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Top 10 Best North America Sailing Trips

Found 684 Sailing Trips activities in North America. Sort by Popularity. - Page 25
 

Private Sailing Tour -2 Hour (Up to 12 Passengers)

(3.5 of 2 reviews)

Christened in 1934, Cloudia is a beautifully restored, rare example of a classic Norwegian double ended ketch. Inspired by the original designs of famed naval architect Colin Archer (1832-1921), from Larvik, Norway, the Cloudia is... More

Free Cancellation
Private Tour
Start From $1,200.00
 
Private Sailing Tour -2 Hour (Up to 12 Passengers)

Private Sailing Tour -2 Hour (Up to 12 Passengers)

  • North America
  • Good2 reviews3.5

Christened in 1934, Cloudia is a beautifully restored, rare example of a classic Norwegian double en....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

Luxury Diamond Head Sunset Sail

(5 of 3 reviews)

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private 50' luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from... More

Free Cancellation
Private Tour
Start From $1,398.00
 
Luxury Diamond Head Sunset Sail

Luxury Diamond Head Sunset Sail

  • North America
  • Superb3 reviews5

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....

    Free Cancellation
    Private Tour
    Start From $1,398.00
 
 

3 Hour Luxury Private Sailing Catamaran for 7-12 People

(5 of 3 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 $1,995.00
 
3 Hour Luxury Private Sailing Catamaran for 7-12 People

3 Hour Luxury Private Sailing Catamaran for 7-12 People

  • North America
  • Superb3 reviews5

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

    Free Cancellation
    Private Tour
    Start From $1,995.00
 
 

BYOB Friday Night Fireworks Cruise

(4.2 of 5 reviews)

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More

Free Cancellation
Private Tour
Start From $138.95
 
BYOB Friday Night Fireworks Cruise

BYOB Friday Night Fireworks Cruise

  • North America
  • Exellent5 reviews4.2

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....

    Free Cancellation
    Private Tour
    Start From $138.95
 
 

2 hours - Private Sunset Sail along Historic Bay Front

(4.9 of 27 reviews)

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to assist in making your experience a wonder memory. This 2-hour sail gives passengers a ... More

Free Cancellation
Private Tour
Start From $795.00
 
2 hours - Private Sunset Sail along Historic Bay Front

2 hours - Private Sunset Sail along Historic Bay Front

  • North America
  • Superb27 reviews4.9

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our sta....

    Free Cancellation
    Private Tour
    Start From $795.00
 
 

90 Minute Sailing Tour of Portland

(3.5 of 4 reviews)

Our tour begins with a cruise across the river to the most expensive floating homes on the Willamette. We then usually head down the historic Holgate channel on Portland's own "Jungle Cruise" to the spectacular city riverfront wh... More

Free Cancellation
Private Tour
Start From $99.00
 
90 Minute Sailing Tour of Portland

90 Minute Sailing Tour of Portland

  • North America
  • Good4 reviews3.5

Our tour begins with a cruise across the river to the most expensive floating homes on the Willamet....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Private Charter 6 Passenger Sandbar, Snorkel, Dolphins

(5 of 4 reviews)

Cowfish offers a smooth and comfortable ride, versatility, and ample space for 6 or fewer in a small package. Whether you want to lounge on the sandbar, snorkel at your own pace, or enjoy dolphin watching, Cowfish provides a great... More

Free Cancellation
Private Tour
Start From $950.00
 
Private Charter 6 Passenger Sandbar, Snorkel, Dolphins Likely to Sell Out

Private Charter 6 Passenger Sandbar, Snorkel, Dolphins

  • North America
  • Superb4 reviews5

Cowfish offers a smooth and comfortable ride, versatility, and ample space for 6 or fewer in a small....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Friday Night Waikiki Fireworks Sail

(3 of 1 review)

Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a spectacular Hawaiian sunset and the Friday Night Fireworks onboard a luxury private yacht.... More

Free Cancellation
Private Tour
Start From $699.00
 
Friday Night Waikiki Fireworks Sail Likely to Sell Out

Friday Night Waikiki Fireworks Sail

  • North America

Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a....

