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Top 10 Best North America Sailing Trips

Found 639 Sailing Trips activities in North America. Sort by Popularity. - Page 3
 

Waikiki Sunset Cocktail Sail with Open Bar

(4.8 of 427 reviews)

This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruise! Strangers become fast friends on this one regardless if your cruising solo or with a crew! We provide juice, soda, bottled wate... More

Free Cancellation
Start From $85.00
 
Waikiki Sunset Cocktail Sail with Open Bar

Waikiki Sunset Cocktail Sail with Open Bar

  • North America
  • Superb427 reviews4.8

This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruis....

    Free Cancellation
    Start From $85.00
 
 

Live Music Sunset Sail with Drinks Included

(4.9 of 73 reviews)

Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sail! Indulge in complimentary beer, wine, soda, water, margaritas, champagne, and a snack, while enjoying live performances by some ... More

Free Cancellation
Start From $63.85
 
Live Music Sunset Sail with Drinks Included

Live Music Sunset Sail with Drinks Included

  • North America
  • Superb73 reviews4.9

Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sai....

    Free Cancellation
    Start From $63.85
 
 

Key West Dolphin & Snorkel Experience

(4.5 of 243 reviews)

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key West Sunset all in one trip.... More

Free Cancellation
Start From $64.95
 
Key West Dolphin & Snorkel Experience

Key West Dolphin & Snorkel Experience

  • North America
  • Exellent243 reviews4.5

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....

    Free Cancellation
    Start From $64.95
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 411 reviews)

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters... More

Free Cancellation
Start From $179.27
 
Deluxe Sail & Snorkel to the Captain Cook Monument

Deluxe Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb411 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....

    Free Cancellation
    Start From $179.27
 
 

Half-Day Luxury Sailing Experience in Tulum with Open Bar

(4.2 of 225 reviews)

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More

Free Cancellation
Start From $149.00
 
Half-Day Luxury Sailing Experience in Tulum with Open Bar

Half-Day Luxury Sailing Experience in Tulum with Open Bar

  • North America
  • Exellent225 reviews4.2

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....

    Free Cancellation
    Start From $149.00
 
 

2-Hour Sunset Sail on the San Francisco Bay

(4.8 of 356 reviews)

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous traditional vessel to take in the sights at the most bewitching time of d... More

Free Cancellation
Start From $129.00
 
2-Hour Sunset Sail on the San Francisco Bay

2-Hour Sunset Sail on the San Francisco Bay

  • North America
  • Superb356 reviews4.8

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....

    Free Cancellation
    Start From $129.00
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 614 reviews)

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Free Cancellation
Start From $141.57
 
Snorkel with Manta Rays Guaranteed

Snorkel with Manta Rays Guaranteed

  • North America
  • Superb614 reviews4.8

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....

    Free Cancellation
    Start From $141.57
 
 

Limited Time Weekday Super Promo, 48ft Private Yacht Rental,

(5 of 1 review)

Discover the vibrant allure of Miami from the luxurious vantage point of our yacht tours. Embark on a journey where turquoise waters meet golden shores, with panoramic views of iconic landmarks like South Beach and the Miami skyli... More

Free Cancellation
Private Tour
Start From $190.00
 
Limited Time Weekday Super Promo, 48ft Private Yacht Rental,

Limited Time Weekday Super Promo, 48ft Private Yacht Rental,

  • North America
  • Superb1 review5

Discover the vibrant allure of Miami from the luxurious vantage point of our yacht tours. Embark on ....

    Free Cancellation
    Private Tour
    Start From $190.00
 
 

Sunset Sail from Ma'alaea Harbor

(4.6 of 189 reviews)

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our  luxury sailing catamaran, Ocean Spirit. It’s the perfect way to ex... More

Free Cancellation
Private Tour
Start From $133.05
 
Sunset Sail from Ma'alaea Harbor Likely to Sell Out

Sunset Sail from Ma'alaea Harbor

  • North America
  • Superb189 reviews4.6

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....

    Free Cancellation
    Private Tour
    Start From $133.05
 
 

Private Luxury Sailing Charters, BYOB & Dolphins

(5 of 335 reviews)

We are a family owned luxury sailing charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the water on one of our sailboats. We offer hourly, daily, or customized tours according to y... More

Free Cancellation
Private Tour
Start From $499.00
 
Private Luxury Sailing Charters, BYOB & Dolphins Likely to Sell Out

Private Luxury Sailing Charters, BYOB & Dolphins

  • North America
  • Superb335 reviews5

We are a family owned luxury sailing charter business. Come enjoy a BYOB day of sailing and seeing t....

    Free Cancellation
    Private Tour
    Start From $499.00
 
 

Moana’s Guided Turtle Snorkel & Sailing Adventure at Waikiki

(4.7 of 864 reviews)

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Free Cancellation
Private Tour
Start From $79.99
 
Moana’s Guided Turtle Snorkel & Sailing Adventure at Waikiki Likely to Sell Out

Moana’s Guided Turtle Snorkel & Sailing Adventure at Waikiki

  • North America
  • Superb864 reviews4.7

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....

    Free Cancellation
    Private Tour
    Start From $79.99
 
 

Boat Tour and Snorkel at Pelican Rock

(4.5 of 6 reviews)

The must do activities in Cabo are tour the arch, whale watching and snorkeling. We have put all of those things in one spot in this bucket list level experience. First take a boat tour of all of the landmarks Cabo boasts on the w... More

Special Offer
Free Cancellation
Private Tour
Start From $63.20
(Saving 20% ) $79.00
 
-20% Boat Tour and Snorkel at Pelican Rock Likely to Sell Out

Boat Tour and Snorkel at Pelican Rock

  • North America
  • Exellent6 reviews4.5

The must do activities in Cabo are tour the arch, whale watching and snorkeling. We have put all of ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $63.20
    (Saving 20% ) $79.00
 
 

Small-Group San Diego Sunset Sailing Excursion

(4.9 of 536 reviews)

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat is limited to six (6) guests allowing you a comfortable, semi-private experience (or, pu... More

Free Cancellation
Private Tour
Start From $127.00
 
Small-Group San Diego Sunset Sailing Excursion Likely to Sell Out

Small-Group San Diego Sunset Sailing Excursion

  • North America
  • Superb536 reviews4.9

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This th....

    Free Cancellation
    Private Tour
    Start From $127.00
 
 

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

(4.5 of 404 reviews)

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall Ship for a unique sailing experience. There is no better way to witness all o... More

Free Cancellation
Private Tour
Start From $56.00
 
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor Likely to Sell Out

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....

  • North America
  • Exellent404 reviews4.5

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....

    Free Cancellation
    Private Tour
    Start From $56.00
 
 

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

(4.9 of 183 reviews)

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat enjoying the fresh air and best that San Diego has to offer. On your adventure yo... More

Free Cancellation
Private Tour
Start From $119.00
 
Luxury Sailing Tour of San Diego's Bay and Coastal Waterways Likely to Sell Out

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

  • North America
  • Superb183 reviews4.9

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Key West Reef Snorkel & Sail Adventure

(4.7 of 490 reviews)

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Free Cancellation
Private Tour
Start From $89.00
 
Key West Reef Snorkel & Sail Adventure Likely to Sell Out

Key West Reef Snorkel & Sail Adventure

  • North America
  • Superb490 reviews4.7

Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

9am Turtle Canyon Snorkel Adventure

(4.9 of 219 reviews)

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

Free Cancellation
Private Tour
Start From $96.30
 
9am Turtle Canyon Snorkel Adventure Likely to Sell Out

9am Turtle Canyon Snorkel Adventure

  • North America
  • Superb219 reviews4.9

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....

    Free Cancellation
    Private Tour
    Start From $96.30
 
 

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor

(4.6 of 125 reviews)

Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your loved ones to experience a beautiful Snorkeling, Sailing Cruise, and Whale Watching (Dec-Apr) on our Small Charming Hawaiian Catamara... More

Free Cancellation
Private Tour
Start From $139.00
 
Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor Likely to Sell Out

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harb....

  • North America
  • Superb125 reviews4.6

Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....

    Free Cancellation
    Private Tour
    Start From $139.00
 
 

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

(4.7 of 39 reviews)

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our cap... More

Free Cancellation
Private Tour
Start From $119.00
 
Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor Likely to Sell Out

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

  • North America
  • Superb39 reviews4.7

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

2-Hour Sunset Sail from San Diego

(4.9 of 67 reviews)

Leave your worries behind as you cruise the San Diego Bay and marvel at the cityscape. The vibrant waterfront offers expansive views of Downtown, Point Loma, and Coronado Island. Experience the setting sun cast its brilliant color... More

Free Cancellation
Private Tour
Start From $130.00
 
2-Hour Sunset Sail from San Diego Likely to Sell Out

2-Hour Sunset Sail from San Diego

  • North America
  • Superb67 reviews4.9

Leave your worries behind as you cruise the San Diego Bay and marvel at the cityscape. The vibrant w....

    Free Cancellation
    Private Tour
    Start From $130.00
 
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