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Top 10 Best North America Sailing Trips

Found 714 Sailing Trips activities in North America. Sort by Popularity. - Page 16
 

Lahaina Maui Midmorning Whale Watch in the Humpback Sanctuary

(3.3 of 3 reviews)

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More

Free Cancellation
Start From $110.28
 
Lahaina Maui Midmorning Whale Watch in the Humpback Sanctuary

Lahaina Maui Midmorning Whale Watch in the Humpback Sanctuary

  • North America
  • Good3 reviews3.3

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....

    Free Cancellation
    Start From $110.28
 
 

Key West Champagne Sunset Sail with Drinks and Hors d Oeuvres

(3.3 of 3 reviews)

Experience the magic of a Key West sunset from the water on this elegant 2-hour sailing cruise departing from the historic Key West Seaport. As the sails are raised and the breeze carries you across the sparkling Gulf waters, unwi... More

Free Cancellation
Start From $129.99
 
Key West Champagne Sunset Sail with Drinks and Hors d Oeuvres

Key West Champagne Sunset Sail with Drinks and Hors d Oeuvres

  • North America
  • Good3 reviews3.3

Experience the magic of a Key West sunset from the water on this elegant 2-hour sailing cruise depar....

    Free Cancellation
    Start From $129.99
 
 

Old Plank Adventures: Sail into Deep Tranquility

(5 of 2 reviews)

Old Plank Sailing Adventures is a boutique luxury sailing charter and aquatic expedition company, delivering gourmet 5-star experiences on the sparkling waters of Santa Monica Bay and beyond. Founded by Captain & Chef Matthew Manc... More

Free Cancellation
Private Tour
Start From $400.00
 
Old Plank Adventures: Sail into Deep Tranquility

Old Plank Adventures: Sail into Deep Tranquility

  • North America
  • Superb2 reviews5

Old Plank Sailing Adventures is a boutique luxury sailing charter and aquatic expedition company, de....

    Free Cancellation
    Private Tour
    Start From $400.00
 
 

Original Cruisin Tikis Shark Tooth and Sea Shell Scavenger Hunt

(5 of 1 review)

This interactive experience is perfect for families, kids, and anyone who loves the thrill of the hunt—whether you’re spotting shark teeth, collecting shells, or simply enjoying time on the water. We provide cooler, ice, bottl... More

Free Cancellation
Private Tour
Start From $79.00
 
Original Cruisin Tikis Shark Tooth and Sea Shell Scavenger Hunt Likely to Sell Out

Original Cruisin Tikis Shark Tooth and Sea Shell Scavenger Hunt

  • North America
  • Superb1 review5

This interactive experience is perfect for families, kids, and anyone who loves the thrill of the hu....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Private Sunset and Eco Tour in Destin Up to 18 Guests

(5 of 44 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 full restroom, as well as a... More

Free Cancellation
Private Tour
Start From $450.00
 
Private Sunset and Eco Tour in Destin Up to 18 Guests Likely to Sell Out

Private Sunset and Eco Tour in Destin Up to 18 Guests

  • North America
  • Superb44 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 $450.00
 
 

2-Hour Relaxing Chesapeake Day Sail on Lady Patty

(5 of 28 reviews)

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in the picturesque views of St. Michaels, MD. Your journey includes gliding throu... More

Free Cancellation
Private Tour
Start From $160.00
 
2-Hour Relaxing Chesapeake Day Sail on Lady Patty Likely to Sell Out

2-Hour Relaxing Chesapeake Day Sail on Lady Patty

  • North America
  • Superb28 reviews5

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise of....

    Free Cancellation
    Private Tour
    Start From $160.00
 
 

JFarwell Sunset Wine and Cheese Yacht Sailing

(4.9 of 174 reviews)

Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to invite our guests to be involved in sailing - take the helm, hoist the sails, or sit back and enjoy the beautiful sights and wines ... More

Free Cancellation
Private Tour
Start From $145.67
 
JFarwell Sunset Wine and Cheese Yacht Sailing Likely to Sell Out

JFarwell Sunset Wine and Cheese Yacht Sailing

  • North America
  • Superb174 reviews4.9

Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to i....

    Free Cancellation
    Private Tour
    Start From $145.67
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.6 of 63 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
  • Superb63 reviews4.6

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

    Free Cancellation
    Private Tour
    Start From $179.00
 
 

Snorkel Adventure through the Sea of Cortez

(4.5 of 10 reviews)

Sail through the Sea of Cortez, a blue and shimmering spectacle around Cabo San Lucas. You will ride a luxurious and comfortable catamaran along the Cabo bays to admire the greatest landscapes of Baja. As you get immerse into Sant... More

Free Cancellation
Private Tour
Start From $149.00
 
Snorkel Adventure through the Sea of Cortez Likely to Sell Out

Snorkel Adventure through the Sea of Cortez

  • North America
  • Exellent10 reviews4.5

Sail through the Sea of Cortez, a blue and shimmering spectacle around Cabo San Lucas. You will ride....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Jungle Tour In Cancun, drive a speedboat through the lagoon

(4.3 of 4 reviews)

Welcome to the most enigmatic activity in Cancun, the famous jungle tour, this is the best and quick way to know Cancun and all its beauty. Here you will know the Nichupte Lagoon that is a marvelous lagoon in Mexico, here you will... More

Free Cancellation
Private Tour
Start From $55.00
 
Jungle Tour In Cancun, drive a speedboat through the lagoon Likely to Sell Out

Jungle Tour In Cancun, drive a speedboat through the lagoon

  • North America
  • Exellent4 reviews4.3

Welcome to the most enigmatic activity in Cancun, the famous jungle tour, this is the best and quick....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Tapas Tasting Sailboat Experience in Houston

(4.3 of 4 reviews)

Enjoy a unique sailing experience with our 2-hour tapas sail in Kemah, Houston. This curated event blends the elegance of sailing with Mediterranean-inspired tapas, allowing you to savor five seasonal dishes while cruising on a cl... More

Free Cancellation
Private Tour
Start From $195.00
 
Tapas Tasting Sailboat Experience in Houston Likely to Sell Out

Tapas Tasting Sailboat Experience in Houston

  • North America
  • Exellent4 reviews4.3

Enjoy a unique sailing experience with our 2-hour tapas sail in Kemah, Houston. This curated event b....

