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Top 10 Best North America Sailing Trips

Found 668 Sailing Trips activities in North America. Sort by Popularity. - Page 7
 

Sunset Sail On A Charming Vintage Yacht - Beer &. Wine Included

(4.9 of 287 reviews)

Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica of a 1904 gaff rigged friendship sloop. She is an elegant sight under sail, featuring; highly finished woodwork, bronze fixtures, a... More

Free Cancellation
Start From $125.00
 
 Sunset Sail On A Charming Vintage Yacht - Beer &. Wine Included

Sunset Sail On A Charming Vintage Yacht - Beer &. Wine Included

  • North America
  • Superb287 reviews4.9

Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica o....

    Free Cancellation
    Start From $125.00
 
 

Suncoast Sailing's Sunset Sailing Experience!

(4.9 of 221 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
Start From $64.99
 
Suncoast Sailing's Sunset Sailing Experience!

Suncoast Sailing's Sunset Sailing Experience!

  • North America
  • Superb221 reviews4.9

Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....

    Free Cancellation
    Start From $64.99
 
 

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

(4.7 of 12 reviews)

Join us on Cozumel's largest and most luxurious catamaran with the First Lady Charters Team! Embark on a guided snorkeling tour at Cozumel's renowned Marine Park Reef, with all necessary snorkeling gear provided in different sizes... More

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

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

  • North America
  • Superb12 reviews4.7

Join us on Cozumel's largest and most luxurious catamaran with the First Lady Charters Team! Embark ....

    Free Cancellation
    Private Tour
    Start From $1,998.65
 
 

El Cielo Cozumel Snorkeling by Catamaran

(4.4 of 273 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 $110.00
 
El Cielo Cozumel Snorkeling by Catamaran

El Cielo Cozumel Snorkeling by Catamaran

  • North America
  • Exellent273 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 $110.00
 
 

2-Hour Seattle Sailing Harbor Tour

(4.7 of 374 reviews)

Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing tour is family-friendly and is an excellent way to see the Seattle skyline, the beauty of the Puget Sound, even mountain views! We ... More

Free Cancellation
Private Tour
Start From $45.00
 
2-Hour Seattle Sailing Harbor Tour

2-Hour Seattle Sailing Harbor Tour

  • North America
  • Superb374 reviews4.7

Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing t....

    Free Cancellation
    Private Tour
    Start From $45.00
 
 

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

(5 of 27 reviews)

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor for over 12 years, our sailing yachts are the highest quality and op... More

Free Cancellation
Private Tour
Start From $599.00
 
Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

  • North America
  • Superb27 reviews5

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

Half Day Luxury Sailing Experience in Riviera Maya with Open Bar

(4.4 of 60 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 Riviera Maya with Open Bar

Half Day Luxury Sailing Experience in Riviera Maya with Open Bar

  • North America
  • Exellent60 reviews4.4

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
 
 

Sunset Sail Aboard the 47 ft Daydreams Sailboat

(4.8 of 12 reviews)

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the way. Wit... More

Free Cancellation
Private Tour
Start From $99.00
 
Sunset Sail Aboard the 47 ft Daydreams Sailboat

Sunset Sail Aboard the 47 ft Daydreams Sailboat

  • North America
  • Superb12 reviews4.8

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Gran....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Boat Tour and Snorkel at Pelican Rock

(4.3 of 12 reviews)

The must do activities in Cabo are tour the arch, whale watching and snorkeling. We have put all of those things in one spot in this bucket list level experience. First take a boat tour of all of the landmarks Cabo boasts on the w... More

Free Cancellation
Private Tour
Start From $79.00
 
Boat Tour and Snorkel at Pelican Rock

Boat Tour and Snorkel at Pelican Rock

  • North America
  • Exellent12 reviews4.3

The must do activities in Cabo are tour the arch, whale watching and snorkeling. We have put all of ....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

(3.7 of 201 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

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

  • North America
  • Very Good201 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
 
 

Private Sailing Tour through the Ten Thousands Islands

(4.9 of 140 reviews)

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos where built in the early 80s and are known through out the sailing community as the fastest, driest, beachable catamaran on the ma... More

Free Cancellation
Private Tour
Start From $440.00
 
Private Sailing Tour through the Ten Thousands Islands Likely to Sell Out

Private Sailing Tour through the Ten Thousands Islands

  • North America
  • Superb140 reviews4.9

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos ....

