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Top 10 Best North America Sailing Trips

Found 755 Sailing Trips activities in North America. Sort by Popularity. - Page 10
 

Private Yacht Charter in Cabo San Lucas – Cruise to The Arch

(5 of 1 review)

Enjoy a private yachting experience in Cabo San Lucas without committing to a full-day tour. Perfect for couples, families, or small groups, this 2-hour cruise offers front-row views of El Arco, Lover’s Beach, and local sea lion... More

Free Cancellation
Private Tour
Start From $1,150.00
 
Private Yacht Charter in Cabo San Lucas – Cruise to The Arch Likely to Sell Out

Private Yacht Charter in Cabo San Lucas – Cruise to The Arch

  • North America
  • Superb1 review5

Enjoy a private yachting experience in Cabo San Lucas without committing to a full-day tour. Perfect....

    Free Cancellation
    Private Tour
    Start From $1,150.00
 
 

Private Guided Sunset and Eco Tour up to 6 Passengers

(5 of 75 reviews)

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a cooler with bottled water a... More

Free Cancellation
Private Tour
Start From $249.99
 
Private Guided Sunset and Eco Tour up to 6 Passengers Likely to Sell Out

Private Guided Sunset and Eco Tour up to 6 Passengers

  • North America
  • Superb75 reviews5

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....

    Free Cancellation
    Private Tour
    Start From $249.99
 
 

Experience Oceanside Sailing with Whales and dolphins!

(5 of 18 reviews)

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and most comfortable sailboats in the Oceanside harbor. We cater to guests from many of the five star hotels in the area. We serve an up... More

Free Cancellation
Private Tour
Start From $160.00
 
Experience Oceanside Sailing with Whales and dolphins! Likely to Sell Out

Experience Oceanside Sailing with Whales and dolphins!

  • North America
  • Superb18 reviews5

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and mo....

    Free Cancellation
    Private Tour
    Start From $160.00
 
 

Suncoast Sailing's Day Sailing Experience!

(4.9 of 112 reviews)

Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. Just wind in the sails, salt in the air, and the kind of quiet glide across t... More

Free Cancellation
Private Tour
Start From $64.99
 
Suncoast Sailing's Day Sailing Experience! Likely to Sell Out

Suncoast Sailing's Day Sailing Experience!

  • North America
  • Superb112 reviews4.9

Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to fe....

    Free Cancellation
    Private Tour
    Start From $64.99
 
 

Luxury Snorkel Adventure in Cabo

(4.8 of 55 reviews)

Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located at Santa Maria Bay or Chileno Bay, at either one of this beach areas is where boat captain will make a stop for snorkeling at one ... More

Free Cancellation
Private Tour
Start From $149.00
 
Luxury Snorkel Adventure in Cabo Likely to Sell Out

Luxury Snorkel Adventure in Cabo

  • North America
  • Superb55 reviews4.8

Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located ....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Portland Tall Ship Cruise on Casco Bay

(4.5 of 235 reviews)

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.... More

Free Cancellation
Private Tour
Start From $101.79
 
Portland Tall Ship Cruise on Casco Bay Likely to Sell Out

Portland Tall Ship Cruise on Casco Bay

  • North America
  • Exellent235 reviews4.5

What better way to see the delights of Portland than from the sea in one of the famous schooner tall....

    Free Cancellation
    Private Tour
    Start From $101.79
 
 

Sailing Charters in Wilmington

(5 of 187 reviews)

After a successful first three seasons I am happy to be here for a fourth season!!! 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 ... More

Free Cancellation
Private Tour
Start From $89.00
 
Sailing Charters in Wilmington Likely to Sell Out

Sailing Charters in Wilmington

  • North America
  • Superb187 reviews5

After a successful first three seasons I am happy to be here for a fourth season!!! Sail in style on....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Catamaran Sailing Cruise in Monterey

(4.8 of 35 reviews)

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind to make for a peaceful and exciting cruise on the bay. On the way out of t... More

Free Cancellation
Private Tour
Start From $65.00
 
Catamaran Sailing Cruise in Monterey Likely to Sell Out

Catamaran Sailing Cruise in Monterey

  • North America
  • Superb35 reviews4.8

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage af....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Best of Halifax Harbour Boat Tour

(4.9 of 77 reviews)

This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside our Captain and Deckhand throughout the relaxed harbour tour as they share Halifax's history and present day facts!... More

Free Cancellation
Private Tour
Start From $44.07
 
Best of Halifax Harbour Boat Tour Likely to Sell Out

Best of Halifax Harbour Boat Tour

  • North America
  • Superb77 reviews4.9

This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside ....

    Free Cancellation
    Private Tour
    Start From $44.07
 
 

Chacahua Afternoon Journey

(4.8 of 47 reviews)

As a team we try to create journeys that are worth investing your time and confidence. We try to do our best to get out of the same schedules that our fellow colleagues offer this tour is whole afternoon experience that show us al... More

Free Cancellation
Private Tour
Start From $88.82
 
Chacahua Afternoon Journey Likely to Sell Out

Chacahua Afternoon Journey

  • North America
  • Superb47 reviews4.8

As a team we try to create journeys that are worth investing your time and confidence. We try to do ....

