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Top 10 Best North America Sailing Trips

Found 722 Sailing Trips activities in North America. Sort by Popularity. - Page 29
 

Friday Night Waikiki Fireworks Sail

(3 of 1 review)

Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a spectacular Hawaiian sunset and the Friday Night Fireworks onboard a luxury private yacht.... More

Free Cancellation
Private Tour
Start From $699.00
 
Friday Night Waikiki Fireworks Sail Likely to Sell Out

Friday Night Waikiki Fireworks Sail

  • North America

Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a....

    Free Cancellation
    Private Tour
    Start From $699.00
 
 

Whale Watching with Lunch and transportation included

(4.4 of 19 reviews)

Experience the "Whale-tastic Adventure" in Cabo San Lucas during the winter season, where you'll have front-row seats to witness the playful and majestic antics of whales in their natural habitat. Setting sail from the Marina, you... More

Free Cancellation
Private Tour
Start From $99.00
 
Whale Watching with Lunch and transportation included Likely to Sell Out

Whale Watching with Lunch and transportation included

  • North America
  • Exellent19 reviews4.4

Experience the "Whale-tastic Adventure" in Cabo San Lucas during the winter season, where you'll hav....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Key West Stargazing Cruise aboard Schooner America 2.0

(5 of 1 review)

Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this stargazing cruise, guests can enjoy unobstructed views of the sweeping night sky and a fun adventure in Key West at night. Please note th... More

Free Cancellation
Private Tour
Start From $83.85
 
Key West Stargazing Cruise aboard Schooner America 2.0 Likely to Sell Out

Key West Stargazing Cruise aboard Schooner America 2.0

  • North America
  • Superb1 review5

Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this stargaz....

    Free Cancellation
    Private Tour
    Start From $83.85
 
 

Cancun Bubble Boat Lagoon Tour

(5 of 1 review)

Set off on a leisurely 90-minute voyage through the mesmerizing mangrove channels of the Nichupté Lagoon on a unique pontoon boat. Treat yourself to a unique escapade that harmoniously combines the excitement of discovery with th... More

Free Cancellation
Private Tour
Start From $45.00
 
Cancun Bubble Boat Lagoon Tour Likely to Sell Out

Cancun Bubble Boat Lagoon Tour

  • North America
  • Superb1 review5

Set off on a leisurely 90-minute voyage through the mesmerizing mangrove channels of the Nichupté L....

    Free Cancellation
    Private Tour
    Start From $45.00
 
 

Cabo Yacht Tour to Lovers or Pelícano Beach + Beach Time

(3 of 2 reviews)

Set sail for a day of relaxation on our yacht tour to Lovers Beach. This 45-minute journey offers you the chance to unwind on the beautiful sands of Pelícano Beach, where you can enjoy a minimum of 2 hours of free time to soak up... More

Free Cancellation
Private Tour
Start From $35.00
 
Cabo Yacht Tour to Lovers or Pelícano Beach + Beach Time Likely to Sell Out

Cabo Yacht Tour to Lovers or Pelícano Beach + Beach Time

  • North America

Set sail for a day of relaxation on our yacht tour to Lovers Beach. This 45-minute journey offers yo....

    Free Cancellation
    Private Tour
    Start From $35.00
 
 

Private Sunset Sail of NYC Skyline and Statue of Liberty

(5 of 2 reviews)

Discover NYC from a completely different perspective on a private sailboat charter during sunset hours when the views are even more spectacular. You and your group will view New York City in ways that are breath taking. See the St... More

Free Cancellation
Private Tour
Start From $725.00
 
Private Sunset Sail of NYC Skyline and Statue of Liberty Likely to Sell Out

Private Sunset Sail of NYC Skyline and Statue of Liberty

  • North America
  • Superb2 reviews5

Discover NYC from a completely different perspective on a private sailboat charter during sunset hou....

    Free Cancellation
    Private Tour
    Start From $725.00
 
 

Spectacular Midday Sail

(5 of 4 reviews)

Join Captain Doyle for an unforgettable 2-hour sailing experience aboard our 35-foot sailboat, Luna. Enjoy wide-open views of the city's skyline and waterfront attractions as we sail among tall ships, mega-yachts, and military ves... More

Free Cancellation
Private Tour
Start From $120.00
 
Spectacular Midday Sail Likely to Sell Out

Spectacular Midday Sail

  • North America
  • Superb4 reviews5

Join Captain Doyle for an unforgettable 2-hour sailing experience aboard our 35-foot sailboat, Luna.....

