Menu

Top 10 Best North America Sailing Trips

Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 15
 

Friday Night Firework Cruise in Waikiki

(4.7 of 23 reviews)

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, truly making this the ultimate party experience. Enjoy the Premium drinks of your choice ... More

Free Cancellation
Start From $69.99
 
Friday Night Firework Cruise in Waikiki

Friday Night Firework Cruise in Waikiki

  • North America
  • Superb23 reviews4.7

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....

    Free Cancellation
    Start From $69.99
 
 

Sailing on Historic Schooner Yacht in Salem, MA

(4.9 of 172 reviews)

Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience the majesty aboard John G. Alden's personal schooner yacht Malabar X. Winner of the 1930 and 1932 Newport to Bermuda race and open... More

Free Cancellation
Start From $55.00
 
Sailing on Historic Schooner Yacht in Salem, MA Likely to Sell Out

Sailing on Historic Schooner Yacht in Salem, MA

  • North America
  • Superb172 reviews4.9

Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience ....

    Free Cancellation
    Start From $55.00
 
 

3 Hours Ultimate Watersports Excursion in Miami

(4.9 of 172 reviews)

All-Inclusive Catamaran Adventure in Miami: 3 Hours of Adrenaline and Party! Board your comfortable and stable Catamaran for an unforgettable all-inclusive water experience. Highlights: - Extreme Watersports: Feel the thrill wi... More

Free Cancellation
Start From $139.00
 
 3 Hours Ultimate Watersports Excursion in Miami Likely to Sell Out

3 Hours Ultimate Watersports Excursion in Miami

  • North America
  • Superb172 reviews4.9

All-Inclusive Catamaran Adventure in Miami: 3 Hours of Adrenaline and Party! Board your comfortable....

    Free Cancellation
    Start From $139.00
 
 

Whale Watching with Lunch and transportation included

(4.4 of 20 reviews)

Experience the "Whale-tastic Adventure" in Cabo San Lucas during the winter season, where you'll have front-row seats to witness the playful and majestic antics of whales in their natural habitat. Setting sail from the Marina, you... More

Free Cancellation
Start From $99.00
 
Whale Watching with Lunch and transportation included Likely to Sell Out

Whale Watching with Lunch and transportation included

  • North America
  • Exellent20 reviews4.4

Experience the "Whale-tastic Adventure" in Cabo San Lucas during the winter season, where you'll hav....

    Free Cancellation
    Start From $99.00
 
 

Sunset sail Aboard Manakai Catamaran

(5 of 14 reviews)

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a smaller guest capacity and open-deck layout, it offers an intimate, lai... More

Free Cancellation
Start From $49.82
 
Sunset sail Aboard Manakai Catamaran Likely to Sell Out

Sunset sail Aboard Manakai Catamaran

  • North America
  • Superb14 reviews5

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Wood....

    Free Cancellation
    Start From $49.82
 
 

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

(4.9 of 42 reviews)

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we... More

Free Cancellation
Start From $59.95
 
Schooner Applejack Sunset Sail Tour in Boothbay Harbor Likely to Sell Out

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

  • North America
  • Superb42 reviews4.9

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

    Free Cancellation
    Start From $59.95
 
 

Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15

(4.5 of 31 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 + Fireworks Festival 3/15 Likely to Sell Out

Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15

  • North America
  • Exellent31 reviews4.5

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

    Free Cancellation
    Start From $60.00
 
 

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

(4.9 of 46 reviews)

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay and National Seashore. Or explore the Condor: walk around, do the Titanic po... More

Free Cancellation
Start From $99.00
 
Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise Likely to Sell Out

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

  • North America
  • Superb46 reviews4.9

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chil....

    Free Cancellation
    Start From $99.00
 
 

Deluxe Turtle Snorkeling Escapade at Waikiki

(4.9 of 8 reviews)

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More

Free Cancellation
Start From $121.00
 
Deluxe Turtle Snorkeling Escapade at Waikiki Likely to Sell Out

Deluxe Turtle Snorkeling Escapade at Waikiki

  • North America
  • Superb8 reviews4.9

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....

    Free Cancellation
    Start From $121.00
 
 

Slow Sailing Bacalar Experience with snack and drinks

(4.9 of 21 reviews)

Step aboard our sailboat and experience Bacalar in most authentic and sustainable way - powered mainly by the wind. By choosing to sail, you help protect the lagoon's fragile ecosystem while enjoying a peaceful and unforgettable j... More

Free Cancellation
Start From $37.79
 
Slow Sailing Bacalar Experience with snack and drinks Likely to Sell Out

Slow Sailing Bacalar Experience with snack and drinks

  • North America
  • Superb21 reviews4.9

Step aboard our sailboat and experience Bacalar in most authentic and sustainable way - powered main....

