Top North America Sailing Trips

Q: Which North America Sailing Trips have Instant Confirmation?

North America Sailing Trips with Instant Confirmation include: Speedboat and Snorkeling Adventure in Cancun Catamaran Sailing and Snorkeling to Isla Mujeres from Cancun Paddle at Dawn with visit to Cenotes and Islands Where Two Seas Meet: Arch Discovery & Free Time at Playa del Amor Sunrise by Paddle or Kayak with Floating Picnic View all Tours with Instant Confirmation →

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 →

Private Oahu Sunset Charter with Tasting and Drinks

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people …More

Oahu, USA

5.0 (55)

Private Oahu Sunset Charter with Tasting and Drinks

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people...

120 to 150 minutes Free Cancellation

5.0 (55)

from
$1,414

Private Sailing Charter: Up to 24 Passengers

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco …More

San Francisco, USA

5.0 (2)

Private Sailing Charter: Up to 24 Passengers

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco...

1 hour 30 minutes

5.0 (2)

from
$1,425

Private luxury catamaran in Tulum with snacks & open bar

It is an incredible and unique experiences because for 4 hours you will be the owner of this incredible sailing catamaran, with a host and …More

Tulum, Mexico

5.0 (338)

Private luxury catamaran in Tulum with snacks & open bar

It is an incredible and unique experiences because for 4 hours you will be the owner of this incredible sailing catamaran, with a host and...

4 hours Free Cancellation

5.0 (338)

from
$1,450

Puerto Vallarta Private Yacht Adventure 5 hours + 1 hour Free

Sail on a private trip on board our private yacht 50 feet, ideal for up to 18 passengers. We are sure that with us you …More

Puerto Vallarta, Mexico

5.0 (10)

Puerto Vallarta Private Yacht Adventure 5 hours + 1 hour Free

Sail on a private trip on board our private yacht 50 feet, ideal for up to 18 passengers. We are sure that with us you...

6 hours

5.0 (10)

from
$1,452

Private Yacht Tour: 5 Hours + 1 Free with Snorkeling and Beach

Sail on a 6-hour private trip aboard our 55-foot private yacht, ideal for up to 12 passengers. We are sure that with us you will …More

Puerto Vallarta, Mexico

Private Yacht Tour: 5 Hours + 1 Free with Snorkeling and Beach

Sail on a 6-hour private trip aboard our 55-foot private yacht, ideal for up to 12 passengers. We are sure that with us you will...

6 hours

from
$1,485

2hr Luxury Private Sailing Catamaran for 7-12 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

5.0 (4)

2hr Luxury Private Sailing Catamaran for 7-12 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

5.0 (4)

from
$1,495

Visit Private Beaches around Puerto Vallarta in a Private Yacht

Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours don’t go. Also enjoy the explanation from our captain …More

Puerto Vallarta, Mexico

5.0 (128)

Visit Private Beaches around Puerto Vallarta in a Private Yacht

Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours don’t go. Also enjoy the explanation from our captain...

4 hours

5.0 (128)

from
$1,500

Private Catamaran Charter for Exclusive Celebrations

Enjoy the luxury of having your own 35-passenger catamaran for a private charter on the Pacific. Perfect for exclusive celebrations or a fun day with …More

Oahu, USA

5.0 (1)

Private Catamaran Charter for Exclusive Celebrations

Enjoy the luxury of having your own 35-passenger catamaran for a private charter on the Pacific. Perfect for exclusive celebrations or a fun day with...

2 hours Free Cancellation

5.0 (1)

from
$1,500

Private Afternoon Harbor Cruise on Kismet for parties up to 20

Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise the harbor, BYOB, awesome stereo, bathroom, history …More

Charleston, USA

5.0 (30)

Private Afternoon Harbor Cruise on Kismet for parties up to 20

Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise the harbor, BYOB, awesome stereo, bathroom, history...

2 hours Free Cancellation

5.0 (30)

from
$1,549

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 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

5.0 (2)

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 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...