    Free Cancellation
    Private Tour
    Start From $120.00
 
 

Private Sailing Experience on Galveston Bay

(5 of 1 review)

See the Texas Gulf Coast in a whole new way. Feel the sea breeze, explore the Texas Gulf Coast, and discover a new way to travel aboard our luxury charter yacht. We offer the perfect blend of comfort and adventure, making it the ... More

Free Cancellation
Private Tour
Start From $800.00
 
Private Sailing Experience on Galveston Bay Likely to Sell Out

Private Sailing Experience on Galveston Bay

  • North America
  • Superb1 review5

See the Texas Gulf Coast in a whole new way. Feel the sea breeze, explore the Texas Gulf Coast, and....

    Free Cancellation
    Private Tour
    Start From $800.00
 
 

Sunday Mimosa Bar Catamaran Sail with Mini Brunch Bites

(5 of 5 reviews)

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard our a spacious and stylish 50-foot catamaran, and set sail for a relaxing and refreshing 2-hour cruise through Charleston’s histor... More

Free Cancellation
Private Tour
Start From $57.00
 
Sunday Mimosa Bar Catamaran Sail with Mini Brunch Bites Likely to Sell Out

Sunday Mimosa Bar Catamaran Sail with Mini Brunch Bites

  • North America
  • Superb5 reviews5

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard ou....

    Free Cancellation
    Private Tour
    Start From $57.00
 
 

Semi-Private Sunset Sail Waikiki

(5 of 5 reviews)

Cruise by the iconic Waikiki coastline and up past our famous Diamond Head State Monument as our crew shares their local knowledge of both the land and sea. Experience the freedom of open ocean blue water sailing as we effortlessl... More

Free Cancellation
Private Tour
Start From $129.00
 
Semi-Private Sunset Sail Waikiki Likely to Sell Out

Semi-Private Sunset Sail Waikiki

  • North America
  • Superb5 reviews5

Cruise by the iconic Waikiki coastline and up past our famous Diamond Head State Monument as our cre....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Super Combo ATV in Cancun with Zipline, Snorkel, Cenote, transfer

(3.7 of 3 reviews)

Welcome to the super combo tour, the best activity in Mexico and the Caribbean. You will start the trip in the town of Puerto Morelos. There you will be able to visit the 2nd biggest barrier reef in the world. Swim and explore the... More

Free Cancellation
Private Tour
Start From $119.00
 
Super Combo ATV in Cancun with Zipline, Snorkel, Cenote, transfer Likely to Sell Out

Super Combo ATV in Cancun with Zipline, Snorkel, Cenote, transfer

  • North America
  • Very Good3 reviews3.7

Welcome to the super combo tour, the best activity in Mexico and the Caribbean. You will start the t....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

JFarwell Sip & Sail aboard the Reverie

(5 of 19 reviews)

This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding in luxury with friends, family or colleagues. Step aboard our 50’ Catamaran and be greeted with a perfect locally crafted bevera... More

Free Cancellation
Private Tour
Start From $857.11
 
JFarwell Sip & Sail aboard the Reverie Likely to Sell Out

JFarwell Sip & Sail aboard the Reverie

  • North America
  • Superb19 reviews5

This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding ....

    Free Cancellation
    Private Tour
    Start From $857.11
 
 

The Best Catamaran tour to Isla Mujeres with Open Bar and Lunch

(3.7 of 3 reviews)

Enjoy the most complete Isla Mujeres experience! Start with round-trip transportation from your hotel, then sail across the Caribbean on a catamaran with open bar and music on board. Snorkel in crystal-clear waters, savor a delici... More

Free Cancellation
Private Tour
Start From $39.90
 
The Best Catamaran tour to Isla Mujeres with Open Bar and Lunch Likely to Sell Out

The Best Catamaran tour to Isla Mujeres with Open Bar and Lunch

  • North America
  • Very Good3 reviews3.7

Enjoy the most complete Isla Mujeres experience! Start with round-trip transportation from your hote....

