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Top 10 Best North America Sailing Trips

Found 714 Sailing Trips activities in North America. Sort by Popularity. - Page 14
 

Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

(4.4 of 42 reviews)

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we set a c... More

Free Cancellation
Start From $64.95
 
Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

  • North America
  • Exellent42 reviews4.4

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....

    Free Cancellation
    Start From $64.95
 
 

JFarwell Adventure Yacht Sailing in the Halifax Harbour

(5 of 163 reviews)

Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the water, and offers a great introduction to sailing. Guests are encouraged to be as hands on with the sailing process as they would... More

Free Cancellation
Start From $80.12
 
JFarwell Adventure Yacht Sailing in the Halifax Harbour Likely to Sell Out

JFarwell Adventure Yacht Sailing in the Halifax Harbour

  • North America
  • Superb163 reviews5

Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the....

    Free Cancellation
    Start From $80.12
 
 

Wednesday Happy Hour Sunset Sail - Drinks Included

(5 of 9 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
Start From $76.00
 
Wednesday Happy Hour Sunset Sail - Drinks Included Likely to Sell Out

Wednesday Happy Hour Sunset Sail - Drinks Included

  • North America
  • Superb9 reviews5

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

    Free Cancellation
    Start From $76.00
 
 

Hilton Hawaiian Village Adventure Sail on the Spirit of Aloha

(5 of 3 reviews)

This cruise is exceptionally family-friendly, with no snorkeling or in-water activities, making it ideal for guests who want to experience the ocean without getting wet. Unlike many Waikiki beach catamarans, the Spirit of Aloha o... More

Free Cancellation
Start From $59.95
 
Hilton Hawaiian Village Adventure Sail on the Spirit of Aloha Likely to Sell Out

Hilton Hawaiian Village Adventure Sail on the Spirit of Aloha

  • North America
  • Superb3 reviews5

This cruise is exceptionally family-friendly, with no snorkeling or in-water activities, making it i....

    Free Cancellation
    Start From $59.95
 
 

Catamaran Sailing and Snorkeling to Isla Mujeres from Cancun

(4.2 of 5 reviews)

This is the most complete tour to Isla Mujeres on board a Catamaran with all the inclusions to give you a real caribbean experience. Discover Isla Mujeres and it's beautiful beach with us, our team is certified and you will spend... More

Free Cancellation
Start From $20.00
 
Catamaran Sailing and Snorkeling to Isla Mujeres from Cancun Likely to Sell Out

Catamaran Sailing and Snorkeling to Isla Mujeres from Cancun

  • North America
  • Exellent5 reviews4.2

This is the most complete tour to Isla Mujeres on board a Catamaran with all the inclusions to give ....

    Free Cancellation
    Start From $20.00
 
 

Schooner Aquidneck Morning Mimosa Sail

(5 of 15 reviews)

Rise and Shine! There’s no better way to start your day in Newport than sailing past stunning sights while sipping a cool Mimosa aboard the schooner Aquidneck! The sightseeing is stunning! You’ll get great views of Fort Adams... More

Free Cancellation
Start From $50.00
 
Schooner Aquidneck Morning Mimosa Sail Likely to Sell Out

Schooner Aquidneck Morning Mimosa Sail

  • North America
  • Superb15 reviews5

Rise and Shine! There’s no better way to start your day in Newport than sailing past stunning sigh....