    Free Cancellation
    Private Tour
    Start From $88.82
 
 

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

(4.8 of 217 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: Mā’alaea Harbor Likely to Sell Out

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

  • North America
  • Superb217 reviews4.8

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
 
 

Private Kelowna Sailing Cruise on Okanagan Lake

(5 of 42 reviews)

Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are welcome to sit back and relax, enjoy the sights, or take a turn at the helm, with instruction from your skipper! I will never forg... More

Free Cancellation
Private Tour
Start From $123.26
 
Private Kelowna Sailing Cruise on Okanagan Lake Likely to Sell Out

Private Kelowna Sailing Cruise on Okanagan Lake

  • North America
  • Superb42 reviews5

Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are w....

    Free Cancellation
    Private Tour
    Start From $123.26
 
 

Halifax Sunset Cruise Ft. a Live Musician

(4.7 of 47 reviews)

Experience golden hour, that magical time of night when the sun makes its way below the horizon, on the Halifax Sunset Cruise aboard our signature ship, the Tall Ship Silva. Purchase wine, beer, cocktails, and other beverages from... More

Free Cancellation
Private Tour
Start From $41.24
 
Halifax Sunset Cruise Ft. a Live Musician Likely to Sell Out

Halifax Sunset Cruise Ft. a Live Musician

  • North America
  • Superb47 reviews4.7

Experience golden hour, that magical time of night when the sun makes its way below the horizon, on ....

    Free Cancellation
    Private Tour
    Start From $41.24
 
 

2-Hour Private Sailing Experience in San Diego Bay

(5 of 171 reviews)

Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing to obtain in today's world. With all the stress life brings we are happy to provide a peacefu... More

Free Cancellation
Private Tour
Start From $675.00
 
2-Hour Private Sailing Experience in San Diego Bay Likely to Sell Out

2-Hour Private Sailing Experience in San Diego Bay

  • North America
  • Superb171 reviews5

Our unique sail displays a peace sign because that is exactly what we share with our customers, peac....

    Free Cancellation
    Private Tour
    Start From $675.00
 
 

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

(4.9 of 101 reviews)

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands... More

Free Cancellation
Private Tour
Start From $119.00
 
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak Likely to Sell Out

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

  • North America
  • Superb101 reviews4.9

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authent....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Sailing Tour through the Lagoon of the 7 Colors

(4.9 of 1,180 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 $39.98
 
Sailing Tour through the Lagoon of the 7 Colors Likely to Sell Out

Sailing Tour through the Lagoon of the 7 Colors

  • North America
  • Superb1,180 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $39.98
 
 

Boat Fishing Tour, Puerto Morelos CIPREA, 25'

(5 of 2 reviews)

We are a team with 20 years of experience in sport fishing tour only. Newbies and experts are welcome. Come and enjoy the beauties of the Caribbean Sea, the setting where we fish We have the best boats in Puerto Morelos. Come an... More

Free Cancellation
Private Tour
Start From $313.83
 
Boat Fishing Tour, Puerto Morelos CIPREA, 25' Likely to Sell Out

Boat Fishing Tour, Puerto Morelos CIPREA, 25'

  • North America
  • Superb2 reviews5

We are a team with 20 years of experience in sport fishing tour only. Newbies and experts are welco....

    Free Cancellation
    Private Tour
    Start From $313.83
 
 

Private sailing tour of Bacalar Lagoon

(5 of 435 reviews)

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a delicious fruit cocktail, water and beer. Our certified guides will make this tour an unfo... More

Free Cancellation
Private Tour
Start From $215.00
 
Private sailing tour of Bacalar Lagoon Likely to Sell Out

Private sailing tour of Bacalar Lagoon

  • North America
  • Superb435 reviews5

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper ....

    Free Cancellation
    Private Tour
    Start From $215.00
 
 

Windjammer Classic Day Sail from Camden, Maine

(4.8 of 407 reviews)

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations on a modern windjammer. With wide ... More

Free Cancellation
Private Tour
Start From $59.95
 
Windjammer Classic Day Sail from Camden, Maine Likely to Sell Out

Windjammer Classic Day Sail from Camden, Maine

  • North America
  • Superb407 reviews4.8

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Los Cabos Sunset Sailing Adventure

(5 of 1 review)

Experience a breathtaking sunset sail on the Cabo San Lucas Bay aboard a luxury catamaran, complete with delicious appetizers and an international open bar. After being picked up from your hotel, embark from the Cabo San Lucas Mar... More

Free Cancellation
Private Tour
Start From $119.00
 
Los Cabos Sunset Sailing Adventure Likely to Sell Out

Los Cabos Sunset Sailing Adventure

  • North America
  • Superb1 review5

Experience a breathtaking sunset sail on the Cabo San Lucas Bay aboard a luxury catamaran, complete ....

    Free Cancellation
    Private Tour
    Start From $119.00
 
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