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Top 10 Best North America Sailing Trips

Found 672 Sailing Trips activities in North America. Sort by Popularity. - Page 33
 

Key West Wreckers Race Aboard Schooner America 2.0

(4.9 of 9 reviews)

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern ... More

Start From $111.80
 
Key West Wreckers Race Aboard Schooner America 2.0

Key West Wreckers Race Aboard Schooner America 2.0

  • North America
  • Superb9 reviews4.9

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse abo....

    Start From $111.80
 
 

Cancun to Isla Mujeres Full Day Tour with Snorkeling

(4.9 of 9 reviews)

Live a fun and relaxed day aboard a catamaran with open bar on board meeting the pearl of the Caribbean – Isla Mujeres, with its paradise beaches. We start the catamaran tour with national open bar included on board throughout ... More

Free Cancellation
Start From $70.00
 
Cancun to Isla Mujeres Full Day Tour with Snorkeling Likely to Sell Out

Cancun to Isla Mujeres Full Day Tour with Snorkeling

  • North America
  • Superb9 reviews4.9

Live a fun and relaxed day aboard a catamaran with open bar on board meeting the pearl of the Carib....

    Free Cancellation
    Start From $70.00
 
 

Private Cruise Swim with Dolphin

(4.9 of 9 reviews)

Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and anniversaries. An Impressive Swimming Experience with Wild Dolphins at the West Coast of Oahu. Learning about the ecosystem of wil... More

Free Cancellation
Private Tour
Start From $3,769.63
 
Private Cruise Swim with Dolphin Likely to Sell Out

Private Cruise Swim with Dolphin

  • North America
  • Superb9 reviews4.9

Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and ....

    Free Cancellation
    Private Tour
    Start From $3,769.63
 
 

Dock Side Adventure Kayak, Paddle Boarding, Sunfish sailboats

(4.9 of 9 reviews)

Enjoy the day hanging out on our 30 ft Double Deck Slide Boat. Have full access to all of our water toys. Relax and listen to music in the shade. Barbecue lunch or dinner and watch the sunset. Swim off the Slide Boat or relax on o... More

Free Cancellation
Private Tour
Start From $350.00
 
Dock Side Adventure Kayak, Paddle Boarding, Sunfish sailboats Likely to Sell Out

Dock Side Adventure Kayak, Paddle Boarding, Sunfish sailboats

  • North America
  • Superb9 reviews4.9

Enjoy the day hanging out on our 30 ft Double Deck Slide Boat. Have full access to all of our water ....

    Free Cancellation
    Private Tour
    Start From $350.00
 
 

Platinum Private Catamaran Sailing Tour

(5 of 3 reviews)

If you like to take the opportunity to meet the amazing whales and are visiting Los Cabos during the dates of December 15th thru April 15th, you can enjoy this amazing adventure for 2 hours departing at 09:00 am in the morning. If... More

Free Cancellation
Private Tour
Start From $237.00
 
Platinum Private Catamaran Sailing Tour Likely to Sell Out

Platinum Private Catamaran Sailing Tour

  • North America
  • Superb3 reviews5

If you like to take the opportunity to meet the amazing whales and are visiting Los Cabos during the....

    Free Cancellation
    Private Tour
    Start From $237.00
 
 

Deluxe Private Boats - Leopard 51

(5 of 17 reviews)

1. 45-foot Lagoon Catamaran, with premium drinks and food included. 2. Open Bar. The price is set from 1 to 20 passengers. 3. Maximum capacity of 35 passengers. 4. We are focused on providing everything you need so you can relax ... More

Free Cancellation
Private Tour
Start From $1,800.00
 
Deluxe Private Boats - Leopard 51 Likely to Sell Out

Deluxe Private Boats - Leopard 51

  • North America
  • Superb17 reviews5

1. 45-foot Lagoon Catamaran, with premium drinks and food included. 2. Open Bar. The price is set f....

    Free Cancellation
    Private Tour
    Start From $1,800.00
 
 

Waikiki private Day Tour and Sunset sail for couples

(5 of 11 reviews)

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples on their honeymoon, celebrating an Anniversary, or just in love, celebrating ... More

Free Cancellation
Private Tour
Start From $300.00
 
Waikiki private Day Tour and Sunset sail for couples Likely to Sell Out

Waikiki private Day Tour and Sunset sail for couples

  • North America
  • Superb11 reviews5

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This privat....

