Menu

Top 10 Best North America Sailing Trips

Found 756 Sailing Trips activities in North America. Sort by Popularity.
 

Miami Millionaires Sightseeing Cruise

(4.3 of 1,688 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
 
Miami Millionaires Sightseeing Cruise

Miami Millionaires Sightseeing Cruise

  • North America
  • Exellent1,688 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, Oahu 2-Hour Whale Watching: Guaranteed Sightings

(4.6 of 1,319 reviews)

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More

Free Cancellation
Start From $53.31
 
Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings

Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings

  • North America
  • Superb1,319 reviews4.6

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....

    Free Cancellation
    Start From $53.31
 
 

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

(4.9 of 4,502 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
  • Superb4,502 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
 
 

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

(4.6 of 3,458 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
  • Superb3,458 reviews4.6

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

    Free Cancellation
    Start From $129.00
 
 

Key West Signature Sunset Sail with Live Music, Open Bar & Food

(4.5 of 356 reviews)

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More

Free Cancellation
Start From $72.00
 
Key West Signature Sunset Sail with Live Music, Open Bar & Food Likely to Sell Out

Key West Signature Sunset Sail with Live Music, Open Bar & Food

  • North America
  • Exellent356 reviews4.5

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. ....

    Free Cancellation
    Start From $72.00
 
 

Kauai: Deluxe Nā Pali Sunset Cruise - aboard Lucky Lady

(4.7 of 1,554 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
 
Kauai: Deluxe Nā Pali Sunset Cruise - aboard Lucky Lady Likely to Sell Out

Kauai: Deluxe Nā Pali Sunset Cruise - aboard Lucky Lady

  • North America
  • Superb1,554 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
 
 

San Francisco Bay Cruise

(4.4 of 328 reviews)

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour excursion heads underneath the Golden Gate Bridge, around Alcatraz Island, past Angel Island State Park, and alongside the cit... More

Special Offer
Free Cancellation
Start From $35.10
(Saving 10% ) $39.00
 
-10% San Francisco Bay Cruise Likely to Sell Out

San Francisco Bay Cruise

  • North America
  • Exellent328 reviews4.4

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hou....

    Special Offer
    Free Cancellation
    Start From $35.10
    (Saving 10% ) $39.00
 
 

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

(4.7 of 3,663 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

Special Offer
Free Cancellation
Start From $79.00
(Saving inf% ) $0.00
 
-inf% Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres Likely to Sell Out

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

  • North America
  • Superb3,663 reviews4.7

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

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

Turtles & Tacos Luxury Catamaran Snorkel

(4.7 of 114 reviews)

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and snorkel alongside Hawaiian green sea turtles and colorful tropical fish at ... More

Special Offer
Free Cancellation
Start From $199.00
(Saving inf% ) $0.00
 
-inf% Turtles & Tacos Luxury Catamaran Snorkel Likely to Sell Out

Turtles & Tacos Luxury Catamaran Snorkel

  • North America
  • Superb114 reviews4.7

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....

    Special Offer
    Free Cancellation
    Start From $199.00
    (Saving inf% ) $0.00
 
 

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

(4.8 of 3,608 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 $119.20
(Saving 20% ) $149.00
 
-20% Los Cabos Luxury Sailing, Snorkel and Lunch Cruise Likely to Sell Out

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

  • North America
  • Superb3,608 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 $119.20
    (Saving 20% ) $149.00
 
 

Kona Signature Catamaran Sunset Sail

(4.8 of 249 reviews)

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean and coastline as the sky transforms with vibrant hues of orange, pink and gold. Relax on d... More

Special Offer
Free Cancellation
Start From $109.00
(Saving inf% ) $0.00
 
-inf% Kona Signature Catamaran Sunset Sail Likely to Sell Out

Kona Signature Catamaran Sunset Sail

  • North America
  • Superb249 reviews4.8

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloh....

