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Top 10 Best North America Sailing Trips

Found 735 Sailing Trips activities in North America. Sort by Popularity. - Page 35
 

Private Yacht for up to 12 People

(5 of 1 review)

Imagine feeling the sea breeze aboard the wonderful Tiara 44 Yacht, it will definitely be a trip that you will enjoy like no other, you cannot miss its comfortable spaces while the beautiful colors of the sea and the sky make thos... More

Private Tour
Start From $2,030.00
 
Private Yacht for up to 12 People

Private Yacht for up to 12 People

  • North America
  • Superb1 review5

Imagine feeling the sea breeze aboard the wonderful Tiara 44 Yacht, it will definitely be a trip tha....

    Private Tour
    Start From $2,030.00
 
 

Private Sailing Trip on Monterey Bay

(5 of 1 review)

Discover the stunning beauty of Monterey Bay aboard your own private sailing charter. This experience caters to all ages and interests. Venture along the coastline, soak in the vibrant wildlife, and enjoy the serene ocean atmosphe... More

Free Cancellation
Private Tour
Start From $895.00
 
Private Sailing Trip on Monterey Bay

Private Sailing Trip on Monterey Bay

  • North America
  • Superb1 review5

Discover the stunning beauty of Monterey Bay aboard your own private sailing charter. This experienc....

    Free Cancellation
    Private Tour
    Start From $895.00
 
 

Fort Myers: Tiki Pub VIP Private Tropical Sandbar Getaway Cruise

(5 of 1 review)

There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Your Captain/Entertainer will make sure you have everything you need, and bring the party with custom curated playlists, Tiki-Oki, a... More

Free Cancellation
Private Tour
Start From $599.00
 
Fort Myers: Tiki Pub VIP Private Tropical Sandbar Getaway Cruise

Fort Myers: Tiki Pub VIP Private Tropical Sandbar Getaway Cruise

  • North America
  • Superb1 review5

There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Yo....

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

Luxury Yacht 58 ft for up to 20 people 4 hrs

(5 of 1 review)

Azimut yachts are designed to pamper the most demanding tastes. Feel the pleasure of sailing aboard this luxury yacht along the coast of Bahía de Banderas. You will enjoy every moment and every place in this tropical paradise. L... More

Free Cancellation
Private Tour
Start From $4,100.00
 
Luxury Yacht 58 ft for up to 20 people 4 hrs

Luxury Yacht 58 ft for up to 20 people 4 hrs

  • North America
  • Superb1 review5

Azimut yachts are designed to pamper the most demanding tastes. Feel the pleasure of sailing aboard ....

    Free Cancellation
    Private Tour
    Start From $4,100.00
 
 

Epic 34 Catamaran Sailing and Snorkeling Adventure

(5 of 1 review)

Epic 34' catamaran sailing and snorkeling in Waikiki Bay. With Diamond as the back drop you lay back and enjoy the amazing views.... More

Free Cancellation
Private Tour
Start From $299.00
 
Epic 34 Catamaran Sailing and Snorkeling Adventure

Epic 34 Catamaran Sailing and Snorkeling Adventure

  • North America
  • Superb1 review5

Epic 34' catamaran sailing and snorkeling in Waikiki Bay. With Diamond as the back drop you lay back....

    Free Cancellation
    Private Tour
    Start From $299.00
 
 

Tiki Pub Glow Party Cruise (Adults only)

(4.9 of 16 reviews)

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, sipping on your BYOB drinks. Experience the magic of the moonlit waters, paired with tunes and laughter. Join us for the most memora... More

Free Cancellation
Private Tour
Start From $79.95
 
Tiki Pub Glow Party Cruise (Adults only)

Tiki Pub Glow Party Cruise (Adults only)

  • North America
  • Superb16 reviews4.9

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, si....

