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Top 10 Best North America Sailing Trips

Found 725 Sailing Trips activities in North America. Sort by Popularity. - Page 13
 

Half Day Luxury Sailing Experience in Riviera Maya with Open Bar

(4.4 of 66 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
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
  • Exellent66 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
    Start From $149.00
 
 

Isla Mujeres Sailing Adventure from Cancun

(3.7 of 6 reviews)

Join the experience of sailing through the Mexican Caribbean Sea from Cancun to Isla Mujeres onboard of an exclusive catamaran...!! This tour is recommended for those who like to have fun, with music for all tastes and open-bar on... More

Free Cancellation
Start From $149.00
 
Isla Mujeres Sailing Adventure from Cancun

Isla Mujeres Sailing Adventure from Cancun

  • North America
  • Very Good6 reviews3.7

Join the experience of sailing through the Mexican Caribbean Sea from Cancun to Isla Mujeres onboard....

    Free Cancellation
    Start From $149.00
 
 
-15% Sailing Tour through the Lagoon of the 7 Colors

Sailing Tour through the Lagoon of the 7 Colors

(4.9 of 1,096 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

Special Offer
Free Cancellation
Start From $31.45
(Saving 15% ) $37.00
 
-15% Sailing Tour through the Lagoon of the 7 Colors

Sailing Tour through the Lagoon of the 7 Colors

  • North America
  • Superb1,096 reviews4.9

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

    Special Offer
    Free Cancellation
    Start From $31.45
    (Saving 15% ) $37.00
 
 

City Tour & Beach Club All Inclusive W Horse Ride & Water Sports

(3.3 of 3 reviews)

Experience the ultimate vacation with our all-inclusive tour! Sit back and relax as you are transported in a luxurious, air-conditioned vehicle, complete with complimentary beverages. Our tour includes visits to the stunning cathe... More

Free Cancellation
Start From $79.00
 
City Tour & Beach Club All Inclusive W Horse Ride & Water Sports

City Tour & Beach Club All Inclusive W Horse Ride & Water Sports

  • North America
  • Good3 reviews3.3

Experience the ultimate vacation with our all-inclusive tour! Sit back and relax as you are transpor....

    Free Cancellation
    Start From $79.00
 
 

Small-Group San Diego Afternoon Sailing Excursion

(5 of 525 reviews)

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends and fill up the whole boat!). Sit back, relax and enjoy the com... More

Free Cancellation
Start From $116.00
 
Small-Group San Diego Afternoon Sailing Excursion Likely to Sell Out

Small-Group San Diego Afternoon Sailing Excursion

  • North America
  • Superb525 reviews5

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing....

    Free Cancellation
    Start From $116.00
 
 

Sunset Sail Tour

(4.9 of 88 reviews)

Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, engage on this classic 42 ft yacht, that accommodates a 6 passenger maximum for an intimate cruise through the waters of Wrightsvill... More

Free Cancellation
Start From $125.00
 
Sunset Sail Tour Likely to Sell Out

Sunset Sail Tour

  • North America
  • Superb88 reviews4.9

Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, enga....

    Free Cancellation
    Start From $125.00
 
 

New York Fall Foliage Sail up the Hudson River

(4.5 of 8 reviews)

Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Schooner America 2.0, both 1800s-style sailboats. Bordering the Hudson River north of Fort Lee, New Jersey, the Palisade Cliffs are am... More

Free Cancellation
Start From $143.27
 
New York Fall Foliage Sail up the Hudson River Likely to Sell Out

New York Fall Foliage Sail up the Hudson River

  • North America
  • Exellent8 reviews4.5

Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Scho....

    Free Cancellation
    Start From $143.27
 
 

Schooner Clearwater- Sailing Cruise-Clearwater Beach

(4.9 of 217 reviews)

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Parti... More

Free Cancellation
Start From $85.00
 
Schooner Clearwater- Sailing Cruise-Clearwater Beach Likely to Sell Out

Schooner Clearwater- Sailing Cruise-Clearwater Beach

  • North America
  • Superb217 reviews4.9

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater wi....

    Free Cancellation
    Start From $85.00
 
 

New York City Sunset Sail to the Statue of Liberty

(4.9 of 65 reviews)

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic sailboat is 105-feet in length and has about 3600 square feet of sail ... More

Free Cancellation
Start From $90.12
 
New York City Sunset Sail to the Statue of Liberty Likely to Sell Out

New York City Sunset Sail to the Statue of Liberty

  • North America
  • Superb65 reviews4.9

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of B....

    Free Cancellation
    Start From $90.12
 
 

Casco Bay: Private Afternoon Charter on Heart's Desire

(4 of 1 review)

This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special event, or a family get-together that will never be forgotten. Ride aboard Heart's Desire: designed by famed yacht designer - John... More

Free Cancellation
Private Tour
Start From $575.00
 
Casco Bay: Private Afternoon Charter on Heart's Desire Likely to Sell Out

Casco Bay: Private Afternoon Charter on Heart's Desire

  • North America
  • Very Good1 review4

This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special ....

