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Top 10 Best North America Sailing Trips

Found 727 Sailing Trips activities in North America. Sort by Popularity. - Page 2
 

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

(4.8 of 3,462 reviews)

Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time to hang out in the pristine water and take it easy aboard the sailboat – you can snorkel with tropical fish, stand atop a paddleb... More

Free Cancellation
Start From $149.00
 
Los Cabos Luxury Sailing, Snorkel and Lunch Cruise Likely to Sell Out

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

  • North America
  • Superb3,462 reviews4.8

Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time t....

    Free Cancellation
    Start From $149.00
 
 

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

(4.6 of 691 reviews)

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More

Free Cancellation
Start From $89.00
 
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas Likely to Sell Out

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

  • North America
  • Superb691 reviews4.6

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....

    Free Cancellation
    Start From $89.00
 
 

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club

(4.5 of 151 reviews)

Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among vibrant tropical fish, then relax on Playa Norte, one of Mexico's finest beaches. Departing from the pier, begin with a 30-minut... More

Free Cancellation
Start From $89.00
 
Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club Likely to Sell Out

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club

  • North America
  • Exellent151 reviews4.5

Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among ....

    Free Cancellation
    Start From $89.00
 
 

San Francisco Bay Cruise

(4.4 of 310 reviews)

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour excursion heads underneath the Golden Gate Bridge, around Alcatraz Island, past Angel Island State Park, and alongside the cit... More

Free Cancellation
Start From $39.00
 
San Francisco Bay Cruise Likely to Sell Out

San Francisco Bay Cruise

  • North America
  • Exellent310 reviews4.4

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hou....

    Free Cancellation
    Start From $39.00
 
 

Puerto Vallarta, Luxury Sunset Sailing

(4.6 of 404 reviews)

Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamarans. Relax and unwind as you enjoy delicious appetizers, a premium open bar, and top-tier service from our attentive crew. This i... More

Free Cancellation
Start From $99.00
 
Puerto Vallarta, Luxury Sunset Sailing Likely to Sell Out

Puerto Vallarta, Luxury Sunset Sailing

  • North America
  • Superb404 reviews4.6

Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamar....

    Free Cancellation
    Start From $99.00
 
 

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

(4.6 of 420 reviews)

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail along the stunning coastline of the Riviera Maya aboard a luxurious catamaran, while Mother Nature prepares for her nightly performan... More

Free Cancellation
Start From $109.00
 
Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar Likely to Sell Out

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

  • North America
  • Superb420 reviews4.6

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail alo....

    Free Cancellation
    Start From $109.00
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 816 reviews)

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More

Free Cancellation
Start From $202.59
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • North America
  • Superb816 reviews4.7

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....

    Free Cancellation
    Start From $202.59
 
 

Day's End Cocktail Sunset Sail

(4.7 of 66 reviews)

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s happy hour reimagined (a true ‘pau hana’ at sea) with handcrafted drin... More

Free Cancellation
Start From $159.00
 
Day's End Cocktail Sunset Sail Likely to Sell Out

Day's End Cocktail Sunset Sail

  • North America
  • Superb66 reviews4.7

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....

    Free Cancellation
    Start From $159.00
 
 

Private Catamaran Escape for 2–6 Guests – Celebrate Your Way”

(4.9 of 319 reviews)

Set sail on a one-of-a-kind ocean escape designed for small, meaningful moments. Whether you’re celebrating a bachelorette, a birthday, or simply enjoying time with your favorite people, this catamaran getaway for up to six gues... More

Free Cancellation
Private Tour
Start From $595.00
 
Private Catamaran Escape for 2–6 Guests – Celebrate Your Way” Likely to Sell Out

Private Catamaran Escape for 2–6 Guests – Celebrate Your Way....

  • North America
  • Superb319 reviews4.9

Set sail on a one-of-a-kind ocean escape designed for small, meaningful moments. Whether you’re ce....

    Free Cancellation
    Private Tour
    Start From $595.00
 
 

Sunset Sail in Key West with Beverages Included

(4.9 of 898 reviews)

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the... More

Free Cancellation
Private Tour
Start From $79.00
 
Sunset Sail in Key West with Beverages Included Likely to Sell Out

Sunset Sail in Key West with Beverages Included

  • North America
  • Superb898 reviews4.9

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

(4.9 of 825 reviews)

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985... More

Free Cancellation
Private Tour
Start From $44.99
 
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB Likely to Sell Out

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

  • North America
  • Superb825 reviews4.9

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....

