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Top 10 Best North America Sailing Trips

Found 693 Sailing Trips activities in North America. Sort by Popularity. - Page 10
 

Private Cabo 35ft cat experience Food and open bar included!

(4.9 of 314 reviews)

Barta is an extremely fun and comfort 36ft catamaran specifically designed to accommodate large groups of up to 20 passengers. Immerse yourself in the scenic wonders of the bay of Cabo San Lucas as Barta gracefully navigates, ensu... More

Free Cancellation
Private Tour
Start From $2,235.00
 
Private Cabo 35ft cat experience Food and open bar included!

Private Cabo 35ft cat experience Food and open bar included!

  • North America
  • Superb314 reviews4.9

Barta is an extremely fun and comfort 36ft catamaran specifically designed to accommodate large grou....

    Free Cancellation
    Private Tour
    Start From $2,235.00
 
 

El Cielo Cozumel Snorkeling by Private Boat

(4.8 of 133 reviews)

TRAVELER'S FAVORITE EXPERIENCE! Have fun aboard your Private boat and experience Cozumel water treasures in this incredible snorkeling adventure. This 4 hours family-friendly Private tour will take you out to the most renowned r... More

Free Cancellation
Private Tour
Start From $789.00
 
El Cielo Cozumel Snorkeling by Private Boat Likely to Sell Out

El Cielo Cozumel Snorkeling by Private Boat

  • North America
  • Superb133 reviews4.8

TRAVELER'S FAVORITE EXPERIENCE! Have fun aboard your Private boat and experience Cozumel water trea....

    Free Cancellation
    Private Tour
    Start From $789.00
 
 

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

(5 of 64 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 $90.00
 
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
  • Superb64 reviews5

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

    Free Cancellation
    Private Tour
    Start From $90.00
 
 

Private Key West Sandbar and Paddle by Boat

(4.9 of 32 reviews)

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats and wildlife refuges as well as spot an abundance of marine birds and sea life. Padd... More

Free Cancellation
Private Tour
Start From $600.00
 
Private Key West Sandbar and Paddle by Boat Likely to Sell Out

Private Key West Sandbar and Paddle by Boat

  • North America
  • Superb32 reviews4.9

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Key West Sailing & Snorkeling: A Reef Adventure

(4.7 of 135 reviews)

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Free Cancellation
Private Tour
Start From $79.00
 
Key West Sailing & Snorkeling: A Reef Adventure Likely to Sell Out

Key West Sailing & Snorkeling: A Reef Adventure

  • North America
  • Superb135 reviews4.7

Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

(5 of 54 reviews)

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More

Free Cancellation
Private Tour
Start From $149.00
 
2hr. INTERACTIVE Sailing Experience on San Francisco Bay Likely to Sell Out

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

  • North America
  • Superb54 reviews5

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Experience Oceanside Sailing with Whales and dolphins!

(5 of 11 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 $130.00
 
Experience Oceanside Sailing with Whales and dolphins! Likely to Sell Out

Experience Oceanside Sailing with Whales and dolphins!

  • North America
  • Superb11 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 $130.00
 
 

Private Sailing Charter with Captain, BYOB

(5 of 56 reviews)

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's scenic Harbor. The golden hour of sunset is our prime booking time, offering... More

Free Cancellation
Private Tour
Start From $500.00
 
Private Sailing Charter with Captain, BYOB Likely to Sell Out

Private Sailing Charter with Captain, BYOB

  • North America
  • Superb56 reviews5

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6....

    Free Cancellation
    Private Tour
    Start From $500.00
 
 

Small-Group San Diego Sunset Sailing Excursion

(4.9 of 562 reviews)

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat is limited to six (6) guests allowing you a comfortable, semi-private experience (or, pu... More

Free Cancellation
Private Tour
Start From $127.00
 
Small-Group San Diego Sunset Sailing Excursion Likely to Sell Out

Small-Group San Diego Sunset Sailing Excursion

  • North America
  • Superb562 reviews4.9

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This th....

    Free Cancellation
    Private Tour
    Start From $127.00
 
 

Shallow Water Snorkeling and Dolphin Watching in Key West

(4.6 of 447 reviews)

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropical waters of Key West on Catamaran Echo - making vacation memories since 1991. Enjoy a premium shallow snorkeling and dolphin-watc... More

Free Cancellation
Private Tour
Start From $108.91
 
Shallow Water Snorkeling and Dolphin Watching in Key West Likely to Sell Out

Shallow Water Snorkeling and Dolphin Watching in Key West

  • North America
  • Superb447 reviews4.6

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropica....