    Free Cancellation
    Private Tour
    Start From $79.95
 
 

Tiki Pub Amazing Dolphin Eco Adventure

(4.7 of 3 reviews)

Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water inhabitants, cruise the bay for Dolphins, Manatee, and a myriad of sea creatures and incredible Birds! The best part is that then y... More

Free Cancellation
Private Tour
Start From $59.95
 
Tiki Pub Amazing Dolphin Eco Adventure Likely to Sell Out

Tiki Pub Amazing Dolphin Eco Adventure

  • North America
  • Superb3 reviews4.7

Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water i....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Luxury Sunset Cruise with Open bar in Vallarta

(3 of 4 reviews)

As the golden hour sets in, step aboard a luxurious 50-foot Beneteau sailboat and cruise along Banderas Bay’s stunning coastline. This sunset sailing experience offers an unforgettable evening of elegance, romance, and breathtak... More

Free Cancellation
Private Tour
Start From $99.00
 
Luxury Sunset Cruise with Open bar in Vallarta Likely to Sell Out

Luxury Sunset Cruise with Open bar in Vallarta

  • North America

As the golden hour sets in, step aboard a luxurious 50-foot Beneteau sailboat and cruise along Bande....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Exciting Public Afternoon Sail on our Newest Sailboat

(3 of 4 reviews)

Looking for a more personal sailing experience without the cost of a private charter? Our Afternoon Public Sail is the perfect balance. With a maximum of just 6 guests onboard, you’ll enjoy an intimate, relaxed atmosphere. Aboar... More

Free Cancellation
Private Tour
Start From $153.85
 
Exciting Public Afternoon Sail on our Newest Sailboat Likely to Sell Out

Exciting Public Afternoon Sail on our Newest Sailboat

  • North America

Looking for a more personal sailing experience without the cost of a private charter? Our Afternoon ....

    Free Cancellation
    Private Tour
    Start From $153.85
 
 

Two Hour Private Sailing Charter

(5 of 3 reviews)

Escape the city on a two hour private sailing charter for up to 6 guests. Our two hour charter option is available morning, afternoon, and evening, and it is a great option for a quick getaway. We sail you around lower Manhattan w... More

Free Cancellation
Private Tour
Start From $625.00
 
Two Hour Private Sailing Charter Likely to Sell Out

Two Hour Private Sailing Charter

  • North America
  • Superb3 reviews5

Escape the city on a two hour private sailing charter for up to 6 guests. Our two hour charter optio....

    Free Cancellation
    Private Tour
    Start From $625.00
 
 

Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran

(5 of 3 reviews)

Your 90 minute sunset sail on 41ft, 32 passenger Lazy Daze Catamaran will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the ... More

Free Cancellation
Private Tour
Start From $40.00
 
Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran Likely to Sell Out

Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran

  • North America
  • Superb3 reviews5

Your 90 minute sunset sail on 41ft, 32 passenger Lazy Daze Catamaran will include a scenic trip thro....

    Free Cancellation
    Private Tour
    Start From $40.00
 
 

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

(5 of 3 reviews)

Set sail on Maui's only floating tiki bar aboard a hand-built catamaran, where sunsets and handcrafted cocktails create unforgettable memories. Enjoy a relaxing evening of island tunes, light snacks, and an open bar as you glide o... More

Free Cancellation
Private Tour
Start From $119.56
 
Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran Likely to Sell Out

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

  • North America
  • Superb3 reviews5

Set sail on Maui's only floating tiki bar aboard a hand-built catamaran, where sunsets and handcraft....

    Free Cancellation
    Private Tour
    Start From $119.56
 
 

Private Sailing for up to 10 people 4 hrs

(5 of 3 reviews)

Sail through the bay of Puerto Vallarta celebrating your birthday, a special date for you or just to have fun with your friends in private. It is a charming classic-style sailboat, where you can enjoy the pleasure of sailing thro... More

Free Cancellation
Private Tour
Start From $1,216.00
 
Private Sailing for up to 10 people 4 hrs Likely to Sell Out

Private Sailing for up to 10 people 4 hrs

  • North America
  • Superb3 reviews5

Sail through the bay of Puerto Vallarta celebrating your birthday, a special date for you or just to....

    Free Cancellation
    Private Tour
    Start From $1,216.00
 
 

Xoximilco Flaoting Fiesta in Canals of Cancun

(5 of 3 reviews)

Celebrate Mexican culture like never before at Xoximilco by Xcaret—a one-of-a-kind floating fiesta through the canals of Cancun! Step aboard a colorful trajinera (traditional gondola-style boat) and get ready for a night full of... More

Free Cancellation
Private Tour
Start From $144.99
 
 Xoximilco Flaoting Fiesta in Canals of Cancun Likely to Sell Out

Xoximilco Flaoting Fiesta in Canals of Cancun

  • North America
  • Superb3 reviews5

Celebrate Mexican culture like never before at Xoximilco by Xcaret—a one-of-a-kind floating fiesta....

