Menu

Top 10 Best North America Sailing Trips

Found 702 Sailing Trips activities in North America. Sort by Popularity.
 

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

(4.9 of 4,069 reviews)

The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great way to have fun in the sun and enjoy the best of what Panama City Beach has to offer! Cruise over to Shell Island where you and the... More

Free Cancellation
Start From $57.59
 
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Tim....

  • North America
  • Superb4,069 reviews4.9

The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great w....

    Free Cancellation
    Start From $57.59
 
 

Official Miami Millionaires Sightseeing Cruise

(4.3 of 986 reviews)

Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmerizing beauty of Biscayne Bay, while getting an exclusive glimpse into the luxurious lifestyle of Miami's elite, with a bilingual com... More

Free Cancellation
Start From $18.00
 
Official Miami Millionaires Sightseeing Cruise Likely to Sell Out

Official Miami Millionaires Sightseeing Cruise

  • North America
  • Exellent986 reviews4.3

Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmeriz....

    Free Cancellation
    Start From $18.00
 
 

Waikiki Turtle Snorkeling Boat Tour and Adventure

(4.7 of 1,085 reviews)

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!** Join us for a **2-hour snorkeling adventure** at **Turtle Canyon**, one of Oahu’s top snorkeling spots! Cruise along the stunning **Waikiki coastlin... More

Special Offer
Free Cancellation
Start From $68.60
(Saving 9% ) $75.00
 
-9% Waikiki Turtle Snorkeling Boat Tour and Adventure Likely to Sell Out

Waikiki Turtle Snorkeling Boat Tour and Adventure

  • North America
  • Superb1,085 reviews4.7

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!** Join us for a **2-ho....

    Special Offer
    Free Cancellation
    Start From $68.60
    (Saving 9% ) $75.00
 
 

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

(4.7 of 3,306 reviews)

Join us for the Luxury Sailing Adventure to Isla Mujeres aboard a state-of-the-art catamaran — with the option to choose between an Adults Only or Family Friendly experience. Snorkel in warm, crystalline waters, then savor a del... More

Free Cancellation
Start From $129.00
 
Isla Mujeres Luxury Sailing: Adults Only or Family Friendly Likely to Sell Out

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

  • North America
  • Superb3,306 reviews4.7

Join us for the Luxury Sailing Adventure to Isla Mujeres aboard a state-of-the-art catamaran — wit....

    Free Cancellation
    Start From $129.00
 
 

Sunset & Dolphin Catamaran Cruise with Island Time

(4.9 of 1,706 reviews)

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in Panama City Beach, FL. Enjoy a rum punch while cruising along the beautiful Gulf Coa... More

Free Cancellation
Start From $57.59
 
Sunset & Dolphin Catamaran Cruise with Island Time Likely to Sell Out

Sunset & Dolphin Catamaran Cruise with Island Time

  • North America
  • Superb1,706 reviews4.9

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....

    Free Cancellation
    Start From $57.59
 
 

2 Hour Sailing Cruise on Lake Tahoe

(4.9 of 793 reviews)

Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing adventure and include complementary local beer and wine, as well as non-alcoholic beverages on all of our daily cruises. Unlike other t... More

Free Cancellation
Start From $140.00
 
2 Hour Sailing Cruise on Lake Tahoe Likely to Sell Out

2 Hour Sailing Cruise on Lake Tahoe

  • North America
  • Superb793 reviews4.9

Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing advent....

    Free Cancellation
    Start From $140.00
 
 

Sightseeing Day Sail around Boston Harbor

(4.8 of 457 reviews)

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport district, Castle... More

Special Offer
Free Cancellation
Start From $56.55
(Saving 15% ) $66.54
 
-15% Sightseeing Day Sail around Boston Harbor Likely to Sell Out

Sightseeing Day Sail around Boston Harbor

  • North America
  • Superb457 reviews4.8

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner....

    Special Offer
    Free Cancellation
    Start From $56.55
    (Saving 15% ) $66.54
 
 

Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

(4.6 of 243 reviews)

Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quality, comfort, and performance. Live the yachting lifestyle, walk barefoot on the deck, feel the sun and breeze on your face, dance ... More

Special Offer
Free Cancellation
Start From $179.10
(Saving 10% ) $199.00
 
-10% Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef Likely to Sell Out

Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

  • North America
  • Superb243 reviews4.6

Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quali....

    Special Offer
    Free Cancellation
    Start From $179.10
    (Saving 10% ) $199.00
 
 

Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres

(4.7 of 3,287 reviews)

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern sailing catamarans while sipping sparkling wine or your favorite cocktail and fea... More

Free Cancellation
Start From $79.00
 
Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres Likely to Sell Out

Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres

  • North America
  • Superb3,287 reviews4.7

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....

