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Top 10 Best USA Sailing Trips

Found 452 Sailing Trips activities in USA. Sort by Popularity. - Page 17
 

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

(4.8 of 18 reviews)

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea, this intimate evening cruise offers stunning views of the coast... More

Free Cancellation
Start From $279.00
 
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

  • USA
  • Superb18 reviews4.8

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experien....

    Free Cancellation
    Start From $279.00
 
 

Private Therapy Sailing Adventure

(4.8 of 46 reviews)

Old Plank Adventures: Sail into Deep Tranquility LUXURY SAILING | THERAPEUTIC ESCAPES | GOURMET CUISINE | INTIMATE WILDLIFE ENCOUNTERS Immerse yourself in the timeless Mediterranean elegance along Southern California’s glitteri... More

Free Cancellation
Private Tour
Start From $400.00
 
Private Therapy Sailing Adventure

Private Therapy Sailing Adventure

  • USA
  • Superb46 reviews4.8

Old Plank Adventures: Sail into Deep Tranquility LUXURY SAILING | THERAPEUTIC ESCAPES | GOURMET CUIS....

    Free Cancellation
    Private Tour
    Start From $400.00
 
 

Experience Oceanside Sailing with Whales and dolphins!

(5 of 18 reviews)

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and most comfortable sailboats in the Oceanside harbor. We cater to guests from many of the five star hotels in the area. We serve an up... More

Free Cancellation
Private Tour
Start From $200.00
 
Experience Oceanside Sailing with Whales and dolphins!

Experience Oceanside Sailing with Whales and dolphins!

  • USA
  • Superb18 reviews5

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and mo....

    Free Cancellation
    Private Tour
    Start From $200.00
 
 

Private Statue of Liberty Sailing Tour

(5 of 14 reviews)

Experience a luxury sailing adventure! Enjoy a spacious deck lounge, sun pad, cabin lounge with table seating for six, Bluetooth sound system, luxury wraps, lavatory, and curated amenities. Fully staffed by USCG licensed captain a... More

Free Cancellation
Private Tour
Start From $800.00
 
Private Statue of Liberty Sailing Tour Likely to Sell Out

Private Statue of Liberty Sailing Tour

  • USA
  • Superb14 reviews5

Experience a luxury sailing adventure! Enjoy a spacious deck lounge, sun pad, cabin lounge with tabl....

    Free Cancellation
    Private Tour
    Start From $800.00
 
 

Ultimate Party in Miami : Boat Party, Party Bus & Nightclub

(3.1 of 16 reviews)

This is not just another night out, it’s Miami’s nightlife on the water. Step aboard a spacious double-decker boat transformed into a moving nightclub with a live DJ, dazzling lights, and a vibrant atmosphere. As the sun sets,... More

Free Cancellation
Private Tour
Start From $189.00
 
Ultimate Party in Miami : Boat Party, Party Bus & Nightclub Likely to Sell Out

Ultimate Party in Miami : Boat Party, Party Bus & Nightclub

  • USA
  • Good16 reviews3.1

This is not just another night out, it’s Miami’s nightlife on the water. Step aboard a spacious ....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay

(4.9 of 13 reviews)

We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We have made a commitment to sustainability and having a minimal impact on the environment ! It is a wholesome adventure that will le... More

Free Cancellation
Private Tour
Start From $600.00
 
Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay Likely to Sell Out

Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay

  • USA
  • Superb13 reviews4.9

We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We ....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Private Sailing on the Miami Bay - Biscayne Bay

(4.9 of 76 reviews)

Let's go Sailing!  Experience Miami's Biscayne Bay aboard one of Destino Charters Beneteau stylish vessels in the company of experienced, but mostly fun, well traveled, passionate captains. A Private Sailing tour aboard Destino ... More

Free Cancellation
Private Tour
Start From $425.00
 
Private Sailing on the Miami Bay - Biscayne Bay Likely to Sell Out

Private Sailing on the Miami Bay - Biscayne Bay

  • USA
  • Superb76 reviews4.9

Let's go Sailing!  Experience Miami's Biscayne Bay aboard one of Destino Charters Beneteau stylish....

    Free Cancellation
    Private Tour
    Start From $425.00
 
 

Baltimore Inner Harbor Sail on Summer Wind

(4.6 of 125 reviews)

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling city from the water. Explore the Inner Harbor and the joy of sailing on t... More

Free Cancellation
Private Tour
Start From $65.00
 
Baltimore Inner Harbor Sail on Summer Wind Likely to Sell Out

Baltimore Inner Harbor Sail on Summer Wind

  • USA
  • Superb125 reviews4.6

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authe....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Nights of Lights Sailboat Tour at St Augustine Sailing

(5 of 18 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 $129.00
 
Nights of Lights Sailboat Tour at St Augustine Sailing Likely to Sell Out

Nights of Lights Sailboat Tour at St Augustine Sailing

  • USA
  • Superb18 reviews5

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

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Private Sailboat Charter on San Francisco Bay

(5 of 8 reviews)

Moving into summer provides calm mornings and what can be a very fresh afternoon breeze. 3 hour PRIVATE Charter with a unique experience aboard Carmelita, our beautiful and pristine Catalina 42 sailboat. We provide our clients wi... More

Free Cancellation
Private Tour
Start From $995.00
 
Private Sailboat Charter on San Francisco Bay Likely to Sell Out

Private Sailboat Charter on San Francisco Bay

  • USA
  • Superb8 reviews5

Moving into summer provides calm mornings and what can be a very fresh afternoon breeze. 3 hour PRI....

