Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 708 Sailing Trips activities in North America. Sort by Popularity. - Page 13Cozumel Luxury Sailing & Snorkeling with Lunch and Open Bar Onboard
• Enjoy the turquoise waters of Cozumel aboard one of our luxury sailing catamarans. • Snorkel and marvel at the wide array of tropical fish and rich marine life that inhabit the colorful reefs of the island. • Paddleboard a... More

Cozumel Luxury Sailing & Snorkeling with Lunch and Open Bar Onboa....
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North America
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Superb224 reviews4.8
• Enjoy the turquoise waters of Cozumel aboard one of our luxury sailing catamarans. • Snorkel a....
Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach
Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Dolphin, Island Swim & Sunset Cruises. Enjoy your Island Sandbar stop at One Tree Island, where you can enjoy the beautiful waters... More

Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach
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North America
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Superb48 reviews4.7
Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Do....
Luxury Catamaran Whale Watch
From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More

Luxury Catamaran Whale Watch
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North America
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Superb40 reviews5
From December through April, the waters off Maui come alive with the sights and sounds of the majest....
New York City Skyline Lights Sail
Experience New York City from the water on classic Schooner Adirondack. Gaze at the city lights from the water and enjoy a peaceful setting as you escape the city and take to a quiet harbor at night. Key points about this activ... More

New York City Skyline Lights Sail
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North America
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Superb13 reviews4.7
Experience New York City from the water on classic Schooner Adirondack. Gaze at the city lights fro....
Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar
Admire the peaceful waters of the Caribbean Sea, aboard a classic or luxury catamaran and enjoy a spectacular day sailing to Isla Mujeres on a fun-filled experience where music, drinks and incredible views will never be lacking. ... More

Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar
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North America
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Very Good35 reviews3.7
Admire the peaceful waters of the Caribbean Sea, aboard a classic or luxury catamaran and enjoy a sp....
2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests
Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to helping families create unforgettable memories. Our vessel is thoughtfully designed to be warm and inviting, featuring handcrafted yel... More
Private Tour

2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests
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North America
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Superb69 reviews5
Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to help....
Private Tour
Sunset Sail from Ma'alaea Harbor
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
Private Tour

Sunset Sail from Ma'alaea Harbor
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North America
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Superb212 reviews4.6
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....
Private Tour
4 hours - Private 48ft Yacht all inclusive in Tulum and Playa del Carmen
We are a Yacht private rental company with more than 15 years of experience in the hospitality industry in Playa del Carmen, Puerto Aventuras and Tulum. Our services are provided with high quality standards to ensure maximum satis... More
Private Tour

4 hours - Private 48ft Yacht all inclusive in Tulum and Playa del....
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North America
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Superb367 reviews5
We are a Yacht private rental company with more than 15 years of experience in the hospitality indus....
Private Tour
Private 2 Hour Sailboat Sunset Charter
When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you plan the perfect experience for you and your guests! You'll sail around Shell Island into the Gulf of Mexico, while you enjoy dol... More
Private Tour

Private 2 Hour Sailboat Sunset Charter
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North America
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Superb1 review5
When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you....
Private Tour
Private Catamaran Charter in Waikiki (1-6 Guests)
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the boat, as well as 2 small nets on the back of the boat. Not only does Hawa... More
Private Tour

Private Catamaran Charter in Waikiki (1-6 Guests)
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North America
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Superb18 reviews5
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....
Private Tour
Deluxe Day Sail in San Diego
Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego Bay offer a perfect blend of adventure and relaxation. With our passionate and kno... More
Private Tour

Deluxe Day Sail in San Diego
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North America
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Superb49 reviews5
Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our person....
Private Tour
Small Group Waikiki Sunset Sailing Tour
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More
Private Tour

Small Group Waikiki Sunset Sailing Tour
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North America
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Superb100 reviews4.9
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....
Private Tour
2 Hour Sunset Sailing Tour in Wrightsville Beach
Our experienced captains will sail you to the most beautiful local spots to watch the sunset on the water. Spot dolphins, seabirds, and other wildlife as you pass by islands and marshlands.... More
Private Tour

2 Hour Sunset Sailing Tour in Wrightsville Beach
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North America
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Superb100 reviews4.9
Our experienced captains will sail you to the most beautiful local spots to watch the sunset on the ....
Private Tour
Sailing Tour through the Laguna de los Siete Colores
Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, being your best option to know this magical place without damaging the ecosystem. Guided by a team of professionals, with whom you ... More
Private Tour

Sailing Tour through the Laguna de los Siete Colores
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North America
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Superb1,389 reviews5
Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, b....
Private Tour
Private Kelowna Sailing Cruise on Okanagan Lake
Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are welcome to sit back and relax, enjoy the sights, or take a turn at the helm, with instruction from your skipper! I will never forg... More
Private Tour

Private Kelowna Sailing Cruise on Okanagan Lake
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North America
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Superb39 reviews5
Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are w....
Private Tour
Statue of Liberty Sunset Cruise and New York City Sky Line
New York City Sightseeing Scenic cruise. Enjoy the Statue of Liberty and Ellis Island up close. View of the Manhattan skyline, One World Trade Center and the Empire State Building.Enjoy a panoramic view of lower Manhattan as you p... More
Private Tour

Statue of Liberty Sunset Cruise and New York City Sky Line
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North America
New York City Sightseeing Scenic cruise. Enjoy the Statue of Liberty and Ellis Island up close. View....
Private Tour
Cabo San Lucas Sunset Party on the Water - Adult Only
Spend an incredible vacation enjoying an adventure you will never forget, sailing through the blue waters of the Cabo San Lucas Bay, taking in the amazing scenery all while you enjoy the music and dancing. This Party Boat is perfe... More
Private Tour

Cabo San Lucas Sunset Party on the Water - Adult Only
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North America
Spend an incredible vacation enjoying an adventure you will never forget, sailing through the blue w....
Private Tour
Sunset sail Aboard Manakai Catamaran
Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a smaller guest capacity and open-deck layout, it offers an intimate, lai... More
Private Tour

Sunset sail Aboard Manakai Catamaran
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North America
Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Wood....
Private Tour
Catamaran Sailing Cruise in Monterey
Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind to make for a peaceful and exciting cruise on the bay. On the way out of t... More
Private Tour

Catamaran Sailing Cruise in Monterey
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North America
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Superb18 reviews4.7
Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage af....
Private Tour
Private Yacht Charter in Cabo San Lucas – Cruise to The Arch
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
Private Tour

Private Yacht Charter in Cabo San Lucas – Cruise to The Arch
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North America
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Superb18 reviews4.7
Enjoy a private yachting experience in Cabo San Lucas without committing to a full-day tour. Perfect....
Private Tour