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Top 10 Best North America Sailing Trips

Found 770 Sailing Trips activities in North America. Sort by Popularity. - Page 7
 

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

(5 of 93 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
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
  • Superb93 reviews5

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

    Free Cancellation
    Start From $149.00
 
 

Vancouver Sailing Experience on a 50 foot Sailboat

(5 of 102 reviews)

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for 20 of those, have extensive sailing and local knowledge, 12 years experience volunteering... More

Free Cancellation
Start From $110.82
 
Vancouver Sailing Experience on a 50 foot Sailboat Likely to Sell Out

Vancouver Sailing Experience on a 50 foot Sailboat

  • North America
  • Superb102 reviews5

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....

    Free Cancellation
    Start From $110.82
 
 

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

(4.6 of 126 reviews)

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More

Free Cancellation
Start From $54.95
 
Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor Likely to Sell Out

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

  • North America
  • Superb126 reviews4.6

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....

    Free Cancellation
    Start From $54.95
 
 

Sunset Sail from Traverse City with Food, Wine & Cocktails

(4.8 of 226 reviews)

Wind down and relax as our captain and crewmates teach you about our elegant schooner and share stories about the history of the lands, people, and waters of the Grand Traverse Bay area. Enjoy complimentary locally sourced food, w... More

Free Cancellation
Start From $229.00
 
Sunset Sail from Traverse City with Food, Wine & Cocktails Likely to Sell Out

Sunset Sail from Traverse City with Food, Wine & Cocktails

  • North America
  • Superb226 reviews4.8

Wind down and relax as our captain and crewmates teach you about our elegant schooner and share stor....

    Free Cancellation
    Start From $229.00
 
 

Daytime Sailing Along San Diego's Skyline

(4.9 of 149 reviews)

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor Sunroad Marina on Harbor Island on San Diego Bay, we often s... More

Free Cancellation
Start From $79.00
 
Daytime Sailing Along San Diego's Skyline Likely to Sell Out

Daytime Sailing Along San Diego's Skyline

  • North America
  • Superb149 reviews4.9

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....

    Free Cancellation
    Start From $79.00
 
 

Windjammer Classic Sunset Sail from Camden, Maine

(4.9 of 425 reviews)

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More

Free Cancellation
Start From $64.95
 
Windjammer Classic Sunset Sail from Camden, Maine Likely to Sell Out

Windjammer Classic Sunset Sail from Camden, Maine

  • North America
  • Superb425 reviews4.9

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....

    Free Cancellation
    Start From $64.95
 
 

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

(4.9 of 987 reviews)

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Incl... More

Free Cancellation
Start From $108.91
 
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses Likely to Sell Out

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

  • North America
  • Superb987 reviews4.9

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....

    Free Cancellation
    Start From $108.91
 
 

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

(4.9 of 108 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pal... More

Free Cancellation
Start From $59.95
 
Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise Likely to Sell Out

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

  • North America
  • Superb108 reviews4.9

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....

    Free Cancellation
    Start From $59.95
 
 

Maui Sunset Sail

(4.6 of 218 reviews)

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing catamaran, Ocean Spirit. It’s the perfect way to expe... More

Free Cancellation
Start From $137.82
 
Maui Sunset Sail Likely to Sell Out

Maui Sunset Sail

  • North America
  • Superb218 reviews4.6

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....

    Free Cancellation
    Start From $137.82
 
 

Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling

(5 of 63 reviews)

Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing cruise. Explore los arcos area while savoring fresh guacamole and a selection of delicious snacks. This personalized sailing expe... More

Special Offer
Free Cancellation
Private Tour
Start From $734.97
(Saving 15% ) $864.67
 
-15% Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling Likely to Sell Out

Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling

  • North America
  • Superb63 reviews5

Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $734.97
    (Saving 15% ) $864.67
 
 

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

(5 of 48 reviews)

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor for over 12 years, our sailing yachts are the highest quality and op... More

Special Offer
Free Cancellation
Private Tour
Start From $599.00
(Saving inf% ) $0.00
 
-inf% Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique Likely to Sell Out

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

  • North America
  • Superb48 reviews5

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $599.00
    (Saving inf% ) $0.00
 
 

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

(4.8 of 58 reviews)

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, you’ll glide along the coastline and experience an exclusive o... More

Special Offer
Free Cancellation
Private Tour
Start From $90.01
(Saving inf% ) $0.00
 
-inf% Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu Likely to Sell Out

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

  • North America
  • Superb58 reviews4.8

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village di....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $90.01
    (Saving inf% ) $0.00
 
