Menu

Top 10 Best North America Sailing Trips

Found 727 Sailing Trips activities in North America. Sort by Popularity. - Page 28
 

Sunset Sailing Tour of San Diego Bay up to 6 Guests

(5 of 1 review)

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sunset sailing charters and boat tours. Our sunset sailin... More

Start From $119.00
 
Sunset Sailing Tour of San Diego Bay up to 6 Guests

Sunset Sailing Tour of San Diego Bay up to 6 Guests

  • North America
  • Superb1 review5

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautifu....

    Start From $119.00
 
 

Luxury Diamond Head Sunset Sail

(5 of 3 reviews)

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private 50' luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from... More

Free Cancellation
Private Tour
Start From $1,398.00
 
Luxury Diamond Head Sunset Sail

Luxury Diamond Head Sunset Sail

  • North America
  • Superb3 reviews5

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....

    Free Cancellation
    Private Tour
    Start From $1,398.00
 
 

Luxury Private Sunset Experience in San Jose

(5 of 3 reviews)

Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour. The Luxury Private Sailing boat have capacity from 1 to 16 people, the rate offered here is for 8 people, if like to add more pl... More

Free Cancellation
Private Tour
Start From $1,600.00
 
Luxury Private Sunset Experience in San Jose

Luxury Private Sunset Experience in San Jose

  • North America
  • Superb3 reviews5

Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour....

    Free Cancellation
    Private Tour
    Start From $1,600.00
 
 

4 Hour Private Sail for up to 6 people

(4.8 of 12 reviews)

This private excursion allows a party of six passengers to cruise the San Diego Bay and Coast on a customizable charter. Create your own adventure on a vintage sailing yacht for 4 hours with an experienced captain.... More

Free Cancellation
Private Tour
Start From $1,100.00
 
4 Hour Private Sail for up to 6 people

4 Hour Private Sail for up to 6 people

  • North America
  • Superb12 reviews4.8

This private excursion allows a party of six passengers to cruise the San Diego Bay and Coast on a c....

    Free Cancellation
    Private Tour
    Start From $1,100.00
 
 

Cabo's Premier Catamaran Snorkeling: Explore the Waters!

(4.8 of 12 reviews)

Embark aboard our CaboMar catamaran for an unforgettable snorkeling adventure. First, we’ll cruise by some of Cabo's most iconic spots: Playa del Amor, El Arco, and the Sea Lion Reserve. At each location, we’ll stop for about ... More

Free Cancellation
Private Tour
Start From $129.00
 
Cabo's Premier Catamaran Snorkeling: Explore the Waters!

Cabo's Premier Catamaran Snorkeling: Explore the Waters!

  • North America
  • Superb12 reviews4.8

Embark aboard our CaboMar catamaran for an unforgettable snorkeling adventure. First, we’ll cruise....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 
-29% Catamaran Cruise in Riviera Maya with Snorkeling and Lunch

Catamaran Cruise in Riviera Maya with Snorkeling and Lunch

(3 of 3 reviews)

Enjoy the cool ocean breeze and the sparkling turquoise sea as you cruise along the Mexican Caribbean on our spacious catamaran. With music, drinks, and a lively host to keep the good vibes going, this isn’t just a tour — itâ€... More

Special Offer
Free Cancellation
Private Tour
Start From $98.69
(Saving 29% ) $139.00
 
-29% Catamaran Cruise in Riviera Maya with Snorkeling and Lunch

Catamaran Cruise in Riviera Maya with Snorkeling and Lunch

  • North America

Enjoy the cool ocean breeze and the sparkling turquoise sea as you cruise along the Mexican Caribbea....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $98.69
    (Saving 29% ) $139.00
 
 

South Beach Miami BACHELORETTE Boat Day!