    Special Offer
    Free Cancellation
    Start From $109.00
    (Saving inf% ) $0.00
 
 

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

(4.5 of 649 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

Special Offer
Free Cancellation
Start From $48.00
(Saving inf% ) $0.00
 
-inf% Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor Likely to Sell Out

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

  • North America
  • Exellent649 reviews4.5

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

    Special Offer
    Free Cancellation
    Start From $48.00
    (Saving inf% ) $0.00
 
 

Pirate Ship Sunset Dinner and Show in Los Cabos

(4.3 of 702 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 $99.00
(Saving inf% ) $0.00
 
-inf% Pirate Ship Sunset Dinner and Show in Los Cabos Likely to Sell Out

Pirate Ship Sunset Dinner and Show in Los Cabos

  • North America
  • Exellent702 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 $99.00
    (Saving inf% ) $0.00
 
 

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

(4.3 of 1,502 reviews)

Award Winning Cozumel Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire the Spectacular marine life on this awarded Cozumel Snorkeling trip. Enjoy Cozumel's top attractions and most visited reefs in the C... More

Special Offer
Free Cancellation
Start From $58.50
(Saving 10% ) $65.00
 
-10% Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs Likely to Sell Out

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

  • North America
  • Exellent1,502 reviews4.3

Award Winning Cozumel Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire th....

    Special Offer
    Free Cancellation
    Start From $58.50
    (Saving 10% ) $65.00
 
 

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,543 reviews)

The water is clean, clear, and safe following the recent storms! Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from Waikiki. ... More

Special Offer
Free Cancellation
Start From $49.95
(Saving inf% ) $0.00
 
-inf% Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Likely to Sell Out

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • North America
  • Superb1,543 reviews4.9

The water is clean, clear, and safe following the recent storms! Experience one Viator's 2025 Top 2....

    Special Offer
    Free Cancellation
    Start From $49.95
    (Saving inf% ) $0.00
 
 

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

(4.6 of 22 reviews)

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience offers breathtaking views of the sunset complemented by deligh... More

Special Offer
Free Cancellation
Start From $141.98
(Saving inf% ) $0.00
 
-inf% Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar Likely to Sell Out

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

  • North America
  • Superb22 reviews4.6

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....

    Special Offer
    Free Cancellation
    Start From $141.98
    (Saving inf% ) $0.00
 
 

Key West Reef Morning Snorkeling with Breakfast and Mimosas

(4.5 of 613 reviews)

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More

Special Offer
Free Cancellation
Start From $35.00
(Saving inf% ) $0.00
 
-inf% Key West Reef Morning Snorkeling with Breakfast and Mimosas Likely to Sell Out

Key West Reef Morning Snorkeling with Breakfast and Mimosas

  • North America
  • Exellent613 reviews4.5

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....

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

Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure

(4.7 of 1,395 reviews)

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

Special Offer
Free Cancellation
Start From $68.60
(Saving 15% ) $80.71
 
-15% Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure Likely to Sell Out

Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure

  • North America
  • Superb1,395 reviews4.7

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join ....

    Special Offer
    Free Cancellation
    Start From $68.60
    (Saving 15% ) $80.71
 
 

Kauai: Leila Na Pali Sunset Dinner Sail

(4.7 of 538 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

Special Offer
Free Cancellation
Start From $263.82
(Saving inf% ) $0.00
 
-inf% Kauai: Leila Na Pali Sunset Dinner Sail Likely to Sell Out

Kauai: Leila Na Pali Sunset Dinner Sail

  • North America
  • Superb538 reviews4.7

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

    Special Offer
    Free Cancellation
    Start From $263.82
    (Saving inf% ) $0.00
 
 

Buccaneer Pirate Cruise in Destin

(4.9 of 110 reviews)

Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family! Enjoy a fun cruise with interactive pirate-themed activities, entertainment, and treasure hunts. Take in the beauty of the Emeral... More

Special Offer
Free Cancellation
Start From $55.00
(Saving inf% ) $0.00
 
-inf% Buccaneer Pirate Cruise in Destin Likely to Sell Out

Buccaneer Pirate Cruise in Destin

  • North America
  • Superb110 reviews4.9

Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family!....

    Special Offer
    Free Cancellation
    Start From $55.00
    (Saving inf% ) $0.00
 
1 2 3 4 5
Booking.com
Booking.com
Booking.com