USA

The 15 Best Sailing Tours in the USA

126 sailing trips  ·  from $35 a head

Key West schooners, San Diego bays, Newport twelve-metres and the Waikiki coast at sunset. These 15 American sailing days are priced and timed, with a note on which ones sail and which motor out.

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - What the route shows you in two hours
Concerts, Key West Sailing Tours, Party and Music Sailing Cruises, Sailing Tours, Sailing Tours with an Open Bar, Sailing Tours with an Open Bar in Key West, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

1.Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

★★★★★★★★★★4.5 · 3,559 reviews · 2 hours (approx.) · from $79Our pick

Key West sunset sail review with open bar, live music, shrimp, spacious catamaran decks, practical tips, value, weather advice, and FAQs.

“The sunset was absolutely divine. We sat outside on the bow, drank wine, and took it all in. The crew were attentive and the company was a good time. 10/10 would do again.”

Check availability →Read our full review

Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail - Sunset views, city lights, and changing weather
Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Oahu Sailing Tours, Sailing Tours, Sailing Tours with an Open Bar, Sailing Tours with an Open Bar in Oahu, Sunset Sailing Cruises, Sunset Sailing Cruises in Oahu, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

Waikiki Turtle Snorkel and Sail on Hawea Catamaran - Sailing out toward Turtle Canyon
Catamaran Sailing Trips, Catamaran Sailing Trips in Oahu, Catamaran Sailing Trips in the USA, 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

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

3.Waikiki Turtle Snorkel and Sail on Hawea Catamaran

★★★★★★★★★★5.0 · 1,655 reviews · 2 hours 30 minutes (approx.) · from $89

Review the Waikiki Turtle Snorkel and Sail on Hawea Catamaran, with turtle sightings, costs, timing, safety tips, and honest advice.

“Awesome tour. Capt Jenna and her team Julia, Nina and Tommy did a great job of showing us where the turtles were but also keeping us safe as there were alot is boats in the area. Seeing all the turtles and flying sh and the reef was spectacular. Ended with a sail around Waikuki. Highly recommend this tour and team.”

Check availability →Read our full review

Key West Afternoon Snorkel Sail with Unlimited Cocktails! - Getting ready at the reef
Key West Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in Key West, Sailing and Snorkeling Trips in the USA, Sailing Tours, Sailing Tours with an Open Bar, Sailing Tours with an Open Bar in Key West, Tour Reviews, USA Sailing Tours

Key West Afternoon Snorkel Sail with Unlimited Cocktails!

4.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

★★★★★★★★★★4.5 · 1,572 reviews · 3 hours (approx.) · from $59

Review of Key West’s 3-hour reef snorkel sail, with catamaran details, drink policy, value, crowding, safety, and practical tips.

“Not cruise ship friendly. If you're traveling on a cruise ship, they dropped us off far from our port and made it a difficult boarding. At least let me know, so I can plan accordingly. Because I would not have selected this experience.”

Check availability →Read our full review

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres - A wine tasting that fits a moving boat
Key West Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours, Wine Tours

Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

Key West Sunset Sail with Live Music, Drinks and Appetizers - Boarding the 65-foot Fury catamaran
Concerts, Key West Sailing Tours, Party and Music Sailing Cruises, Sailing Tours, Sailing Tours with an Open Bar, Sailing Tours with an Open Bar in Key West, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Key West Sunset Sail with Live Music, Drinks and Appetizers

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure - A catamaran built for comfort, not just transport
Guided, 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

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Sunset Sail in Key West with Beverages Included - Sailing through Key West Harbor
Key West Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Sunset Sail in Key West with Beverages Included

8.Sunset Sail in Key West with Beverages Included

★★★★★★★★★★5.0 · 907 reviews · 1 hour 30 minutes (approx.) · from $79

Sail from Key West Harbor aboard a small boat, sip included drinks, and watch the famous sunset with attentive crew and room to relax.

“Very relaxing, smaller group makes it feel much more personal. The captain and his first mate were great. My husband & I very much enjoyed it.”

Check availability →Read our full review

2 Hour Sailing Cruise on Lake Tahoe - The two-hour route across Lake Tahoe
2-Hour Experiences, Sailing Tours, Tour Reviews, USA Sailing Tours

2 Hour Sailing Cruise on Lake Tahoe

9.2 Hour Sailing Cruise on Lake Tahoe

★★★★★★★★★★5.0 · 886 reviews · 2 hours (approx.) · from $140

Review of Sail Tahoe Blue's two-hour Lake Tahoe cruise, with small groups, local drinks, safety details, value, tips, and booking advice.

“The crew took very good care of us. From their extensive knowledge about the lake to always keeping our glass filled. I highly recommend this.”

Check availability →Read our full review

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres - The early route: Fort Zachary and the Key West shore
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

Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail - Snorkeling in the Florida Keys backcountry
Canoes & Kayaks, Full-Day, Key West Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in Key West, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours

Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

Afternoon Sail & Snorkel to the Captain Cook Monument - What the snorkeling is like
Big Island Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours

Afternoon Sail & Snorkel to the Captain Cook Monument

Sunset Dolphin Sail Aboard the Privateer Catamaran - Meeting at Paradise Adventures on Jan Cooley Drive
Catamaran Sailing Trips, Catamaran Sailing Trips in the USA, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Sunset Dolphin Sail Aboard the Privateer Catamaran

13.Sunset Dolphin Sail Aboard the Privateer Catamaran

★★★★★★★★★★5.0 · 709 reviews · 2 hours (approx.) · from $45Best value

Review of Panama City Beach’s Privateer sunset dolphin sail, with pricing, views, drinks, music, logistics, drawbacks, and booking advice.

“Mike, Lamar, Jess and Jeff (singer/guitarist) were the best at Sunset Paradise Adventure!!! Even though it was raining the best experience ever, my family loved it and we saw SO MANY GROUPS OF DOLPHINS!!! This has to be the best experience we ever had. Thank you for making this the most memorable experience!”

Check availability →Read our full review

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas - Looking for dolphins along Key West’s water
Key West Sailing Tours, Sailing Tours, Sailing Tours with Lunch and BBQ, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA, Wine Tours

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

14.Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

★★★★★★★★★★4.5 · 699 reviews · 2 hours 30 minutes (approx.) · from $89

Key West sunset sail review with dolphin watching, wine, champagne, tapas, landmark views, practical tips, pricing, and honest drawbacks.

“Wonderful experience, excellent hors d’oevres, drinks, beautiful sunset, well worth the price - would have liked to be under sail instead of engine for the trip”

Check availability →Read our full review

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure - The 8:30 a.m. start and check-in routine
Bay, Harbour and Coastal Sailing, Big Island Sailing Tours, Coastal Sailing Tours in the USA, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

Scroll to Top

Every kind of day on the water

Pick a rig, a coast or an afternoon.