Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 692 Sailing Trips activities in North America. Sort by Popularity. - Page 28Sunset Sailing Tour of San Diego Bay up to 6 Guests
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

Sunset Sailing Tour of San Diego Bay up to 6 Guests
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North America
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Superb1 review5
A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautifu....
Afternoon Ali'i Adventure
Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. ... More

Afternoon Ali'i Adventure
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North America
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Superb5 reviews5
Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....
Bachelorette Sailing Party on San Diego Bay up to 6 Guests
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
Private Tour

Bachelorette Sailing Party on San Diego Bay up to 6 Guests
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North America
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Superb5 reviews5
Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking....
Private Tour
Private Afternoon Harbor Cruise on Kismet for parties up to 15
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
Private Tour

Private Afternoon Harbor Cruise on Kismet for parties up to 15
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North America
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Superb19 reviews5
Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise....
Private Tour
Exclusive Private Sailing Luxury Tour in Los Cabos
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
Private Tour

Exclusive Private Sailing Luxury Tour in Los Cabos
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North America
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Superb19 reviews5
Experience snorkeling in crystal waters, the beach Palmilla has a blue flag recognition and is one o....
Private Tour
Luxury Private Sunset Experience in San Jose
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
Private Tour

Luxury Private Sunset Experience in San Jose
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North America
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Superb19 reviews5
Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour....
Private Tour
The Hamptons Date Night Dining Hot Spots
This Hamptons hotspot dining boat tour allows guests to visit multiple dining hotspots in a single excursion hassle-free, maximizing their time and providing a convenient way to explore the Hamptons. Guests won't have to worry abo... More
Private Tour

The Hamptons Date Night Dining Hot Spots
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North America
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Superb1 review5
This Hamptons hotspot dining boat tour allows guests to visit multiple dining hotspots in a single e....
Private Tour
Snorkel in the beautiful reef of Puerto Morelos with transport
The most amazing and exciting tour in the Mexican Caribbean is here. Visit the national park of reefs in Puerto Morelos. Sail through the turquoise clear water of the Caribbean Sea and arrive to the Mesoamerican reef. Our captain... More
Private Tour

Snorkel in the beautiful reef of Puerto Morelos with transport
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North America
The most amazing and exciting tour in the Mexican Caribbean is here. Visit the national park of reef....
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
2 Hours Private Guided Sailing Adventure in Pensacola Beach
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
Private Tour

2 Hours Private Guided Sailing Adventure in Pensacola Beach
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North America
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Superb2 reviews5
This 2 hour sailing excursion may take place in Pensacola Bay, passing by areas of Sabine Island, De....
Private Tour
San Francisco City Lights Sail
The Golden Gate isn’t the only bridge in town! Once the sun sets and the lights come on, join us for a city-front cruise to enjoy the majestic sites of San Francisco in the night sky. See the Bay Bridge lit in all its glory, alo... More
Private Tour

San Francisco City Lights Sail
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North America
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Superb5 reviews5
The Golden Gate isn’t the only bridge in town! Once the sun sets and the lights come on, join us f....
Private Tour
Private Catamaran Sunset Cruise with Dolphin watching
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
Private Tour

Private Catamaran Sunset Cruise with Dolphin watching
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North America
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Superb4 reviews5
One of the best ways to relax on your vacation is to view a sunset aboard Destin sailing Adventures.....
Private Tour
Private Paddle Tour at Sunrise
With this amazing experience through the Bacalar Lagoon you will live unbeatable moments for 3.5 hours, we have all the necessary equipment for this activity to be complete. We are an ecologically responsible company that promotes... More
Private Tour

Private Paddle Tour at Sunrise
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North America
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Superb206 reviews5
With this amazing experience through the Bacalar Lagoon you will live unbeatable moments for 3.5 hou....
Private Tour

Private Transparent Boat Tour in the Sea of Cozumel
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
(Saving 20% )

Private Transparent Boat Tour in the Sea of Cozumel
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North America
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Superb206 reviews5
Incredible experience in a 100% transparent boat, we are also the only tour currently that offers sn....
Free Cancellation
Private Tour
(Saving 20% )
Live this unique snorkeling experience. El Cielo in Cozumel a magical tour.
If we tell you that you can be near the sky while you are at the paradisiacal Caribbean Sea, could believe us? On this tour that is completely possible! Adventure with us through the coast of the Cozumel Island, visit three of th... More
Private Tour

Live this unique snorkeling experience. El Cielo in Cozumel a mag....
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North America
If we tell you that you can be near the sky while you are at the paradisiacal Caribbean Sea, could b....
Private Tour
Private Sunset Sailing
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
Private Tour

Private Sunset Sailing
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North America
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Superb1 review5
A private and exclusive Sunset Sailing Adventure discovering a Sunset that will never repeat. Premiu....
Private Tour
2hr Luxury Private Sailing Catamaran for 7-12 People
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
Private Tour

2hr Luxury Private Sailing Catamaran for 7-12 People
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North America
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Superb1 review5
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
Aloha Wednesday Sunset Sail - Drinks Included - Lux Catamaran
Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha Wednesday Sunset Sail. This midweek escape combines tropical charm with st... More
Private Tour

Aloha Wednesday Sunset Sail - Drinks Included - Lux Catamaran
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North America
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Superb2 reviews5
Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit....
Private Tour
Sailing Adventures 3-Hour Activity in Destin
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
Private Tour

Sailing Adventures 3-Hour Activity in Destin
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North America
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Superb4 reviews5
There’s nothing like seeing the clear emerald waters pass under the hull while sailing on the Stil....
Private Tour
Private Sunset Sail of NYC Skyline and Statue of Liberty
Discover NYC from a completely different perspective on a private sailboat charter during sunset hours when the views are even more spectacular. You and your group will view New York City in ways that are breath taking. See the St... More
Private Tour

Private Sunset Sail of NYC Skyline and Statue of Liberty
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North America
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Superb2 reviews5
Discover NYC from a completely different perspective on a private sailboat charter during sunset hou....
Private Tour