Top North America Sailing Trips

633 Results
Best Private Luxury Daytime Boat Tour in New York City - 2 Hour

Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manhattan aboard a 30' luxurious powerboat. Get an unobstructed view …More

New York City, USA

Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manhattan aboard a 30' luxurious powerboat. Get an unobstructed view...

2 hours Free Cancellation
5.0 (99)
from
$500
El Cielo Snorkel by Private Boat

- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and coral formations - Stop over at a secluded pristine …More

Likely to Sell Out
Likely to Sell Out
Cozumel, Mexico

- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and coral formations - Stop over at a secluded pristine...

4 hours Free Cancellation
4.9 (341)
from
$500
Private Sailing Charter on San Diego Bay

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural …More

San Diego, USA

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural...

3 hours Free Cancellation
4.9 (50)
from
$499
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the …More

Hilton Head Island, USA

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the...

2 hours Free Cancellation
5.0 (122)
from
$485
6hrs of Sailing in Bacalar Lagoon: discover Cenotes, Islands and Stromatolites.

Ideal for adventurers and sailing lovers! Explore the most emblematic points of the lagoon, or modify the route to discover areas far from tourism. 6 …More

Bacalar, Mexico

Ideal for adventurers and sailing lovers! Explore the most emblematic points of the lagoon, or modify the route to discover areas far from tourism. 6...

6 hours Free Cancellation
5.0 (19)
from
$468
2 - Hour Private Hilton Head Morning Dolphin Watching / Sail

This 2 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side of the island - generally best conditions …More

Hilton Head Island, USA

This 2 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side of the island - generally best conditions...

2 hours Free Cancellation
5.0 (37)
from
$465
Private Catamaran: Snorkel, Swim and Dolphin Watching

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take …More

Likely to Sell Out
Likely to Sell Out
Destin, USA

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take...

3 hours Free Cancellation
5.0 (1)
from
$465
Private Sunset and Eco Tour in Destin Up to 18 Guests

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset …More

Likely to Sell Out
Likely to Sell Out
Destin, USA

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset...

1 hour 30 minutes Free Cancellation
5.0 (45)
from
$450
Marco Island Private Catamaran Sailing Tour

It’s your own private sail with Captain Nick, the owner of Easy Breezy Charters. Breezy is a 30-foot Stiletto sailing catamaran with open nets at …More

Likely to Sell Out
Likely to Sell Out
Naples, USA

It’s your own private sail with Captain Nick, the owner of Easy Breezy Charters. Breezy is a 30-foot Stiletto sailing catamaran with open nets at...

2 hours
5.0 (154)
from
$450
Isla Mujeres, Cancún Private Sunset Trip

Our tours are suited to your needs, as we want you to enjoy yourself, to simply let go, to watch the sunset and experience the …More

Isla Mujeres, Mexico

Our tours are suited to your needs, as we want you to enjoy yourself, to simply let go, to watch the sunset and experience the...

5 hours Hotel pickup offered Free Cancellation
5.0 (82)
from
$450
Private Sailing Charters in Oceanside CA

Explore the stunning Pacific waters with a private sailing charter in Oceanside, California. Enjoy a customizable sailing adventure tailored to your pace and interests, guided …More

Carlsbad, USA

Explore the stunning Pacific waters with a private sailing charter in Oceanside, California. Enjoy a customizable sailing adventure tailored to your pace and interests, guided...

2 hours Free Cancellation
5.0 (4)
from
$450
#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed …More

Oahu, USA

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed...

2 hours Free Cancellation
5.0 (4)
from
$450
Fort Myers: Tiki Pub VIP Private Dolphin & Sunset Cruise

Spend the most amazing time of day in the best place to enjoy it. Our custom tiki boat has it all. Whether you want to …More

Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

Spend the most amazing time of day in the best place to enjoy it. Our custom tiki boat has it all. Whether you want to...

2 hours Free Cancellation
5.0 (4)
from
$449
Private Yacht Charter in Cabo for Up to 8 People

Experience Cabo San Lucas exclusively aboard a private yacht for up to 8 people. Enjoy a personalized experience sailing in front of the iconic Arch, …More

Cabo San Lucas, Mexico

Experience Cabo San Lucas exclusively aboard a private yacht for up to 8 people. Enjoy a personalized experience sailing in front of the iconic Arch,...

2 hours Free Cancellation
5.0 (4)
from
$429
Private 90-Minute Harbor Sailing Charter in Key West

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida …More

Key West, USA

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida...

1 hour 30 minutes Free Cancellation
4.9 (20)
from
$425
Private Therapy Sailing Adventure

Old Plank Adventures: Sail into Deep Tranquility LUXURY SAILING | THERAPEUTIC ESCAPES | GOURMET CUISINE | INTIMATE WILDLIFE ENCOUNTERS Immerse yourself in the timeless Mediterranean …More

Santa Monica, USA

Old Plank Adventures: Sail into Deep Tranquility LUXURY SAILING | THERAPEUTIC ESCAPES | GOURMET CUISINE | INTIMATE WILDLIFE ENCOUNTERS Immerse yourself in the timeless Mediterranean...

2 to 3 hours
4.8 (49)
from
$400
Old Plank Adventures: Sail into Deep Tranquility

Old Plank Sailing Adventures is a boutique luxury sailing charter and aquatic expedition company, delivering gourmet 5-star experiences on the sparkling waters of Santa Monica …More

Santa Monica, USA

Old Plank Sailing Adventures is a boutique luxury sailing charter and aquatic expedition company, delivering gourmet 5-star experiences on the sparkling waters of Santa Monica...

2 hours Free Cancellation
5.0 (3)
from
$400
Luxury Private Yacht Charter in Cabo San Lucas Mexico

You will take a 2-hour tour of the bay of Cabo San Lucas aboard "Reel Tequila" our 31ft boat with a capacity of up to …More

Cabo San Lucas, Mexico

You will take a 2-hour tour of the bay of Cabo San Lucas aboard "Reel Tequila" our 31ft boat with a capacity of up to...

2 hours Free Cancellation
5.0 (8)
from
$400
SUNSET CRUISE in Key Largo,FL.

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need to worry about large crowds or waiting …More

Likely to Sell Out
Likely to Sell Out
Key Largo, USA

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need to worry about large crowds or waiting...

1 hour 30 minutes Free Cancellation
5.0 (2)
from
$389
Private Sailboat Charter from San Pedro: Port of Los Angeles

Experience the beauty of the Pacific Ocean with a private yacht charter in San Pedro, CA. Enjoy a sunset sailing adventure on a Beneteau Oceanis …More

Los Angeles, USA

Experience the beauty of the Pacific Ocean with a private yacht charter in San Pedro, CA. Enjoy a sunset sailing adventure on a Beneteau Oceanis...

2 to 4 hours Free Cancellation
5.0 (1)
from
$380

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