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Top 10 Best USA Sailing Trips

Found 452 Sailing Trips activities in USA. Sort by Popularity. - Page 11
 

2 Hour Sailing Adventure in Lake Michigan (up to 6 people)

(5 of 12 reviews)

Our trips are perfect for starters or advanced sailors. We offer a 2 -hour sailing trip overlooking views of the city of Racine and on clear day views of Milwaukee and Kenosha You can lay back and relax to the sounds of the wave... More

Free Cancellation
Start From $95.00
 
2 Hour Sailing Adventure in Lake Michigan (up to 6 people)

2 Hour Sailing Adventure in Lake Michigan (up to 6 people)

  • USA
  • Superb12 reviews5

Our trips are perfect for starters or advanced sailors. We offer a 2 -hour sailing trip overlooking ....

    Free Cancellation
    Start From $95.00
 
 

San Diego Sailing Cruise Small Group 6 Guests Classic Yacht

(5 of 84 reviews)

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with Captain Phil, a USCG-licensed captain with 55 years of sailing experience. ... More

Free Cancellation
Start From $125.00
 
San Diego Sailing Cruise Small Group 6 Guests Classic Yacht Likely to Sell Out

San Diego Sailing Cruise Small Group 6 Guests Classic Yacht

  • USA
  • Superb84 reviews5

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San ....

    Free Cancellation
    Start From $125.00
 
 

Private Sunset and Eco Tour in Destin-Up to 16 Guests

(5 of 44 reviews)

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a full restroom, as well as a... More

Free Cancellation
Private Tour
Start From $450.00
 
Private Sunset and Eco Tour in Destin-Up to 16 Guests Likely to Sell Out

Private Sunset and Eco Tour in Destin-Up to 16 Guests

  • USA
  • Superb44 reviews5

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....

    Free Cancellation
    Private Tour
    Start From $450.00
 
 

Maui Turtle Snorkel & Sail with Lunch & Open Bar

(4.8 of 39 reviews)

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear waters teeming with vibrant coral reefs a... More

Free Cancellation
Private Tour
Start From $122.40
 
Maui Turtle Snorkel & Sail with Lunch & Open Bar Likely to Sell Out

Maui Turtle Snorkel & Sail with Lunch & Open Bar

  • USA
  • Superb39 reviews4.8

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine lan....

    Free Cancellation
    Private Tour
    Start From $122.40
 
 

Private Sailing Charter on San Diego Bay

(4.9 of 48 reviews)

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural wonder aboard a beautiful sailing yacht with a knowledgeable and friendly Captain? This private charterÂ... More

Free Cancellation
Private Tour
Start From $475.00
 
Private Sailing Charter on San Diego Bay Likely to Sell Out

Private Sailing Charter on San Diego Bay

  • USA
  • Superb48 reviews4.9

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. W....

    Free Cancellation
    Private Tour
    Start From $475.00
 
 

2 Hours Cocktail Sail Aboard Bella

(4.9 of 48 reviews)

Our experienced captains will sail you to the most beautiful local spots to watch the sunset on the water. Spot dolphins, seabirds, and other wildlife as you pass by islands and marshlands. The boat is fully equipped with air con... More

Free Cancellation
Private Tour
Start From $150.00
 
2 Hours Cocktail Sail Aboard Bella Likely to Sell Out

2 Hours Cocktail Sail Aboard Bella

  • USA
  • Superb48 reviews4.9

Our experienced captains will sail you to the most beautiful local spots to watch the sunset on the ....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

Small Group Waikiki Sunset Sailing Tour

(4.9 of 115 reviews)

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More

Free Cancellation
Private Tour
Start From $99.00
 
Small Group Waikiki Sunset Sailing Tour Likely to Sell Out

Small Group Waikiki Sunset Sailing Tour

  • USA
  • Superb115 reviews4.9

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Private Classic Sailboat Tour in New York City

(5 of 2 reviews)

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a unique and immersive experience on the Hudson River. You'll enjoy stunning views of iconic landmarks like the Statue of Liberty, E... More

Free Cancellation
Private Tour
Start From $700.00
 
Private Classic Sailboat Tour in New York City Likely to Sell Out

Private Classic Sailboat Tour in New York City

  • USA
  • Superb2 reviews5

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a ....

    Free Cancellation
    Private Tour
    Start From $700.00
 
 

Waikiki small group turtle snorkeling & sailing

(5 of 100 reviews)

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of dawn during their Hawaiian vacation due to time zone changes. As we start out our tour from ... More

Free Cancellation
Private Tour
Start From $99.00
 
Waikiki small group turtle snorkeling & sailing Likely to Sell Out

Waikiki small group turtle snorkeling & sailing

  • USA
  • Superb100 reviews5

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Daytime Charleston Harbor Sail - Lux Catamatan w/Bar

(4.7 of 9 reviews)

Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s historic harbor. This 55-foot catamaran offers the perfect vantage point to experience the city’s charm from the water, away from the ... More

Free Cancellation
Private Tour
Start From $64.00
 
Daytime Charleston Harbor Sail - Lux Catamatan w/Bar Likely to Sell Out

Daytime Charleston Harbor Sail - Lux Catamatan w/Bar

  • USA
  • Superb9 reviews4.7

Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s histor....