(5 of 1 review)

Enjoy a yacht-day bachelorette trip where everything is already set to go right from the biggest and best marina in SOUTH BEACH... We've found the boats, brought on the food and drinks, and made sure that everything that a good y... More

Free Cancellation
Private Tour
Start From $1,795.00
 
South Beach Miami BACHELORETTE Boat Day!

South Beach Miami BACHELORETTE Boat Day!

  • North America
  • Superb1 review5

Enjoy a yacht-day bachelorette trip where everything is already set to go right from the biggest and....

    Free Cancellation
    Private Tour
    Start From $1,795.00
 
 

Snorkel in the beautiful reef of Puerto Morelos with transport

(3 of 1 review)

The most amazing and exciting tour in the Mexican Caribbean is here. Visit the national park of reefs in Puerto Morelos. Sail through the turquoise clear water of the Caribbean Sea and arrive to the Mesoamerican reef. Our captain... More

Free Cancellation
Private Tour
Start From $42.14
 
Snorkel in the beautiful reef of Puerto Morelos with transport Likely to Sell Out

Snorkel in the beautiful reef of Puerto Morelos with transport

  • North America

The most amazing and exciting tour in the Mexican Caribbean is here. Visit the national park of reef....

    Free Cancellation
    Private Tour
    Start From $42.14
 
 

2 Hours Private Guided Sailing Adventure in Pensacola Beach

(5 of 4 reviews)

This 2 hour sailing excursion may take place in Pensacola Bay, passing by areas of Sabine Island, Deer Point, Fair Point and Deadman's Island. We may also sail east under the Bob Sikes (Pensacola Beach) Bridge, exploring areas of ... More

Free Cancellation
Private Tour
Start From $375.00
 
2 Hours Private Guided Sailing Adventure in Pensacola Beach Likely to Sell Out

2 Hours Private Guided Sailing Adventure in Pensacola Beach

  • North America
  • Superb4 reviews5

This 2 hour sailing excursion may take place in Pensacola Bay, passing by areas of Sabine Island, De....

    Free Cancellation
    Private Tour
    Start From $375.00
 
 

Private Catamaran Sunset Cruise with Dolphin watching

(5 of 4 reviews)

One of the best ways to relax on your vacation is to view a sunset aboard Destin sailing Adventures. Sit back and relax while Captain Kip takes you to the best spots to view the sunset, and see a dolphin.... More

Free Cancellation
Private Tour
Start From $360.00
 
Private Catamaran Sunset Cruise with Dolphin watching Likely to Sell Out

Private Catamaran Sunset Cruise with Dolphin watching

  • North America
  • Superb4 reviews5

One of the best ways to relax on your vacation is to view a sunset aboard Destin sailing Adventures.....

    Free Cancellation
    Private Tour
    Start From $360.00
 
 

Private Yacht Charter in Cabo San Lucas – Cruise to The Arch

(5 of 4 reviews)

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 $999.00
 
Private Yacht Charter in Cabo San Lucas – Cruise to The Arch Likely to Sell Out

Private Yacht Charter in Cabo San Lucas – Cruise to The Arch

  • North America
  • Superb4 reviews5

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

    Free Cancellation
    Private Tour
    Start From $999.00
 
 

Private Paddle Tour at Sunrise

(5 of 211 reviews)

With this amazing experience through the Bacalar Lagoon you will live unbeatable moments for 3.5 hours, we have all the necessary equipment for this activity to be complete. We are an ecologically responsible company that promotes... More

Free Cancellation
Private Tour
Start From $69.69
 
Private Paddle Tour at Sunrise Likely to Sell Out

Private Paddle Tour at Sunrise

  • North America
  • Superb211 reviews5

With this amazing experience through the Bacalar Lagoon you will live unbeatable moments for 3.5 hou....

