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Top 10 Best North America Sailing Trips

Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 4
 

Two Hour Coastal Sailing Cruise

(5 of 26 reviews)

What makes this tour unique is the custom experience aboard our 43-foot, 27-foot wide trimaran—one of the largest and most stable sailing vessels in Savannah. Unlike crowded tour boats, our open-deck layout offers plenty of room... More

Free Cancellation
Start From $124.99
 
Two Hour Coastal Sailing Cruise

Two Hour Coastal Sailing Cruise

  • North America
  • Superb26 reviews5

What makes this tour unique is the custom experience aboard our 43-foot, 27-foot wide trimaran—one....

    Free Cancellation
    Start From $124.99
 
 

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

(4.9 of 958 reviews)

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Incl... More

Free Cancellation
Start From $108.91
 
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

  • North America
  • Superb958 reviews4.9

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....

    Free Cancellation
    Start From $108.91
 
 

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

(4.8 of 45 reviews)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More

Free Cancellation
Start From $289.00
 
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

  • North America
  • Superb45 reviews4.8

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....

    Free Cancellation
    Start From $289.00
 
 

Key West Sailing & Snorkeling: A Reef Adventure

(4.8 of 186 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
Start From $79.00
 
Key West Sailing & Snorkeling: A Reef Adventure

Key West Sailing & Snorkeling: A Reef Adventure

  • North America
  • Superb186 reviews4.8

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

    Free Cancellation
    Start From $79.00
 
 

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

(4.8 of 214 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
Start From $200.00
 
Molokini Snorkel and Performance Sail: Mā’alaea Harbor

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

  • North America
  • Superb214 reviews4.8

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

    Free Cancellation
    Start From $200.00
 
 
-15% Deluxe Sunset & Day Sail Small Group

Deluxe Sunset & Day Sail Small Group

(5 of 247 reviews)

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as the sky transforms into a masterpiece of color. Keep an eye out for playfu... More

Special Offer
Free Cancellation
Start From $101.15
(Saving 15% ) $119.00
 
-15% Deluxe Sunset & Day Sail Small Group

Deluxe Sunset & Day Sail Small Group

  • North America
  • Superb247 reviews5

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....

    Special Offer
    Free Cancellation
    Start From $101.15
    (Saving 15% ) $119.00
 
 

Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music

(4.6 of 107 reviews)

Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. In Cancun, you have an incredible opportunity to fall in love again at the rhythm of the live sax with a sunset as enchanting as t... More

Free Cancellation
Start From $95.00
 
Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music Likely to Sell Out

Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music

  • North America
  • Superb107 reviews4.6

Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. ....

    Free Cancellation
    Start From $95.00
 
 

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

(4.9 of 445 reviews)

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay for over 15 years, just for the fun of it. We started this eco-tour in 2018 to share the ama... More

Free Cancellation
Start From $129.00
 
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling Likely to Sell Out

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

  • North America
  • Superb445 reviews4.9

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....

    Free Cancellation
    Start From $129.00
 
 

Private 6 Hrs 47 ft. Catamaran Snorkel & Cielo Charter (30p. max)

(4.8 of 20 reviews)

Sail in style aboard Cozumel’s largest and most spacious catamaran—a 47ft Nautitech—on an unforgettable journey to the famous El Cielo sandbar! Just 5–10 minutes by taxi from any cruise terminal or downtown, enjoy award-wi... More

Free Cancellation
Private Tour
Start From $1,998.65
 
Private 6 Hrs 47 ft. Catamaran Snorkel & Cielo Charter (30p. max) Likely to Sell Out

Private 6 Hrs 47 ft. Catamaran Snorkel & Cielo Charter (30p. max)

  • North America
  • Superb20 reviews4.8

Sail in style aboard Cozumel’s largest and most spacious catamaran—a 47ft Nautitech—on an unfo....

    Free Cancellation
    Private Tour
    Start From $1,998.65
 
 

Waikiki Sunset Boat Cruise

(4.9 of 104 reviews)

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More

Free Cancellation
Private Tour
Start From $50.00
 
Waikiki Sunset Boat Cruise Likely to Sell Out

Waikiki Sunset Boat Cruise

  • North America
  • Superb104 reviews4.9

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....

    Free Cancellation
    Private Tour
    Start From $50.00
 
 

Key West Reef Snorkel & Sail Adventure

(4.7 of 541 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 $79.00
 
Key West Reef Snorkel & Sail Adventure Likely to Sell Out

Key West Reef Snorkel & Sail Adventure

  • North America
  • Superb541 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 $79.00
 
 

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

(4.4 of 372 reviews)

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant sailing experience. Guests board a spacious Fury Catamaran, part of the largest luxury fleet in the Florida Keys, and sail to North Ame... More

Free Cancellation
Private Tour
Start From $59.95
 
Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail Likely to Sell Out

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

  • North America
  • Exellent372 reviews4.4

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.8 of 173 reviews)

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views ... More

Free Cancellation
Private Tour
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks Likely to Sell Out

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • North America
  • Superb173 reviews4.8

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....

    Free Cancellation
    Private Tour
    Start From $61.50
 
 

2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

(5 of 111 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pal... More

Free Cancellation
Private Tour
Start From $69.00
 
2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only) Likely to Sell Out

2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

  • North America
  • Superb111 reviews5

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....

    Free Cancellation
    Private Tour
    Start From $69.00
 
 

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

(3.7 of 206 reviews)

Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the best reefs and see beautiful tropical fish. Enjoy a delicious buffet lunch on our private beach club, and then tour Isla Mujeres to s... More

Free Cancellation
Private Tour
Start From $69.99
 
Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar Likely to Sell Out

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

  • North America
  • Very Good206 reviews3.7

Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the bes....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

(4.9 of 166 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
Private Tour
Start From $79.50
 
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans Likely to Sell Out

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

  • North America
  • Superb166 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $79.50
 
 

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

(5 of 30 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pals on ou... More

Free Cancellation
Private Tour
Start From $89.00
 
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise Likely to Sell Out

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

  • North America
  • Superb30 reviews5

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get so....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

El Cielo Cozumel Snorkeling trip by Catamaran

(4.4 of 279 reviews)

TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnificent reefs and great snorkeling and after, head back to a secluded Beach to relax and enjoy the beauty of Cozumel turquoise waters.... More

Free Cancellation
Private Tour
Start From $95.00
 
El Cielo Cozumel Snorkeling trip by Catamaran Likely to Sell Out

El Cielo Cozumel Snorkeling trip by Catamaran

  • North America
  • Exellent279 reviews4.4

TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnific....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Akialoa Mā’alaea Sunset Sail

(4.5 of 8 reviews)

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque inter-island channel, showcasing the beauty of Maui, Lāna‘i, and Kah... More

Free Cancellation
Private Tour
Start From $108.11
 
Akialoa Mā’alaea Sunset Sail Likely to Sell Out

Akialoa Mā’alaea Sunset Sail

  • North America
  • Exellent8 reviews4.5

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sun....

    Free Cancellation
    Private Tour
    Start From $108.11
 
 

Private Sailboat tour in Cabo San Lucas with Papillon Yachts

(5 of 199 reviews)

Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care of you to make this an unforgettable experience. Our all-inclusive and all-private tour will make sure you have everything you need... More

Free Cancellation
Private Tour
Start From $800.00
 
Private Sailboat tour in Cabo San Lucas with Papillon Yachts Likely to Sell Out

Private Sailboat tour in Cabo San Lucas with Papillon Yachts

  • North America
  • Superb199 reviews5

Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care o....

    Free Cancellation
    Private Tour
    Start From $800.00
 
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