Top activities
Top landmarks
Trip ideas
Nearby places
Port schedule

Top USA Sailing Trips

375 Results
Baltimore History Sail on the Summer Wind

Learn about the maritime history of Baltimore and the Chesapeake Bay on this 1.5-hour sailing tour. Enjoy being on the water and listening to the …More

Baltimore, USA

Learn about the maritime history of Baltimore and the Chesapeake Bay on this 1.5-hour sailing tour. Enjoy being on the water and listening to the...

1 hour 30 minutes Free Cancellation
4.9 (72)
from
$65
Baltimore Inner Harbor Sail on the Unforgettable

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
4.8 (25)
from
$65
Waikiki Sunset Cruise and Iconic Views with Swimming

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide …More

Oahu, USA

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide...

2 hours Free Cancellation
5.0 (4)
from
$65
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
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
Waikiki 2 Hour Sunset Whale Watching Cruise Sightings Guaranteed

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden …More

Oahu, USA

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden...

2 hours Free Cancellation
4.6 (87)
from
$68
2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play …More

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

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play...

2 hours Free Cancellation
4.9 (157)
from
$69
Two Hour Scenic Sail on the Liberty Clipper

A voyage aboard the 125' Schooner Liberty Clipper offers a unique opportunity to connect with maritime history while exploring the stunning views of Long Island …More

Likely to Sell Out
Likely to Sell Out
Long Island, USA

A voyage aboard the 125' Schooner Liberty Clipper offers a unique opportunity to connect with maritime history while exploring the stunning views of Long Island...

2 hours Free Cancellation
5.0 (9)
from
$69
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
Glass Bottom Boat Fireworks and After Dark Reef Walker Cruise

Waikiki transforms into a vibrant spectacle on Friday nights, and the Friday Fireworks Cruise offers a unique vantage point to experience this magic. Departing from …More

Oahu, USA

Waikiki transforms into a vibrant spectacle on Friday nights, and the Friday Fireworks Cruise offers a unique vantage point to experience this magic. Departing from...

1 hour 30 minutes Free Cancellation
5.0 (3)
from
$69
Glass Bottom Boat Morning Coffee Cruise in Waikiki

Wake up to the serene beauty of Waikiki on the Morning Coffee Cruise, where you can savor locally roasted Ali’i Coffee Co. and fresh pastries …More

Oahu, USA

Wake up to the serene beauty of Waikiki on the Morning Coffee Cruise, where you can savor locally roasted Ali’i Coffee Co. and fresh pastries...

1 hour 30 minutes Free Cancellation
5.0 (3)
from
$69
Key West Dolphin and Snorkel Experience

The Cool Shore ExcursionsDolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous …More

Key West, USA

The Cool Shore ExcursionsDolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous...

3 hours Free Cancellation
4.7 (345)
from
$70
Monterey Bay Whale Watching

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey …More

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

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey...

2 to 3 hours Free Cancellation
4.8 (366)
from
$70
Suncoast Sailing's Sunset Sailing Experience!

Step aboard Suncoast Horizon, a real working schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. …More

St Petersburg, USA

Step aboard Suncoast Horizon, a real working schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script....

2 hours 30 minutes Free Cancellation
4.9 (285)
from
$70
Friday Night Firework Cruise in Waikiki

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, …More

Oahu, USA

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline,...

1 hour Free Cancellation
4.8 (35)
from
$70
1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises. …More

Bar Harbor, USA

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises....

2 hours Free Cancellation
4.2 (730)
from
$70
Southwest Florida Sunset Sail

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The …More

Fort Myers, USA

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The...

2 hours Free Cancellation
5.0 (509)
from
$70
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather …More

Naples, USA

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather...

2 hours 30 minutes Free Cancellation
4.9 (196)
from
$70
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from …More

Oahu, USA

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from...

2 hours Free Cancellation
4.9 (18)
from
$70
2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). Our snorkel, swim and …More

Oahu, USA

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). Our snorkel, swim and...

2 hours Free Cancellation
5.0 (3)
from
$70

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

Recent tour reviews
Activity name

Discover USA