    Free Cancellation
    Start From $79.00
 
 

Toronto Tall Ship Boat Cruise

(4.3 of 619 reviews)

This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the 'Tall Ship Kajama,' a traditional 165-foot, 3-masted schooner boat, and sit back and relax with a cold drink from the bar or order from the re... More

Free Cancellation
Start From $31.92
 
Toronto Tall Ship Boat Cruise Likely to Sell Out

Toronto Tall Ship Boat Cruise

  • North America
  • Exellent619 reviews4.3

This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the 'Tall Ship K....

    Free Cancellation
    Start From $31.92
 
 

Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

(4.9 of 2,029 reviews)

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with premium drinks, indescribable views, and music. As we sail alongside Oa... More

Free Cancellation
Start From $89.99
 
Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast Likely to Sell Out

Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

  • North America
  • Superb2,029 reviews4.9

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....

    Free Cancellation
    Start From $89.99
 
 

Evening Colors Sunset Sail Tour in Seattle

(4.8 of 514 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
Start From $65.00
 
Evening Colors Sunset Sail Tour in Seattle Likely to Sell Out

Evening Colors Sunset Sail Tour in Seattle

  • North America
  • Superb514 reviews4.8

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

    Free Cancellation
    Start From $65.00
 
 

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

(4.8 of 3,008 reviews)

Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time to hang out in the pristine water and take it easy aboard the sailboat – you can snorkel with tropical fish, stand atop a paddleb... More

Special Offer
Free Cancellation
Start From $126.65
(Saving 15% ) $149.00
 
-15% Los Cabos Luxury Sailing, Snorkel and Lunch Cruise Likely to Sell Out

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

  • North America
  • Superb3,008 reviews4.8

Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time t....

    Special Offer
    Free Cancellation
    Start From $126.65
    (Saving 15% ) $149.00
 
 

2-Hour Seattle Sailing Harbor Tour

(4.7 of 421 reviews)

Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing tour is family-friendly and is an excellent way to see the Seattle skyline, the beauty of the Puget Sound, even mountain views! We ... More

Free Cancellation
Start From $49.30
 
2-Hour Seattle Sailing Harbor Tour Likely to Sell Out

2-Hour Seattle Sailing Harbor Tour

  • North America
  • Superb421 reviews4.7

Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing t....

    Free Cancellation
    Start From $49.30
 
 

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,017 reviews)

2025 VIATOR TOP 20 BEST EXCURSIONS award in the UNITED STATES including the TOP RATED SNORKEL EXCURSION in the US!! Best value in Waikiki! See turtles GUARANTEED or receive a FULL REFUND! Brand new PREMIUM snorkel equipment inclu... More

Free Cancellation
Start From $59.95
 
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Likely to Sell Out

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • North America
  • Superb1,017 reviews4.9

2025 VIATOR TOP 20 BEST EXCURSIONS award in the UNITED STATES including the TOP RATED SNORKEL EXCURS....

    Free Cancellation
    Start From $59.95
 
 

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

(4.8 of 1,518 reviews)

This is the best way to start your day on Oahu! Complimentary cold brew coffee from Honolulu’s local favorite ARVO Café, served with a selection of Anahola Granola bars—Original, Chocolate Chip, Tropical, and Mango & Ginger. ... More

Free Cancellation
Start From $84.77
 
Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran Likely to Sell Out

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

  • North America
  • Superb1,518 reviews4.8

This is the best way to start your day on Oahu! Complimentary cold brew coffee from Honolulu’s loc....

    Free Cancellation
    Start From $84.77
 
 

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

(4.1 of 451 reviews)

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises.... More

Free Cancellation
Start From $70.00
 
1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain Likely to Sell Out

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

  • North America
  • Exellent451 reviews4.1

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....

    Free Cancellation
    Start From $70.00
 
 

Leila Na Pali Sunset Dinner Sail

(4.7 of 488 reviews)

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will s... More

Free Cancellation
Start From $263.82
 
Leila Na Pali Sunset Dinner Sail Likely to Sell Out

Leila Na Pali Sunset Dinner Sail

  • North America
  • Superb488 reviews4.7

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....

    Free Cancellation
    Start From $263.82
 
 

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

(4.5 of 524 reviews)

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall Ship for a unique sailing experience. There is no better way to witness all o... More

Free Cancellation
Start From $44.00
 
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor Likely to Sell Out

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....

  • North America
  • Exellent524 reviews4.5

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....

    Free Cancellation
    Start From $44.00
 
 

Pirate Ship Sunset Dinner and Show in Los Cabos

(4.3 of 599 reviews)

Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic sunset cruise with a show that is the joy for children and grown-ups alike. Our pirates, dance, chant, climb the ropes, while you... More

Special Offer
Free Cancellation
Start From $94.05
(Saving 5% ) $99.00
 
-5% Pirate Ship Sunset Dinner and Show in Los Cabos Likely to Sell Out

Pirate Ship Sunset Dinner and Show in Los Cabos

  • North America
  • Exellent599 reviews4.3

Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic ....

    Special Offer
    Free Cancellation
    Start From $94.05
    (Saving 5% ) $99.00
 
1 2 3 4 5
Booking.com
Booking.com
Booking.com