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Top 10 Best North America Sailing Trips

Found 735 Sailing Trips activities in North America. Sort by Popularity. - Page 28
 

Sailing Adventures 3-Hour Activity in Destin

(5 of 5 reviews)

There’s nothing like seeing the clear emerald waters pass under the hull while sailing on the Stiletto Catamaran. Harnessing the power of the wind as we sail along these beautiful waters is magical. You might even get to experie... More

Free Cancellation
Private Tour
Start From $525.00
 
Sailing Adventures 3-Hour Activity in Destin

Sailing Adventures 3-Hour Activity in Destin

  • North America
  • Superb5 reviews5

There’s nothing like seeing the clear emerald waters pass under the hull while sailing on the Stil....

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

Private Afternoon Harbor Cruise on Kismet for parties up to 20

(5 of 26 reviews)

Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise the harbor, BYOB, awesome stereo, bathroom, history tours, swim and float on rafts. Kismet does it all! Kismet is a custom-built ... More

Free Cancellation
Private Tour
Start From $1,549.00
 
Private Afternoon Harbor Cruise on Kismet for parties up to 20

Private Afternoon Harbor Cruise on Kismet for parties up to 20

  • North America
  • Superb26 reviews5

Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise....

    Free Cancellation
    Private Tour
    Start From $1,549.00
 
 

Private Luxury Yacht Charter with Snorkeling in Los Cabos

(5 of 26 reviews)

Experience snorkeling in crystal waters, the beach Palmilla has a blue flag recognition and is one of the best beach areas to discover the underwater world of the Los Cabos area. During the months of December thru March, you can w... More

Free Cancellation
Private Tour
Start From $1,600.00
 
Private Luxury Yacht Charter with Snorkeling in Los Cabos

Private Luxury Yacht Charter with Snorkeling in Los Cabos

  • North America
  • Superb26 reviews5

Experience snorkeling in crystal waters, the beach Palmilla has a blue flag recognition and is one o....

    Free Cancellation
    Private Tour
    Start From $1,600.00
 
 

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
 
 

Fishing and snorkel tour in Puerto Vallarta and Nuevo Vallarta

(4.3 of 17 reviews)

Our crew will support you on board the boat, in the water and during your visit. They will teach you all the basics for fishing and they will take you to unique places in the bay so you can enjoy a good dip in the salty sea water... More

Free Cancellation
Private Tour
Start From $1,075.00
 
Fishing and snorkel tour in Puerto Vallarta and Nuevo Vallarta

Fishing and snorkel tour in Puerto Vallarta and Nuevo Vallarta

  • North America
  • Exellent17 reviews4.3

Our crew will support you on board the boat, in the water and during your visit. They will teach yo....

    Free Cancellation
    Private Tour
    Start From $1,075.00
 
 

Private Luxury Sunset Sail in San Jose del Cabo Marina

(4.3 of 17 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
 
Private Luxury Sunset Sail in San Jose del Cabo Marina

Private Luxury Sunset Sail in San Jose del Cabo Marina

  • North America
  • Exellent17 reviews4.3

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

    Free Cancellation
    Private Tour
    Start From $1,600.00
 
 

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

Free Cancellation
Private Tour
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....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Cabo San Lucas Sailing Snorkeling Adventure

(5 of 1 review)

ELEGANCE MEETS ADVENTURE – A FAMILY EXPERIENCE LIKE NO OTHER Treat yourself and your loved ones to an unforgettable day at sea aboard our luxurious double-deck Whether you're snorkeling alongside tropical fish, paddleboarding ... More

Free Cancellation
Private Tour
Start From $159.00
 
Cabo San Lucas Sailing Snorkeling Adventure

Cabo San Lucas Sailing Snorkeling Adventure

  • North America
  • Superb1 review5

ELEGANCE MEETS ADVENTURE – A FAMILY EXPERIENCE LIKE NO OTHER Treat yourself and your loved ones to....

    Free Cancellation
    Private Tour
    Start From $159.00
 
 

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
 
 

Cabo's Premier Catamaran Snorkeling: Explore the Waters!

(5 of 3 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
  • Superb3 reviews5

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

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

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

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
 
 

Bachelorette Sailing Party on San Diego Bay up to 6 Guests

(5 of 1 review)

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, not to mention an incredible abundance of sea l... More

Free Cancellation
Private Tour
Start From $750.00
 
Bachelorette Sailing Party on San Diego Bay up to 6 Guests

Bachelorette Sailing Party on San Diego Bay up to 6 Guests

  • North America
  • Superb1 review5

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking....

    Free Cancellation
    Private Tour
    Start From $750.00
 
 

4th of July Sunset Sail on the Black Pearl

(5 of 1 review)

Join us for the 4th of July for Fireworks over Cedar Point from a beautiful 47' Sailing yacht - The Black Pearl! Sail magestically across the water as we find our most perfect spot for viewing the fireworks while watching the suns... More

Free Cancellation
Private Tour
Start From $1,195.00
 
4th of July Sunset Sail on the Black Pearl

4th of July Sunset Sail on the Black Pearl

  • North America
  • Superb1 review5

Join us for the 4th of July for Fireworks over Cedar Point from a beautiful 47' Sailing yacht - The ....

    Free Cancellation
    Private Tour
    Start From $1,195.00
 
 

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
 
 

2 Island Adventure: Contoy & Mujeres with Snorkeling & open bar

(4.3 of 6 reviews)

What makes this tour unique? Unlike most tours that visit only one island, our experience takes you to two stunning Caribbean islands in a single day—Isla Contoy, a protected ecological reserve with limited daily visitors, and t... More

Free Cancellation
Private Tour
Start From $80.00
 
2 Island Adventure: Contoy & Mujeres with Snorkeling & open bar Likely to Sell Out

2 Island Adventure: Contoy & Mujeres with Snorkeling & open bar

  • North America
  • Exellent6 reviews4.3

What makes this tour unique? Unlike most tours that visit only one island, our experience takes you ....

    Free Cancellation
    Private Tour
    Start From $80.00
 
 

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 Transparent Boat Tour in the Sea of Cozumel

(5 of 4 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 $663.56
 
Private Transparent Boat Tour in the Sea of Cozumel Likely to Sell Out

Private Transparent Boat Tour in the Sea of Cozumel

  • North America
  • Superb4 reviews5

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

    Free Cancellation
    Private Tour
    Start From $663.56
 
 

Full-Day Gray Whale Watching tour from Cabo to Mag Bay

(5 of 11 reviews)

Led by passionate marine biologist, this full day journey takes you from Cabo to remote, unspoiled waters of Magdalena Bay- one of the best places on earth to meet gray whales up close. With expert guidance, you´ll gain fascina... More

Free Cancellation
Private Tour
Start From $436.09
 
Full-Day Gray Whale Watching tour from Cabo to Mag Bay Likely to Sell Out

Full-Day Gray Whale Watching tour from Cabo to Mag Bay

  • North America
  • Superb11 reviews5

Led by passionate marine biologist, this full day journey takes you from Cabo to remote, unspoiled w....

    Free Cancellation
    Private Tour
    Start From $436.09
 
 

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 $750.00
 
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 $750.00
 
 

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
 
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