Start From $69.95
 
Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine Likely to Sell Out

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

  • USA
  • Superb188 reviews4.7

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....

    Free Cancellation
    Start From $69.95
 
 

'Alihilani Lahaina Sunset Sail

(4.9 of 156 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 $117.30
 
'Alihilani Lahaina Sunset Sail Likely to Sell Out

'Alihilani Lahaina Sunset Sail

  • USA
  • Superb156 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 $117.30
 
 

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

(4.7 of 1,598 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 Likely to Sell Out

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

  • USA
  • Superb1,598 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
 
 

Seattle's Original Sunset Sail (Est. 1984) - 70ft Boat - BYOB

(4.9 of 211 reviews)

Our Sunset Sail is one of the most relaxing and affordable activities in Downtown Seattle. The Sunset Sail is powered by the wind, so it is extremally Eco-Friendly. We are one of the only cruises in the area that allow you to brin... More

Free Cancellation
Start From $71.00
 
Seattle's Original Sunset Sail (Est. 1984) - 70ft Boat - BYOB Likely to Sell Out

Seattle's Original Sunset Sail (Est. 1984) - 70ft Boat - BYOB

  • USA
  • Superb211 reviews4.9

Our Sunset Sail is one of the most relaxing and affordable activities in Downtown Seattle. The Sunse....

    Free Cancellation
    Start From $71.00
 
 

St. Augustine Live Music Sail with Drinks & Sunset Option

(4.7 of 384 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
  • Superb384 reviews4.7

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

    Free Cancellation
    Start From $66.49
 
 

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

(4.6 of 452 reviews)

If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise on a classic Boston tall ship! We depart Fan Pier Marina and raise the sails, then it’s time to just chill out and relax. Get a... More

Free Cancellation
Start From $71.35
 
Sunset Sailing Cruise on a Tall Ship in Boston Harbor Likely to Sell Out

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

  • USA
  • Superb452 reviews4.6

If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise....

    Free Cancellation
    Start From $71.35
 
 

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

(4.9 of 965 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 $54.98
 
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB Likely to Sell Out

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

  • USA
  • Superb965 reviews4.9

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

    Free Cancellation
    Start From $54.98
 
 

Kauai: Leila Na Pali Sunset Dinner Sail

(4.6 of 582 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
  • Superb582 reviews4.6

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
 
 

2.5-Hour Small-Group Catamaran Sail with Drinks

(5 of 314 reviews)

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail. Designed for comfort and stability, these modern catamarans featu... More

Free Cancellation
Start From $119.00
 
2.5-Hour Small-Group Catamaran Sail with Drinks Likely to Sell Out

2.5-Hour Small-Group Catamaran Sail with Drinks

  • USA
  • Superb314 reviews5

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your ....

    Free Cancellation
    Start From $119.00
 
 

Newport Sightseeing Day Sailing Experience on Schooner Adirondack

(4.9 of 110 reviews)

See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schooner Adirondack. You'll pass by many iconic sights, bridges, lighthouses and more during this 1.5-hour experience!... More

Free Cancellation
Start From $57.24
 
Newport Sightseeing Day Sailing Experience on Schooner Adirondack Likely to Sell Out

Newport Sightseeing Day Sailing Experience on Schooner Adirondack

  • USA
  • Superb110 reviews4.9

See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schoone....

    Free Cancellation
    Start From $57.24
 
 

New York Sunset Schooner Cruise on the Hudson River

(4.9 of 231 reviews)

Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known as Schooner Adirondack - inspired by the pilot schooners of... More

Free Cancellation
Start From $90.12
 
New York Sunset Schooner Cruise on the Hudson River Likely to Sell Out

New York Sunset Schooner Cruise on the Hudson River

  • USA
  • Superb231 reviews4.9

Experience a New York City sunset from the water on this evening sightseeing sail past many famous w....

    Free Cancellation
    Start From $90.12
 
 

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

(4.8 of 25 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
  • Superb25 reviews4.8

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
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.8 of 200 reviews)

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views ... More

Free Cancellation
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks Likely to Sell Out

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • USA
  • Superb200 reviews4.8

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....

    Free Cancellation
    Start From $61.50
 
 

Kauai’s Na Pali Coast Snorkel and Sail Tour

(4.8 of 569 reviews)

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making it the top choice for fami... More

Free Cancellation
Start From $292.48
 
Kauai’s Na Pali Coast Snorkel and Sail Tour Likely to Sell Out

Kauai’s Na Pali Coast Snorkel and Sail Tour

  • USA
  • Superb569 reviews4.8

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour cat....

    Free Cancellation
    Start From $292.48
 
 

Sunset Sail in Key West with Beverages Included

(4.9 of 974 reviews)

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the... More

Free Cancellation
Start From $79.00
 
Sunset Sail in Key West with Beverages Included Likely to Sell Out

Sunset Sail in Key West with Beverages Included

  • USA
  • Superb974 reviews4.9

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....

    Free Cancellation
    Start From $79.00
 
 

Sailing on Historic Schooner Yacht in Salem, MA

(4.9 of 206 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 $47.81
 
Sailing on Historic Schooner Yacht in Salem, MA Likely to Sell Out

Sailing on Historic Schooner Yacht in Salem, MA

  • USA
  • Superb206 reviews4.9

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

    Free Cancellation
    Start From $47.81
 
 

Sunset Catamaran Cruise in Ft. Lauderdale

(4.8 of 706 reviews)

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach as the sun slips slowly behind the lights of the city. This evening cruise calls for sun ... More

Free Cancellation
Start From $129.00
 
Sunset Catamaran Cruise in Ft. Lauderdale Likely to Sell Out

Sunset Catamaran Cruise in Ft. Lauderdale

  • USA
  • Superb706 reviews4.8

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....

    Free Cancellation
    Start From $129.00
 
 

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

(4.9 of 711 reviews)

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk like a pirate then climb aboard the Black Sparrow and set sail in search of treasure! But wait it's no... More

Free Cancellation
Start From $47.99
 
Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger Likely to Sell Out

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

  • USA
  • Superb711 reviews4.9

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos.....

    Free Cancellation
    Start From $47.99
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 844 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 Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • USA
  • Superb844 reviews4.7

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

    Free Cancellation
    Start From $213.41
 
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