USA Sailing Trips

Deluxe Sunset & Day Sail Small Group

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as …More

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

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as...

2 hours 30 minutes Free Cancellation
5.0 (371)
from
$119
Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical …More

Maui, USA

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical...

5 hours Free Cancellation
5.0 (135)
from
$269
2.5-Hour Small-Group Catamaran Sail with Drinks

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail. …More

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

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail....

2 hours 30 minutes Free Cancellation
5.0 (370)
from
$119
St. Augustine Live Music Sail with Drinks & Sunset Option

Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience! Opt for a two-hour live music sunset sail with all sails raised, …More

St Augustine, USA

Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience! Opt for a two-hour live music sunset sail with all sails raised,...

1 hour 45 minutes Free Cancellation
4.8 (417)
from
$66
Shallow Water Snorkeling and Dolphin Watching in Key West

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s …More

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

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s...

4 hours
4.8 (438)
from
$109
Windjammer Classic Day Sail from Camden, Maine

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations …More

Camden, USA

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations...

2 hours Free Cancellation
4.8 (461)
from
$65
Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk …More

Hilton Head Island, USA

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk...

1 hour 30 minutes Free Cancellation
4.9 (720)
from
$48
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 City Balloon Tours TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for …More

Oahu, USA

2025 City Balloon Tours TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for...

2 hours Free Cancellation
4.9 (1,013)
from
$55
Small-Group San Diego Sunset Sailing Excursion

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat …More

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

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat...

3 hours Free Cancellation
5.0 (638)
from
$127
Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never …More

Oahu, USA

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never...

2 hours Free Cancellation
4.7 (1,265)
from
$53
2hr. INTERACTIVE Sailing Experience on San Francisco Bay

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and …More

Likely to Sell Out
Likely to Sell Out
Sausalito, USA

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and...

2 hours Free Cancellation
5.0 (106)
from
$149
Newport Sunset Sail on Schooner Adirondack

Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of the best evening activities to do during …More

Newport, USA

Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of the best evening activities to do during...

1 hour 30 minutes
4.8 (140)
from
$74
Day Sails and Sunset tours on Schooner Surprise in Camden Maine

Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at most and have cushioned seating on board …More

Camden, USA

Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at most and have cushioned seating on board...

2 hours Free Cancellation
4.9 (167)
from
$73
San Diego Whale Watching Cruise

Whale watching season is all year long in San Diego! Our team at Next Level Sailing provides the optimal experience with guides so experienced we …More

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

Whale watching season is all year long in San Diego! Our team at Next Level Sailing provides the optimal experience with guides so experienced we...

4 hours Free Cancellation
4.8 (2,470)
from
$85
Sunset Sail Cruise in Key West

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's …More

Key West, USA

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's...

2 hours Free Cancellation
5.0 (292)
from
$102
Fort Lauderdale Sailing Charter

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a …More

Fort Lauderdale, USA

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a...

4 hours Free Cancellation
5.0 (401)
from
$95
Kona Manta Ray Night Snorkel — 85–95% Sighting Rate

• 85–95% manta ray sighting rate at Manta Village, Kona • Return free within 7 days if no mantas seen — space available • Owner …More

Big Island of Hawaii, USA

• 85–95% manta ray sighting rate at Manta Village, Kona • Return free within 7 days if no mantas seen — space available • Owner...

1 hour 30 minutes Free Cancellation
4.8 (744)
from
$141
Baltimore Inner Harbor Sail on Summer Wind

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling …More

Baltimore, USA

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling...

1 hour 30 minutes Free Cancellation
4.7 (118)
from
$65
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 (121)
from
$485
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay …More

Miami, USA

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay...

3 hours 30 minutes Free Cancellation
4.9 (458)
from
$101
4-Hour Fort Lauderdale Sailing Charter

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have …More

Fort Lauderdale, USA

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have...

4 hours Free Cancellation
4.9 (323)
from
$110

Frequently Asked Questions

These answers are based on answers previously given to City Balloon Tours customers' questions.

Recent tour reviews
Activity name

USA Tours
Attractions
Guides
Calendar