    Free Cancellation
    Start From $50.00
 
 

Maui Midday Whale Watch in the Humpback Sanctuary out of Maalaea

(4.9 of 104 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 $110.27
 
Maui Midday Whale Watch in the Humpback Sanctuary out of Maalaea Likely to Sell Out

Maui Midday Whale Watch in the Humpback Sanctuary out of Maalaea

  • North America
  • Superb104 reviews4.9

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

    Free Cancellation
    Start From $110.27
 
 

Where Two Seas Meet: Arch Discovery & Free Time at Playa del Amor

(4.8 of 12 reviews)

Why This is a "Must-Do" Experience: Unrivaled Views: Get up close to the Arch and see the diverse marine life, including tropical fish and occasionally breaching whales in season. Flexible Adventure: Enjoy guided insights into the... More

Free Cancellation
Start From $27.00
 
Where Two Seas Meet: Arch Discovery & Free Time at Playa del Amor Likely to Sell Out

Where Two Seas Meet: Arch Discovery & Free Time at Playa del Amor

  • North America
  • Superb12 reviews4.8

Why This is a "Must-Do" Experience: Unrivaled Views: Get up close to the Arch and see the diverse ma....

    Free Cancellation
    Start From $27.00
 
 

San Diego Whale Watching Cruise

(4.4 of 720 reviews)

Each year approximately 20,000 gray whales migrate from the Bering Sea to the lagoons of Baja California and back again. Come witness this amazing journey off the coast of San Diego on this educational whale watching excursion.... More

Free Cancellation
Start From $54.00
 
San Diego Whale Watching Cruise Likely to Sell Out

San Diego Whale Watching Cruise

  • North America
  • Exellent720 reviews4.4

Each year approximately 20,000 gray whales migrate from the Bering Sea to the lagoons of Baja Califo....

    Free Cancellation
    Start From $54.00
 
 

Catamaran in Cozumel with snorkeling at El Cielo and open Bar

(3.9 of 19 reviews)

Snorkel, Sip & Celebrate in Cozumel’s Caribbean Paradise Your captain and crew welcome you aboard with open arms—and an open bar. Margaritas, beer, soft drinks, and bottled water flow as music fills the air and the sea sets t... More

Free Cancellation
Start From $38.50
 
Catamaran in Cozumel with snorkeling at El Cielo and open Bar Likely to Sell Out

Catamaran in Cozumel with snorkeling at El Cielo and open Bar

  • North America
  • Very Good19 reviews3.9

Snorkel, Sip & Celebrate in Cozumel’s Caribbean Paradise Your captain and crew welcome you aboard....

    Free Cancellation
    Start From $38.50
 
 

2hr. SUNSET Sailing Experience on San Francisco Bay

(4.9 of 35 reviews)

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sailing Experience is "interactive" which means we want you to get the full experience of sailing so you'll have an opportunity to tak... More

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

2hr. SUNSET Sailing Experience on San Francisco Bay

  • North America
  • Superb35 reviews4.9

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sail....

    Free Cancellation
    Start From $149.00
 
 

Waikiki Friday Night Fireworks Cruise NYE SPECIAL CRUISE!

(4.6 of 32 reviews)

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring your favorite beverages and join us for Waikiki's weekly fireworks displ... More

Free Cancellation
Start From $60.00
 
Waikiki Friday Night Fireworks Cruise NYE SPECIAL CRUISE! Likely to Sell Out

Waikiki Friday Night Fireworks Cruise NYE SPECIAL CRUISE!

  • North America
  • Superb32 reviews4.6

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....

    Free Cancellation
    Start From $60.00
 
 

Half-Day Luxury Sailing in Puerto Morelos with Open Bar

(4.8 of 4 reviews)

Set sail on the tranquil turquoise waters of Puerto Morelos aboard a luxury catamaran for an unforgettable half-day adventure. This experience offers a guided snorkeling session at a vibrant reef in the Mesoamerican Barrier Reef, ... More

Free Cancellation
Start From $149.00
 
Half-Day Luxury Sailing in Puerto Morelos with Open Bar Likely to Sell Out

Half-Day Luxury Sailing in Puerto Morelos with Open Bar

  • North America
  • Superb4 reviews4.8

Set sail on the tranquil turquoise waters of Puerto Morelos aboard a luxury catamaran for an unforge....

