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Top 10 Best North America Sailing Trips

Found 754 Sailing Trips activities in North America. Sort by Popularity. - Page 22
 

2hr Shared Sailing Experience in Toronto

(5 of 23 reviews)

On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out for the ferry, reported to be the shortest commercial one in the world. Below the water is a walking tunnel connecting the two for t... More

Free Cancellation
Start From $148.81
 
2hr Shared Sailing Experience in Toronto

2hr Shared Sailing Experience in Toronto

  • North America
  • Superb23 reviews5

On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out fo....

    Free Cancellation
    Start From $148.81
 
 

Romantic Sunset Dinner Cruising Experience

(4.2 of 40 reviews)

Sail away on Cancun's only romantic dinner cruise, a magnificent way to pamper your loved one or to enjoy a classy supper with your friends. With the magnificent backdrop that no restaurant can provide, indulge in a fine meal unde... More

Free Cancellation
Start From $109.00
 
Romantic Sunset Dinner Cruising Experience

Romantic Sunset Dinner Cruising Experience

  • North America
  • Exellent40 reviews4.2

Sail away on Cancun's only romantic dinner cruise, a magnificent way to pamper your loved one or to ....

    Free Cancellation
    Start From $109.00
 
 

New York Day Sail to the Statue of Liberty on Schooner America

(4.8 of 65 reviews)

Offering a premium sailing experience, the Schooner America is a tribute to the original America that won the America's Cup in 1851. This classic sailboat is comfortable, elegant and smooth at 105-feet in length with 3600 square... More

Free Cancellation
Start From $60.08
 
New York Day Sail to the Statue of Liberty on Schooner America Likely to Sell Out

New York Day Sail to the Statue of Liberty on Schooner America

  • North America
  • Superb65 reviews4.8

Offering a premium sailing experience, the Schooner America is a tribute to the original America t....

    Free Cancellation
    Start From $60.08
 
 

Deluxe Turtle Snorkeling Escapade at Waikiki

(4.9 of 8 reviews)

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More

Free Cancellation
Start From $100.00
 
Deluxe Turtle Snorkeling Escapade at Waikiki Likely to Sell Out

Deluxe Turtle Snorkeling Escapade at Waikiki

  • North America
  • Superb8 reviews4.9

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....

    Free Cancellation
    Start From $100.00
 
 

4th of July Fireworks on Clipper City Tall Ship

(3.7 of 6 reviews)

Celebrate Independence Day in unforgettable style aboard America's largest Tall Ship. This exclusive 4.5-hour experience combines gourmet hors d’oeuvres, open bar, themed cocktails, and live music. Sail through New York Harbor a... More

Free Cancellation
Start From $702.08
 
4th of July Fireworks on Clipper City Tall Ship Likely to Sell Out

4th of July Fireworks on Clipper City Tall Ship

  • North America
  • Very Good6 reviews3.7

Celebrate Independence Day in unforgettable style aboard America's largest Tall Ship. This exclusive....

    Free Cancellation
    Start From $702.08
 
 

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

(4.9 of 12 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

  • North America
  • Superb12 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
 
 

Isla Mujeres Platinum by Albatros Catamarans

(4.1 of 296 reviews)

The Platinum Tour is unique because it offers an unparalleled experience of luxury, adventure, and relaxation in the Mexican Caribbean. What sets it apart is the perfect blend of sophistication and fun, with attention to every det... More

Free Cancellation
Private Tour
Start From $129.00
 
Isla Mujeres Platinum by Albatros Catamarans Likely to Sell Out

Isla Mujeres Platinum by Albatros Catamarans

  • North America
  • Exellent296 reviews4.1

The Platinum Tour is unique because it offers an unparalleled experience of luxury, adventure, and r....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Private 32' Catamaran: Cabo Arch, Sea Lions & Beach for 12 Guest

(4.7 of 14 reviews)

Our boat excursions in Cabo San Lucas are the perfect way to explore the wonders of the Sea of Cortez. Our well-trained bilingual crew will ensure you have the best time on board. Choosing our charter means more than just avoidin... More

Free Cancellation
Private Tour
Start From $970.00
 
Private 32' Catamaran: Cabo Arch, Sea Lions & Beach for 12 Guest Likely to Sell Out

Private 32' Catamaran: Cabo Arch, Sea Lions & Beach for 12 Guest

  • North America
  • Superb14 reviews4.7

Our boat excursions in Cabo San Lucas are the perfect way to explore the wonders of the Sea of Corte....

    Free Cancellation
    Private Tour
    Start From $970.00
 
 

Polynesian Canoe Day Sail

(4.9 of 29 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

Free Cancellation
Private Tour
Start From $200.00
 
Polynesian Canoe Day Sail Likely to Sell Out

Polynesian Canoe Day Sail

  • North America
  • Superb29 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $200.00
 
 

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

(4.7 of 68 reviews)

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above Honolulu to snorkeling off a catamaran off Waikiki. Explore lush rainforest and... More

Free Cancellation
Private Tour
Start From $196.63
 
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel Likely to Sell Out

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

  • North America
  • Superb68 reviews4.7

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour....

