Top North America Sailing Trips

Q: What are the best options for North America Sailing Trips?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best North America Sailing Trips are: Crystal Boat Tour with Snorkeling and Drinks in Cozumel Cancun Mangrove Jet Ski Tour Ultimate Bay Tours -Private 25 Travelers- Trimaran Experience Cabo San Lucas Private Custom Snorkel or Sunset Adventure Excursion to Reefs in a transparent boat from Cancun

Q: What are the best kid-friendly options for North America Sailing Trips Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly North America Sailing Trips are: 3 Hour Xpuha-60' Neptunus-Tulum, Playa del Carmen, Riviera Maya 4th of July Fireworks on Clipper City Tall Ship #1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson The Nāpali Coast Snorkel Excursion Pirate Ship by Day View all kid-friendly Tours →

Q: Which North America Sailing Trips have Instant Confirmation?

North America Sailing Trips with Instant Confirmation include: Private Luxury Yacht Charter aboard Tu Enamorado Private Catamaran from Cancun to Isla Mujeres | For up to 100 pp Luxury Yacht 58 ft for up to 20 people 4 hrs Private Cruise Swim with Dolphin Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs View all Tours with Instant Confirmation →

Q: I need a ride! Which North America Sailing Trips have Hotel Pickup?

No problem. These North America Sailing Trips include Hotel Pickup: Private Cruise Swim with Dolphin Private Romantic Sailing Sunset Experience Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar Private Luxury Sunset Sail in San Jose del Cabo Marina Private Luxury Yacht Charter with Snorkeling in Los Cabos View all Tours with Hotel Pickup →

Q: Got any more North America trip ideas?

We sure do. Check out our curated lists of hand-picked North America Tours. Top 10 North America 2026 Senior-friendly tours North America The best tours and activities for culture lovers in North America Top Day Trips from North America Things to do in North America this summer View all North America Trip Ideas →

Q: What are the most popular styles of Tours and Activities in North America?

Based on our sales data over the past year, the most popular styles of tours and activities in North America are: North America Luxury & Special Occasions North America Luxury Tours North America Tours & Sightseeing North America Kid Friendly North America Cruises, Sailing & Water Tours View all tour styles in North America →

Waikiki 2 Hour Sunset Whale Watching Cruise Sightings Guaranteed

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden …More

Oahu, USA

4.6 (87)

Waikiki 2 Hour Sunset Whale Watching Cruise Sightings Guaranteed

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden...

2 hours Free Cancellation

4.6 (87)

from
$57

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana …More

Cocoa Beach, USA

4.9 (206)

Sunset Catamaran Sail in Cocoa Beach

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana...

2 hours Free Cancellation

4.9 (206)

from
$56

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

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 …More

Charleston, USA

4.6 (858)

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

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...

1 hour 30 minutes Free Cancellation

4.6 (858)

from
$56

Daytime Charleston Harbor Sail - Lux Catamatan w/Bar

Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s historic harbor. This 55-foot catamaran offers the perfect vantage point to …More

Mount Pleasant, USA

4.7 (11)

Daytime Charleston Harbor Sail - Lux Catamatan w/Bar

Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s historic harbor. This 55-foot catamaran offers the perfect vantage point to...

2 hours Free Cancellation

4.7 (11)

from
$56

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by …More

Hilton Head Island, USA

4.7 (565)

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by...

1 hour 30 minutes Free Cancellation

4.7 (565)

from
$55

Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon

Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters in the Caribbean and has the most fascinating tropical …More

Bacalar, Mexico

4.9 (111)

Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon

Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters in the Caribbean and has the most fascinating tropical...

3 hours Free Cancellation

4.9 (111)

from
$55

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

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 …More

Isla Mujeres, Mexico

4.8 (3,830)

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

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...

