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Top 10 Best USA Sailing Trips

Found 426 Sailing Trips activities in USA. Sort by Popularity. - Page 17
 

Sunset Sailing Cruise on San Diego Bay | Champagne Included

(5 of 1 review)

What makes this experience truly special is the blend of refined European luxury and a relaxed, intimate atmosphere without the feel of a large group tour. You will be sailing aboard a beautifully crafted French yacht designed for... More

Free Cancellation
Start From $199.00
 
Sunset Sailing Cruise on San Diego Bay | Champagne Included

Sunset Sailing Cruise on San Diego Bay | Champagne Included

  • USA
  • Superb1 review5

What makes this experience truly special is the blend of refined European luxury and a relaxed, inti....

    Free Cancellation
    Start From $199.00
 
 

All Inclusive St Pete Private Half Day Catamaran Charter

(5 of 1 review)

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks,... More

Free Cancellation
Private Tour
Start From $1,700.00
 
All Inclusive St Pete Private Half Day Catamaran Charter

All Inclusive St Pete Private Half Day Catamaran Charter

  • USA
  • Superb1 review5

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and cr....

    Free Cancellation
    Private Tour
    Start From $1,700.00
 
 

Afternoon Ali'i Adventure

(5 of 6 reviews)

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. ... More

Free Cancellation
Private Tour
Start From $276.00
 
Afternoon Ali'i Adventure

Afternoon Ali'i Adventure

  • USA
  • Superb6 reviews5

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....

    Free Cancellation
    Private Tour
    Start From $276.00
 
 

Private Morning Sail in San Diego up to 12 guests $975

(5 of 33 reviews)

This private morning sail is a great way to start the day. Mornings are best to go see San Diego's wildlife because there is little wind and few waves, allowing us to easily cross over to Point Loma. The bay will most likely have ... More

Free Cancellation
Private Tour
Start From $487.50
 
Private Morning Sail in San Diego up to 12 guests $975

Private Morning Sail in San Diego up to 12 guests $975

  • USA
  • Superb33 reviews5

This private morning sail is a great way to start the day. Mornings are best to go see San Diego's w....

    Free Cancellation
    Private Tour
    Start From $487.50
 
 

Private Sunset & Dolphin Sightseeing Sail on Daydreams Sailboat

(5 of 3 reviews)

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you plan the perfect experience for you and your guests! You'll sail around Shell Island into the Gulf of Mexico, while you enjoy dol... More

Free Cancellation
Private Tour
Start From $759.96
 
Private Sunset & Dolphin Sightseeing Sail on Daydreams Sailboat

Private Sunset & Dolphin Sightseeing Sail on Daydreams Sailboat

  • USA
  • Superb3 reviews5

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you....

    Free Cancellation
    Private Tour
    Start From $759.96
 
 

Maui: Catamaran Sunset Whale Watch with Cocktails

(5 of 2 reviews)

Experience the best of whale season at sunset! Watch humpbacks breach and play from the deck of a 65' luxury catamaran as the sun sets with an ice-cold cocktail in hand. Guaranteed humpback whale sightings on every charter. Expe... More

Free Cancellation
Private Tour
Start From $189.00
 
Maui: Catamaran Sunset Whale Watch with Cocktails

Maui: Catamaran Sunset Whale Watch with Cocktails

  • USA
  • Superb2 reviews5

Experience the best of whale season at sunset! Watch humpbacks breach and play from the deck of a 65....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Private Catamaran: Snorkel, Swim and Dolphin Watching

(5 of 1 review)

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take you to some of the best spots the area has to offer while you are visiting the Emerald Coast.... More

Free Cancellation
Private Tour
Start From $465.00
 
Private Catamaran: Snorkel, Swim and Dolphin Watching

Private Catamaran: Snorkel, Swim and Dolphin Watching

  • USA
  • Superb1 review5

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion....

    Free Cancellation
    Private Tour
    Start From $465.00
 
 

2hr Luxury Private Sailing Catamaran for 7-12 People

(5 of 4 reviews)

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More

Free Cancellation
Private Tour
Start From $1,495.00
 
2hr Luxury Private Sailing Catamaran for 7-12 People

2hr Luxury Private Sailing Catamaran for 7-12 People

  • USA
  • Superb4 reviews5

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....

    Free Cancellation
    Private Tour
    Start From $1,495.00
 
 

2 - Hour Private Hilton Head Morning Dolphin Watching / Sail

(5 of 37 reviews)

This 2 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side of the island - generally best conditions for sailing). During the MORNING, this is generally a calm - light wind relaxing sail, a... More

Free Cancellation
Private Tour
Start From $465.00
 
2 - Hour Private Hilton Head Morning Dolphin Watching / Sail

2 - Hour Private Hilton Head Morning Dolphin Watching / Sail

  • USA
  • Superb37 reviews5

This 2 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side ....

    Free Cancellation
    Private Tour
    Start From $465.00
 
 

Sailing Charter

(5 of 9 reviews)

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make an adventure out of it, and sail a living legend out of scenic Sequim Bay! Ingrid Princess is an ocean going, full keel ketch avail... More

Free Cancellation
Private Tour
Start From $240.00
 
Sailing Charter

Sailing Charter

  • USA
  • Superb9 reviews5

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make a....