    Free Cancellation
    Private Tour
    Start From $575.00
 
 

Tulum: Snorkeling and Private Sailing Tour

(4.9 of 155 reviews)

We will enjoy a wonderful catamaran tour, powered only by the wind, we will be able to enjoy a spectacular view of the Tulum ruins from the sea... More

Free Cancellation
Private Tour
Start From $50.22
 
Tulum: Snorkeling and Private Sailing Tour Likely to Sell Out

Tulum: Snorkeling and Private Sailing Tour

  • North America
  • Superb155 reviews4.9

We will enjoy a wonderful catamaran tour, powered only by the wind, we will be able to enjoy a spect....

    Free Cancellation
    Private Tour
    Start From $50.22
 
 

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

(4.8 of 14 reviews)

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More

Free Cancellation
Private Tour
Start From $1,150.00
 
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People Likely to Sell Out

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

  • North America
  • Superb14 reviews4.8

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....

    Free Cancellation
    Private Tour
    Start From $1,150.00
 
 

Private Sunset Sail for 3-6 People

(4.7 of 12 reviews)

Experience a private group charter with up to six passengers while sailing along the San Diego Bay. If you’re looking for a night of family fun, or to celebrate with your friends look no further. Leave your worries behind as yo... More

Free Cancellation
Private Tour
Start From $776.00
 
Private Sunset Sail for 3-6 People Likely to Sell Out

Private Sunset Sail for 3-6 People

  • North America
  • Superb12 reviews4.7

Experience a private group charter with up to six passengers while sailing along the San Diego Bay.....

    Free Cancellation
    Private Tour
    Start From $776.00
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.8 of 58 reviews)

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More

Free Cancellation
Private Tour
Start From $179.00
 
Hawaiian Canoe Sailing Experience in Maui Likely to Sell Out

Hawaiian Canoe Sailing Experience in Maui

  • North America
  • Superb58 reviews4.8

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....

    Free Cancellation
    Private Tour
    Start From $179.00
 
 

2 Island Adventure: Contoy & Mujeres with Snorkeling & open bar

(4.3 of 6 reviews)

What makes this tour unique? Unlike most tours that visit only one island, our experience takes you to two stunning Caribbean islands in a single day—Isla Contoy, a protected ecological reserve with limited daily visitors, and t... More

Free Cancellation
Private Tour
Start From $80.00
 
2 Island Adventure: Contoy & Mujeres with Snorkeling & open bar Likely to Sell Out

2 Island Adventure: Contoy & Mujeres with Snorkeling & open bar

  • North America
  • Exellent6 reviews4.3

What makes this tour unique? Unlike most tours that visit only one island, our experience takes you ....

    Free Cancellation
    Private Tour
    Start From $80.00
 
 

San Diego Afternoon Sail

(5 of 9 reviews)

Join Captain Doyle for an unforgettable 2-hour sailing experience aboard our 35-foot sailboat, Luna. Enjoy wide-open views of the city's skyline and waterfront attractions as we sail among tall ships, mega-yachts, and military ves... More

Free Cancellation
Private Tour
Start From $120.00
 
San Diego Afternoon Sail Likely to Sell Out

San Diego Afternoon Sail

  • North America
  • Superb9 reviews5

Join Captain Doyle for an unforgettable 2-hour sailing experience aboard our 35-foot sailboat, Luna.....

    Free Cancellation
    Private Tour
    Start From $120.00
 
 

Waikiki small group turtle snorkeling & sailing

(5 of 78 reviews)

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of dawn during their Hawaiian vacation due to time zone changes. As we start out our tour from ... More

Free Cancellation
Private Tour
Start From $99.00
 
Waikiki small group turtle snorkeling & sailing Likely to Sell Out

Waikiki small group turtle snorkeling & sailing

  • North America
  • Superb78 reviews5

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Catamaran Sailing Cruise in Monterey

(4.7 of 27 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
  • Superb27 reviews4.7

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

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Private 2-Hour Sunset Sailing Tour on Lake Fairview

(5 of 32 reviews)

Sunset Sailing Tour in Orlando | The Perfect Date Night Experience! Looking for something different to do in Orlando besides theme parks? Escape the crowds and experience the hidden beauty of Central Florida with an unforgettabl... More

Special Offer
Free Cancellation
Private Tour
Start From $84.15
(Saving 15% ) $99.00
 
-15% Private 2-Hour Sunset Sailing Tour on Lake Fairview Likely to Sell Out

Private 2-Hour Sunset Sailing Tour on Lake Fairview

  • North America
  • Superb32 reviews5

Sunset Sailing Tour in Orlando | The Perfect Date Night Experience! Looking for something differen....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $84.15
    (Saving 15% ) $99.00
 
 

12pm Turtle Canyon Snorkel Adventure

(4.8 of 298 reviews)

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

Free Cancellation
Private Tour
Start From $84.77
 
12pm Turtle Canyon Snorkel Adventure Likely to Sell Out

12pm Turtle Canyon Snorkel Adventure

  • North America
  • Superb298 reviews4.8

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....

    Free Cancellation
    Private Tour
    Start From $84.77
 
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