    Free Cancellation
    Private Tour
    Start From $39.90
 
 

Cancun ATV Jungle Adventure & Isla Mujeres Catamaran Combo

(3.7 of 3 reviews)

Embark on two unforgettable Cancun adventures with this incredible combo package! Day 1: Unleash your inner thrill-seeker on a wild ATV Jungle Tour. Race through the Mayan jungle, soar through the treetops on ziplines, and refres... More

Free Cancellation
Private Tour
Start From $119.00
 
Cancun ATV Jungle Adventure & Isla Mujeres Catamaran Combo Likely to Sell Out

Cancun ATV Jungle Adventure & Isla Mujeres Catamaran Combo

  • North America
  • Very Good3 reviews3.7

Embark on two unforgettable Cancun adventures with this incredible combo package! Day 1: Unleash yo....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

San Diego Bay Harbor Cruise: Private 2-Hour Experience

(3.7 of 3 reviews)

Explore the stunning San Diego Bay on a 2-hour harbor cruise designed for up to 6 guests. Perfect for special occasions or a relaxing outing with friends and family, this charter offers breathtaking views of downtown San Diego and... More

Free Cancellation
Private Tour
Start From $1,100.00
 
San Diego Bay Harbor Cruise: Private 2-Hour Experience Likely to Sell Out

San Diego Bay Harbor Cruise: Private 2-Hour Experience

  • North America
  • Very Good3 reviews3.7

Explore the stunning San Diego Bay on a 2-hour harbor cruise designed for up to 6 guests. Perfect fo....

    Free Cancellation
    Private Tour
    Start From $1,100.00
 
 

Waikiki Sunset Cruise and Iconic Views with Swimming

(5 of 1 review)

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 $47.00
 
Waikiki Sunset Cruise and Iconic Views with Swimming Likely to Sell Out

Waikiki Sunset Cruise and Iconic Views with Swimming

  • North America
  • Superb1 review5

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

    Free Cancellation
    Private Tour
    Start From $47.00
 
 

Oyster Bay Two Hour Sailing Experience

(5 of 2 reviews)

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and the impressive estates that line the bay. WINDSWEPT is metic... More

Free Cancellation
Private Tour
Start From $595.00
 
Oyster Bay Two Hour Sailing Experience Likely to Sell Out

Oyster Bay Two Hour Sailing Experience

  • North America
  • Superb2 reviews5

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oys....

    Free Cancellation
    Private Tour
    Start From $595.00
 
 

Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres

(5 of 2 reviews)

A Caribbean Escape Like No Other! Experience the beauty of the Caribbean on this all-inclusive catamaran tour from Cancun to Isla Mujeres. The day begins with a leisurely sail across the turquoise waters, where you'll enjoy drinks... More

Free Cancellation
Private Tour
Start From $65.00
 
Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres Likely to Sell Out

Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres

  • North America
  • Superb2 reviews5

A Caribbean Escape Like No Other! Experience the beauty of the Caribbean on this all-inclusive catam....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Private Sailing Adventure in Bacalar

(5 of 21 reviews)

Join us on an exciting sailing adventure. Learn about the Lagoon and the art of moving with wind. We explore mangroves, shoreline and Cenotes. Our guides are knowledgeable about the area, each point we visit comes with a detail ex... More

Free Cancellation
Private Tour
Start From $273.48
 
Private Sailing Adventure in Bacalar Likely to Sell Out

Private Sailing Adventure in Bacalar

  • North America
  • Superb21 reviews5

Join us on an exciting sailing adventure. Learn about the Lagoon and the art of moving with wind. We....

    Free Cancellation
    Private Tour
    Start From $273.48
 
 

Romantic Experience Sunset Dinner Columbus in Cancun (2x1 price)

(4.3 of 6 reviews)

During this dream date, you will have a romantic atmosphere with your lover. Saxophone or Trova music with live romantic songs, delicious food and good wine and the sunset behind you or a twilight that is perfect for this type of ... More

Free Cancellation
Private Tour
Start From $250.00
 
Romantic Experience Sunset Dinner Columbus in Cancun (2x1 price) Likely to Sell Out

Romantic Experience Sunset Dinner Columbus in Cancun (2x1 price)

  • North America
  • Exellent6 reviews4.3

During this dream date, you will have a romantic atmosphere with your lover. Saxophone or Trova musi....

    Free Cancellation
    Private Tour
    Start From $250.00
 
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