    Free Cancellation
    Private Tour
    Start From $440.00
 
 

Luxury Catamaran Whale Watch

(5 of 39 reviews)

Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback whale. The waters off West Maui have long been the favored vacation spot of these massive marine mammals. The Alii Class Yachts pro... More

Free Cancellation
Private Tour
Start From $159.00
 
Luxury Catamaran Whale Watch Likely to Sell Out

Luxury Catamaran Whale Watch

  • North America
  • Superb39 reviews5

Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback w....

    Free Cancellation
    Private Tour
    Start From $159.00
 
 

4-Hour St. Pete Pier to Egmont Key Experience by Ferry

(4.7 of 289 reviews)

From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stunning Sunshine Skyway bridge and perhaps see a dolphin or two! This is the only charter offering service from downtown St. Petersb... More

Free Cancellation
Private Tour
Start From $66.67
 
4-Hour St. Pete Pier to Egmont Key Experience by Ferry Likely to Sell Out

4-Hour St. Pete Pier to Egmont Key Experience by Ferry

  • North America
  • Superb289 reviews4.7

From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stu....

    Free Cancellation
    Private Tour
    Start From $66.67
 
 

Seattle's Best Private Sailing Adventure on the Puget Sound BYOB!

(5 of 104 reviews)

Escape the hustle and bustle of city life and embark on an exclusive 3-hour private sailing tour in the Puget Sound. This personalized voyage is designed for up to six passengers, offering an intimate and unforgettable experience ... More

Free Cancellation
Private Tour
Start From $549.00
 
Seattle's Best Private Sailing Adventure on the Puget Sound BYOB! Likely to Sell Out

Seattle's Best Private Sailing Adventure on the Puget Sound BYOB!

  • North America
  • Superb104 reviews5

Escape the hustle and bustle of city life and embark on an exclusive 3-hour private sailing tour in ....

    Free Cancellation
    Private Tour
    Start From $549.00
 
 

Small Group Waikiki Sunset Sailing Tour

(4.9 of 90 reviews)

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

Free Cancellation
Private Tour
Start From $99.00
 
Small Group Waikiki Sunset Sailing Tour Likely to Sell Out

Small Group Waikiki Sunset Sailing Tour

  • North America
  • Superb90 reviews4.9

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

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
 
 

Private Boat Tour Adventure in Miami Celeb Homes, Snorkeling, Fun

(4.7 of 56 reviews)

DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews on Google. What you will get: Nature Immersion: Encounter dolphins, turtles, manatees, and more as you explore Miami's waters Cel... More

Free Cancellation
Private Tour
Start From $65.00
 
Private Boat Tour Adventure in Miami Celeb Homes, Snorkeling, Fun Likely to Sell Out

Private Boat Tour Adventure in Miami Celeb Homes, Snorkeling, Fun

  • North America
  • Superb56 reviews4.7

DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews ....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Monterey Bay Whale Watching

(4.7 of 277 reviews)

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey Bay Canyon, one of the largest underwater canyons in the wor... More

Free Cancellation
Private Tour
Start From $69.95
 
Monterey Bay Whale Watching Likely to Sell Out

Monterey Bay Whale Watching

  • North America
  • Superb277 reviews4.7

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watchi....

    Free Cancellation
    Private Tour
    Start From $69.95
 
 

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

(4.9 of 11 reviews)

Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the flagship 420 Outrage a boat like no other. From the expansive bow with innovative seating galore, to the beautifully designed convert... More

Free Cancellation
Private Tour
Start From $284.09
 
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests Likely to Sell Out

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

  • North America
  • Superb11 reviews4.9

Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the fla....

    Free Cancellation
    Private Tour
    Start From $284.09
 
 

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

(4.8 of 22 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
Private Tour
Start From $289.00
 
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only) Likely to Sell Out

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

  • North America
  • Superb22 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $289.00
 
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