USA Sailing Trips

Private Sailing on the Miami Bay - Biscayne Bay

Let's go Sailing!  Experience Miami's Biscayne Bay aboard one of City Sky Diving Beneteau stylish vessels in the company of experienced, but mostly fun, well …More

Likely to Sell Out
Likely to Sell Out
Miami, USA

Let's go Sailing!  Experience Miami's Biscayne Bay aboard one of City Sky Diving Beneteau stylish vessels in the company of experienced, but mostly fun, well...

4 to 12 hours Free Cancellation
5.0 (67)
from
$175
2.5 hr Sailboat Tour aboard Orion's Child

City Sky Diving Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. …More

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

City Sky Diving Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel....

2 hours 30 minutes Free Cancellation
5.0 (93)
from
$130
Sunset Sailing Cruise in Monterey Bay

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience …More

Likely to Sell Out
Likely to Sell Out
Monterey & Carmel, USA

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience...

1 hour 30 minutes Free Cancellation
4.8 (62)
from
$95
Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran

Your 90 minute sunset sail on 41ft, 32 passenger Lazy Daze Catamaran will include a scenic trip through Grand Lagoon and along the coast of …More

Panama City Beach, USA

Your 90 minute sunset sail on 41ft, 32 passenger Lazy Daze Catamaran will include a scenic trip through Grand Lagoon and along the coast of...

1 hour 30 minutes Free Cancellation
5.0 (6)
from
$38
Private Hilton Head Sunset Sailing Tour with Dolphin Watching

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island - …More

Hilton Head Island, USA

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island -...

2 hours Free Cancellation
5.0 (125)
from
$525
New York City Sunset Sail to the Statue of Liberty

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic …More

Likely to Sell Out
Likely to Sell Out
New York City, USA

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic...

2 hours Free Cancellation
4.9 (75)
from
$90
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far …More

Oahu, USA

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far...

2 hours Free Cancellation
4.9 (264)
from
$50
Private Sunset Sail in San Diego up to 12 guests

Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to helping families create unforgettable memories. Our vessel is thoughtfully designed to be …More

Likely to Sell Out
Likely to Sell Out
San Diego, USA

Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to helping families create unforgettable memories. Our vessel is thoughtfully designed to be...

2 hours 30 minutes Free Cancellation
5.0 (73)
from
$85
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, …More

Maui, USA

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers,...

5 hours Free Cancellation
5.0 (141)
from
$193
Kona Morning Snorkel to Captain Cook Monument

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along …More

Big Island of Hawaii, USA

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along...

4 hours 30 minutes Free Cancellation
4.9 (480)
from
$179
Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with …More

San Diego, USA

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with...

2 hours 30 minutes Free Cancellation
5.0 (359)
from
$125
Sailboat Cruise on Chesapeake Bay

Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay, powered …More

Likely to Sell Out
Likely to Sell Out

Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay, powered...

2 hours 30 minutes Free Cancellation
5.0 (40)
from
$116
Key West Dolphin Watch and Sunset Sail on Catamaran

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of …More

Likely to Sell Out
Likely to Sell Out
Key West, USA

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of...

3 hours Free Cancellation
4.9 (40)
from
$124
Maui Molokini Snorkeling Sailing Adventure with Breakfast & Lunch

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, …More

Maui, USA

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve,...

5 hours Free Cancellation
4.9 (220)
from
$221
Key West: Sunset Sail + Reef Snorkel & Sandbar

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • …More

Likely to Sell Out
Likely to Sell Out
Key West, USA

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? •...

4 hours 30 minutes Free Cancellation
5.0 (56)
from
$150
Private Sailing Charter with Captain, BYOB

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's …More

Charleston, USA

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's...

2 hours 30 minutes Free Cancellation
5.0 (97)
from
$500
90 Minute Sailing Tour of Portland

Our tour begins with a cruise across the river to the most expensive floating homes on the Willamette. We then usually head down the historic Holgate …More

Portland, USA

Our tour begins with a cruise across the river to the most expensive floating homes on the Willamette. We then usually head down the historic Holgate...

1 hour 30 minutes Free Cancellation
4.5 (4)
from
$99
Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on City Sky Diving …More

Charleston, USA

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on City Sky Diving...

2 to 4 hours Free Cancellation
5.0 (62)
from
$599
Snorkel Sail Adventure off Ka'anapali Beach in Maui aboard Gemini

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, …More

Likely to Sell Out
Likely to Sell Out
Lahaina, USA

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky,...

4 hours Free Cancellation
5.0 (55)
from
$193
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

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

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