    Free Cancellation
    Private Tour
    Start From $300.00
 
 

Scientific and Cultural Tour in Bacalar with an Expert

(5 of 1 review)

Embark on an exclusive journey to the enchanting Bacalar Lagoon with our private tour, guided by a local expert and dedicated naturalist committed to the preservation and study of this unique ecosystem. Our guide, fluent in Englis... More

Free Cancellation
Private Tour
Start From $315.94
 
Scientific and Cultural Tour in Bacalar with an Expert Likely to Sell Out

Scientific and Cultural Tour in Bacalar with an Expert

  • North America
  • Superb1 review5

Embark on an exclusive journey to the enchanting Bacalar Lagoon with our private tour, guided by a l....

    Free Cancellation
    Private Tour
    Start From $315.94
 
 

Pirates Sunset Cruise at the Cabo San Lucas Arch

(5 of 1 review)

You'll love visiting the Arch of Cabo San Lucas! - Experience breathtaking views of the stunning sunset where the Sea of Cortez meets the Pacific Ocean. - If you visit during the winter months, you might catch a glimpse of whales ... More

Free Cancellation
Private Tour
Start From $119.00
 
Pirates Sunset Cruise at the Cabo San Lucas Arch Likely to Sell Out

Pirates Sunset Cruise at the Cabo San Lucas Arch

  • North America
  • Superb1 review5

You'll love visiting the Arch of Cabo San Lucas! - Experience breathtaking views of the stunning sun....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Private Luxury Yacht Cruise on Tu Enamorado

(3.5 of 4 reviews)

Pamper yourself, your friends and family to an unforgettable sailing cruise around scenic Cabo San Lucas Bay aboard the beautifully crafted Tu Enamorado. Live the yachting lifestyle, walk barefoot on the deck, feel the sun and bre... More

Free Cancellation
Private Tour
Start From $199.00
 
Private Luxury Yacht Cruise on Tu Enamorado Likely to Sell Out

Private Luxury Yacht Cruise on Tu Enamorado

  • North America
  • Good4 reviews3.5

Pamper yourself, your friends and family to an unforgettable sailing cruise around scenic Cabo San L....

    Free Cancellation
    Private Tour
    Start From $199.00
 
 

San Francisco Private Yacht Tour Oracle Sail Grand Prix SailGP

(3.5 of 4 reviews)

High speed, high tech, high drama. SailGP is back in the Bay! View the racing from aboard your own private sailing yacht - your Captain spent four seasons setting the SailGP race course around the world, so I can provide with an... More

Free Cancellation
Private Tour
Start From $195.00
 
San Francisco Private Yacht Tour Oracle Sail Grand Prix SailGP Likely to Sell Out

San Francisco Private Yacht Tour Oracle Sail Grand Prix SailGP

  • North America
  • Good4 reviews3.5

High speed, high tech, high drama. SailGP is back in the Bay! View the racing from aboard your own....

    Free Cancellation
    Private Tour
    Start From $195.00
 
 

Private Classic Sailboat Tour in New York City

(3.5 of 4 reviews)

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a unique and immersive experience on the Hudson River. You'll enjoy stunning views of iconic landmarks like the Statue of Liberty, E... More

Free Cancellation
Private Tour
Start From $800.00
 
Private Classic Sailboat Tour in New York City Likely to Sell Out

Private Classic Sailboat Tour in New York City

  • North America
  • Good4 reviews3.5

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a ....

    Free Cancellation
    Private Tour
    Start From $800.00
 
 

Nights of Lights Sailboat Tour St Augustine Sailing

(5 of 3 reviews)

What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours offer a simple ride, St Augustine Sailing provides an intimate, serene setting ... More

Free Cancellation
Private Tour
Start From $774.00
 
Nights of Lights Sailboat Tour St Augustine Sailing Likely to Sell Out

Nights of Lights Sailboat Tour St Augustine Sailing

  • North America
  • Superb3 reviews5

What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experien....

