USA Sailing Trips

2-Hour Private Sailing Experience in San Diego Bay

Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing …More

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

Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing...

2 hours Free Cancellation
5.0 (188)
from
$675
2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on …More

Likely to Sell Out
Likely to Sell Out
La Jolla, USA

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on...

2 hours 30 minutes Free Cancellation
5.0 (114)
from
$119
Maui Midday Whale Watch in the Humpback Sanctuary out of Maalaea

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

Likely to Sell Out
Likely to Sell Out
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
4.9 (103)
from
$110
Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique …More

Likely to Sell Out
Likely to Sell Out
Honolulu, USA

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique...

2 hours Free Cancellation
4.9 (223)
from
$67
Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail on Boothbay Harbor’s …More

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail on Boothbay Harbor’s...

2 hours Free Cancellation
4.5 (41)
from
$65
Waikiki small group turtle snorkeling & sailing

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of...

2 hours Free Cancellation
5.0 (109)
from
$99
Original Cruisin Tikis Shark Tooth and Sea Shell Scavenger Hunt

This interactive experience is perfect for families, kids, and anyone who loves the thrill of the hunt—whether you’re spotting shark teeth, collecting shells, or simply …More

Likely to Sell Out
Likely to Sell Out
Destin, USA

This interactive experience is perfect for families, kids, and anyone who loves the thrill of the hunt—whether you’re spotting shark teeth, collecting shells, or simply...

3 hours
5.0 (1)
from
$79
Original Cruisin Tikis Snorkeling Safari

The Snorkeling Safari is a must-do when visiting Destin. Pop open your favorite drinks and let your professional, USCG-licensed captain cruise you through the heart …More

Likely to Sell Out
Likely to Sell Out
Destin, USA

The Snorkeling Safari is a must-do when visiting Destin. Pop open your favorite drinks and let your professional, USCG-licensed captain cruise you through the heart...

3 hours
5.0 (1)
from
$89
New York Sunset Schooner Cruise on the Hudson River

Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known …More

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

Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known...

2 hours Free Cancellation
4.9 (224)
from
$90
New York City Sailboat Day Cruise to the Statue of Liberty

Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as …More

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

Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as...

1 hour 45 minutes Free Cancellation
4.9 (174)
from
$60
Daytime Sailing Along San Diego's Skyline

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor …More

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

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor...

2 hours Free Cancellation
5.0 (161)
from
$99
Maui Sunset Sail

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.8 (213)

Maui Sunset Sail

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing...

2 hours Free Cancellation
4.8 (213)
from
$138
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
2-Hour Oahu Sunset Catamaran Sail

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu....

2 hours Free Cancellation
4.8 (142)
from
$130
Small Group Waikiki Sunset Sailing Tour

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come...

2 hours Free Cancellation
4.9 (121)
from
$99
Experience Oceanside Sailing with Whales and dolphins!

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and most comfortable sailboats in the …More

Carlsbad, USA

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and most comfortable sailboats in the...

2 hours Free Cancellation
5.0 (18)
from
$150
Wednesday Happy Hour Sunset Sail - Drinks Included

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha …More

Mount Pleasant, USA

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha...

2 hours Free Cancellation
5.0 (10)
from
$76
Private Sailing Charter in Savannah GA

Set sail on a private trimaran charter in Savannah, where every moment is tailored just for you. Whether it's a family outing, an intimate wedding, …More

Savannah, USA

Set sail on a private trimaran charter in Savannah, where every moment is tailored just for you. Whether it's a family outing, an intimate wedding,...

2 hours Free Cancellation
5.0 (7)
from
$650
Miami Private Boat Tour- Millionaire’s Row and Celebration Cruise

Discover Miami from a whole new perspective aboard one of the top-rated private boat experiences in the city, rated 4.9⭐ with 1.2k+ reviews on Google. …More

Miami, USA

Discover Miami from a whole new perspective aboard one of the top-rated private boat experiences in the city, rated 4.9⭐ with 1.2k+ reviews on Google....

4 hours Free Cancellation
4.9 (259)
from
$150
New York Day Sail to the Statue of Liberty on Schooner America

Offering a premium sailing experience, the Schooner America is a tribute to the original America that won the America's Cup in 1851. This classic sailboat is comfortable, …More

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

Offering a premium sailing experience, the Schooner America is a tribute to the original America that won the America's Cup in 1851. This classic sailboat is comfortable,...

1 hour 45 minutes Free Cancellation
4.9 (64)
from
$60
Private Sailing on the Miami Bay - Biscayne Bay

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

4 to 12 hours Free Cancellation
5.0 (67)
from
$175

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