    Free Cancellation
    Private Tour
    Start From $699.00
 
 

The Best Catamaran Tour to Isla Mujeres from Cancún

(4.8 of 5 reviews)

Discover Isla Mujeres and visit one of the beutiful beaches in the world, from incredible catamaran equipped with all the comforts! Enjoy with your family and your friends a quiet ride catamaran sailing on the crystal clear waters... More

Free Cancellation
Private Tour
Start From $68.00
 
The Best Catamaran Tour to Isla Mujeres from Cancún Likely to Sell Out

The Best Catamaran Tour to Isla Mujeres from Cancún

  • North America
  • Superb5 reviews4.8

Discover Isla Mujeres and visit one of the beutiful beaches in the world, from incredible catamaran ....

    Free Cancellation
    Private Tour
    Start From $68.00
 
 

Bacalar - Gourmet Tour in Private Catamaran with Cocktails Included

(5 of 41 reviews)

During this experience you will try star dishes from the best restaurants in the area aboard a comfortable private boat. You will enjoy a rich signature cocktail bar while navigating the crystal clear waters of Bacalar with a fine... More

Free Cancellation
Private Tour
Start From $525.00
 
Bacalar - Gourmet Tour in Private Catamaran with Cocktails Included Likely to Sell Out

Bacalar - Gourmet Tour in Private Catamaran with Cocktails Includ....

  • North America
  • Superb41 reviews5

During this experience you will try star dishes from the best restaurants in the area aboard a comfo....

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

Private Sailing Charter in Brooklyn

(5 of 4 reviews)

Are you ready to set sail on a one-of-a-kind tour of New York Harbor? We've got an unforgettable adventure waiting for you! Departing from Brooklyn Bridge Park against the breathtaking backdrop of Lower Manhattan, Tantara sails s... More

Free Cancellation
Private Tour
Start From $660.00
 
Private Sailing Charter in Brooklyn Likely to Sell Out

Private Sailing Charter in Brooklyn

  • North America
  • Superb4 reviews5

Are you ready to set sail on a one-of-a-kind tour of New York Harbor? We've got an unforgettable adv....

    Free Cancellation
    Private Tour
    Start From $660.00
 
 

Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Drinks

(5 of 12 reviews)

Sail along the coast, enjoying the refreshing breeze in this exclusive sailing experience. Marvel at the beauty that makes Los Cabos a unique destination and enjoy this adventure aboard our luxurious French-made sailboats and cat... More

Free Cancellation
Private Tour
Start From $175.00
 
Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Drinks Likely to Sell Out

Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Dr....

  • North America
  • Superb12 reviews5

Sail along the coast, enjoying the refreshing breeze in this exclusive sailing experience. Marvel a....

    Free Cancellation
    Private Tour
    Start From $175.00
 
 

Half-Day Private Snorkel Sailing Adventure in Cabo San Lucas

(5 of 12 reviews)

A Private Adventure with a scent of exclusivity. Go snorkeling in style with Premium Open bar and fine exquisite snacks. Discover Marine Life or bath in the Sea of Cortes. A fantastic Private Adventure.... More

Free Cancellation
Private Tour
Start From $940.00
 
Half-Day Private Snorkel Sailing Adventure in Cabo San Lucas Likely to Sell Out

Half-Day Private Snorkel Sailing Adventure in Cabo San Lucas

  • North America
  • Superb12 reviews5

A Private Adventure with a scent of exclusivity. Go snorkeling in style with Premium Open bar and fi....