3 hours Free Cancellation

5.0 (2)

from
$1,595

Private Luxury Sunset Sail 39Ft Catamaran in Cozumel – 3 Hours

This is more than a sunset cruise it's a completely private evening aboard a spacious 39 foot Lagoon catamaran. Unlike shared sunset tours, your boat …More

Cozumel, Mexico

5.0 (26)

Private Luxury Sunset Sail 39Ft Catamaran in Cozumel – 3 Hours

This is more than a sunset cruise it's a completely private evening aboard a spacious 39 foot Lagoon catamaran. Unlike shared sunset tours, your boat...

3 hours Free Cancellation

5.0 (26)

from
$1,600

We are a company that understands privacy, attention to detail, and quality in everything we get our hands-on. We want you to feel relaxed and …More

Cozumel, Mexico

5.0 (109)

Deluxe Private Boats - 40 ft Catamaran

We are a company that understands privacy, attention to detail, and quality in everything we get our hands-on. We want you to feel relaxed and...

3 to 8 hours Free Cancellation

5.0 (109)

from
$1,600

Private Luxury Sunset Sail in San Jose del Cabo Marina

Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour. The Luxury Private Sailing boat have capacity from 1 to 16 …More

San Jose del Cabo, Mexico

5.0 (1)

Private Luxury Sunset Sail in San Jose del Cabo Marina

Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour. The Luxury Private Sailing boat have capacity from 1 to 16...

3 hours Hotel pickup offered

5.0 (1)

from
$1,600

Private Luxury Yacht Charter with Snorkeling in Los Cabos

Experience snorkeling in crystal waters, the beach Palmilla has a blue flag recognition and is one of the best beach areas to discover the underwater …More

San Jose del Cabo, Mexico

Private Luxury Yacht Charter with Snorkeling in Los Cabos

Experience snorkeling in crystal waters, the beach Palmilla has a blue flag recognition and is one of the best beach areas to discover the underwater...

4 hours Hotel pickup offered

from
$1,600

Private Catamaran Ride in Los Cabos Food and Bar Outdoors

Enjoy a complete catamaran experience combining scenic sailing, snorkeling and onboard dining. Sail in front of the Cabo San Lucas Arch while enjoying open bar …More

Cabo San Lucas, Mexico

5.0 (18)

Private Catamaran Ride in Los Cabos Food and Bar Outdoors

Enjoy a complete catamaran experience combining scenic sailing, snorkeling and onboard dining. Sail in front of the Cabo San Lucas Arch while enjoying open bar...

3 hours Free Cancellation

5.0 (18)

from
$1,687

All Inclusive St Pete Private Half Day Catamaran Charter

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter …More

St Petersburg, USA

5.0 (1)

All Inclusive St Pete Private Half Day Catamaran Charter

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter...

5 hours Free Cancellation

5.0 (1)

from
$1,700

4hrs / 46ft Catamaran Private Charter From Cancun to Isla Mujeres

This catamaran has capacity up to 45 people. We provide a high quality service, nice boat and we take care of customer during the all …More

Cancun, Mexico

5.0 (6)

4hrs / 46ft Catamaran Private Charter From Cancun to Isla Mujeres

This catamaran has capacity up to 45 people. We provide a high quality service, nice boat and we take care of customer during the all...

4 hours Free Cancellation

5.0 (6)

from
$1,700

Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar

Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great photo opportunities as you pass by the famous …More

San Jose del Cabo, Mexico

5.0 (390)

Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar

Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great photo opportunities as you pass by the famous...

4 hours Hotel pickup offered Free Cancellation

5.0 (390)

from
$1,799

3 Hour Luxury Private Sailing Catamaran for 7-12 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

5.0 (1)

3 Hour Luxury Private Sailing Catamaran for 7-12 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...

3 hours Free Cancellation

5.0 (1)

from
$1,995

All Inclusive Half Day Sunset Catamaran Adventure

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter …More

St Petersburg, USA

5.0 (1)

All Inclusive Half Day Sunset Catamaran Adventure

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter...

6 hours Free Cancellation

5.0 (1)

from
$2,000