    Free Cancellation
    Private Tour
    Start From $108.91
 
 

Molokini Snorkel and Performance Sail from Ma'alaea Harbor

(4.9 of 198 reviews)

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More

Free Cancellation
Private Tour
Start From $200.00
 
Molokini Snorkel and Performance Sail from Ma'alaea Harbor Likely to Sell Out

Molokini Snorkel and Performance Sail from Ma'alaea Harbor

  • North America
  • Superb198 reviews4.9

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....

    Free Cancellation
    Private Tour
    Start From $200.00
 
 

Schooner Fame Sailing Tour

(4.9 of 528 reviews)

FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per TripAdvisor. Don't miss the very best of what Salem has to offer! There's more to our town than witches! FAME is a full-scale replica... More

Free Cancellation
Private Tour
Start From $50.65
 
Schooner Fame Sailing Tour Likely to Sell Out

Schooner Fame Sailing Tour

  • North America
  • Superb528 reviews4.9

FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per Trip....

    Free Cancellation
    Private Tour
    Start From $50.65
 
 

12pm Turtle Canyon Snorkel Adventure

(4.8 of 279 reviews)

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

Free Cancellation
Private Tour
Start From $96.30
 
12pm Turtle Canyon Snorkel Adventure Likely to Sell Out

12pm Turtle Canyon Snorkel Adventure

  • North America
  • Superb279 reviews4.8

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....

    Free Cancellation
    Private Tour
    Start From $96.30
 
 

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

(4.7 of 17 reviews)

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from December-March, of course, the annual humpback whales!... More

Free Cancellation
Private Tour
Start From $83.40
 
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu Likely to Sell Out

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

  • North America
  • Superb17 reviews4.7

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (LÄ“â€....

    Free Cancellation
    Private Tour
    Start From $83.40
 
 

The Boat People Cruise Private Harbor Cruises

(5 of 34 reviews)

Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We strive to create an unforgettable evening with contagious laughter and panoramic views of the Newport Bay. Bring your plus one or ... More

Free Cancellation
Private Tour
Start From $100.00
 
The Boat People Cruise Private Harbor Cruises Likely to Sell Out

The Boat People Cruise Private Harbor Cruises

  • North America
  • Superb34 reviews5

Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We ....

    Free Cancellation
    Private Tour
    Start From $100.00
 
 

See a Fireworks Show aboard Tall Ship Windy in Chicago!

(5 of 34 reviews)

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a lei... More

Free Cancellation
Private Tour
Start From $113.73
 
See a Fireworks Show aboard Tall Ship Windy in Chicago! Likely to Sell Out

See a Fireworks Show aboard Tall Ship Windy in Chicago!

  • North America
  • Superb34 reviews5

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Na....

    Free Cancellation
    Private Tour
    Start From $113.73
 
 

Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan

(5 of 24 reviews)

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

Free Cancellation
Private Tour
Start From $507.96
 
Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan Likely to Sell Out

Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan

  • North America
  • Superb24 reviews5

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....

    Free Cancellation
    Private Tour
    Start From $507.96
 
 

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

(4.9 of 60 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 $59.00
 
Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise Likely to Sell Out

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

  • North America
  • Superb60 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 $59.00
 
 

Private Kelowna Sailing Cruise on Okanagan Lake

(5 of 35 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 $124.30
 
Private Kelowna Sailing Cruise on Okanagan Lake Likely to Sell Out

Private Kelowna Sailing Cruise on Okanagan Lake

  • North America
  • Superb35 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 $124.30
 
 

All Inclusive Beach Club, Water Sports HorseBack Ride Food Drinks

(4.5 of 4 reviews)

Introducing the ultimate beach getaway - Stone Island! This all-inclusive package offers an unbeatable experience with unlimited drinks, mouth-watering lunch, and your choice of two exciting activities. Whether you want to ride ho... More

Free Cancellation
Private Tour
Start From $55.00
 
All Inclusive Beach Club, Water Sports HorseBack Ride Food Drinks Likely to Sell Out

All Inclusive Beach Club, Water Sports HorseBack Ride Food Drinks

  • North America
  • Exellent4 reviews4.5

Introducing the ultimate beach getaway - Stone Island! This all-inclusive package offers an unbeatab....

    Free Cancellation
    Private Tour
    Start From $55.00
 
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