 

1-Hour Interactive Pirate Cruise (arrive 30 minutes early)

(4.9 of 1,516 reviews)

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along Florida’s Intracoastal Waterway that’s fun for the whole family! T... More

Special Offer
Free Cancellation
Private Tour
Start From $35.00
(Saving inf% ) $0.00
 
-inf% 1-Hour Interactive Pirate Cruise (arrive 30 minutes early) Likely to Sell Out

1-Hour Interactive Pirate Cruise (arrive 30 minutes early)

  • North America
  • Superb1,516 reviews4.9

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $35.00
    (Saving inf% ) $0.00
 
 

Premium Private Catamaran Sail, Snorkel & "El Cielo" Charter

(4.8 of 23 reviews)

Sail in style aboard Cozumel’s largest and most spacious catamaran—a 47ft Nautitech—on an unforgettable journey to the famous El Cielo sandbar! Just 5–10 minutes by taxi from any cruise terminal or downtown, enjoy award-wi... More

Special Offer
Free Cancellation
Private Tour
Start From $1,998.65
(Saving inf% ) $0.00
 
-inf% Premium Private Catamaran Sail, Snorkel & Likely to Sell Out

Premium Private Catamaran Sail, Snorkel & "El Cielo" Charter

  • North America
  • Superb23 reviews4.8

Sail in style aboard Cozumel’s largest and most spacious catamaran—a 47ft Nautitech—on an unfo....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,998.65
    (Saving inf% ) $0.00
 
 

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

(4.8 of 21 reviews)

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air! Fun for all ... More

Special Offer
Free Cancellation
Private Tour
Start From $91.23
(Saving inf% ) $0.00
 
-inf% Sail on Tall Ship Windy, join us for our Likely to Sell Out

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

  • North America
  • Superb21 reviews4.8

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $91.23
    (Saving inf% ) $0.00
 
 

Puerto Vallarta Luxury Sailing with Premium Open bar & lunch

(4.8 of 312 reviews)

Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breathtaking views of Puerto Vallarta’s coastline and the majestic Sierra Madre mountains. This small-group experience offers a perfe... More

Special Offer
Free Cancellation
Private Tour
Start From $79.00
(Saving inf% ) $0.00
 
-inf% Puerto Vallarta Luxury Sailing with Premium Open bar & lunch Likely to Sell Out

Puerto Vallarta Luxury Sailing with Premium Open bar & lunch

  • North America
  • Superb312 reviews4.8

Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breat....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $79.00
    (Saving inf% ) $0.00
 
 

Sail & Splash Excursion in Ft. Lauderdale

(4.8 of 278 reviews)

Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion aboard our state of the art catamaran, the Spirit of Lauderdale. Enjoy one of the best cruise Ft Lauderdale has to offer . Sit back... More

Special Offer
Free Cancellation
Private Tour
Start From $129.00
(Saving inf% ) $0.00
 
-inf% Sail & Splash Excursion in Ft. Lauderdale Likely to Sell Out

Sail & Splash Excursion in Ft. Lauderdale

  • North America
  • Superb278 reviews4.8

Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion a....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $129.00
    (Saving inf% ) $0.00
 
 

Paragon Lahaina Sunset Sail

(4.6 of 9 reviews)

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the glassy, miraculous ‘au’au Channel is like floating inside an infinite ... More

Special Offer
Free Cancellation
Private Tour
Start From $102.00
(Saving inf% ) $0.00
 
-inf% Paragon Lahaina Sunset Sail Likely to Sell Out

Paragon Lahaina Sunset Sail

  • North America
  • Superb9 reviews4.6

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from L....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $102.00
    (Saving inf% ) $0.00
 
 

Sunset Dolphin Sail Aboard the Privateer Catamaran

(4.8 of 731 reviews)

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, our 78-passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mex... More

Special Offer
Free Cancellation
Private Tour
Start From $45.00
(Saving inf% ) $0.00
 
-inf% Sunset Dolphin Sail Aboard the Privateer Catamaran Likely to Sell Out

Sunset Dolphin Sail Aboard the Privateer Catamaran

  • North America
  • Superb731 reviews4.8

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $45.00
    (Saving inf% ) $0.00
 
 

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 963 reviews)

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Special Offer
Free Cancellation
Private Tour
Start From $84.99
(Saving inf% ) $0.00
 
-inf% Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure Likely to Sell Out

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....

  • North America
  • Superb963 reviews4.7

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $84.99
    (Saving inf% ) $0.00
 
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