    Free Cancellation
    Start From $37.79
 
 

Catamaran Sailing Cruise in Monterey

(4.8 of 30 reviews)

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind to make for a peaceful and exciting cruise on the bay. On the way out of t... More

Free Cancellation
Start From $65.00
 
Catamaran Sailing Cruise in Monterey Likely to Sell Out

Catamaran Sailing Cruise in Monterey

  • North America
  • Superb30 reviews4.8

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage af....

    Free Cancellation
    Start From $65.00
 
 

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
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
    Start From $119.00
 
 

Tour Sailing boat 4 Hours

(5 of 10 reviews)

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
Start From $37.07
(Saving 15% ) $43.61
 
-15% Tour Sailing boat 4 Hours Likely to Sell Out

Tour Sailing boat 4 Hours

  • North America
  • Superb10 reviews5

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

    Special Offer
    Free Cancellation
    Start From $37.07
    (Saving 15% ) $43.61
 
 

Romantic Dinner Touring the Nichupté Lagoon in Galeón

(5 of 1 review)

Love will fall at the foot of the Nichupté Lagoon, as you discover its most precious secrets aboard the Columbus Romantic Dinner Cruise. This is a unique romance tour in Cancun, as it offers a very special evening, surrounded by ... More

Free Cancellation
Start From $125.00
 
Romantic Dinner Touring the Nichupté Lagoon in Galeón Likely to Sell Out

Romantic Dinner Touring the Nichupté Lagoon in Galeón

  • North America
  • Superb1 review5

Love will fall at the foot of the Nichupté Lagoon, as you discover its most precious secrets aboard....

    Free Cancellation
    Start From $125.00
 
 

Your Private Miami Yacht Charter with Music and Fun

(4.6 of 65 reviews)

Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate like never before. This VIP experience is designed for fun, style, and unforgettable memories with your group. Adventure Highlig... More

Free Cancellation
Private Tour
Start From $300.00
 
Your Private Miami Yacht Charter with Music and Fun Likely to Sell Out

Your Private Miami Yacht Charter with Music and Fun

  • North America
  • Superb65 reviews4.6

Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate....

    Free Cancellation
    Private Tour
    Start From $300.00
 
 

New York City Sailboat Day Cruise to the Statue of Liberty

(4.8 of 152 reviews)

Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as the crew raises sail and the boat effortlessly glides along the Hudson Rive... More

Free Cancellation
Private Tour
Start From $60.08
 
New York City Sailboat Day Cruise to the Statue of Liberty Likely to Sell Out

New York City Sailboat Day Cruise to the Statue of Liberty

  • North America
  • Superb152 reviews4.8

Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by t....

    Free Cancellation
    Private Tour
    Start From $60.08
 
 

Los Cabos Sunset Sailing Adventure

(4.8 of 152 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

Free Cancellation
Private Tour
Start From $119.00
 
Los Cabos Sunset Sailing Adventure Likely to Sell Out

Los Cabos Sunset Sailing Adventure

  • North America
  • Superb152 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

The Boat People Cruise Private Harbor Cruises

(5 of 44 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
  • Superb44 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
 
 

Escape from the Rock! Cruise around Alcatraz

(4.2 of 157 reviews)

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and past Angel Island State Park before circling Alcatraz Island for an in-depth view of the prison. Take in the sights and sounds of ... More

Free Cancellation
Private Tour
Start From $48.00
 
Escape from the Rock! Cruise around Alcatraz Likely to Sell Out

Escape from the Rock! Cruise around Alcatraz

  • North America
  • Exellent157 reviews4.2

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and ....

    Free Cancellation
    Private Tour
    Start From $48.00
 
 

Sail San Francisco Bay on the Historic Brigantine Matthew Turner

(5 of 2 reviews)

Set sail on the San Francisco Bay aboard the historic brigantine Matthew Turner, the largest sailboat in the area. Experience the beauty of the bay as you glide past iconic landmarks like the Golden Gate Bridge, Alcatraz, and Ange... More

Free Cancellation
Private Tour
Start From $99.00
 
Sail San Francisco Bay on the Historic Brigantine Matthew Turner Likely to Sell Out

Sail San Francisco Bay on the Historic Brigantine Matthew Turner

  • North America
  • Superb2 reviews5

Set sail on the San Francisco Bay aboard the historic brigantine Matthew Turner, the largest sailboa....

    Free Cancellation
    Private Tour
    Start From $99.00
 
Booking.com
Booking.com
Booking.com