Sailing Tours with Drinks in the USA: 15 Worth the Sea Air

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 $79Top of the fleet

Spend about two hours sailing from Key West with an open liquor bar, champagne, sangria, wine, premium beer, soft drinks, and chef-prepared hors d’oeuvres. A local musician provides live entertainment while you pass Mallory Square, Fort Zachary Taylor, Sunset Key, and the Key West harbor. Arrive 30 minutes early and bring a sweater.

“Wonderful experience, drinks food and music all terrific and the sunset was breathtaking. Bring a sweater”

Check sailing dates →Read the whole sail review

Oahu Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Oahu, Sailing Tours with Drinks in the USA, 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

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

★★★★★★★★★★5.0 · 2,205 reviews · 2 hours (approx.) · from $89Best loved

Join the Hawaii-built Moana Catamaran at Kewalo Basin Harbor for a barefoot sunset sail along Waikiki and past Diamond Head. Your first premium drink is included, with more available for $8. The crew, including staff such as Viv and Eli, serves drinks while you watch for dolphins, humpback whales from November to May, and changing sunset colors.

“Great experience, great crew, very satisfied. The positive attitude of the crew made for a very enjoyable and relaxing trip. They were very attentive, boat is clean and well kept. They went to extra efforts to see a whale off of Diamond Head and we were successful at capturing whale flukes with a gorgeous sunset in the background”

Check sailing dates →Read the whole sail review

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 Drinks, Sailing Tours with Drinks in Key West, Sailing Tours with Drinks in the USA, Tour Reviews, USA Sailing Tours

Key West Afternoon Snorkel Sail with Unlimited Cocktails!

3.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

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

Sail from Key West’s historic seaport aboard the 69-foot Marquesa to the Florida Reef, about 7.5 miles offshore. The crew provides gear, safety instruction, and time to snorkel in shallow reef water. After swimming, enjoy included beer, wine, soft drinks, and cocktails on the return trip. The boat has restrooms and a freshwater rinse.

“The boat was great as well as the captain and mates! I didn't see a lot of fish that was a bit disappointing. Other than that it was fun!”

Check sailing dates →Read the whole sail review

Key West Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Key West, Sailing Tours with Drinks in the USA, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

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

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

★★★★★★★★★★5.0 · 1,366 reviews · 2 hours (approx.) · from $125

Join Danger Charters at 255 Front Street for a two-hour sunset sail with up to eight wines, five beers, soft drinks, and wine-paired hors d’oeuvres. Crews including Mary, James, Connor, and Molly are known for warm service, stories, blankets on cool evenings, and a relaxed small-boat setting.

“Great crew, excellent wine, delicious hors d’oeuvres, beautiful sunset ~ perfect evening! Plus, the limited number of guests was definitely preferred.”

Check sailing dates →Read the whole sail review

Key West Sunset Sail with Live Music, Drinks and Appetizers

5.Key West Sunset Sail with Live Music, Drinks and Appetizers

★★★★★★★★★★4.5 · 952 reviews · 2 hours (approx.) · from $79

Spend about two hours aboard Fury’s 65-foot catamaran as local musicians play popular cover songs, crew serve unlimited margaritas, beer, wine, champagne, soda, and seasonal appetizers. You can dance, sit in the shade, or watch the sunset near Mallory Square and Fort Zachary Taylor. Arrive early for a better seat.

“Great fun! Drinks flowed freely, great apps, but mostly awesome band & dancing under the beauty of Gods Key West sunset!!!”

Check sailing dates →Read the whole sail review

Key West Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Key West, Sailing Tours with Drinks in the USA, Sailing Tours with Lunch, 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

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

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

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

Set out from Key West’s Historic Seaport for a 2.5-hour catamaran cruise past Mallory Square, Fort Zachary Taylor, and Sunset Key. The crew, including captains such as Daniel and hosts such as Jordan or Gracie, serves wine, champagne, beer, soda, and small bites. Dolphins are possible, not promised.

“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 sailing dates →Read the whole sail review

Waikiki Sunset Cocktail Sail with Open Bar

7.Waikiki Sunset Cocktail Sail with Open Bar

★★★★★★★★★★4.5 · 554 reviews · 1 hour 30 minutes (approx.) · from $84

Set sail from Waikiki aboard the Holokai Catamaran for 90 minutes of sunset views, conversation, and unlimited drinks. Choose wine, champagne, beer, soda, juice, or the signature Holokai Hooch. Crew members including Ryan, Chase, Kevin, Kayla, Bridget, and Alec have been praised for keeping the mood friendly and the bar moving.

“I would definitely recommend thus to everyone, no matter the age! Our entire family loved it! The crew were all extremely friendly and the sunset was beautiful! Will definitely do this again the next time we come back!”

Check sailing dates →Read the whole sail review

Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in the USA, Sailing Yacht Charters, San Diego Sailing Tours, Tour Reviews, USA Sailing Tours

San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

8.San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

★★★★★★★★★★5.0 · 331 reviews · 2 hours 30 minutes (approx.) · from $115

Join Captain Phillip aboard Liberty, a hand-restored reproduction of a 1904 sailboat, for a two-and-a-half-hour San Diego Bay cruise. With no more than six passengers, you can help sail the boat, sip beer or white wine, spot sea lions and dolphins, and watch the skyline glow near sunset.

“The sunset sail with Captain Phillip is the highlight of our trip so far. