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Top 10 Best North America Sailing Trips

Found 687 Sailing Trips activities in North America. Sort by Popularity. - Page 7
 

Mexico City: Xochimilco at sunrise + Breakfast and transportation

(5 of 65 reviews)

Navigating through the channels of Xochimilco while the sun rises behind living volcanoes is an activity that can only be experienced in Xochimilco Mexico, and doing it by experts committed to sustainability and history makes it a... More

Free Cancellation
Start From $147.39
 
Mexico City: Xochimilco at sunrise + Breakfast and transportation

Mexico City: Xochimilco at sunrise + Breakfast and transportation

  • North America
  • Superb65 reviews5

Navigating through the channels of Xochimilco while the sun rises behind living volcanoes is an acti....

    Free Cancellation
    Start From $147.39
 
 

Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar

(4.7 of 63 reviews)

*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting from our crew who will provide you with unmatched service throughout the excursion. *Take a moment for a photo opportunity with y... More

Free Cancellation
Start From $109.00
 
Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar Likely to Sell Out

Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open....

  • North America
  • Superb63 reviews4.7

*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting ....

    Free Cancellation
    Start From $109.00
 
 

Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience

(5 of 509 reviews)

Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own private catamaran. Complete with a professional captain & crew , your group will enjoy spacious accommodations and a premium, pers... More

Free Cancellation
Private Tour
Start From $2,200.00
 
Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience Likely to Sell Out

Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience

  • North America
  • Superb509 reviews5

Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own ....

    Free Cancellation
    Private Tour
    Start From $2,200.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 223 reviews)

A three hour tour you won't want to miss! 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 adve... More

Free Cancellation
Private Tour
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb223 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....

    Free Cancellation
    Private Tour
    Start From $136.19
 
 

Pau Hana Sunset Cocktail Cruise

(4.8 of 48 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed catamaran. This cruise includes unlimited soft drinks, tropical juices, beers, wines, cocktails and a variety of appetizers.. Great f... More

Free Cancellation
Private Tour
Start From $165.00
 
Pau Hana Sunset Cocktail Cruise Likely to Sell Out

Pau Hana Sunset Cocktail Cruise

  • North America
  • Superb48 reviews4.8

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed cat....

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

Molokini Snorkel and Performance Sail from Ma'alaea Harbor

(4.9 of 198 reviews)

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More

Free Cancellation
Private Tour
Start From $200.00
 
Molokini Snorkel and Performance Sail from Ma'alaea Harbor Likely to Sell Out

Molokini Snorkel and Performance Sail from Ma'alaea Harbor

  • North America
  • Superb198 reviews4.9

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....

    Free Cancellation
    Private Tour
    Start From $200.00
 
 

Polynesian Canoe Sunset Sail

(4.9 of 118 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Special Offer
Free Cancellation
Private Tour
Start From $225.00
(Saving 10% ) $250.00
 
-10% Polynesian Canoe Sunset Sail Likely to Sell Out

Polynesian Canoe Sunset Sail

  • North America
  • Superb118 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $225.00
    (Saving 10% ) $250.00
 
 

Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres

(4.4 of 286 reviews)

Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a delicious drink and the entertainment from the crew. Unique and quality service is our priority. We are sure that you will love all... More

Free Cancellation
Private Tour
Start From $62.00
 
Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres Likely to Sell Out

Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres

  • North America
  • Exellent286 reviews4.4

Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a d....

    Free Cancellation
    Private Tour
    Start From $62.00
 
 

Visit Private Beaches around Puerto Vallarta in a Private Yacht

(5 of 81 reviews)

Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours don’t go. Also enjoy the explanation from our captain on the art of sailing. This is not a boat trip, this is an experience to enj... More

Free Cancellation
Private Tour
Start From $1,500.00
 
Visit Private Beaches around Puerto Vallarta in a Private Yacht Likely to Sell Out

Visit Private Beaches around Puerto Vallarta in a Private Yacht

  • North America
  • Superb81 reviews5

Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours do....

    Free Cancellation
    Private Tour
    Start From $1,500.00
 
 

Mangrove Kayak + Snorkel & Sunset Sail hosted by Honest Eco

(5 of 150 reviews)

I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world with a blue sea too alluring to ignore. I arrived to Key West in 2005. Now I have 10+ years of experience studying Biology and bein... More

Free Cancellation
Private Tour
Start From $156.00
 
Mangrove Kayak + Snorkel & Sunset Sail hosted by Honest Eco Likely to Sell Out

Mangrove Kayak + Snorkel & Sunset Sail hosted by Honest Eco

  • North America
  • Superb150 reviews5

I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world w....

    Free Cancellation
    Private Tour
    Start From $156.00
 
 

Sailing Tour through the Lagoon of the 7 Colors

(4.9 of 996 reviews)

Sail with people who share your passion for adventure! You will explore fascinating places along the lagoon of the 7 colors. Our small groups guarantee you excellent attention and service from our crew. Disconnect from the world ... More

Free Cancellation
Private Tour
Start From $36.00
 
Sailing Tour through the Lagoon of the 7 Colors Likely to Sell Out

Sailing Tour through the Lagoon of the 7 Colors

  • North America
  • Superb996 reviews4.9

Sail with people who share your passion for adventure! You will explore fascinating places along the....

    Free Cancellation
    Private Tour
    Start From $36.00
 
 

Sightseeing Day Sail around Boston Harbor

(4.7 of 382 reviews)

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport district, Castle... More

Free Cancellation
Private Tour
Start From $66.54
 
Sightseeing Day Sail around Boston Harbor Likely to Sell Out

Sightseeing Day Sail around Boston Harbor

  • North America
  • Superb382 reviews4.7

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner....

    Free Cancellation
    Private Tour
    Start From $66.54
 
 

Sailing Charters in Wilmington

(5 of 145 reviews)

After a successful first season I am happy to be here for back to back seasons. Sail in style on the historic Wilmington river walk. Enjoy a personalized Charter experience with up to six guests. Very few sailboats are up for publ... More

Free Cancellation
Private Tour
Start From $89.99
 
Sailing Charters in Wilmington Likely to Sell Out

Sailing Charters in Wilmington

  • North America
  • Superb145 reviews5

After a successful first season I am happy to be here for back to back seasons. Sail in style on the....

    Free Cancellation
    Private Tour
    Start From $89.99
 
 

Windjammer Classic Sunset Sail from Camden, Maine

(4.9 of 332 reviews)

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More

Free Cancellation
Private Tour
Start From $64.95
 
Windjammer Classic Sunset Sail from Camden, Maine Likely to Sell Out

Windjammer Classic Sunset Sail from Camden, Maine

  • North America
  • Superb332 reviews4.9

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....

    Free Cancellation
    Private Tour
    Start From $64.95
 
 

Sailing Tour through the Laguna de los Siete Colores

(5 of 1,324 reviews)

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

Free Cancellation
Private Tour
Start From $38.00
 
Sailing Tour through the Laguna de los Siete Colores Likely to Sell Out

Sailing Tour through the Laguna de los Siete Colores

  • North America
  • Superb1,324 reviews5

Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, b....

    Free Cancellation
    Private Tour
    Start From $38.00
 
 

Afternoon Half-Day Catmaran Sailing and Snorkel Adventure

(4.5 of 70 reviews)

Want to enjoy a sailing tour, where you can snorkel and visit Isla Mujeres in just half a day? This is the tour for you! Enjoy sailing in one of our Catamarans and we will ensure that you enjoy your afternoon to the maximum. We wi... More

Free Cancellation
Private Tour
Start From $69.99
 
Afternoon Half-Day Catmaran Sailing and Snorkel Adventure Likely to Sell Out

Afternoon Half-Day Catmaran Sailing and Snorkel Adventure

  • North America
  • Exellent70 reviews4.5

Want to enjoy a sailing tour, where you can snorkel and visit Isla Mujeres in just half a day? This ....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

2.5-hour Guided Sailboat Tour

(4.9 of 164 reviews)

2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, 159 Bridge Park Drive. Views of the Brooklyn Bridge, Statue of Liberty, World Trade Center, Ellis Island, Governor's Island and M... More

Free Cancellation
Private Tour
Start From $118.00
 
2.5-hour Guided Sailboat Tour Likely to Sell Out

2.5-hour Guided Sailboat Tour

  • North America
  • Superb164 reviews4.9

2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, ....

    Free Cancellation
    Private Tour
    Start From $118.00
 
 

Reef Snorkel, underwater adventure in Puerto Morelos With Transportation & Lunch

(4 of 3 reviews)

Snorkel activity in a caribbean reef. Amazing sightseeing and shore excursion. This is consider a must activity in Cancun. You will visit one of the most bigger reef in the world, this is consider as the 2nd one worldwide. Imagi... More

Free Cancellation
Private Tour
Start From $55.00
 
Reef Snorkel, underwater adventure in Puerto Morelos With Transportation & Lunch Likely to Sell Out

Reef Snorkel, underwater adventure in Puerto Morelos With Transpo....

  • North America
  • Very Good3 reviews4

Snorkel activity in a caribbean reef. Amazing sightseeing and shore excursion. This is consider a mu....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Suncoast Sailing's Sunset Sailing Experience!

(4.9 of 220 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
  • Superb220 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
 
 

Luxury Catamaran Sailing Charters in Maine

(4.9 of 85 reviews)

Sail in luxury on a 44-ft catamaran yacht! We are one of the only sailing catamaran charters in Maine, and our luxurious yacht makes for a relaxing and fun experience. Our catamaran is stable and does not bounce in waves, providin... More

Free Cancellation
Private Tour
Start From $135.00
 
Luxury Catamaran Sailing Charters in Maine Likely to Sell Out

Luxury Catamaran Sailing Charters in Maine

  • North America
  • Superb85 reviews4.9

Sail in luxury on a 44-ft catamaran yacht! We are one of the only sailing catamaran charters in Main....

    Free Cancellation
    Private Tour
    Start From $135.00
 
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