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Top 10 Best North America Sailing Trips

Found 676 Sailing Trips activities in North America. Sort by Popularity. - Page 7
 

Polynesian Canoe Sunset Sail

(4.9 of 118 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Free Cancellation
Start From $250.00
 
Polynesian Canoe Sunset Sail

Polynesian Canoe Sunset Sail

  • North America
  • Superb118 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Free Cancellation
    Start From $250.00
 
 

Shallow Water Snorkeling and Dolphin Watching in Key West

(4.6 of 432 reviews)

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropical waters of Key West on Catamaran Echo - making vacation memories since 1991. Enjoy a premium shallow snorkeling and dolphin-watc... More

Free Cancellation
Start From $108.91
 
Shallow Water Snorkeling and Dolphin Watching in Key West Likely to Sell Out

Shallow Water Snorkeling and Dolphin Watching in Key West

  • North America
  • Superb432 reviews4.6

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropica....

    Free Cancellation
    Start From $108.91
 
 

Pau Hana Sunset Cruise with the Whales

(4.8 of 45 reviews)

Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the biggest guests of all -- the Humpback Whales -- and you have perfect way to begin your evening in paradise! Cruise along the Kohala... More

Free Cancellation
Start From $165.00
 
Pau Hana Sunset Cruise with the Whales Likely to Sell Out

Pau Hana Sunset Cruise with the Whales

  • North America
  • Superb45 reviews4.8

Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the b....

    Free Cancellation
    Start From $165.00
 
 

Sunset Sail Cruise in Key West

(4.9 of 211 reviews)

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail scho... More

Free Cancellation
Start From $91.38
 
Sunset Sail Cruise in Key West Likely to Sell Out

Sunset Sail Cruise in Key West

  • North America
  • Superb211 reviews4.9

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....

    Free Cancellation
    Start From $91.38
 
 

Private Boat Tour Adventure in Miami Celeb Homes, Snorkeling, Fun

(4.8 of 52 reviews)

DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews on Google. What you will get: Nature Immersion: Encounter dolphins, turtles, manatees, and more as you explore Miami's waters Cel... More

Free Cancellation
Private Tour
Start From $55.00
 
Private Boat Tour Adventure in Miami Celeb Homes, Snorkeling, Fun Likely to Sell Out

Private Boat Tour Adventure in Miami Celeb Homes, Snorkeling, Fun

  • North America
  • Superb52 reviews4.8

DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews ....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Sunset Sail on Historic Schooner in Key West

(4.8 of 95 reviews)

Set sail for a beautiful Key West sunset on the historic schooner When And If! Commissioned by then Colonel George Patton "When the war is over and if I return, Bea and I will sail around the world!" Step foot on the gorgeous teak... More

Free Cancellation
Private Tour
Start From $109.00
 
Sunset Sail on Historic Schooner in Key West Likely to Sell Out

Sunset Sail on Historic Schooner in Key West

  • North America
  • Superb95 reviews4.8

Set sail for a beautiful Key West sunset on the historic schooner When And If! Commissioned by then ....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Evening Colors Sunset Sail Tour in Seattle

(4.8 of 416 reviews)

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hoist the sails, then we will shut the engine down and enjoy the quiet of our beautiful schooner cutting through the tranquil Puget So... More

Free Cancellation
Private Tour
Start From $65.00
 
Evening Colors Sunset Sail Tour in Seattle Likely to Sell Out

Evening Colors Sunset Sail Tour in Seattle

  • North America
  • Superb416 reviews4.8

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hois....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Key West Sunset Snorkel with Unlimited Draft Beer & Wine

(4.7 of 114 reviews)

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More

Free Cancellation
Private Tour
Start From $56.95
 
Key West Sunset Snorkel with Unlimited Draft Beer & Wine Likely to Sell Out

Key West Sunset Snorkel with Unlimited Draft Beer & Wine

  • North America
  • Superb114 reviews4.7

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....

    Free Cancellation
    Private Tour
    Start From $56.95
 
 

Panama City Beach Sunset Sail on The Footloose Catamaran

(4.8 of 387 reviews)

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on SV Footloose, our 38 passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico ... More

Free Cancellation
Private Tour
Start From $45.00
 
Panama City Beach Sunset Sail on The Footloose Catamaran Likely to Sell Out

Panama City Beach Sunset Sail on The Footloose Catamaran

  • North America
  • Superb387 reviews4.8

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....