    Free Cancellation
    Private Tour
    Start From $196.63
 
 

Key West's Locals' Top Sandbar and Sailing Experience

(4.2 of 15 reviews)

Join us on Sebago's newest trip, designed to allow guests to experience the waters around Key West as so many locals do, visiting little known, breathtakingly beautiful spots with small groups of friends while enjoying great food ... More

Free Cancellation
Private Tour
Start From $169.00
 
Key West's Locals' Top Sandbar and Sailing Experience Likely to Sell Out

Key West's Locals' Top Sandbar and Sailing Experience

  • North America
  • Exellent15 reviews4.2

Join us on Sebago's newest trip, designed to allow guests to experience the waters around Key West a....

    Free Cancellation
    Private Tour
    Start From $169.00
 
 

2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests

(5 of 73 reviews)

Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to helping families create unforgettable memories. Our vessel is thoughtfully designed to be warm and inviting, featuring handcrafted yel... More

Free Cancellation
Private Tour
Start From $260.00
 
2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests Likely to Sell Out

2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests

  • North America
  • Superb73 reviews5

Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to help....

    Free Cancellation
    Private Tour
    Start From $260.00
 
 

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 $99.00
 
Nights of Lights Sailboat Tour at St Augustine Sailing Likely to Sell Out

Nights of Lights Sailboat Tour at St Augustine Sailing

  • North America
  • 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 $99.00
 
 

Private Sailboat Charter on San Francisco Bay

(5 of 8 reviews)

Sunny winter days can be the Best on San Francisco Bay! No Fog, gentle breeze and sunshine! 3 hour PRIVATE Charter with a unique experience aboard Carmelita, our beautiful and pristine Catalina 42 sailboat. We provide our clients ... 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

  • North America
  • Superb8 reviews5

Sunny winter days can be the Best on San Francisco Bay! No Fog, gentle breeze and sunshine! 3 hour P....

    Free Cancellation
    Private Tour
    Start From $995.00
 
 

4-Hour Sailing Adventure on The Strait of Juan de Fuca

(4.7 of 27 reviews)

Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbacks, Orcas, Sea lions, Seals, Eagles and water birds there is always something to see while you are learning the skills to sail one... More

Free Cancellation
Private Tour
Start From $134.60
 
4-Hour Sailing Adventure on The Strait of Juan de Fuca Likely to Sell Out

4-Hour Sailing Adventure on The Strait of Juan de Fuca

  • North America
  • Superb27 reviews4.7

Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbac....

    Free Cancellation
    Private Tour
    Start From $134.60
 
 

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

  • North America
  • 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 14 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

  • North America
  • Superb14 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
 
 

Sail Away: Explore Maine's Coastal Beauty on a 2-Hour Excursion

(4.9 of 42 reviews)

Step aboard for an unforgettable journey along Maine's stunning coastline! Join us for a two-hour sail and create memories to cherish forever. Experience the beauty of Maine as you glide through the waters of the Saco River and Sa... More

Free Cancellation
Private Tour
Start From $139.00
 
Sail Away: Explore Maine's Coastal Beauty on a 2-Hour Excursion Likely to Sell Out

Sail Away: Explore Maine's Coastal Beauty on a 2-Hour Excursion

  • North America
  • Superb42 reviews4.9

Step aboard for an unforgettable journey along Maine's stunning coastline! Join us for a two-hour sa....

    Free Cancellation
    Private Tour
    Start From $139.00
 
 

Whale Shark Encounter Experience in Cancun (Snack Lunch included)

(4.3 of 4 reviews)

If you like awesome and unique activities, then this activity is for you. Welcome to the Whale Shark experience, this is a unique activity in the world and is the most enigmatic activity in Mexico. Imagine swimming next to an imme... More

Free Cancellation
Private Tour
Start From $189.00
 
Whale Shark Encounter Experience in Cancun (Snack Lunch included) Likely to Sell Out

Whale Shark Encounter Experience in Cancun (Snack Lunch included)

  • North America
  • Exellent4 reviews4.3

If you like awesome and unique activities, then this activity is for you. Welcome to the Whale Shark....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

New York City Skyline Lights Sail

(4.7 of 13 reviews)

Experience New York City from the water on classic Schooner Adirondack. Gaze at the city lights from the water and enjoy a peaceful setting as you escape the city and take to a quiet harbor at night. Key points about this activ... More

Free Cancellation
Private Tour
Start From $67.01
 
New York City Skyline Lights Sail Likely to Sell Out

New York City Skyline Lights Sail

  • North America
  • Superb13 reviews4.7

Experience New York City from the water on classic Schooner Adirondack. Gaze at the city lights fro....

    Free Cancellation
    Private Tour
    Start From $67.01
 
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