    Free Cancellation
    Private Tour
    Start From $774.00
 
 

Private Sunset Tour in Marina La Cruz by Yacht

(5 of 17 reviews)

Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours don’t go. Also enjoy the explanation from our captain on the art of sailing. This is not a boat trip, this is an experience to enj... More

Free Cancellation
Private Tour
Start From $1,300.00
 
Private Sunset Tour in Marina La Cruz by Yacht Likely to Sell Out

Private Sunset Tour in Marina La Cruz by Yacht

  • North America
  • Superb17 reviews5

Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours do....

    Free Cancellation
    Private Tour
    Start From $1,300.00
 
 

Luxury Yacht 58 ft for up to 20 people 4 hrs

(5 of 17 reviews)

Azimut yachts are designed to pamper the most demanding tastes. Feel the pleasure of sailing aboard this luxury yacht along the coast of Bahía de Banderas. You will enjoy every moment and every place in this tropical paradise. L... More

Free Cancellation
Private Tour
Start From $4,100.00
 
Luxury Yacht 58 ft for up to 20 people 4 hrs Likely to Sell Out

Luxury Yacht 58 ft for up to 20 people 4 hrs

  • North America
  • Superb17 reviews5

Azimut yachts are designed to pamper the most demanding tastes. Feel the pleasure of sailing aboard ....

    Free Cancellation
    Private Tour
    Start From $4,100.00
 
 

4 Day Alaskan Excursion

(5 of 17 reviews)

This is a Tour that no other Company in the World offers. You will be sailing and enjoying the Alaskan wilderness. Each day is unknown because the climate here is so unpredictable. But we always make the best with what we have got... More

Free Cancellation
Private Tour
Start From $6,000.00
 
4 Day Alaskan Excursion Likely to Sell Out

4 Day Alaskan Excursion

  • North America
  • Superb17 reviews5

This is a Tour that no other Company in the World offers. You will be sailing and enjoying the Alask....

    Free Cancellation
    Private Tour
    Start From $6,000.00
 
 

Private Sunset Sail for Two

(5 of 5 reviews)

Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise along the vibrant waterfront and marvel at the cityscape. Create a memory of a lifetime while sailing past Downtown, Point Loma, an... More

Free Cancellation
Private Tour
Start From $462.00
 
Private Sunset Sail for Two Likely to Sell Out

Private Sunset Sail for Two

  • North America
  • Superb5 reviews5

Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise a....

    Free Cancellation
    Private Tour
    Start From $462.00
 
 

Private 2-Hour Wind and Wine Sunset Sail in Key West

(4.9 of 81 reviews)

This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from around the world and a variety of beers. You will be sailing on a 65-foot schooner while watching the sunset into the ocean. There... More

Free Cancellation
Private Tour
Start From $4,000.00
 
Private 2-Hour Wind and Wine Sunset Sail in Key West Likely to Sell Out

Private 2-Hour Wind and Wine Sunset Sail in Key West

  • North America
  • Superb81 reviews4.9

This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from ....

    Free Cancellation
    Private Tour
    Start From $4,000.00
 
 

Private Sunset Catamaran: 3-Hour Exclusive Cruise in Los Cabos

(4.9 of 81 reviews)

Highlights of Your Private Sunset Cruise: Exclusive Private Catamaran: Perfect for couples, friends, or family. Breathtaking Sunset Views: Watch the sky light up with vibrant colors over Cabo. Iconic Landmarks: Sail past The Arch,... More

Free Cancellation
Private Tour
Start From $1,295.00
 
Private Sunset Catamaran: 3-Hour Exclusive Cruise in Los Cabos Likely to Sell Out

Private Sunset Catamaran: 3-Hour Exclusive Cruise in Los Cabos

  • North America
  • Superb81 reviews4.9

Highlights of Your Private Sunset Cruise: Exclusive Private Catamaran: Perfect for couples, friends,....

    Free Cancellation
    Private Tour
    Start From $1,295.00
 
 

Private Afternoon Snorkel with Sunset Sail in Key West

(5 of 4 reviews)

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's a... More

Free Cancellation
Private Tour
Start From $995.00
 
Private Afternoon Snorkel with Sunset Sail in Key West Likely to Sell Out

Private Afternoon Snorkel with Sunset Sail in Key West

  • North America
  • Superb4 reviews5

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that sp....

    Free Cancellation
    Private Tour
    Start From $995.00
 
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