    Free Cancellation
    Private Tour
    Start From $45.00
 
 

12pm Turtle Canyon Snorkel Adventure

(4.8 of 265 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 $96.30
 
12pm Turtle Canyon Snorkel Adventure Likely to Sell Out

12pm Turtle Canyon Snorkel Adventure

  • North America
  • Superb265 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 $96.30
 
 

Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat

(5 of 28 reviews)

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for f... More

Free Cancellation
Private Tour
Start From $999.00
 
Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat Likely to Sell Out

Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat

  • North America
  • Superb28 reviews5

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bo....

    Free Cancellation
    Private Tour
    Start From $999.00
 
 

Small Group Waikiki Sunset Sailing Tour

(4.9 of 86 reviews)

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More

Free Cancellation
Private Tour
Start From $99.00
 
Small Group Waikiki Sunset Sailing Tour Likely to Sell Out

Small Group Waikiki Sunset Sailing Tour

  • North America
  • Superb86 reviews4.9

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar

(4.7 of 63 reviews)

*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting from our crew who will provide you with unmatched service throughout the excursion. *Take a moment for a photo opportunity with y... More

Free Cancellation
Private Tour
Start From $109.00
 
Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar Likely to Sell Out

Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open....

  • North America
  • Superb63 reviews4.7

*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting ....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Boston Harbor Sunset Sail Tour

(4.7 of 62 reviews)

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. This elegant sailing experience will be aboard either Schooner Adirondack III or Adir... More

Free Cancellation
Private Tour
Start From $75.48
 
Boston Harbor Sunset Sail Tour Likely to Sell Out

Boston Harbor Sunset Sail Tour

  • North America
  • Superb62 reviews4.7

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....

    Free Cancellation
    Private Tour
    Start From $75.48
 
 

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

(5 of 48 reviews)

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More

Free Cancellation
Private Tour
Start From $149.00
 
2hr. INTERACTIVE Sailing Experience on San Francisco Bay Likely to Sell Out

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

  • North America
  • Superb48 reviews5

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Sailing Tour through the Laguna de los Siete Colores

(5 of 1,289 reviews)

Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, being your best option to know this magical place without damaging the ecosystem. Guided by a team of professionals, with whom you ... More

Free Cancellation
Private Tour
Start From $38.00
 
Sailing Tour through the Laguna de los Siete Colores Likely to Sell Out

Sailing Tour through the Laguna de los Siete Colores

  • North America
  • Superb1,289 reviews5

Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, b....

    Free Cancellation
    Private Tour
    Start From $38.00
 
 

Portland Tall Ship Cruise on Casco Bay

(4.5 of 222 reviews)

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.... More

Free Cancellation
Private Tour
Start From $97.43
 
Portland Tall Ship Cruise on Casco Bay Likely to Sell Out

Portland Tall Ship Cruise on Casco Bay

  • North America
  • Exellent222 reviews4.5

What better way to see the delights of Portland than from the sea in one of the famous schooner tall....

    Free Cancellation
    Private Tour
    Start From $97.43
 
 

Sailing Tour through the Lagoon of the 7 Colors

(4.9 of 977 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

Free Cancellation
Private Tour
Start From $36.00
 
Sailing Tour through the Lagoon of the 7 Colors Likely to Sell Out

Sailing Tour through the Lagoon of the 7 Colors

  • North America
  • Superb977 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $36.00
 
 

Private boat for 6 hours with snorkeling & beaches in Puerto Vallarta

(5 of 1 review)

Sail on a private trip aboard our 26-foot boat. Ideal for up to 8 passengers. We are sure that with us you will know the best part of our beautiful bay of Puerto Vallarta. Do not miss the opportunity we offer you to make this rese... More

Free Cancellation
Private Tour
Start From $871.45
 
Private boat for 6 hours with snorkeling & beaches in Puerto Vallarta Likely to Sell Out

Private boat for 6 hours with snorkeling & beaches in Puerto Vall....

  • North America
  • Superb1 review5

Sail on a private trip aboard our 26-foot boat. Ideal for up to 8 passengers. We are sure that with ....

    Free Cancellation
    Private Tour
    Start From $871.45
 
 

BYOB Waikiki Sunset Swim and Diamond Head Sailing

(5 of 143 reviews)

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Free Cancellation
Private Tour
Start From $79.00
 
BYOB Waikiki Sunset Swim and Diamond Head Sailing Likely to Sell Out

BYOB Waikiki Sunset Swim and Diamond Head Sailing

  • North America
  • Superb143 reviews5

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....

    Free Cancellation
    Private Tour
    Start From $79.00
 
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