Sailing Trips in USA
Top 10 Best USA Sailing Trips
Found 426 Sailing Trips activities in USA. Sort by Popularity. - Page 2Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience offers breathtaking views of the sunset complemented by deligh... More
Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui
-
USA
-
Superb88 reviews4.6
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....
Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full Open Bar
Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based on weather, tides, and ocean conditions. • Explore Lana... More
Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full Open Bar
-
USA
-
Superb88 reviews5
Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where ....
Lahaina Maui Sunset Sail on 'Alihilani
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for a luxurious experience, allowing for incredible views of Maui and the inter islands from the... More
Lahaina Maui Sunset Sail on 'Alihilani
-
USA
-
Superb214 reviews4.9
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....
Waikiki Turtle Snorkel and Sail on Hawea Catamaran
Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island relaxation in one extraordinary outing. Swim among sea turtles and tropical fi... More
Waikiki Turtle Snorkel and Sail on Hawea Catamaran
-
USA
-
Superb1,786 reviews4.8
Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This pop....
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985... More
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
-
USA
-
Superb1,014 reviews4.9
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....
Sunset Windjammer Cruise Along the Coast of Portland Maine
Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. (NOTE: This is NOT a narrated tour, bu... More
Sunset Windjammer Cruise Along the Coast of Portland Maine
-
USA
-
Superb218 reviews4.7
Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to exper....
Waikiki 2 hour Turtle Canyon Snorkeling Adventure
Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard the either 55-ft open-style catamaran or 50-ft double-decker power catamaran and ... More
Waikiki 2 hour Turtle Canyon Snorkeling Adventure
-
USA
-
Superb1,518 reviews4.7
Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cr....
Key West Afternoon Reef Snorkeling with Open Bar
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More
Key West Afternoon Reef Snorkeling with Open Bar
-
USA
-
Exellent491 reviews4.5
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds (NOTE: This is NOT a narrated tour,... More
Afternoon Windjammer Cruise Along the Coast of Portland Maine
-
USA
-
Superb301 reviews4.7
Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to e....
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 the sky transforms into a masterpiece of color. Keep an eye out for playfu... More
Deluxe Sunset & Day Sail Small Group
-
USA
-
Superb368 reviews5
Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....
Happy Hour Sunset Sail on Maui's Luxury Catamaran
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted drinks, vibrant music, and a relaxed-yet-refined vibe that turns every pour ... More
Happy Hour Sunset Sail on Maui's Luxury Catamaran
-
USA
-
Superb101 reviews4.8
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu
-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boarding — no harbor shuttle, no bus, no wasted time -Spacious 45-foot catamaran with near 360 degree view -Families welcome: Keiki ra... More
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu
-
USA
-
Superb625 reviews4.7
-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boardi....
Sailing on Historic Schooner Yacht in Salem, MA
Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience the majesty aboard John G. Alden's personal schooner yacht Malabar X. Winner of the 1930 and 1932 Newport to Bermuda race and open... More
Sailing on Historic Schooner Yacht in Salem, MA
-
USA
-
Superb308 reviews4.9
Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience ....
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
-
USA
-
Superb862 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
Dolphin Sunset Cruise in Panama City Beach on the "Island Time"
The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in Panama City Beach, FL. Enjoy a rum punch while cruising along the beautiful Gulf Coa... More
Dolphin Sunset Cruise in Panama City Beach on the "Island Time"
-
USA
-
Superb2,135 reviews4.9
The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....
Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing
Experience a romantic Maui evening aboard Paragon, Sail Maui's flagship 47-foot performance sailing catamaran. Settle in together and experience the peace and serenity of sailing the beautiful ʻAuʻau Channel, surrounded by the s... More
Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing
-
USA
-
Superb45 reviews4.9
Experience a romantic Maui evening aboard Paragon, Sail Maui's flagship 47-foot performance sailing ....
Sunset Sail Along the San Diego Skyline
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water. Our San Diego Bay Sunset Sailing Cruises provide an up-close and personal view o... More
Likely to Sell Out Sunset Sail Along the San Diego Skyline
-
USA
-
Superb659 reviews4.9
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....
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, or unwind on a 90-minute After Dark Live Music Cruise (no sailin... More
Likely to Sell Out St. Augustine Live Music Sail with Drinks & Sunset Option
-
USA
-
Superb419 reviews4.7
Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience!....
2-Hour Sunset Sail on the San Francisco Bay
Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous traditional vessel to take in the sights at the most bewitching time of d... More
Likely to Sell Out 2-Hour Sunset Sail on the San Francisco Bay
-
USA
-
Superb435 reviews4.7
Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More
Likely to Sell Out Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
-
USA
-
Superb40 reviews4.9
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....