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Top 10 Best North America Sailing Trips

Found 692 Sailing Trips activities in North America. Sort by Popularity. - Page 29
 

Private Cancun Sailboat Cruise with Beers and Sodas Included

(5 of 1 review)

Escape to paradise with our exclusive private sailing boat cruise to Isla Mujeres, a pristine island gem just off the coast of Cancun. Step aboard our fine vessel and embark on a journey of discovery and relaxation in the breathta... More

Free Cancellation
Private Tour
Start From $579.00
 
Private Cancun Sailboat Cruise with Beers and Sodas Included

Private Cancun Sailboat Cruise with Beers and Sodas Included

  • North America
  • Superb1 review5

Escape to paradise with our exclusive private sailing boat cruise to Isla Mujeres, a pristine island....

    Free Cancellation
    Private Tour
    Start From $579.00
 
 

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

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
 
 

Key West Christmas Cruise with Live Band and Drinks

(5 of 3 reviews)

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our live band and celebrate the holidays and Christmas in Key West. E... More

Free Cancellation
Private Tour
Start From $88.15
 
Key West Christmas Cruise with Live Band and Drinks Likely to Sell Out

Key West Christmas Cruise with Live Band and Drinks

  • North America
  • Superb3 reviews5

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christ....

    Free Cancellation
    Private Tour
    Start From $88.15
 
 

Luxury Catamaran tour to Isla Mujeres with transportation from Playa del Carmen

(4.3 of 60 reviews)

Because it's an amazing place where you can relax in the beautiful Caribbean Sea, we offer you a personal assistance from our incredible crew that will make you have a great time, you will snorkel in an amazing part of the second ... More

Free Cancellation
Private Tour
Start From $93.87
 
Luxury Catamaran tour to Isla Mujeres with transportation from Playa del Carmen Likely to Sell Out

Luxury Catamaran tour to Isla Mujeres with transportation from Pl....

  • North America
  • Exellent60 reviews4.3

Because it's an amazing place where you can relax in the beautiful Caribbean Sea, we offer you a per....

    Free Cancellation
    Private Tour
    Start From $93.87
 
 

Cancun ATV Jungle Adventure & Isla Mujeres Catamaran Combo

(4.3 of 60 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
  • Exellent60 reviews4.3

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

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Luxury Camden Sailing Experience

(4.3 of 60 reviews)

Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Fastest boat in the harbor... More

Free Cancellation
Private Tour
Start From $125.00
 
Luxury Camden Sailing Experience Likely to Sell Out

Luxury Camden Sailing Experience

  • North America
  • Exellent60 reviews4.3

Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Faste....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres

(4.3 of 60 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 $79.00
 
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
  • Exellent60 reviews4.3

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

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

2.5 hr Sailboat Tour aboard Orion's Child

(5 of 58 reviews)

TripAdvisor SPECIAL MONDAY ONLY Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. Multiple daily sails that include a quarter day and sunset sa... More

Free Cancellation
Private Tour
Start From $99.00
 
2.5 hr Sailboat Tour aboard Orion's Child Likely to Sell Out

2.5 hr Sailboat Tour aboard Orion's Child

  • North America
  • Superb58 reviews5

TripAdvisor SPECIAL MONDAY ONLY Sail. SEE OUR WEBSITE for other options and availability. Since 2009....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Tour in a Catamaran To Isla Mujeres

(5 of 1 review)

We are the most complete tour of the Riviera Maya since we offer round transportation from your hotel to the marina, open bar with national drinks on the Catamaran, snorkeling activity, buffet lunch at the beach club and free time... More

Free Cancellation
Private Tour
Start From $39.00
 
Tour in a Catamaran To Isla Mujeres Likely to Sell Out

Tour in a Catamaran To Isla Mujeres

  • North America
  • Superb1 review5

We are the most complete tour of the Riviera Maya since we offer round transportation from your hote....

    Free Cancellation
    Private Tour
    Start From $39.00
 
 

Incredible Party in Unlimited Catamaran to Isla Mujeres! + Transportation

(5 of 1 review)

Are you ready for a wonderful day sailing through the Caribbean Sea? aboard a great boat. During the tour you can feel the sun and the breeze while sailing towards a reef, where you will have the opportunity to snorkel and admire ... More

Free Cancellation
Private Tour
Start From $88.00
 
Incredible Party in Unlimited Catamaran to Isla Mujeres! + Transportation Likely to Sell Out

Incredible Party in Unlimited Catamaran to Isla Mujeres! + Transp....

  • North America
  • Superb1 review5

Are you ready for a wonderful day sailing through the Caribbean Sea? aboard a great boat. During the....

    Free Cancellation
    Private Tour
    Start From $88.00
 
 

Private Sailing Adventure in Bacalar

(5 of 10 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 $247.96
 
Private Sailing Adventure in Bacalar Likely to Sell Out

Private Sailing Adventure in Bacalar

  • North America
  • Superb10 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 $247.96
 
 

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

(4.2 of 5 reviews)

Love will surrender to the most cherished secrets of Nichupte Lagoon aboard Columbus Lobster Dinner Cruise. This is one of a kind romance tour in Cancun offering a special evening surrounded by breathtaking views, live saxophone m... More

Free Cancellation
Private Tour
Start From $224.00
 
Romantic Experience Sunset Dinner Columbus in Cancun (2x1 price) Likely to Sell Out

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

  • North America
  • Exellent5 reviews4.2

Love will surrender to the most cherished secrets of Nichupte Lagoon aboard Columbus Lobster Dinner ....

