Top North America Sailing Trips

632 Results
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

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
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

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
All Inclusive Full Day Luxury 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

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...

7 hours Free Cancellation
5.0 (1)
from
$2,100
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
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

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 (1)
from
$1,995
Cancun Half Day Sailing Cataman Cruise to Isla Mujeres

Original Half Day Sailing since 2012, No need to invest your whole day to visit Isla Mujeres! Lite Tour to Isla Mujeres provides full sailing, …More

Likely to Sell Out
Likely to Sell Out
Punta Sam, Mexico

Original Half Day Sailing since 2012, No need to invest your whole day to visit Isla Mujeres! Lite Tour to Isla Mujeres provides full sailing,...

4 hours 30 minutes Hotel pickup offered Free Cancellation
5.0 (1)
from
$79
Themed and Special Event Cruise in Chesapeake Bay

This cruise is a unique way to celebrate that special event in your life while cruising on your very own private sailing yacht. You and …More

Likely to Sell Out
Likely to Sell Out

This cruise is a unique way to celebrate that special event in your life while cruising on your very own private sailing yacht. You and...

2 hours 30 minutes Free Cancellation
5.0 (1)
from
$790
Amazing Romantic Dinner In Cancun On A Spanish Galeon

Have you run out of ideas to celebrate love with your partner? Imagine to reconquer your true love. In Cancun you have an incredible opportunity …More

Likely to Sell Out
Likely to Sell Out
Punta Sam, Mexico

Have you run out of ideas to celebrate love with your partner? Imagine to reconquer your true love. In Cancun you have an incredible opportunity...

3 hours Free Cancellation
5.0 (1)
from
$99
Super ATVs and Romantic Dinner Combo, with transport & dinner

Would you like to give your partner the best birthday or anniversary gift during the holidays? Join us in this great adventure that takes you …More

Punta Sam, Mexico

Would you like to give your partner the best birthday or anniversary gift during the holidays? Join us in this great adventure that takes you...

13 hours Hotel pickup offered Free Cancellation
5.0 (1)
from
$184
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
2.5 Hour Karaoke Cruise Experience in Lake Chatuge

Join us for an amazing karaoke cruise across the gorgeous waters of Lake Chatuge! Belt out your favorite tunes or just kick back and enjoy …More

Join us for an amazing karaoke cruise across the gorgeous waters of Lake Chatuge! Belt out your favorite tunes or just kick back and enjoy...

3 hours Free Cancellation
5.0 (1)
from
$530
Glass Bottom Boat Sunset and After Dark Reef Walker Cruise

Enjoy a stunning sunset cruise along the Waikiki coastline, where the heat softens and Diamond Head transforms into a silhouette against the vibrant sky. Departing …More

Oahu, USA

Enjoy a stunning sunset cruise along the Waikiki coastline, where the heat softens and Diamond Head transforms into a silhouette against the vibrant sky. Departing...

1 hour 30 minutes Free Cancellation
5.0 (1)
from
$69
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

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 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
Afternoon Catamaran to Isla Mujeres: Snorkel, Open Bar & Sunset

This is one of the few afternoon catamaran experiences available in Cancun. Discover Isla Mujeres on a relaxed afternoon catamaran tour from Cancun. Avoid the …More

Cancun, Mexico

This is one of the few afternoon catamaran experiences available in Cancun. Discover Isla Mujeres on a relaxed afternoon catamaran tour from Cancun. Avoid the...

7 hours Free Cancellation
5.0 (1)
from
$89
Luxury Sailboat at Sunset in Cancun

To cross the calm waters of the Caribbean, there is no better means of transportation than a catamaran. These specialized sailboats have multiple hulls so …More

Cancun, Mexico

To cross the calm waters of the Caribbean, there is no better means of transportation than a catamaran. These specialized sailboats have multiple hulls so...

2 hours 30 minutes Hotel pickup offered
5.0 (1)
from
$150
Lahaina Maui Afternoon Whale Watch Sail in Humpback Sanctuary

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, …More

Maui, USA

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii,...

2 hours Free Cancellation
5.0 (1)
from
$102
Private Sailing Experience on Galveston Bay

See the Texas Gulf Coast in a whole new way. Feel the sea breeze, explore the Texas Gulf Coast, and discover a new way to …More

Houston, USA

See the Texas Gulf Coast in a whole new way. Feel the sea breeze, explore the Texas Gulf Coast, and discover a new way to...

4 hours Free Cancellation
5.0 (1)
from
$800
Private Sunset Sail in Key West Florida

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch …More

Key West, USA

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch...

2 hours Free Cancellation
5.0 (1)
from
$750
Romantic Dinner Touring the Nichupté Lagoon in Galeón

Love will fall at the foot of the Nichupté Lagoon, as you discover its most precious secrets aboard the Columbus Romantic Dinner Cruise. This is …More

Cancun, Mexico

Love will fall at the foot of the Nichupté Lagoon, as you discover its most precious secrets aboard the Columbus Romantic Dinner Cruise. This is...

3 hours Free Cancellation
5.0 (1)
from
$125

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