    Free Cancellation
    Private Tour
    Start From $240.00
 
 

Private Sunset Sail on San Diego Bay with Champagne

(5 of 9 reviews)

What makes this experience truly unique is the combination of refined European luxury and a relaxed, intimate atmosphere. You will be sailing aboard a beautifully crafted French yacht, designed for comfort, performance, and elegan... More

Free Cancellation
Private Tour
Start From $975.00
 
Private Sunset Sail on San Diego Bay with Champagne

Private Sunset Sail on San Diego Bay with Champagne

  • USA
  • Superb9 reviews5

What makes this experience truly unique is the combination of refined European luxury and a relaxed,....

    Free Cancellation
    Private Tour
    Start From $975.00
 
 

2 hours - Private Day Sail along Historic St Augustine Bayfront

(5 of 20 reviews)

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to assist in making your experience a wonder memory. This 2-hour sail gives passengers a ... More

Free Cancellation
Private Tour
Start From $795.00
 
2 hours - Private Day Sail along Historic St Augustine Bayfront

2 hours - Private Day Sail along Historic St Augustine Bayfront

  • USA
  • Superb20 reviews5

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our sta....

    Free Cancellation
    Private Tour
    Start From $795.00
 
 

Private Sail Around New York City and The Statue of Liberty

(5 of 9 reviews)

Discover NYC from a completely different perspective on a private sailboat charter. You and your group will view New York City in ways that are breath taking. See the Statue of Liberty up close like you can almost touch it. Sit ba... More

Free Cancellation
Private Tour
Start From $650.00
 
Private Sail Around New York City and The Statue of Liberty

Private Sail Around New York City and The Statue of Liberty

  • USA
  • Superb9 reviews5

Discover NYC from a completely different perspective on a private sailboat charter. You and your gro....

    Free Cancellation
    Private Tour
    Start From $650.00
 
 

Nights of Lights Sailboat Tour St Augustine Sailing

(5 of 4 reviews)

What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours offer a simple ride, St Augustine Sailing provides an intimate, serene setting ... More

Free Cancellation
Private Tour
Start From $774.00
 
Nights of Lights Sailboat Tour St Augustine Sailing

Nights of Lights Sailboat Tour St Augustine Sailing

  • USA
  • Superb4 reviews5

What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experien....

    Free Cancellation
    Private Tour
    Start From $774.00
 
 

SUNSET CRUISE in Key Largo,FL.

(5 of 3 reviews)

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need to worry about large crowds or waiting in long lines. Personalize the trip to your liking. A private charter makes it more personab... More

Free Cancellation
Private Tour
Start From $389.00
 
SUNSET CRUISE in Key Largo,FL. Likely to Sell Out

SUNSET CRUISE in Key Largo,FL.

  • USA
  • Superb3 reviews5

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need t....

    Free Cancellation
    Private Tour
    Start From $389.00
 
 

Sunset Sailing Tour of San Diego Bay up to 6 Guests

(5 of 1 review)

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sunset sailing charters and boat tours. Our sunset sailin... More

Free Cancellation
Private Tour
Start From $800.00
 
Sunset Sailing Tour of San Diego Bay up to 6 Guests Likely to Sell Out

Sunset Sailing Tour of San Diego Bay up to 6 Guests

  • USA
  • Superb1 review5

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautifu....

    Free Cancellation
    Private Tour
    Start From $800.00
 
 

Key West Christmas Cruise with Live Band and Drinks

(5 of 6 reviews)

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our live band and celebrate the holidays and Christmas in Key West. E... More

Free Cancellation
Private Tour
Start From $97.61
 
Key West Christmas Cruise with Live Band and Drinks Likely to Sell Out

Key West Christmas Cruise with Live Band and Drinks

  • USA
  • Superb6 reviews5

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christ....

    Free Cancellation
    Private Tour
    Start From $97.61
 
 

Private Key West Sunset Sail

(4.7 of 52 reviews)

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for up to 12 passengers, the Sloop High Tide and Sunset Sail Key West make for t... More

Free Cancellation
Private Tour
Start From $695.00
 
Private Key West Sunset Sail Likely to Sell Out

Private Key West Sunset Sail

  • USA
  • Superb52 reviews4.7

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, ....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

4th of July Sunset Sail on the Black Pearl

(4.7 of 52 reviews)

Join us for the 4th of July for Fireworks over Cedar Point from a beautiful 47' Sailing yacht - The Black Pearl! Sail magestically across the water as we find our most perfect spot for viewing the fireworks while watching the suns... More

Free Cancellation
Private Tour
Start From $1,195.00
 
4th of July Sunset Sail on the Black Pearl Likely to Sell Out

4th of July Sunset Sail on the Black Pearl

  • USA
  • Superb52 reviews4.7

Join us for the 4th of July for Fireworks over Cedar Point from a beautiful 47' Sailing yacht - The ....

    Free Cancellation
    Private Tour
    Start From $1,195.00
 
 

Waikiki Sunset Cruise and Iconic Views with Swimming

(5 of 4 reviews)

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide along the iconic Gold Coast as the sun sets, painting the sky with vibrant co... More

Free Cancellation
Private Tour
Start From $65.00
 
Waikiki Sunset Cruise and Iconic Views with Swimming Likely to Sell Out

Waikiki Sunset Cruise and Iconic Views with Swimming

  • USA
  • Superb4 reviews5

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in....

    Free Cancellation
    Private Tour
    Start From $65.00
 
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