Top activities
Top landmarks
Trip ideas
Nearby places

Top USA Sailing Trips

374 Results
Hilton Hawaiian Village Adventure Sail on the Spirit of Aloha

This cruise is exceptionally family-friendly, with no snorkeling or in-water activities, making it ideal for guests who want to experience the ocean without getting wet. …More

Oahu, USA

This cruise is exceptionally family-friendly, with no snorkeling or in-water activities, making it ideal for guests who want to experience the ocean without getting wet....

1 hour Free Cancellation
5.0 (3)
from
$60
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
SUNSET CRUISE in Key Largo,FL.

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need to worry about large crowds or waiting …More

Likely to Sell Out
Likely to Sell Out
Key Largo, USA

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need to worry about large crowds or waiting...

1 hour 30 minutes Free Cancellation
5.0 (2)
from
$389
Private Sailing Charter: Up to 24 Passengers

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco …More

Likely to Sell Out
Likely to Sell Out
San Francisco, USA

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco...

1 hour 30 minutes
5.0 (2)
from
$1,425
Private Daytime Picnic Boat Cruise (Up to 6 Passengers)

Set sail on Lake Champlain for a one-of-a-kind adventure where the route is guided entirely by the wind—ensuring no two cruises are ever the same. …More

Likely to Sell Out
Likely to Sell Out
Burlington, USA

Set sail on Lake Champlain for a one-of-a-kind adventure where the route is guided entirely by the wind—ensuring no two cruises are ever the same....

2 hours
5.0 (2)
from
$550
Private Sunset Catamaran Sail in Cocoa Beach

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a stunning evening on the serene waters of …More

Likely to Sell Out
Likely to Sell Out
Cocoa Beach, USA

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a stunning evening on the serene waters of...

2 hours Free Cancellation
5.0 (2)
from
$338
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 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 (2)
from
$1,595
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6...

2 hours Free Cancellation
5.0 (2)
from
$1,200
Fort Myers: Tiki Pub VIP Private Tropical Sandbar Getaway Cruise

There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Your Captain/Entertainer will make sure you have everything …More

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

There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Your Captain/Entertainer will make sure you have everything...

3 hours Free Cancellation
5.0 (2)
from
$599
San Diego Wild Life Sailing Adventure Private

Join GoSailing San Diego for a private 4-hour wildlife sail aboard Wolf, a classic 1967 Cal 34 sailboat, with Captain Sal and First Mate Sharon. …More

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

Join GoSailing San Diego for a private 4-hour wildlife sail aboard Wolf, a classic 1967 Cal 34 sailboat, with Captain Sal and First Mate Sharon....

4 hours Free Cancellation
5.0 (2)
from
$503
Morning Charleston Harbor Sail Lux Catamaran Shade and Seating

Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the Charleston's premier 50-foot catamaran. Designed for stunning views in …More

Mount Pleasant, USA

Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the Charleston's premier 50-foot catamaran. Designed for stunning views in...

2 hours Free Cancellation
5.0 (2)
from
$38
Old Plank Adventures: Sail into Deep Tranquility

Old Plank Sailing Adventures is a boutique luxury sailing charter and aquatic expedition company, delivering gourmet 5-star experiences on the sparkling waters of Santa Monica …More

Santa Monica, USA

Old Plank Sailing Adventures is a boutique luxury sailing charter and aquatic expedition company, delivering gourmet 5-star experiences on the sparkling waters of Santa Monica...

2 hours Free Cancellation
5.0 (2)
from
$400
Portland ME: Casco Bay Boat Tour w/ Island Yoga + Mimosas or Wine

This experience combines three things you rarely get in one outing: a small-group boat tour, yoga on a Casco Bay island, and a celebratory drink …More

Portland, USA

This experience combines three things you rarely get in one outing: a small-group boat tour, yoga on a Casco Bay island, and a celebratory drink...

3 hours Free Cancellation
5.0 (2)
from
$185
Private Sunset Sail of NYC Skyline and Statue of Liberty

Discover NYC from a completely different perspective on a private sailboat charter during sunset hours when the views are even more spectacular. You and your …More

Jersey City, USA

Discover NYC from a completely different perspective on a private sailboat charter during sunset hours when the views are even more spectacular. You and your...

2 hours Free Cancellation
5.0 (2)
from
$800
Oyster Bay Two Hour Sailing Experience

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and …More

Long Island, USA

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and...

2 hours Free Cancellation
5.0 (2)
from
$650
Sound of the Ocean Whale Watch Sail

Step aboard a boat and experience whale watching like never before. On this special cruise, see humpback whales in their natural habitat and hear them …More

Maui, USA

Step aboard a boat and experience whale watching like never before. On this special cruise, see humpback whales in their natural habitat and hear them...

2 hours Free Cancellation
5.0 (2)
from
$164
Sail Seattle's Iconic Lake Union All Year Around

Relax, take in the views, and discover why Lake Union, in the very heart of Seattle, is one of the city's most fascinating—and beautiful—places to …More

Seattle, USA

Relax, take in the views, and discover why Lake Union, in the very heart of Seattle, is one of the city's most fascinating—and beautiful—places to...

2 hours Free Cancellation
5.0 (2)
from
$125
Sailing Charter on san diego bay for up to 6 guests

While sailing on your private boat tour on the San Diego bay, enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, …More

San Diego, USA

While sailing on your private boat tour on the San Diego bay, enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines,...

2 hours
5.0 (2)
from
$800
Private Sailing Charters on La Vie Dansante

Jump aboard Hannah Banana Boat Charters for the ultimate small-group water adventure! Gather your favorite people and set sail on our spacious 48' private yacht …More

Daytona Beach, USA

Jump aboard Hannah Banana Boat Charters for the ultimate small-group water adventure! Gather your favorite people and set sail on our spacious 48' private yacht...

3 hours Free Cancellation
5.0 (2)
from
$800

Frequently Asked Questions

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

Recent tour reviews
Activity name

USA Tours
Attractions
Guides
Calendar