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Top 10 Best North America Sailing Trips

Found 692 Sailing Trips activities in North America. Sort by Popularity. - Page 28
 

Sunset Sailing Tour of San Diego Bay up to 6 Guests

(5 of 1 review)

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sunset sailing charters and boat tours. Our sunset sailin... More

Start From $600.00
 
Sunset Sailing Tour of San Diego Bay up to 6 Guests

Sunset Sailing Tour of San Diego Bay up to 6 Guests

  • North America
  • Superb1 review5

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautifu....

    Start From $600.00
 
 

Afternoon Ali'i Adventure

(5 of 5 reviews)

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. ... More

Free Cancellation
Start From $276.00
 
Afternoon Ali'i Adventure

Afternoon Ali'i Adventure

  • North America
  • Superb5 reviews5

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....

    Free Cancellation
    Start From $276.00
 
 

Bachelorette Sailing Party on San Diego Bay up to 6 Guests

(5 of 5 reviews)

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, not to mention an incredible abundance of sea l... More

Free Cancellation
Private Tour
Start From $1,200.00
 
Bachelorette Sailing Party on San Diego Bay up to 6 Guests

Bachelorette Sailing Party on San Diego Bay up to 6 Guests

  • North America
  • Superb5 reviews5

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

Private Afternoon Harbor Cruise on Kismet for parties up to 15

(5 of 19 reviews)

Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise the harbor, BYOB, awesome stereo, bathroom, history tours, swim and float on rafts. Kismet does it all! Kismet is a custom-built ... More

Free Cancellation
Private Tour
Start From $1,549.00
 
Private Afternoon Harbor Cruise on Kismet for parties up to 15 Likely to Sell Out

Private Afternoon Harbor Cruise on Kismet for parties up to 15

  • North America
  • Superb19 reviews5

Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise....

    Free Cancellation
    Private Tour
    Start From $1,549.00
 
 

Exclusive Private Sailing Luxury Tour in Los Cabos

(5 of 19 reviews)

Experience snorkeling in crystal waters, the beach Palmilla has a blue flag recognition and is one of the best beach areas to discover the underwater world of the Los Cabos area. During the months of December thru March, you can w... More

Free Cancellation
Private Tour
Start From $1,600.00
 
Exclusive Private Sailing Luxury Tour in Los Cabos Likely to Sell Out

Exclusive Private Sailing Luxury Tour in Los Cabos

  • North America
  • Superb19 reviews5

Experience snorkeling in crystal waters, the beach Palmilla has a blue flag recognition and is one o....

    Free Cancellation
    Private Tour
    Start From $1,600.00
 
 

Luxury Private Sunset Experience in San Jose

(5 of 19 reviews)

Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour. The Luxury Private Sailing boat have capacity from 1 to 16 people, the rate offered here is for 8 people, if like to add more pl... More

Free Cancellation
Private Tour
Start From $1,600.00
 
Luxury Private Sunset Experience in San Jose Likely to Sell Out

Luxury Private Sunset Experience in San Jose

  • North America
  • Superb19 reviews5

Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour....

    Free Cancellation
    Private Tour
    Start From $1,600.00
 
 

The Hamptons Date Night Dining Hot Spots

(5 of 1 review)

This Hamptons hotspot dining boat tour allows guests to visit multiple dining hotspots in a single excursion hassle-free, maximizing their time and providing a convenient way to explore the Hamptons. Guests won't have to worry abo... More

Free Cancellation
Private Tour
Start From $1,790.00
 
The Hamptons Date Night Dining Hot Spots Likely to Sell Out

The Hamptons Date Night Dining Hot Spots

  • North America
  • Superb1 review5

This Hamptons hotspot dining boat tour allows guests to visit multiple dining hotspots in a single e....

    Free Cancellation
    Private Tour
    Start From $1,790.00
 
 

Snorkel in the beautiful reef of Puerto Morelos with transport

(3 of 1 review)

The most amazing and exciting tour in the Mexican Caribbean is here. Visit the national park of reefs in Puerto Morelos. Sail through the turquoise clear water of the Caribbean Sea and arrive to the Mesoamerican reef. Our captain... More

Free Cancellation
Private Tour
Start From $55.00
 
Snorkel in the beautiful reef of Puerto Morelos with transport Likely to Sell Out

Snorkel in the beautiful reef of Puerto Morelos with transport

  • North America

The most amazing and exciting tour in the Mexican Caribbean is here. Visit the national park of reef....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Private 2 Hour Sailboat Sunset Charter

(5 of 1 review)

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you plan the perfect experience for you and your guests! You'll sail around Shell Island into the Gulf of Mexico, while you enjoy dol... More

Free Cancellation
Private Tour
Start From $699.00
 
Private 2 Hour Sailboat Sunset Charter Likely to Sell Out

Private 2 Hour Sailboat Sunset Charter

  • North America
  • Superb1 review5

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you....

    Free Cancellation
    Private Tour
    Start From $699.00
 
 

2 Hours Private Guided Sailing Adventure in Pensacola Beach

(5 of 2 reviews)

This 2 hour sailing excursion may take place in Pensacola Bay, passing by areas of Sabine Island, Deer Point, Fair Point and Deadman's Island. We may also sail east under the Bob Sikes (Pensacola Beach) Bridge, exploring areas of ... More

Free Cancellation
Private Tour
Start From $375.00
 
2 Hours Private Guided Sailing Adventure in Pensacola Beach Likely to Sell Out

2 Hours Private Guided Sailing Adventure in Pensacola Beach

  • North America
  • Superb2 reviews5

This 2 hour sailing excursion may take place in Pensacola Bay, passing by areas of Sabine Island, De....