    Free Cancellation
    Private Tour
    Start From $69.69
 
 

Private Transparent Boat Tour in the Sea of Cozumel

(5 of 211 reviews)

Incredible experience in a 100% transparent boat, we are also the only tour currently that offers snorkeling, sunken ships, there is more probability of finding marine life on this tour since we are on the second largest reef in t... More

Free Cancellation
Private Tour
Start From $636.23
 
Private Transparent Boat Tour in the Sea of Cozumel Likely to Sell Out

Private Transparent Boat Tour in the Sea of Cozumel

  • North America
  • Superb211 reviews5

Incredible experience in a 100% transparent boat, we are also the only tour currently that offers sn....

    Free Cancellation
    Private Tour
    Start From $636.23
 
 

Private Sail on the Cape Fear River Aboard a Classic Yacht

(5 of 211 reviews)

Our private charters offer insider access to the Cape Fear River under the guidance of a local captain who has sailed these waters - and the wide Atlantic beyond - professionally for more than a decade. Our steward's comparable ex... More

Free Cancellation
Private Tour
Start From $515.00
 
Private Sail on the Cape Fear River Aboard a Classic Yacht Likely to Sell Out

Private Sail on the Cape Fear River Aboard a Classic Yacht

  • North America
  • Superb211 reviews5

Our private charters offer insider access to the Cape Fear River under the guidance of a local capta....

    Free Cancellation
    Private Tour
    Start From $515.00
 
 

6-Hour Sailing Charter from Fort Lauderdale

(5 of 3 reviews)

Enjoy some time on the water with this 6-Hour Full Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option to use their time docked or sailing out to sea. Once on the water... More

Free Cancellation
Private Tour
Start From $400.00
 
6-Hour Sailing Charter from Fort Lauderdale Likely to Sell Out

6-Hour Sailing Charter from Fort Lauderdale

  • North America
  • Superb3 reviews5

Enjoy some time on the water with this 6-Hour Full Day Sailing Charter located in Fort Lauderdale. Y....

    Free Cancellation
    Private Tour
    Start From $400.00
 
 

Marina Del Rey Luxury Yacht Experience

(3 of 2 reviews)

Discover the perfect blend of relaxation, fun, and local insight on the water with our exclusive Marina del Rey yacht experience, hosted by our friendly and knowledgeable captains. Whether you’re seeking a laid-back day cruising... More

Free Cancellation
Private Tour
Start From $99.00
 
Marina Del Rey Luxury Yacht Experience Likely to Sell Out

Marina Del Rey Luxury Yacht Experience

  • North America

Discover the perfect blend of relaxation, fun, and local insight on the water with our exclusive Mar....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Private Sunset Sailing

(5 of 1 review)

A private and exclusive Sunset Sailing Adventure discovering a Sunset that will never repeat. Premium Open Bar and a Cheese and Cold Cuts table as snacks. Go in style and go Private. Since Covid-19 additional measures and precauti... More

Free Cancellation
Private Tour
Start From $999.00
 
Private Sunset Sailing Likely to Sell Out

Private Sunset Sailing

  • North America
  • Superb1 review5

A private and exclusive Sunset Sailing Adventure discovering a Sunset that will never repeat. Premiu....

    Free Cancellation
    Private Tour
    Start From $999.00
 
 

Whale Shark Snorkel Tour in Cancun (Snack Lunch included)

(5 of 1 review)

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
  • Superb1 review5

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
 
 

Discover Hobie-Cat Sailing and Fish your own Lunch

(5 of 6 reviews)

Becoming able to sail a sailboat only with the wind is a skill that will give you the sense of Freedom that only the ocean can give. You'll realize that you will be able to get to some of the most beautiful places on the planet wi... More

Free Cancellation
Private Tour
Start From $225.00
 
Discover Hobie-Cat Sailing and Fish your own Lunch Likely to Sell Out

Discover Hobie-Cat Sailing and Fish your own Lunch

  • North America
  • Superb6 reviews5

Becoming able to sail a sailboat only with the wind is a skill that will give you the sense of Freed....

    Free Cancellation
    Private Tour
    Start From $225.00
 
 

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
 
Booking.com
Booking.com
Booking.com