    Free Cancellation
    Start From $149.00
 
 

Afternoon Half-Day Catmaran Sailing and Snorkel Adventure

(4.5 of 73 reviews)

Want to enjoy a sailing tour, where you can snorkel and visit Isla Mujeres in just half a day? This is the tour for you! Enjoy sailing in one of our Catamarans and we will ensure that you enjoy your afternoon to the maximum. The t... More

Free Cancellation
Start From $59.99
 
Afternoon Half-Day Catmaran Sailing and Snorkel Adventure Likely to Sell Out

Afternoon Half-Day Catmaran Sailing and Snorkel Adventure

  • North America
  • Exellent73 reviews4.5

Want to enjoy a sailing tour, where you can snorkel and visit Isla Mujeres in just half a day? This ....

    Free Cancellation
    Start From $59.99
 
 

Speedboat and Snorkeling Adventure in Cancun

(4.3 of 3 reviews)

Explore the vibrant Cancun jungle with an exhilarating water adventure that combines speed and serenity. Hop into a 2-passenger speedboat and zip around the stunning Nichupte Lagoon, feeling the thrill of the wind and water. Then,... More

Free Cancellation
Start From $16.00
 
Speedboat and Snorkeling Adventure in Cancun Likely to Sell Out

Speedboat and Snorkeling Adventure in Cancun

  • North America
  • Exellent3 reviews4.3

Explore the vibrant Cancun jungle with an exhilarating water adventure that combines speed and seren....

    Free Cancellation
    Start From $16.00
 
 

Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams

(5 of 3 reviews)

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 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 fu... More

Free Cancellation
Start From $124.05
 
Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams Likely to Sell Out

Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams

  • North America
  • Superb3 reviews5

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow....

    Free Cancellation
    Start From $124.05
 
 

Let's Go Sail the York River in Gloucester Point Virginia

(5 of 170 reviews)

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the cockpit or up on the bow of the boat for greater privacy. Great idea for engagement, bi... More

Free Cancellation
Start From $96.42
 
Let's Go Sail the York River in Gloucester Point Virginia Likely to Sell Out

Let's Go Sail the York River in Gloucester Point Virginia

  • North America
  • Superb170 reviews5

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern ....

    Free Cancellation
    Start From $96.42
 
 

Amazing Snorkeling Experience + Real Mexican Tacos

(4.2 of 15 reviews)

This is the classic snorkeling experience when you come to Cancun, it is a must tour in your Itinerary. When you do this experience you feel a connection with nature, it is like taking a little bit of Cancun with you back home. Se... More

Free Cancellation
Start From $39.61
 
Amazing Snorkeling Experience + Real Mexican Tacos Likely to Sell Out

Amazing Snorkeling Experience + Real Mexican Tacos

  • North America
  • Exellent15 reviews4.2

This is the classic snorkeling experience when you come to Cancun, it is a must tour in your Itinera....

    Free Cancellation
    Start From $39.61
 
 

kayaking in Huatulco

(5 of 7 reviews)

The geographical position favors us to observe whales, dolphins, turtles and much more while sailing in the kayak in calm waters, we have contact with the most 95% of the time on the tour, so it is highly recommended for biologist... More

Free Cancellation
Private Tour
Start From $71.41
 
kayaking in Huatulco Likely to Sell Out

kayaking in Huatulco

  • North America
  • Superb7 reviews5

The geographical position favors us to observe whales, dolphins, turtles and much more while sailing....

    Free Cancellation
    Private Tour
    Start From $71.41
 
 

The Boat People Cruise Private Harbor Cruises

(5 of 53 reviews)

Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We strive to create an unforgettable evening with contagious laughter and panoramic views of the Newport Bay. Bring your plus one or ... More

Free Cancellation
Private Tour
Start From $100.00
 
The Boat People Cruise Private Harbor Cruises Likely to Sell Out

The Boat People Cruise Private Harbor Cruises

  • North America
  • Superb53 reviews5

Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We ....

    Free Cancellation
    Private Tour
    Start From $100.00
 
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