All USA Sailing Tours

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Orange Beach: Dolphin & Sailing Cruise Aboard 52′ Catamaran

★ 4.6Orange Beach: Dolphin & Sailing Cruise Aboard 52′ CatamaranFrom $5515 reviews

Oahu Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in Oahu, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in Oahu, Whale and Dolphin Watching Sails in the USA

Oahu: Waikiki Turtle Snorkel Sail

★ 4.7Waikiki Turtle Snorkel SailFrom $99103 reviews

Honolulu Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Oahu: Sunset sailing in small intimate groups

★ 5.0Sunset sailing in small intimate groupsFrom $1037 reviews

New York City Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

NYC: Sunset Jazz Sail aboard the ‘Clipper City’

★ 3.8Sunset Jazz Sail aboard the ‘Clipper City’From $14634 reviews

Newport Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours

Newport Sunset Sail on Schooner Adirondack

★ 4.9Newport Sunset Sail on Schooner AdirondackFrom $6715 reviews

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Oahu: Sunset Sail Cruise in Waikiki

★ 4.8Sunset Sail Cruise in WaikikiFrom $546 reviews

Newport Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours

Newport: Sunset Sail on Schooner Madeleine

★ 4.9Sunset Sail on Schooner MadeleineFrom $6734 reviews

Newport Sailing Tours, Sailing Tours, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, Tours, USA Sailing Tours

Newport: Day Sailing and Sightseeing Boat Tour on a Schooner

★ 5.0Day Sailing and Sightseeing Boat Tour on a SchoonerFrom $5719 reviews

Newport Sailing Tours, Sailing Tours, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, Tours, USA Sailing Tours

Newport: Schooner Sailing Tour

★ 4.8Schooner Sailing TourFrom $5524 reviews

New York City Sailing Tours, Sailing Tours, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours

New York City Lights Schooner Sail

★ 4.9New York City Lights Schooner SailFrom $677 reviews

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Monterey: Private Whale Watching/Sailing Tour for 6

★ 4.8Monterey: Private Whale Watching/Sailing Tour for 6From $950 whole boat, up to 63 reviews

Bay, Harbour and Coastal Sailing, Catamaran Sailing Trips, Catamaran Sailing Trips in the USA, Coastal Sailing Tours in the USA, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Monterey Bay: Sunset Catamaran Sailing Cruise

★ 4.8Monterey Bay: Sunset Catamaran Sailing CruiseFrom $9531 reviews

Catamaran Sailing Trips, Catamaran Sailing Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours

Monterey: Catamaran Sailing Cruise

★ 4.6Monterey: Catamaran Sailing CruiseFrom $6514 reviews

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Miami: Hobie Cat Sailing

★ 4.0Hobie Cat SailingFrom $594 reviews

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Maui: Snorkeling and Sailing Adventure with Buffet Lunch

★ 4.8Snorkeling and Sailing Adventure with Buffet LunchFrom $172115 reviews

Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Food, Food & Drink, Miami Sailing Tours, Sailing Tours, Sailing Tours with an Open Bar, Tour Reviews, USA Sailing Tours

Miami: Intimate Sailing in Biscayne Bay w/ Food and Drinks

★ 4.7Intimate Sailing in Biscayne Bay w/ Food and DrinksFrom $13934 reviews

Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Maui: Midday Sail with the Whales Māʻalaea Harbor

★ 4.5Midday Sail with the Whales Māʻalaea HarborFrom $922 reviews

Catamaran Sailing Trips, Catamaran Sailing Trips in the USA, Maui Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Maui: Ma’alaea Catamaran Sunset Sail with Appetizers

★ 4.7Ma’alaea Catamaran Sunset Sail with AppetizersFrom $13716 reviews

Dining Experiences, Dinner and Evening Sailing Cruises, Maui Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Maui: Ka’anapali Luxury Sunset Dinner Sail

★ 4.8Ka’anapali Luxury Sunset Dinner SailFrom $169123 reviews

Maui Sailing Tours, Sailing Tours, Sailing Tours with an Open Bar, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Maui: Ka’anapali Luxury Sunset Cocktail Sail with Open Bar

★ 4.7Ka’anapali Luxury Sunset Cocktail Sail with Open BarFrom $134150 reviews

2-Hour Experiences, Dining Experiences, Dinner and Evening Sailing Cruises, Maui Sailing Tours, Sailing Tours, Sailing Tours with an Open Bar, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Maui: 2 Hour Sunset Dinner Sail with Open Bar and Appetizers

★ 4.72 Hour Sunset Dinner Sail with Open Bar and AppetizersFrom $14965 reviews

Maui Sailing Tours, Sailing Tours, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Maui: Ka’anapali Whale Watching Cruise on Luxury Sailboat

