Top North America Sailing Trips

632 Results
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

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

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
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

Likely to Sell Out
Likely to Sell Out
Oahu, USA

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 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

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
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

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

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
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

Likely to Sell Out
Likely to Sell Out
Oahu, USA

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
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

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
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

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 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

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
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

Likely to Sell Out
Likely to Sell Out
San Francisco, USA

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 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

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 Yacht in Tulum with Snacks and Open Bar

What truly sets this tour apart is the level of privacy and customization we offer. Whether you're celebrating a special occasion or simply seeking a …More

Playa del Carmen, Mexico

What truly sets this tour apart is the level of privacy and customization we offer. Whether you're celebrating a special occasion or simply seeking a...

4 hours Free Cancellation
5.0 (5)
from
$1,400
Private Catamaran to Isla Mujeres– Snorkel, Beach Club & Open Bar

The fun starts the moment you step on board. Enjoy a private catamaran experience with open bar from the very beginning, good music, refreshing drinks, …More

Cancun, Mexico

The fun starts the moment you step on board. Enjoy a private catamaran experience with open bar from the very beginning, good music, refreshing drinks,...

7 hours Free Cancellation
from
$1,400
4 hours - Private 48ft Yacht all inclusive in Tulum and Playa del Carmen

We are a Yacht private rental company with more than 15 years of experience in the hospitality industry in Playa del Carmen, Puerto Aventuras and …More

Playa del Carmen, Mexico

We are a Yacht private rental company with more than 15 years of experience in the hospitality industry in Playa del Carmen, Puerto Aventuras and...

4 hours
5.0 (456)
from
$1,398
3 Hour Xpuha-60' Neptunus-Tulum, Playa del Carmen, Riviera Maya

We know you’re not just looking for a yacht—you’re looking for an experience. We’re in the business of making dreams come true! Our new yacht …More

Playa del Carmen, Mexico

We know you’re not just looking for a yacht—you’re looking for an experience. We’re in the business of making dreams come true! Our new yacht...

3 hours
5.0 (221)
from
$1,349
Private Sunset Tour in Marina La Cruz by Yacht

Prepare for a unique experience that combines elegance with relaxation as we navigate as the sun begins to rise on the horizon. On our yacht, …More

Prepare for a unique experience that combines elegance with relaxation as we navigate as the sun begins to rise on the horizon. On our yacht,...

3 hours
5.0 (40)
from
$1,300
Ultimate Bay Tours -Private 25 Travelers- Trimaran Experience

Hey there! Just wanted to share this amazing find with you - a private 43 feet Trimaran in Mazatlan that can accommodate up to 25 …More

Mazatlán, Mexico

Hey there! Just wanted to share this amazing find with you - a private 43 feet Trimaran in Mazatlan that can accommodate up to 25...

4 to 5 hours Hotel pickup offered Free Cancellation
5.0 (1)
from
$1,250
Private Fishing & Snorkeling Boat Charter (Up to 12 pax)

Set sail on the ultimate private marine adventure departing from Nuevo Vallarta! Perfect for families or friend groups (1 to 12 passengers), your party will …More

Puerto Vallarta, Mexico

Set sail on the ultimate private marine adventure departing from Nuevo Vallarta! Perfect for families or friend groups (1 to 12 passengers), your party will...

5 hours Free Cancellation
4.4 (14)
from
$1,219
Private Sailing for up to 10 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

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
$1,216

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