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Top 10 Best North America Sailing Trips

Found 692 Sailing Trips activities in North America. Sort by Popularity. - Page 8
 

Sea to Sky Afternoon Sail

(5 of 206 reviews)

Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds with the breathtaking views of the Coastal and Tantalus mountain ranges. We will depart from the docks in Squamish (about 40 minut... More

Free Cancellation
Start From $134.85
 
Sea to Sky Afternoon Sail Likely to Sell Out

Sea to Sky Afternoon Sail

  • North America
  • Superb206 reviews5

Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds w....

    Free Cancellation
    Start From $134.85
 
 

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

(4.9 of 139 reviews)

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather permitting) while taking in the sun and spectacular views. Our beautifully, well appointed ... More

Free Cancellation
Start From $70.00
 
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans Likely to Sell Out

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

  • North America
  • Superb139 reviews4.9

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....

    Free Cancellation
    Start From $70.00
 
 

Private Cabo 35ft cat experience Food and open bar included!

(4.9 of 314 reviews)

Barta is an extremely fun and comfort 36ft catamaran specifically designed to accommodate large groups of up to 20 passengers. Immerse yourself in the scenic wonders of the bay of Cabo San Lucas as Barta gracefully navigates, ensu... More

Free Cancellation
Private Tour
Start From $2,235.00
 
Private Cabo 35ft cat experience Food and open bar included! Likely to Sell Out

Private Cabo 35ft cat experience Food and open bar included!

  • North America
  • Superb314 reviews4.9

Barta is an extremely fun and comfort 36ft catamaran specifically designed to accommodate large grou....

    Free Cancellation
    Private Tour
    Start From $2,235.00
 
 

JFarwell Sunset Wine and Cheese Yacht Sailing

(4.9 of 121 reviews)

Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to invite our guests to be involved in sailing - take the helm, hoist the sails, or sit back and enjoy the beautiful sights and wines ... More

Free Cancellation
Private Tour
Start From $150.67
 
JFarwell Sunset Wine and Cheese Yacht Sailing Likely to Sell Out

JFarwell Sunset Wine and Cheese Yacht Sailing

  • North America
  • Superb121 reviews4.9

Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to i....

    Free Cancellation
    Private Tour
    Start From $150.67
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.8 of 58 reviews)

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More

Free Cancellation
Private Tour
Start From $179.00
 
Hawaiian Canoe Sailing Experience in Maui Likely to Sell Out

Hawaiian Canoe Sailing Experience in Maui

  • North America
  • Superb58 reviews4.8

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....

    Free Cancellation
    Private Tour
    Start From $179.00
 
 

Sunset Cruise on the Scenic & Calming Chesapeake Bay

(4.7 of 11 reviews)

Watching the sunset over the twin beaches on the Western Shores of the Chesapeake Bay! A great way to close out a summer day with beautiful photos of the sunset. You must call 24 hours before your cruise time to see if the minimum... More

Free Cancellation
Private Tour
Start From $123.00
 
Sunset Cruise on the Scenic & Calming Chesapeake Bay Likely to Sell Out

Sunset Cruise on the Scenic & Calming Chesapeake Bay

  • North America
  • Superb11 reviews4.7

Watching the sunset over the twin beaches on the Western Shores of the Chesapeake Bay! A great way t....

    Free Cancellation
    Private Tour
    Start From $123.00
 
 

Sunset Sail from Ma'alaea Harbor

(4.6 of 208 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
  • Superb208 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
 
 

FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry

(3.4 of 11 reviews)

Take advantage of the vicinity of the Bahamas Islands during your Florida visit to experience the world's best beaches. The ocean crossing is provided with our comfortable Express-Ferry featuring restrooms, comfortable seats, air ... More

Free Cancellation
Private Tour
Start From $299.00
 
FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry Likely to Sell Out

FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry

  • North America
  • Good11 reviews3.4

Take advantage of the vicinity of the Bahamas Islands during your Florida visit to experience the wo....

    Free Cancellation
    Private Tour
    Start From $299.00
 
 

Sunset Catamaran Sail in Cocoa Beach

(5 of 146 reviews)

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the beauty of Floridaâ... More

Free Cancellation
Private Tour
Start From $55.37
 
Sunset Catamaran Sail in Cocoa Beach Likely to Sell Out

Sunset Catamaran Sail in Cocoa Beach

  • North America
  • Superb146 reviews5

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....

    Free Cancellation
    Private Tour
    Start From $55.37
 
 

Suncoast Sailing's Sunset Sailing Experience!