★ 4.8Ka’anapali Whale Watching Cruise on Luxury SailboatFrom $10889 reviews

Catamaran Sailing Trips, Catamaran Sailing Trips in the USA, Maui Sailing Tours, Sailing Tours, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Maui: Luxury Catamaran Whale Watch & Sail

★ 5.0Luxury Catamaran Whale Watch & SailFrom $1192 reviews

Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Lunch Experiences, Maui Sailing Tours, Sailing Tours, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Maui: Deluxe Whale Watch Sail & Lunch from Ma`alaea Harbor

★ 5.0Deluxe Whale Watch Sail & Lunch from Ma`alaea HarborFrom $13733 reviews

New York City Sailing Tours, Sailing Tours, Sailing Tours with an Open Bar, Tour Reviews, USA Sailing Tours, Wine Tours

NYC: Private Champagne Sail to the Statue of Liberty

★ 5.0Private Champagne Sail to the Statue of LibertyFrom $850 whole boat, up to 610 reviews

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Maalaea Harbor: Sunset Sail on a Charming Hawaiin Catamaran

★ 5.0Maalaea Harbor: Sunset Sail on a Charming Hawaiin CatamaranFrom $1295 reviews

Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Los Angeles: Sunset Sailing

★ 5.0Los Angeles: Sunset SailingFrom $13015 reviews

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Long Beach: Private Sailboat Rental with Licensed Captain

★ 4.9Long Beach: Private Sailboat Rental with Licensed CaptainFrom $425 whole boat, up to 619 reviews

2-Hour Experiences, Sailing Tours, Sailing Tours with an Open Bar, Tour Reviews, USA Sailing Tours

Lake Tahoe: 2-Hour Sailing Cruise with Drinks

★ 5.0Lake Tahoe: 2-Hour Sailing Cruise with DrinksFrom $1527 reviews

Maui Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Lahaina: Private Sunset Sailing Trip & West Maui Mountains

★ 5.0Lahaina: Private Sunset Sailing Trip & West Maui MountainsFrom $1,936 whole boat, up to 63 reviews

Lunch Experiences, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Sailing Tours with an Open Bar, Sailing Tours with Lunch and BBQ, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Kona Turtle Snorkel Sail with Lunch and Drinks

★ 4.9Kona Turtle Snorkel Sail with Lunch and DrinksFrom $16919 reviews

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Kailua-Kona: Kealakekua Bay Snorkel and Sail with Lunch

★ 5.0Kailua-Kona: Kealakekua Bay Snorkel and Sail with LunchFrom $1885 reviews

Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Kailua-Kona: Manta Ray Snorkeling and Sunset Sailing Cruise

★ 5.0Kailua-Kona: Manta Ray Snorkeling and Sunset Sailing CruiseFrom $1543 reviews

Key West Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tall Ship and Schooner Sailing, Tall Ship Sailing in Key West, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours, Wine Tours

Key West Wind and Wine Sunset Sail aboard classic Schooner

★ 5.0Key West Wind and Wine Sunset Sail aboard classic SchoonerFrom $13316 reviews

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Key West: Windjammer Champagne Sunset Sail

★ 5.0Windjammer Champagne Sunset SailFrom $8918 reviews

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Key West: Schooner Full Moon Night Sail with Drinks

★ 5.0Schooner Full Moon Night Sail with DrinksFrom $832 reviews

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Key West’s Schooner Appledore Star Champagne Sunset Sail

★ 5.0Key West’s Schooner Appledore Star Champagne Sunset SailFrom $1093 reviews

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Key West: Catamaran Champagne Sunset Sail

★ 4.7Catamaran Champagne Sunset SailFrom $793 reviews

Catamaran Sailing Trips, Catamaran Sailing Trips in the USA, Key West Sailing Tours, Sailing Tours, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Key West: Afternoon Catamaran Sail and Dolphin Watch

★ 4.5Afternoon Catamaran Sail and Dolphin WatchFrom $59116 reviews

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Key West: 2-Hour Sunset Sail with Live Music

★ 4.72-Hour Sunset Sail with Live MusicFrom $79130 reviews

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Key West Afternoon Sail, Snorkel, Kayak & Sunset Excursion

★ 5.0Key West Afternoon Sail, Snorkel, Kayak & Sunset ExcursionFrom $13313 reviews

Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, Tours, USA Sailing Tours

Kauai: Napali Coast Sail & Snorkel Tour from Port Allen

★ 4.8Napali Coast Sail & Snorkel Tour from Port AllenFrom $27490 reviews