    Free Cancellation
    Private Tour
    Start From $940.00
 
 

Private Cabo San Lucas Sunset Cruise

(4.9 of 55 reviews)

You will enjoy watching the sun set on the horizon from your very own private boat with our accommodating and knowledgeable crew. Every tour includes sightseeing along the spectacular Finisterra Rocky point where you will see the ... More

Free Cancellation
Private Tour
Start From $600.00
 
Private Cabo San Lucas Sunset Cruise Likely to Sell Out

Private Cabo San Lucas Sunset Cruise

  • North America
  • Superb55 reviews4.9

You will enjoy watching the sun set on the horizon from your very own private boat with our accommod....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Private Sunset Sailing

(5 of 1 review)

A private and exclusive Sunset Sailing Adventure discovering a Sunset that will never repeat. Premium Open Bar and a Cheese and Cold Cuts table as snacks. Go in style and go Private. Since Covid-19 additional measures and precauti... More

Free Cancellation
Private Tour
Start From $999.00
 
Private Sunset Sailing Likely to Sell Out

Private Sunset Sailing

  • North America
  • Superb1 review5

A private and exclusive Sunset Sailing Adventure discovering a Sunset that will never repeat. Premiu....

    Free Cancellation
    Private Tour
    Start From $999.00
 
 

2hr. PRIVATE Sailing Experience on San Francisco Bay (6 Guests)

(5 of 1 review)

This is a "Private Charter" Sailing Experience on San Francisco Bay for up to 6 guests, with a USCG licensed captain and crew where you'll sail past the Golden Gate Bridge, Alcatraz and Angel Islands and across the San Francisco w... More

Free Cancellation
Private Tour
Start From $795.00
 
2hr. PRIVATE Sailing Experience on San Francisco Bay (6 Guests) Likely to Sell Out

2hr. PRIVATE Sailing Experience on San Francisco Bay (6 Guests)

  • North America
  • Superb1 review5

This is a "Private Charter" Sailing Experience on San Francisco Bay for up to 6 guests, with a USCG ....

    Free Cancellation
    Private Tour
    Start From $795.00
 
 

Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii

(4.9 of 10 reviews)

Welcome to the only place in Hawaii where the spirit of ancient Hawaiian seafaring meets modern expectations on the pristine waters of the Kona coast. Immerse yourself in a unique and unforgettable experience as we invite you to j... More

Free Cancellation
Private Tour
Start From $125.00
 
Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii Likely to Sell Out

Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii

  • North America
  • Superb10 reviews4.9

Welcome to the only place in Hawaii where the spirit of ancient Hawaiian seafaring meets modern expe....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Cancun Half Day Sailing Cataman Cruise to Isla Mujeres

(5 of 1 review)

Original Half Day Sailing since 2012, No need to invest your whole day to visit Isla Mujeres! Lite Tour to Isla Mujeres provides full sailing, snorkeling & enough time to visit Isla Mujeres for shopping or just enjoy this wonderf... More

Free Cancellation
Private Tour
Start From $79.00
 
Cancun Half Day Sailing Cataman Cruise to Isla Mujeres Likely to Sell Out

Cancun Half Day Sailing Cataman Cruise to Isla Mujeres

  • North America
  • Superb1 review5

Original Half Day Sailing since 2012, No need to invest your whole day to visit Isla Mujeres! Lite ....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

JFarwell Sip & Sail aboard the Reverie

(5 of 18 reviews)

This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding in luxury with friends, family or colleagues. Step aboard our 50’ Catamaran and be greeted with a perfect locally crafted bevera... More

Free Cancellation
Private Tour
Start From $852.45
 
JFarwell Sip & Sail aboard the Reverie Likely to Sell Out

JFarwell Sip & Sail aboard the Reverie

  • North America
  • Superb18 reviews5

This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding ....

    Free Cancellation
    Private Tour
    Start From $852.45
 
 

Private Whale Watching Sailing Adventure

(3.5 of 2 reviews)

From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback whales. Departing near Waikiki, enjoy a leisurely sail against the majestic backdrop of Diamond Head as you scan the water for maj... More

Free Cancellation
Private Tour
Start From $695.00
 
Private Whale Watching Sailing Adventure Likely to Sell Out

Private Whale Watching Sailing Adventure

  • North America
  • Good2 reviews3.5

From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback ....

    Free Cancellation
    Private Tour
    Start From $695.00
 
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