    Free Cancellation
    Private Tour
    Start From $44.99
 
 

Leila Na Pali Sunset Dinner Sail

(4.7 of 519 reviews)

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will s... More

Free Cancellation
Private Tour
Start From $263.82
 
Leila Na Pali Sunset Dinner Sail Likely to Sell Out

Leila Na Pali Sunset Dinner Sail

  • North America
  • Superb519 reviews4.7

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....

    Free Cancellation
    Private Tour
    Start From $263.82
 
 

Waikiki Sunset Cocktail Sail with Open Bar

(4.8 of 547 reviews)

Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This lively evening cruise invites solo travelers and groups alike to unwind with unlimited drinks—including Maui Brewing beers, wine... More

Free Cancellation
Private Tour
Start From $84.77
 
Waikiki Sunset Cocktail Sail with Open Bar Likely to Sell Out

Waikiki Sunset Cocktail Sail with Open Bar

  • North America
  • Superb547 reviews4.8

Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This ....

    Free Cancellation
    Private Tour
    Start From $84.77
 
 

Luxury Catamaran Whale Watch

(4.9 of 54 reviews)

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

Free Cancellation
Private Tour
Start From $119.00
 
Luxury Catamaran Whale Watch Likely to Sell Out

Luxury Catamaran Whale Watch

  • North America
  • Superb54 reviews4.9

From December through April, the waters off Maui come alive with the sights and sounds of the majest....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Half-Day Luxury Sailing Experience in Tulum with Open Bar

(4.2 of 248 reviews)

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More

Free Cancellation
Private Tour
Start From $149.00
 
Half-Day Luxury Sailing Experience in Tulum with Open Bar Likely to Sell Out

Half-Day Luxury Sailing Experience in Tulum with Open Bar

  • North America
  • Exellent248 reviews4.2

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

St. Augustine Live Music Cruise with Drinks and Sunset Option

(4.8 of 310 reviews)

**45' Corinthian Power Catamaran will be operating this tour from January 13th - March 1st 2026.** Sailing Catamaran tours will resume on March 2nd. Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all ... More

Free Cancellation
Private Tour
Start From $69.17
 
St. Augustine Live Music Cruise with Drinks and Sunset Option Likely to Sell Out

St. Augustine Live Music Cruise with Drinks and Sunset Option

  • North America
  • Superb310 reviews4.8

**45' Corinthian Power Catamaran will be operating this tour from January 13th - March 1st 2026.** S....

    Free Cancellation
    Private Tour
    Start From $69.17
 
 

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

(4.9 of 808 reviews)

✨ Discover Los Cabos Like Never Before! Sail the turquoise waters of the Sea of Cortez on an unforgettable snorkeling, sightseeing and sailing adventure. Begin at Pelican’s Rock, dive into crystal-clear waters filled with hun... More

Free Cancellation
Private Tour
Start From $105.00
 
Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas Likely to Sell Out

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

  • North America
  • Superb808 reviews4.9

✨ Discover Los Cabos Like Never Before! Sail the turquoise waters of the Sea of Cortez on an unfor....

    Free Cancellation
    Private Tour
    Start From $105.00
 
 

Sunset Boat Cruise: Swim and Cruise Waikiki

(4.7 of 533 reviews)

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the ocean, with the iconic Waikiki coastline as your backdrop. As the sun begins to se... More

Free Cancellation
Private Tour
Start From $58.64
 
Sunset Boat Cruise: Swim and Cruise Waikiki Likely to Sell Out

Sunset Boat Cruise: Swim and Cruise Waikiki

  • North America
  • Superb533 reviews4.7

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....

    Free Cancellation
    Private Tour
    Start From $58.64
 
 

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

(4.8 of 2,234 reviews)

Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This romantic sunset cruise on Cabo San Lucas Bay includes unlimited drinks from an open bar, accompanied by a delightful menu of small b... More

Free Cancellation
Private Tour
Start From $109.00
 
Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar Likely to Sell Out

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

  • North America
  • Superb2,234 reviews4.8

Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This ro....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Cabo San Lucas Sunset Sailing Shared Cruise

(4.9 of 772 reviews)

Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated at night, and see the wonderful sunset contrasting with Cabo San Lucas amazing waters. This is a family-friendly tour and includes... More

Free Cancellation
Private Tour
Start From $105.00
 
Cabo San Lucas Sunset Sailing Shared Cruise Likely to Sell Out

Cabo San Lucas Sunset Sailing Shared Cruise

  • North America
  • Superb772 reviews4.9

Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated ....

    Free Cancellation
    Private Tour
    Start From $105.00
 
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