    Free Cancellation
    Private Tour
    Start From $995.00
 
 

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

(4.8 of 14 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 $1,150.00
 
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People Likely to Sell Out

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

  • USA
  • Superb14 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $1,150.00
 
 

New York City Live Jazz Sail

(4.9 of 16 reviews)

Step aboard 105-foot Schooner America 2.0, a modern tribute to the first boat that won the America's Cup in 1851, for a 2-hour sail around New York Harbor. Sit back and relax while enjoying live Jazz music played throughout this s... More

Free Cancellation
Private Tour
Start From $134.03
 
New York City Live Jazz Sail Likely to Sell Out

New York City Live Jazz Sail

  • USA
  • Superb16 reviews4.9

Step aboard 105-foot Schooner America 2.0, a modern tribute to the first boat that won the America's....

    Free Cancellation
    Private Tour
    Start From $134.03
 
 

Diamond Head Sunset Sail

(4.7 of 15 reviews)

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from the... More

Free Cancellation
Private Tour
Start From $695.00
 
Diamond Head Sunset Sail Likely to Sell Out

Diamond Head Sunset Sail

  • USA
  • Superb15 reviews4.7

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

Key West Dolphin Watch and Sunset Sail on Catamaran

(4.7 of 43 reviews)

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of wind. This tour is perfect for all ages and offers a wide-open, unobs... More

Free Cancellation
Private Tour
Start From $117.17
 
Key West Dolphin Watch and Sunset Sail on Catamaran Likely to Sell Out

Key West Dolphin Watch and Sunset Sail on Catamaran

  • USA
  • Superb43 reviews4.7

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the ligh....

    Free Cancellation
    Private Tour
    Start From $117.17
 
 

Deluxe private Sunset & Day Sail

(5 of 3 reviews)

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks, and into the heart of coastal paradise. Feel the wind in your... More

Free Cancellation
Private Tour
Start From $714.00
 
Deluxe private Sunset & Day Sail Likely to Sell Out

Deluxe private Sunset & Day Sail

  • USA
  • Superb3 reviews5

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling ....

    Free Cancellation
    Private Tour
    Start From $714.00
 
 

Baltimore Inner Harbor Sail on the Unforgettable

(4.8 of 25 reviews)

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling city from the water. Explore the Inner Harbor and the joy of sailing on t... More

Free Cancellation
Private Tour
Start From $65.00
 
Baltimore Inner Harbor Sail on the Unforgettable Likely to Sell Out

Baltimore Inner Harbor Sail on the Unforgettable

  • USA
  • Superb25 reviews4.8

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authe....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Polynesian Canoe Morning Sail

(5 of 18 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Special Offer
Free Cancellation
Private Tour
Start From $180.00
(Saving 10% ) $200.00
 
-10% Polynesian Canoe Morning Sail Likely to Sell Out

Polynesian Canoe Morning Sail

  • USA
  • Superb18 reviews5

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $180.00
    (Saving 10% ) $200.00
 
 

Key West Private Charter: Sandbar and Snorkeling

(5 of 14 reviews)

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a formal, guided eco-tour, this trip offers a more laid-back vibe, allowing you t... More

Special Offer
Free Cancellation
Private Tour
Start From $950.00
(Saving inf% ) $0.00
 
-inf% Key West Private Charter: Sandbar and Snorkeling Likely to Sell Out

Key West Private Charter: Sandbar and Snorkeling

  • USA
  • Superb14 reviews5

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who wa....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $950.00
    (Saving inf% ) $0.00
 
 

Honolua Snorkel Sail from Lahaina

(4.9 of 61 reviews)

Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Marine Life Conservation District. Along the way, watch for wild dolphins, then snorkel among Hawaiian green sea turtles in this vib... More

Special Offer
Free Cancellation
Private Tour
Start From $180.92
(Saving inf% ) $0.00
 
-inf% Honolua Snorkel Sail from Lahaina Likely to Sell Out

Honolua Snorkel Sail from Lahaina

  • USA
  • Superb61 reviews4.9

Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Ma....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $180.92
    (Saving inf% ) $0.00
 
 

Golden Gate Bridge Sailing Tour

(4.8 of 54 reviews)

Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail off to the Golden Gate Bridge and enjoy panoramic views of the San Francisco skyline, Sausalito, Angel Island, Tiburon, and Marin... More

Special Offer
Free Cancellation
Private Tour
Start From $129.00
(Saving inf% ) $0.00
 
-inf% Golden Gate Bridge Sailing Tour Likely to Sell Out

Golden Gate Bridge Sailing Tour

  • USA
  • Superb54 reviews4.8

Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $129.00
    (Saving inf% ) $0.00
 
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