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: San Francisco Bay Cruise Suncoast Sailing's Day Sailing Experience! Halifax Sunset Cruise Ft. a Live Musician Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

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 →

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 …More

Oahu, USA

5.0 (2)

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6...

2 hours Free Cancellation

5.0 (2)

from
$1,200

Private Luxury Sailboat for 12 people 4 hrs

Sail through the bay of Puerto Vallarta celebrating your birthday, a special date for you or just to have fun with your friends in private. …More

Puerto Vallarta, Mexico

Private Luxury Sailboat for 12 people 4 hrs

Sail through the bay of Puerto Vallarta celebrating your birthday, a special date for you or just to have fun with your friends in private....

4 hours

from
$1,200

Private Sailing Tour -2 Hour (Up to 12 Passengers)

Christened in 1934, Cloudia is a beautifully restored, rare example of a classic Norwegian double ended ketch. Inspired by the original designs of famed naval …More

San Diego, USA

Private Sailing Tour -2 Hour (Up to 12 Passengers)

Christened in 1934, Cloudia is a beautifully restored, rare example of a classic Norwegian double ended ketch. Inspired by the original designs of famed naval...

2 hours Free Cancellation

from
$1,200

4th of July Sunset Sail on the Black Pearl

Join us for the 4th of July for Fireworks over Cedar Point from a beautiful 47' Sailing yacht - The Black Pearl! Sail magestically across …More

Sandusky, USA

4th of July Sunset Sail on the Black Pearl

Join us for the 4th of July for Fireworks over Cedar Point from a beautiful 47' Sailing yacht - The Black Pearl! Sail magestically across...

4 to 5 hours

from
$1,195

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and …More

Oahu, USA

4.8 (14)

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

2 hours Free Cancellation

4.8 (14)

from
$1,150

4 Hours Private Yacht in Puerto Vallarta with Snorkeling and Beach

Enjoy an exclusive getaway on a private yacht in Puerto Vallarta, where adventure and relaxation meet. On this 4-hour tour, sail to the stunning Arches …More

Puerto Vallarta, Mexico

4 Hours Private Yacht in Puerto Vallarta with Snorkeling and Beach

Enjoy an exclusive getaway on a private yacht in Puerto Vallarta, where adventure and relaxation meet. On this 4-hour tour, sail to the stunning Arches...

4 hours

from
$1,096

Private Afternoon Snorkel with Sunset Sail in Key West

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon …More

Key West, USA

5.0 (4)

Private Afternoon Snorkel with Sunset Sail in Key West

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon...

4 hours Free Cancellation

5.0 (4)

from
$1,070

Portland Tall Ship Private Charter on Casco Bay

What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the …More

Portland, USA

Portland Tall Ship Private Charter on Casco Bay

What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the...

2 hours Free Cancellation

from
$1,069

6 Hour Private Fishing Charter in the Riviera Maya

Unlike many destinations, your fishing time starts within minutes of departure—no long boat rides—maximizing your time with lines in the water. This is a fully …More

Playa del Carmen, Mexico

5.0 (21)

6 Hour Private Fishing Charter in the Riviera Maya

Unlike many destinations, your fishing time starts within minutes of departure—no long boat rides—maximizing your time with lines in the water. This is a fully...

6 hours

5.0 (21)

from
$1,050

Private Morning Ceremony Sailing Charter

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to …More

Oahu, USA

Private Morning Ceremony Sailing Charter

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to...

1 hour 30 minutes Free Cancellation

from
$1,000

Cabo Private Sunset Sailing with Open Bar and Appetizers

Unlike crowded sightseeing boats, you will enjoy a private luxury sailboat experience with personalized service and a relaxed atmosphere designed for comfort and exclusivity. The …More

Cabo San Lucas, Mexico

4.9 (27)

Cabo Private Sunset Sailing with Open Bar and Appetizers

Unlike crowded sightseeing boats, you will enjoy a private luxury sailboat experience with personalized service and a relaxed atmosphere designed for comfort and exclusivity. The...

2 hours 30 minutes Free Cancellation

4.9 (27)

from
$999

A private and exclusive Sunset Sailing Adventure discovering a Sunset that will never repeat. Premium Open Bar and a Cheese and Cold Cuts table as …More

Cabo San Lucas, Mexico

5.0 (1)

Private Sunset Sailing

A private and exclusive Sunset Sailing Adventure discovering a Sunset that will never repeat. Premium Open Bar and a Cheese and Cold Cuts table as...

2 hours Free Cancellation

5.0 (1)

from
$999

Private Sailboat Charter on San Francisco Bay

Fall and winter typically provide lighter breezes on SF Bay. Great days on the Bay. 3 hour PRIVATE Charter with a unique experience aboard Carmelita, …More

5.0 (9)

Private Sailboat Charter on San Francisco Bay

Fall and winter typically provide lighter breezes on SF Bay. Great days on the Bay. 3 hour PRIVATE Charter with a unique experience aboard Carmelita,...

3 hours Free Cancellation

5.0 (9)

from
$995

Our starting point is Carmelita Lagoon Club, a privileged space on the shores of Bacalar Lagoon, with incredible views and an ideal atmosphere to begin …More

Bacalar, Mexico

5.0 (175)

Private Catamaran Tour

Our starting point is Carmelita Lagoon Club, a privileged space on the shores of Bacalar Lagoon, with incredible views and an ideal atmosphere to begin...

4 hours Free Cancellation

5.0 (175)

from
$990

Premium Isla Mujeres Tour by Private Catamaran

We specialize in making this all-day trip unique, a unique and beautiful experience for all our guests. This trip can always be customized as desired, …More

Cancun, Mexico

5.0 (251)

Premium Isla Mujeres Tour by Private Catamaran

We specialize in making this all-day trip unique, a unique and beautiful experience for all our guests. This trip can always be customized as desired,...

5 hours Free Cancellation

5.0 (251)

from
$990

Private Family Catamaran From Isla Mujeres

Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all day when you can do it in less time? …More

Isla Mujeres, Mexico

5.0 (1)

Private Family Catamaran From Isla Mujeres

Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all day when you can do it in less time?...

3 hours Free Cancellation

5.0 (1)

from
$985

Private Sunset Sail on San Diego Bay with Champagne

What makes this experience truly unique is the combination of refined European luxury and a relaxed, intimate atmosphere. You will be sailing aboard a beautifully …More

San Diego, USA

5.0 (1)

Private Sunset Sail on San Diego Bay with Champagne

What makes this experience truly unique is the combination of refined European luxury and a relaxed, intimate atmosphere. You will be sailing aboard a beautifully...

2 hours 30 minutes Free Cancellation

5.0 (1)

from
$975

San Diego's first ever Family Sailing Tours

We are based in San Diego and we are designed for families. Our whole mission is to bring families closer together. We want to put …More

La Jolla, USA

5.0 (6)

San Diego's first ever Family Sailing Tours

We are based in San Diego and we are designed for families. Our whole mission is to bring families closer together. We want to put...

2 hours 30 minutes Free Cancellation

5.0 (6)

from
$975

Discover the stunning beauty of Monterey Bay aboard your own private sailing charter. This experience caters to all ages and interests. Venture along the coastline, …More

Monterey & Carmel, USA

5.0 (1)

Private Sailing Trip on Monterey Bay

Discover the stunning beauty of Monterey Bay aboard your own private sailing charter. This experience caters to all ages and interests. Venture along the coastline,...

2 hours Free Cancellation

5.0 (1)

from
$965