5 hours 30 minutes Free Cancellation

4.8 (3,830)

from
$55

Scenic Day Sails in Newport Harbor and Narragansett Bay Aquidneck

Set sail aboard Aquidneck on a memorable journey through Newport Harbor and Narragansett Bay, where the winds are perfect for an afternoon adventure. Guests can …More

Newport, USA

5.0 (4)

Scenic Day Sails in Newport Harbor and Narragansett Bay Aquidneck

Set sail aboard Aquidneck on a memorable journey through Newport Harbor and Narragansett Bay, where the winds are perfect for an afternoon adventure. Guests can...

1 hour 40 minutes Free Cancellation

5.0 (4)

from
$55

San Diego Harbor Cruise on the Largest Catamaran in San Diego

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by …More

San Diego, USA

4.9 (55)

San Diego Harbor Cruise on the Largest Catamaran in San Diego

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by...

2 hours 30 minutes Free Cancellation

4.9 (55)

from
$55

Jungle Tour In Cancun, drive a speedboat through the lagoon

Welcome to the most enigmatic activity in Cancun, the famous jungle tour, this is the best and quick way to know Cancun and all its …More

Cancun, Mexico

4.3 (3)

Jungle Tour In Cancun, drive a speedboat through the lagoon

Welcome to the most enigmatic activity in Cancun, the famous jungle tour, this is the best and quick way to know Cancun and all its...

3 hours Hotel pickup offered Free Cancellation

4.3 (3)

from
$55

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 Cool Shore Excursions TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for …More

Oahu, USA

4.9 (1,015)

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 Cool Shore Excursions TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for...

2 hours Free Cancellation

4.9 (1,015)

from
$55

Crystal Boat Tour with Snorkeling and Drinks in Cozumel

Dare to live this incredible experience aboard our Transparent Boat! Sail the Caribbean Sea and discover the emblematic sites of Cozumel such as the first …More

Cozumel, Mexico

4.5 (4)

Crystal Boat Tour with Snorkeling and Drinks in Cozumel

Dare to live this incredible experience aboard our Transparent Boat! Sail the Caribbean Sea and discover the emblematic sites of Cozumel such as the first...

1 hour 30 minutes Free Cancellation

4.5 (4)

from
$55

Sightseeing Day Sail around Boston Harbor

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 …More

Boston, USA

4.8 (654)

Sightseeing Day Sail around Boston Harbor

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...

90 to 120 minutes Free Cancellation

4.8 (654)

from
$54

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 …More

Seattle, USA

4.8 (591)

Seattle Sailing Harbor Tour

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...

2 hours Free Cancellation

4.8 (591)

from
$54

Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers. Cruise through the prestigious Port Royal neighborhood in …More

Naples, USA

5.0 (71)

Sunset Cruise Tour

Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers. Cruise through the prestigious Port Royal neighborhood in...

2 hours Free Cancellation

5.0 (71)

from
$54

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 …More

San Diego, USA

4.6 (681)

San Diego Whale Watching Cruise

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...

3 hours 30 minutes Free Cancellation

4.6 (681)

from
$54

Schooner Appledore Day Sail with Full Bar in Key West

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern …More

Key West, USA

5.0 (113)

Schooner Appledore Day Sail with Full Bar in Key West

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern...

2 hours Free Cancellation

5.0 (113)

from
$54

Key West Reef Morning Snorkeling with Breakfast and Mimosas

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 …More

Key West, USA

4.7 (694)

Key West Reef Morning Snorkeling with Breakfast and Mimosas

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...

3 hours Free Cancellation

4.7 (694)

from
$54

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while …More

Oahu, USA

5.0 (13)

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while...

1 hour 30 minutes Free Cancellation

5.0 (13)

from
$53

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboard a spacious sailing catamaran. This family-friendly adventure includes …More

Panama City Beach, USA

4.9 (5,050)

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboard a spacious sailing catamaran. This family-friendly adventure includes...

3 hours Free Cancellation

4.9 (5,050)

from
$52