(4.9 of 222 reviews)

Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Treasure Island, Florida! You’ll set sail about an hour before sunset to give you plenty of time to catch the full range of hues p... More

Free Cancellation
Private Tour
Start From $64.99
 
Suncoast Sailing's Sunset Sailing Experience! Likely to Sell Out

Suncoast Sailing's Sunset Sailing Experience!

  • North America
  • Superb222 reviews4.9

Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....

    Free Cancellation
    Private Tour
    Start From $64.99
 
 

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico

(4.7 of 303 reviews)

Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all-inclusive fishing tour offers you a unique opportunity to immerse yourself in an authentic, action-packed fishing experience, wit... More

Free Cancellation
Private Tour
Start From $625.00
 
Private Fishing Trip Likely to Sell Out

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico

  • North America
  • Superb303 reviews4.7

Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all....

    Free Cancellation
    Private Tour
    Start From $625.00
 
 

Newport Sunset Sail on Classic Sailboat

(4.8 of 21 reviews)

Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailboat and see all of Newport's iconic sights from the water including histor... More

Free Cancellation
Private Tour
Start From $67.84
 
Newport Sunset Sail on Classic Sailboat Likely to Sell Out

Newport Sunset Sail on Classic Sailboat

  • North America
  • Superb21 reviews4.8

Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a ....

    Free Cancellation
    Private Tour
    Start From $67.84
 
 

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

(4.9 of 185 reviews)

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More

Free Cancellation
Private Tour
Start From $49.99
 
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast Likely to Sell Out

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

  • North America
  • Superb185 reviews4.9

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....

    Free Cancellation
    Private Tour
    Start From $49.99
 
 

Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling

(5 of 177 reviews)

Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical waters alongside colorful sea life. The bilingual crew is happy to accommodate any special occasion or request. This unforgettable ex... More

Free Cancellation
Private Tour
Start From $750.00
 
Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling Likely to Sell Out

Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling

  • North America
  • Superb177 reviews5

Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical water....

    Free Cancellation
    Private Tour
    Start From $750.00
 
 

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

(5 of 31 reviews)

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor for over 12 years, our sailing yachts are the highest quality and op... More

Free Cancellation
Private Tour
Start From $599.00
 
Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique Likely to Sell Out

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

  • North America
  • Superb31 reviews5

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

Monterey Private 3 - 4 Hour Whale Watching Cruise

(5 of 2 reviews)

Enjoy a 3 - 4 hour sailing cruise on the Monterey Bay. This Marine Mammal and Wildlife Safari is a private guided tour and can accommodate up to 6 people. Whale sightings are NOT guaranteed. However, this tour is designed to give... More

Free Cancellation
Private Tour
Start From $950.00
 
Monterey Private 3 - 4 Hour Whale Watching Cruise Likely to Sell Out

Monterey Private 3 - 4 Hour Whale Watching Cruise

  • North America
  • Superb2 reviews5

Enjoy a 3 - 4 hour sailing cruise on the Monterey Bay. This Marine Mammal and Wildlife Safari is a p....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

9am Turtle Canyon Snorkel Adventure

(4.9 of 254 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
  • Superb254 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
 
 

Schooner Fame Sailing Tour

(4.9 of 528 reviews)

FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per TripAdvisor. Don't miss the very best of what Salem has to offer! There's more to our town than witches! FAME is a full-scale replica... More

Free Cancellation
Private Tour
Start From $50.65
 
Schooner Fame Sailing Tour Likely to Sell Out

Schooner Fame Sailing Tour

  • North America
  • Superb528 reviews4.9

FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per Trip....

    Free Cancellation
    Private Tour
    Start From $50.65
 
 

Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling

(4.9 of 108 reviews)

Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Vallarta´s Bay. You will be able to Sail, Snorkel, Swim and even Paddelboard in Los Arcos National Park, capturing beautiful views ... More

Free Cancellation
Private Tour
Start From $785.88
 
Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling Likely to Sell Out

Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling

  • North America
  • Superb108 reviews4.9

Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Va....

    Free Cancellation
    Private Tour
    Start From $785.88
 
 

Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline

(4.8 of 23 reviews)

Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Miami Beach experience. Connect with nature, discover new landscapes, & create lasting memories as you explore the stunning coastline... More

Free Cancellation
Private Tour
Start From $600.00
 
Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline Likely to Sell Out

Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline

  • North America
  • Superb23 reviews4.8

Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Mia....

    Free Cancellation
    Private Tour
    Start From $600.00
 
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