    Free Cancellation
    Private Tour
    Start From $195.00
 
 

Sunset Sail in the Gulf of Mexico for up to 6 Guests

(5 of 11 reviews)

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the sun dips below the horizon. For two and a half hours, enjoy the stunning views along Fort ... More

Free Cancellation
Private Tour
Start From $149.00
 
Sunset Sail in the Gulf of Mexico for up to 6 Guests Likely to Sell Out

Sunset Sail in the Gulf of Mexico for up to 6 Guests

  • North America
  • Superb11 reviews5

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the roman....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

2 Hours Cocktail Sail Aboard Bella

(5 of 2 reviews)

Our experienced captains will sail you to the most beautiful local spots to watch the sunset on the water. Spot dolphins, seabirds, and other wildlife as you pass by islands and marshlands. The boat is fully equipped with air con... More

Free Cancellation
Private Tour
Start From $150.00
 
2 Hours Cocktail Sail Aboard Bella Likely to Sell Out

2 Hours Cocktail Sail Aboard Bella

  • North America
  • Superb2 reviews5

Our experienced captains will sail you to the most beautiful local spots to watch the sunset on the ....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

Afternoon Catamaran to Isla Mujeres: Snorkel, Open Bar & Sunset

(5 of 1 review)

This is one of the few afternoon catamaran experiences available in Cancun. Discover Isla Mujeres on a relaxed afternoon catamaran tour from Cancun. Avoid the morning crowds and enjoy snorkeling, an open bar, beach club access, a... More

Free Cancellation
Private Tour
Start From $89.00
 
Afternoon Catamaran to Isla Mujeres: Snorkel, Open Bar & Sunset Likely to Sell Out

Afternoon Catamaran to Isla Mujeres: Snorkel, Open Bar & Sunset

  • North America
  • Superb1 review5

This is one of the few afternoon catamaran experiences available in Cancun. Discover Isla Mujeres o....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Sea Daddy Private Yacht - 50 ft

(5 of 1 review)

Enjoy a day cruising with friends and family on the open water, explore local scenery, and experience the beautiful Cancun weather! Charter this amazing luxury Sea Ray Flybridge combining comfort & style for up to 16 people. Cab... More

Free Cancellation
Private Tour
Start From $899.00
 
Sea Daddy Private Yacht - 50 ft Likely to Sell Out

Sea Daddy Private Yacht - 50 ft

  • North America
  • Superb1 review5

Enjoy a day cruising with friends and family on the open water, explore local scenery, and experienc....

    Free Cancellation
    Private Tour
    Start From $899.00
 
 

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 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 $1,595.00
 
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People Likely to Sell Out

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 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 $1,595.00
 
 

Tour Sailing 4 Hours Private Magic Bacalar Up to 7 People

(5 of 1 review)

We will sail in a beautiful, clean sailboat, with full safety equipment and in good condition, boat equipped with bathroom for emergencies. Surrounded by lush nature and crystal clear waters of the most beautiful lagoon in the wor... More

Special Offer
Free Cancellation
Private Tour
Start From $192.81
(Saving 10% ) $214.23
 
-10% Tour Sailing 4 Hours Private Magic Bacalar Up to 7 People Likely to Sell Out

Tour Sailing 4 Hours Private Magic Bacalar Up to 7 People

  • North America
  • Superb1 review5

We will sail in a beautiful, clean sailboat, with full safety equipment and in good condition, boat ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $192.81
    (Saving 10% ) $214.23
 
 

Cabo Private Sunset Sailing with Open Bar and Appetizers

(4.9 of 28 reviews)

Unlike crowded sightseeing boats, you will enjoy a private luxury sailboat experience with personalized service and a relaxed atmosphere designed for comfort and exclusivity. The experience includes an unlimited open bar, freshly ... More

Special Offer
Free Cancellation
Private Tour
Start From $999.00
(Saving inf% ) $0.00
 
-inf% Cabo Private Sunset Sailing with Open Bar and Appetizers Likely to Sell Out

Cabo Private Sunset Sailing with Open Bar and Appetizers

  • North America
  • Superb28 reviews4.9

Unlike crowded sightseeing boats, you will enjoy a private luxury sailboat experience with personali....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $999.00
    (Saving inf% ) $0.00
 
 

Private Key West Sandbar and Paddle by Boat

(4.9 of 41 reviews)

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats and wildlife refuges as well as spot an abundance of marine birds and sea life. Padd... More

Special Offer
Free Cancellation
Private Tour
Start From $600.00
(Saving inf% ) $0.00
 
-inf% Private Key West Sandbar and Paddle by Boat Likely to Sell Out

Private Key West Sandbar and Paddle by Boat

  • North America
  • Superb41 reviews4.9

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $600.00
    (Saving inf% ) $0.00
 
 

Los Cabos Sunset Sailing Adventure

(4.5 of 2 reviews)

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

Special Offer
Free Cancellation
Private Tour
Start From $119.00
(Saving inf% ) $0.00
 
-inf% Los Cabos Sunset Sailing Adventure Likely to Sell Out

Los Cabos Sunset Sailing Adventure

  • North America
  • Exellent2 reviews4.5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $119.00
    (Saving inf% ) $0.00
 
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