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Top 10 Best North America Sailing Trips

Found 765 Sailing Trips activities in North America. Sort by Popularity. - Page 11
 

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

(4.9 of 463 reviews)

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay for over 15 years, just for the fun of it. We started this eco-tour in 2018 to share the ama... More

Free Cancellation
Start From $129.00
 
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling Likely to Sell Out

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

  • North America
  • Superb463 reviews4.9

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....

    Free Cancellation
    Start From $129.00
 
 

Whale Shark Sightseeing Adventure from Cancun

(5 of 1 review)

Experience an unforgettable whale shark encounter in the Mexican Caribbean, with the opportunity to enjoy swimming or sightseeing depending on natural conditions. Enjoy a more personalized adventure aboard a small-group boat with... More

Free Cancellation
Start From $159.00
 
Whale Shark Sightseeing Adventure from Cancun Likely to Sell Out

Whale Shark Sightseeing Adventure from Cancun

  • North America
  • Superb1 review5

Experience an unforgettable whale shark encounter in the Mexican Caribbean, with the opportunity to ....

    Free Cancellation
    Start From $159.00
 
 

Catamaran Sailing Cruise in Monterey

(4.8 of 40 reviews)

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind to make for a peaceful and exciting cruise on the bay. On the way out of t... More

Free Cancellation
Start From $65.00
 
Catamaran Sailing Cruise in Monterey Likely to Sell Out

Catamaran Sailing Cruise in Monterey

  • North America
  • Superb40 reviews4.8

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage af....

    Free Cancellation
    Start From $65.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 250 reviews)

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adve... More

Free Cancellation
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb250 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....

    Free Cancellation
    Start From $136.19
 
 

Deluxe Day Sail in San Diego

(5 of 74 reviews)

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego Bay offer a perfect blend of adventure and relaxation. With our passionate and kno... More

Free Cancellation
Start From $119.00
 
Deluxe Day Sail in San Diego Likely to Sell Out

Deluxe Day Sail in San Diego

  • North America
  • Superb74 reviews5

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our person....

    Free Cancellation
    Start From $119.00
 
 

4-Hour Fort Lauderdale Sailing Charter

(4.9 of 322 reviews)

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option(PRIVATE CRUISES) to use their time docked or sailing out to sea. ... More

Free Cancellation
Start From $148.00
 
4-Hour Fort Lauderdale Sailing Charter Likely to Sell Out

4-Hour Fort Lauderdale Sailing Charter

  • North America
  • Superb322 reviews4.9

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....

    Free Cancellation
    Start From $148.00
 
 

Private Sailing Charter: Up to 24 Passengers

(5 of 1 review)

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco Bay. While our boats are coast guard licensed for 34 passengers, we are limiting... More

Free Cancellation
Private Tour
Start From $1,207.50
 
Private Sailing Charter: Up to 24 Passengers Likely to Sell Out

Private Sailing Charter: Up to 24 Passengers

  • North America
  • Superb1 review5

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a ....

    Free Cancellation
    Private Tour
    Start From $1,207.50
 
 

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

(4.8 of 17 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 $840.00
 
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
  • Superb17 reviews4.8

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 $840.00
 
 

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

(5 of 1 review)

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 $1,595.00
 
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People Likely to Sell Out

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

  • North America
  • Superb1 review5

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

    Free Cancellation
    Private Tour
    Start From $1,595.00
 
 

Private Yacht Charter to the Arch in Cabo San Lucas

(5 of 1 review)

Enjoy a private yachting experience in Cabo San Lucas without committing to a full-day tour. Perfect for couples, families, or small groups, this 2-hour cruise offers front-row views of El Arco, Lover’s Beach, and local sea lion... More

Free Cancellation
Private Tour
Start From $1,150.00
 
Private Yacht Charter to the Arch in Cabo San Lucas Likely to Sell Out

Private Yacht Charter to the Arch in Cabo San Lucas

  • North America
  • Superb1 review5

Enjoy a private yachting experience in Cabo San Lucas without committing to a full-day tour. Perfect....