    Free Cancellation
    Private Tour
    Start From $224.00
 
 

Key West Nighttime Full Moon Sail

(5 of 7 reviews)

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or an evening out with family and friends. Departing in the evening as the moo... More

Free Cancellation
Private Tour
Start From $83.85
 
Key West Nighttime Full Moon Sail Likely to Sell Out

Key West Nighttime Full Moon Sail

  • North America
  • Superb7 reviews5

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1....

    Free Cancellation
    Private Tour
    Start From $83.85
 
 

Whale Shark Snorkel Tour in Cancun (Snack Lunch included)

(5 of 7 reviews)

Experience this must-do activity in the Caribbean Sea and swim with this impressive animal. The whale shark adventure is the most enigmatic activity in Mexico. It is a very docile animal that is just as impressive as any other a... More

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

Whale Shark Snorkel Tour in Cancun (Snack Lunch included)

  • North America
  • Superb7 reviews5

Experience this must-do activity in the Caribbean Sea and swim with this impressive animal. The whal....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Private Tour Isla Mujeres excursion in Transparent Boat

(3.3 of 3 reviews)

We have a great diversity of marine life, which can be enjoyed throughout our journey thanks to our 100% transparent boat. It will be a unique activity for you, where you will be given a guided tour of different reefs to apprecia... More

Special Offer
Free Cancellation
Private Tour
Start From $336.87
(Saving 10% ) $374.30
 
-10% Private Tour Isla Mujeres excursion in Transparent Boat Likely to Sell Out

Private Tour Isla Mujeres excursion in Transparent Boat

  • North America
  • Good3 reviews3.3

We have a great diversity of marine life, which can be enjoyed throughout our journey thanks to our ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $336.87
    (Saving 10% ) $374.30
 
 

Two Fantastic Islands To Discover: Tour To Contoy & Isla Mujeres

(3.3 of 3 reviews)

Begin your adventure with hotel pickup and a light breakfast at our private marina in Punta Sam. From there, set sail to the charming Isla Mujeres, a Pueblo Mágico (Magical Town), where you’ll have an hour to explore its vibran... More

Free Cancellation
Private Tour
Start From $192.86
 
Two Fantastic Islands To Discover: Tour To Contoy & Isla Mujeres Likely to Sell Out

Two Fantastic Islands To Discover: Tour To Contoy & Isla Mujeres

  • North America
  • Good3 reviews3.3

Begin your adventure with hotel pickup and a light breakfast at our private marina in Punta Sam. Fro....

    Free Cancellation
    Private Tour
    Start From $192.86
 
 

Full-Day Reef Snorkeling in Cozumel from Cancun with Lunch

(3 of 1 review)

Expore famous Cozumel's top snorkeling locations within the same day on this complete quest featuring the island's most spectacular reefs. Discover the stunning marine flora and fauna of the Dzul-Ha, Casa Blanca and Dalila Reefs,... More

Free Cancellation
Private Tour
Start From $99.00
 
Full-Day Reef Snorkeling in Cozumel from Cancun with Lunch Likely to Sell Out

Full-Day Reef Snorkeling in Cozumel from Cancun with Lunch

  • North America

Expore famous Cozumel's top snorkeling locations within the same day on this complete quest featurin....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Private South Shore Sail Charter

(5 of 2 reviews)

Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and enjoy complimentary drinks while getting the ocean breeze, some Hawaiian sunshine, and even a splash or two! Experience the south ... More

Free Cancellation
Private Tour
Start From $1,000.00
 
Private South Shore Sail Charter Likely to Sell Out

Private South Shore Sail Charter

  • North America
  • Superb2 reviews5

Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and ....

    Free Cancellation
    Private Tour
    Start From $1,000.00
 
 

3 Hour Xpuha-60' Neptunus-Tulum, Playa del Carmen, Riviera Maya

(4.8 of 74 reviews)

We know you’re not just looking for a yacht—you’re looking for an experience. We’re in the business of making dreams come true! Our new yacht is the hottest new addition to our fleet. The Canadian built Neptunus is truly ... More

Free Cancellation
Private Tour
Start From $1,349.00
 
3 Hour Xpuha-60' Neptunus-Tulum, Playa del Carmen, Riviera Maya Likely to Sell Out

3 Hour Xpuha-60' Neptunus-Tulum, Playa del Carmen, Riviera Maya

  • North America
  • Superb74 reviews4.8

We know you’re not just looking for a yacht—you’re looking for an experience. We’re in the ....

    Free Cancellation
    Private Tour
    Start From $1,349.00
 
 

Sunset Sailing for Couples and Small Groups

(5 of 2 reviews)

Embark on a magical sunset sailing tour, a luxurious sailboat designed for intimate, small-group experiences. Perfect for couples or small groups looking to share the beauty of a sunset at sea with like-minded sunset and sailing e... More

Free Cancellation
Private Tour
Start From $156.49
 
Sunset Sailing for Couples and Small Groups Likely to Sell Out

Sunset Sailing for Couples and Small Groups

  • North America
  • Superb2 reviews5

Embark on a magical sunset sailing tour, a luxurious sailboat designed for intimate, small-group exp....

    Free Cancellation
    Private Tour
    Start From $156.49
 
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