    Free Cancellation
    Private Tour
    Start From $64.00
 
 

Guided Seattle Sailing Adventure from Bainbridge Island

(5 of 83 reviews)

Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning waterfront homes, and maybe even spot whales. Or we could see a nuclear submarine, inbound container ships, or century-old schooners... More

Free Cancellation
Private Tour
Start From $360.00
 
Guided Seattle Sailing Adventure from Bainbridge Island Likely to Sell Out

Guided Seattle Sailing Adventure from Bainbridge Island

  • USA
  • Superb83 reviews5

Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning wa....

    Free Cancellation
    Private Tour
    Start From $360.00
 
 

Tiki Pub Amazing Dolphin Eco Adventure

(4.4 of 8 reviews)

Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water inhabitants, cruise the bay for Dolphins, Manatee, and a myriad of sea creatures and incredible Birds! The best part is that then y... More

Free Cancellation
Private Tour
Start From $49.95
 
Tiki Pub Amazing Dolphin Eco Adventure Likely to Sell Out

Tiki Pub Amazing Dolphin Eco Adventure

  • USA
  • Exellent8 reviews4.4

Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water i....

    Free Cancellation
    Private Tour
    Start From $49.95
 
 

Private Swim, Snorkel & Sail on the Daydreams Sailboat

(5 of 32 reviews)

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for f... More

Free Cancellation
Private Tour
Start From $899.00
 
Private Swim, Snorkel & Sail on the Daydreams Sailboat Likely to Sell Out

Private Swim, Snorkel & Sail on the Daydreams Sailboat

  • USA
  • Superb32 reviews5

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bo....

    Free Cancellation
    Private Tour
    Start From $899.00
 
 

Public Sunset Sailing Cruise on Lake Champlain

(5 of 4 reviews)

Witness the captivating Burlington sunset while sailing across Lake Champlain on a classic Friendship Sloop. This two-hour cruise offers an unparalleled view of the Adirondack Mountains as you relax and enjoy the charming atmosphe... More

Free Cancellation
Private Tour
Start From $95.00
 
Public Sunset Sailing Cruise on Lake Champlain Likely to Sell Out

Public Sunset Sailing Cruise on Lake Champlain

  • USA
  • Superb4 reviews5

Witness the captivating Burlington sunset while sailing across Lake Champlain on a classic Friendshi....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise

(5 of 2 reviews)

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, bar seating for 6 people, on board sound system with Tiki-Oki, and the friendliest most fun captains around. You'll be sure to have... More

Free Cancellation
Private Tour
Start From $349.00
 
Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise Likely to Sell Out

Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise

  • USA
  • Superb2 reviews5

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, b....

    Free Cancellation
    Private Tour
    Start From $349.00
 
 

Spectacular Afternoon Sail on San Diego Bay

(5 of 20 reviews)

A unique small group two-hour sailing experience aboard our 35-foot sailboat, Luna. Enjoy spectacular views as your fun-loving, informative Captain shares his knowledge of sailing and San Diego. Get hands-on or sit back and enjoy ... More

Free Cancellation
Private Tour
Start From $108.00
 
Spectacular Afternoon Sail on San Diego Bay Likely to Sell Out

Spectacular Afternoon Sail on San Diego Bay

  • USA
  • Superb20 reviews5

A unique small group two-hour sailing experience aboard our 35-foot sailboat, Luna. Enjoy spectacula....

    Free Cancellation
    Private Tour
    Start From $108.00
 
 

San Diego Sailing Sunset and Afternoon Classic Yacht

(5 of 6 reviews)

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with Captain Phil, a USCG-licensed captain with 55 years of sailing experience. ... More

Free Cancellation
Private Tour
Start From $125.00
 
San Diego Sailing Sunset and Afternoon Classic Yacht Likely to Sell Out

San Diego Sailing Sunset and Afternoon Classic Yacht

  • USA
  • Superb6 reviews5

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San ....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.6 of 63 reviews)

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More

Free Cancellation
Private Tour
Start From $179.00
 
Hawaiian Canoe Sailing Experience in Maui Likely to Sell Out

Hawaiian Canoe Sailing Experience in Maui

  • USA
  • Superb63 reviews4.6

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....

    Free Cancellation
    Private Tour
    Start From $179.00
 
 

Friday Night Firework Cruise in Waikiki

(4.8 of 34 reviews)

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, truly making this the ultimate party experience. Enjoy the Premium drinks of your choice ... More

Free Cancellation
Private Tour
Start From $69.99
 
Friday Night Firework Cruise in Waikiki Likely to Sell Out

Friday Night Firework Cruise in Waikiki

  • USA
  • Superb34 reviews4.8

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

2 Hours Sunset Private Charter on Heart's Desire in Casco Bay

(5 of 2 reviews)

This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Sail aboard Heart's Desire, a 101 year old schooner, designed by famed yacht designe... More

Free Cancellation
Private Tour
Start From $675.00
 
2 Hours Sunset Private Charter on Heart's Desire in Casco Bay Likely to Sell Out

2 Hours Sunset Private Charter on Heart's Desire in Casco Bay

  • USA
  • Superb2 reviews5

This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - com....

    Free Cancellation
    Private Tour
    Start From $675.00
 
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