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Top 10 Best North America Sailing Trips

Found 690 Sailing Trips activities in North America. Sort by Popularity.
 

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

(4.8 of 3,677 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 $52.43
 
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time Likely to Sell Out

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

  • North America
  • Superb3,677 reviews4.8

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

    Free Cancellation
    Start From $52.43
 
 

Official Miami Millionaires Sightseeing Cruise

(4.3 of 840 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
  • Exellent840 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
 
 

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

(4.7 of 3,278 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 $149.00
 
Isla Mujeres Luxury Sailing: Adults Only or Family Friendly Likely to Sell Out

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

  • North America
  • Superb3,278 reviews4.7

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

    Free Cancellation
    Start From $149.00
 
 

Deluxe Na Pali Sunset Tour on the Lucky Lady

(4.7 of 1,339 reviews)

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look for dolphins, whales, and other marine critters as you sip a drink, snap som... More

Free Cancellation
Start From $222.86
 
Deluxe Na Pali Sunset Tour on the Lucky Lady Likely to Sell Out

Deluxe Na Pali Sunset Tour on the Lucky Lady

  • North America
  • Superb1,339 reviews4.7

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....

    Free Cancellation
    Start From $222.86
 
 

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

(4.8 of 2,857 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

Free Cancellation
Start From $149.00
 
Los Cabos Luxury Sailing, Snorkel and Lunch Cruise Likely to Sell Out

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

  • North America
  • Superb2,857 reviews4.8

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

    Free Cancellation
    Start From $149.00
 
 

Sunset & Dolphin Catamaran Cruise with Island Time

(4.9 of 1,614 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 $52.43
 
Sunset & Dolphin Catamaran Cruise with Island Time Likely to Sell Out

Sunset & Dolphin Catamaran Cruise with Island Time

  • North America
  • Superb1,614 reviews4.9

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

    Free Cancellation
    Start From $52.43
 
 

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

(4.7 of 3,224 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
  • Superb3,224 reviews4.7

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

    Free Cancellation
    Start From $79.00
 
 

Evening Colors Sunset Sail Tour in Seattle

(4.8 of 451 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
  • Superb451 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
 
 

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

(4.9 of 1,967 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 $99.99
 
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
  • Superb1,967 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 $99.99
 
 

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 926 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 $59.99
 
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Likely to Sell Out

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • North America
  • Superb926 reviews4.9

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

    Free Cancellation
    Start From $59.99
 
 

2 Hour Sailing Cruise on Lake Tahoe

(4.9 of 713 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
  • Superb713 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
 
 

Waikiki Catamaran Turtle Snorkel Sail

(4.7 of 2,081 reviews)

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More

Free Cancellation
Start From $108.62
 
Waikiki Catamaran Turtle Snorkel Sail Likely to Sell Out

Waikiki Catamaran Turtle Snorkel Sail

  • North America
  • Superb2,081 reviews4.7

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....

    Free Cancellation
    Start From $108.62
 
 

Leila Na Pali Sunset Dinner Sail

(4.7 of 473 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
  • Superb473 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
 
 

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

(4.8 of 1,475 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
  • Superb1,475 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
 
 

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

(4.6 of 643 reviews)

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More

Free Cancellation
Start From $89.00
 
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas Likely to Sell Out

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

  • North America
  • Superb643 reviews4.6

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....

    Free Cancellation
    Start From $89.00
 
 

50ft Luxury Yacht Tour in Miami Beach Captain, Champagne & Party!

(4.5 of 39 reviews)

Ready for the party of a lifetime? Hop aboard our luxurious yacht in Miami Beach to party like never before! Perfect for any special occasion, this VIP experience promises unforgettable memories Adventure Highlights Biscayne Bay ... More

Free Cancellation
Private Tour
Start From $599.99
 
50ft Luxury Yacht Tour in Miami Beach Captain, Champagne & Party! Likely to Sell Out

50ft Luxury Yacht Tour in Miami Beach Captain, Champagne & Party!

  • North America
  • Exellent39 reviews4.5

Ready for the party of a lifetime? Hop aboard our luxurious yacht in Miami Beach to party like never....

    Free Cancellation
    Private Tour
    Start From $599.99
 
 

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

(4.5 of 488 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
Private Tour
Start From $54.50
 
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor Likely to Sell Out

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

  • North America
  • Exellent488 reviews4.5

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

    Free Cancellation
    Private Tour
    Start From $54.50
 
 

Pirate Ship Sunset Dinner and Show in Los Cabos

(4.3 of 585 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

Free Cancellation
Private Tour
Start From $99.00
 
Pirate Ship Sunset Dinner and Show in Los Cabos Likely to Sell Out

Pirate Ship Sunset Dinner and Show in Los Cabos

  • North America
  • Exellent585 reviews4.3

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

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Boston Harbor Sunset Sail Tour

(4.7 of 72 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 $82.27
 
Boston Harbor Sunset Sail Tour Likely to Sell Out

Boston Harbor Sunset Sail Tour

  • North America
  • Superb72 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 $82.27
 
 

Sunset Sail in Key West with Beverages Included

(4.9 of 824 reviews)

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the... More

Free Cancellation
Private Tour
Start From $79.00
 
Sunset Sail in Key West with Beverages Included Likely to Sell Out

Sunset Sail in Key West with Beverages Included

  • North America
  • Superb824 reviews4.9

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....

    Free Cancellation
    Private Tour
    Start From $79.00
 
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