    Free Cancellation
    Private Tour
    Start From $375.00
 
 

San Francisco City Lights Sail

(5 of 5 reviews)

The Golden Gate isn’t the only bridge in town! Once the sun sets and the lights come on, join us for a city-front cruise to enjoy the majestic sites of San Francisco in the night sky. See the Bay Bridge lit in all its glory, alo... More

Free Cancellation
Private Tour
Start From $85.00
 
San Francisco City Lights Sail Likely to Sell Out

San Francisco City Lights Sail

  • North America
  • Superb5 reviews5

The Golden Gate isn’t the only bridge in town! Once the sun sets and the lights come on, join us f....

    Free Cancellation
    Private Tour
    Start From $85.00
 
 

Private Catamaran Sunset Cruise with Dolphin watching

(5 of 4 reviews)

One of the best ways to relax on your vacation is to view a sunset aboard Destin sailing Adventures. Sit back and relax while Captain Kip takes you to the best spots to view the sunset, and see a dolphin.... More

Free Cancellation
Private Tour
Start From $360.00
 
Private Catamaran Sunset Cruise with Dolphin watching Likely to Sell Out

Private Catamaran Sunset Cruise with Dolphin watching

  • North America
  • Superb4 reviews5

One of the best ways to relax on your vacation is to view a sunset aboard Destin sailing Adventures.....

    Free Cancellation
    Private Tour
    Start From $360.00
 
 

Private Paddle Tour at Sunrise

(5 of 206 reviews)

With this amazing experience through the Bacalar Lagoon you will live unbeatable moments for 3.5 hours, we have all the necessary equipment for this activity to be complete. We are an ecologically responsible company that promotes... More

Free Cancellation
Private Tour
Start From $68.88
 
Private Paddle Tour at Sunrise Likely to Sell Out

Private Paddle Tour at Sunrise

  • North America
  • Superb206 reviews5

With this amazing experience through the Bacalar Lagoon you will live unbeatable moments for 3.5 hou....

    Free Cancellation
    Private Tour
    Start From $68.88
 
 

Private Transparent Boat Tour in the Sea of Cozumel

(5 of 206 reviews)

Incredible experience in a 100% transparent boat, we are also the only tour currently that offers snorkeling, sunken ships, there is more probability of finding marine life on this tour since we are on the second largest reef in t... More

Special Offer
Free Cancellation
Private Tour
Start From $503.06
(Saving 20% ) $628.83
 
-20% Private Transparent Boat Tour in the Sea of Cozumel Likely to Sell Out

Private Transparent Boat Tour in the Sea of Cozumel

  • North America
  • Superb206 reviews5

Incredible experience in a 100% transparent boat, we are also the only tour currently that offers sn....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $503.06
    (Saving 20% ) $628.83
 
 

Live this unique snorkeling experience. El Cielo in Cozumel a magical tour.

(3 of 1 review)

If we tell you that you can be near the sky while you are at the paradisiacal Caribbean Sea, could believe us? On this tour that is completely possible! Adventure with us through the coast of the Cozumel Island, visit three of th... More

Free Cancellation
Private Tour
Start From $165.00
 
Live this unique snorkeling experience. El Cielo in Cozumel a magical tour. Likely to Sell Out

Live this unique snorkeling experience. El Cielo in Cozumel a mag....

  • North America

If we tell you that you can be near the sky while you are at the paradisiacal Caribbean Sea, could b....

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

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 Luxury Private Sailing Catamaran for 7-12 People

(5 of 1 review)

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 $1,495.00
 
2hr Luxury Private Sailing Catamaran for 7-12 People Likely to Sell Out

2hr Luxury Private Sailing Catamaran for 7-12 People

  • North America
  • Superb1 review5

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

    Free Cancellation
    Private Tour
    Start From $1,495.00
 
 

Aloha Wednesday Sunset Sail - Drinks Included - Lux Catamaran

(5 of 2 reviews)

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha Wednesday Sunset Sail. This midweek escape combines tropical charm with st... More

Free Cancellation
Private Tour
Start From $76.00
 
Aloha Wednesday Sunset Sail - Drinks Included - Lux Catamaran Likely to Sell Out

Aloha Wednesday Sunset Sail - Drinks Included - Lux Catamaran

  • North America
  • Superb2 reviews5

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit....

    Free Cancellation
    Private Tour
    Start From $76.00
 
 

Sailing Adventures 3-Hour Activity in Destin

(5 of 4 reviews)

There’s nothing like seeing the clear emerald waters pass under the hull while sailing on the Stiletto Catamaran. Harnessing the power of the wind as we sail along these beautiful waters is magical. You might even get to experie... More

Free Cancellation
Private Tour
Start From $525.00
 
Sailing Adventures 3-Hour Activity in Destin Likely to Sell Out

Sailing Adventures 3-Hour Activity in Destin

  • North America
  • Superb4 reviews5

There’s nothing like seeing the clear emerald waters pass under the hull while sailing on the Stil....

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

Private Sunset Sail of NYC Skyline and Statue of Liberty

(5 of 2 reviews)

Discover NYC from a completely different perspective on a private sailboat charter during sunset hours when the views are even more spectacular. You and your group will view New York City in ways that are breath taking. See the St... More

Free Cancellation
Private Tour
Start From $725.00
 
Private Sunset Sail of NYC Skyline and Statue of Liberty Likely to Sell Out

Private Sunset Sail of NYC Skyline and Statue of Liberty

  • North America
  • Superb2 reviews5

Discover NYC from a completely different perspective on a private sailboat charter during sunset hou....

    Free Cancellation
    Private Tour
    Start From $725.00
 
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