    Free Cancellation
    Private Tour
    Start From $1,150.00
 
 

Waikiki Sail and Snorkel Adventure Best of Hawaii 2023

(4 of 4 reviews)

Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with an array of tropical fish. The clear waters of Turtle Canyons reveal a kaleidoscope of colors, from dazzling schools of fish to vi... More

Free Cancellation
Private Tour
Start From $695.00
 
Waikiki Sail and Snorkel Adventure Best of Hawaii 2023 Likely to Sell Out

Waikiki Sail and Snorkel Adventure Best of Hawaii 2023

  • North America
  • Very Good4 reviews4

Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with ....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran

(5 of 5 reviews)

Your 90 minute sunset sail on 41ft, 32 passenger Lazy Daze Catamaran will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the ... More

Free Cancellation
Private Tour
Start From $40.00
 
Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran Likely to Sell Out

Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran

  • North America
  • Superb5 reviews5

Your 90 minute sunset sail on 41ft, 32 passenger Lazy Daze Catamaran will include a scenic trip thro....

    Free Cancellation
    Private Tour
    Start From $40.00
 
 

Private Kelowna Sailing Cruise on Okanagan Lake

(5 of 50 reviews)

Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are welcome to sit back and relax, enjoy the sights, or take a turn at the helm, with instruction from your skipper! I will never forg... More

Free Cancellation
Private Tour
Start From $120.35
 
Private Kelowna Sailing Cruise on Okanagan Lake Likely to Sell Out

Private Kelowna Sailing Cruise on Okanagan Lake

  • North America
  • Superb50 reviews5

Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are w....

    Free Cancellation
    Private Tour
    Start From $120.35
 
 

Daytime Sailing Along San Diego's Skyline

(4.9 of 151 reviews)

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor Sunroad Marina on Harbor Island on San Diego Bay, we often s... More

Free Cancellation
Private Tour
Start From $99.00
 
Daytime Sailing Along San Diego's Skyline Likely to Sell Out

Daytime Sailing Along San Diego's Skyline

  • North America
  • Superb151 reviews4.9

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Best Private Luxury Sunset Boat Tour in New York City - 2 Hour

(5 of 29 reviews)

Experience the breathtaking beauty of New York City as the sun sets behind the Statue of Liberty and reflects off of the city skyline on this magical 2-hour sunset cruise around lower Manhattan! Get an unobstructed view of the Man... More

Free Cancellation
Private Tour
Start From $599.99
 
Best Private Luxury Sunset Boat Tour in New York City - 2 Hour Likely to Sell Out

Best Private Luxury Sunset Boat Tour in New York City - 2 Hour

  • North America
  • Superb29 reviews5

Experience the breathtaking beauty of New York City as the sun sets behind the Statue of Liberty and....

    Free Cancellation
    Private Tour
    Start From $599.99
 
 

HipHop Catamaran Party from Cancun to Isla Mujeres

(3.9 of 20 reviews)

Unlike other tours, we combine adventure, relaxation, and an unforgettable party vibe. Start by snorkeling in one of the Caribbean's top reefs, surrounded by vibrant marine life. Then, head to a secluded sandbank—a hidden gem pe... More

Free Cancellation
Private Tour
Start From $65.00
 
HipHop Catamaran Party from Cancun to Isla Mujeres Likely to Sell Out

HipHop Catamaran Party from Cancun to Isla Mujeres

  • North America
  • Very Good20 reviews3.9

Unlike other tours, we combine adventure, relaxation, and an unforgettable party vibe. Start by snor....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

(4.9 of 144 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pal... More

Free Cancellation
Private Tour
Start From $69.00
 
2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only) Likely to Sell Out

2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

  • North America
  • Superb144 reviews4.9

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....

    Free Cancellation
    Private Tour
    Start From $69.00
 
 

1.5-Hour San Francisco Bay Sailing Tour

(4.8 of 401 reviews)

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with beer and wine. This double-masted, teak-decked, bronze-fitted beauty hold... More

Free Cancellation
Private Tour
Start From $99.00
 
1.5-Hour San Francisco Bay Sailing Tour Likely to Sell Out

1.5-Hour San Francisco Bay Sailing Tour

  • North America
  • Superb401 reviews4.8

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

(4.9 of 47 reviews)

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we... More

Free Cancellation
Private Tour
Start From $59.95
 
Schooner Applejack Sunset Sail Tour in Boothbay Harbor Likely to Sell Out

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

  • North America
  • Superb47 reviews4.9

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Waikiki Friday Night Fireworks Cruise

(4.5 of 31 reviews)

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring your favorite beverages and join us for Waikiki's weekly fireworks displ... More

Free Cancellation
Private Tour
Start From $60.00
 
Waikiki Friday Night Fireworks Cruise Likely to Sell Out

Waikiki Friday Night Fireworks Cruise

  • North America
  • Exellent31 reviews4.5

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....

    Free Cancellation
    Private Tour
    Start From $60.00
 
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