    Free Cancellation
    Private Tour
    Start From $144.99
 
 

Half Day Sunset Catamaran Adventure

(5 of 3 reviews)

Escape the crowds aboard a private luxury catamaran! Sail through Tampa Bay to hidden islands like Egmont Key and Fort De Soto then end your day with a beautiful sunset. Swim, snorkel, and relax on floating mats while your captain... More

Free Cancellation
Private Tour
Start From $1,100.00
 
Half Day Sunset Catamaran Adventure Likely to Sell Out

Half Day Sunset Catamaran Adventure

  • North America
  • Superb3 reviews5

Escape the crowds aboard a private luxury catamaran! Sail through Tampa Bay to hidden islands like E....

    Free Cancellation
    Private Tour
    Start From $1,100.00
 
 

Original Cruisin Tikis Snorkeling Safari

(5 of 3 reviews)

The Snorkeling Safari is a must-do when visiting Destin. Pop open your favorite drinks and let your professional, USCG-licensed captain cruise you through the heart of Destin Harbor while you soak in the scenery and the good vibes... More

Free Cancellation
Private Tour
Start From $89.00
 
Original Cruisin Tikis Snorkeling Safari Likely to Sell Out

Original Cruisin Tikis Snorkeling Safari

  • North America
  • Superb3 reviews5

The Snorkeling Safari is a must-do when visiting Destin. Pop open your favorite drinks and let your ....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Luxury 40' Van Dutch Private Yacht Experience – Cancun 4 Hours

(4.8 of 22 reviews)

Enjoy an unforgettable day at sea with our exclusive 9-hour luxury yacht tour in Cancun. This full-day experience offers the perfect combination of relaxation, comfort, and first-class service. As the day winds down, guests will b... More

Free Cancellation
Private Tour
Start From $1,650.00
 
Luxury 40' Van Dutch Private Yacht Experience – Cancun 4 Hours Likely to Sell Out

Luxury 40' Van Dutch Private Yacht Experience – Cancun 4 Hours

  • North America
  • Superb22 reviews4.8

Enjoy an unforgettable day at sea with our exclusive 9-hour luxury yacht tour in Cancun. This full-d....

    Free Cancellation
    Private Tour
    Start From $1,650.00
 
 

Private Dolphin Catamaran Sail In Cocoa Beach

(4.8 of 22 reviews)

Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter playful dolph... More

Free Cancellation
Private Tour
Start From $337.87
 
Private Dolphin Catamaran Sail In Cocoa Beach Likely to Sell Out

Private Dolphin Catamaran Sail In Cocoa Beach

  • North America
  • Superb22 reviews4.8

Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforg....

    Free Cancellation
    Private Tour
    Start From $337.87
 
 

Cabo San Lucas Private Custom Snorkel or Sunset Adventure

(5 of 1 review)

First, you meet on the dock to meet the best crew that Cabo has! You will get boarded and the crew will make sure that you have a drink in your hand within minutes. You will get to see the world famous Arch, Lover's Beach, Divorce... More

Special Offer
Free Cancellation
Private Tour
Start From $2,000.00
(Saving 20% ) $2,500.00
 
-20% Cabo San Lucas Private Custom Snorkel or Sunset Adventure Likely to Sell Out

Cabo San Lucas Private Custom Snorkel or Sunset Adventure

  • North America
  • Superb1 review5

First, you meet on the dock to meet the best crew that Cabo has! You will get boarded and the crew w....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $2,000.00
    (Saving 20% ) $2,500.00
 
 

Private Monohull Sailboat

(5 of 1 review)

Take your sailing adventures to the next level with a guided private tour on a trusty Monohull boat. This tour features top of the line service from fresh fruits and a bottle of wine to breathtaking views and complete privacy. Ta... More

Free Cancellation
Private Tour
Start From $212.23
 
Private Monohull Sailboat Likely to Sell Out

Private Monohull Sailboat

  • North America
  • Superb1 review5

Take your sailing adventures to the next level with a guided private tour on a trusty Monohull boat.....

    Free Cancellation
    Private Tour
    Start From $212.23
 
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