USA Sailing Trips

385 Results
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
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
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
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
Sunset Sailing Cruise on San Diego Bay | Champagne Included

What makes this experience truly special is the blend of refined European luxury and a relaxed, intimate atmosphere without the feel of a large group …More

San Diego, USA

What makes this experience truly special is the blend of refined European luxury and a relaxed, intimate atmosphere without the feel of a large group...

2 hours 30 minutes Free Cancellation
5.0 (1)
from
$199
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
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
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

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
Spend the Day on Buzzards Bay - Powerboat Cruises

Embark on an unforgettable journey aboard our private powerboat "Petrel" Pricing is just $375 per hour for a two-hour trip. Up to 6 passengers are …More

Embark on an unforgettable journey aboard our private powerboat "Petrel" Pricing is just $375 per hour for a two-hour trip. Up to 6 passengers are...

2 hours Free Cancellation
5.0 (1)
from
$540
Private Half Day Sailing Charter in Portland Maine

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa, …More

Portland, USA

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa,...

4 hours Free Cancellation
5.0 (1)
from
$158
Private Sailing Trip on Monterey Bay

Discover the stunning beauty of Monterey Bay aboard your own private sailing charter. This experience caters to all ages and interests. Venture along the coastline, …More

Monterey & Carmel, USA

Discover the stunning beauty of Monterey Bay aboard your own private sailing charter. This experience caters to all ages and interests. Venture along the coastline,...

2 hours Free Cancellation
5.0 (1)
from
$965
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
Bachelorette Sailing Party on San Diego Bay up to 6 Guests

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, …More

San Diego, USA

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers,...

2 hours
5.0 (1)
from
$800
6-Night Private Charter in Lake Clark National Park

Spend six nights and seven days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group …More

Spend six nights and seven days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group...

7 days
5.0 (1)
from
$30,769
3-Night Private Charter in Lake Clark National Park

Spend three nights and four days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group …More

Spend three nights and four days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group...

4 days
5.0 (1)
from
$20,513
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
Sunset Sailing Tour of San Diego Bay up to 6 Guests

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers …More

San Diego, USA

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers...

2 hours
5.0 (1)
from
$800
Waikiki Catamaran Snorkel with Lunch: Turtles Guaranteed

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and …More

Oahu, USA

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and...

2 to 3 hours Free Cancellation
4.7 (2,102)
from
$170

Frequently Asked Questions

These answers are based on answers previously given to City Sky Diving customers' questions.

Recent tour reviews
Activity name

USA Tours
Attractions
Guides
Calendar