Top North America Sailing Trips

632 Results
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

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
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 …More

Cabo San Lucas, Mexico

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 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

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
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

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
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

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
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

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
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

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
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

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
4.8 (14)
from
$1,150
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

Likely to Sell Out
Likely to Sell Out
Sandusky, USA

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
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

Likely to Sell Out
Likely to Sell Out
Oahu, USA

(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

Likely to Sell Out
Likely to Sell Out
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
$1,200
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

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
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
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
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 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
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
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
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

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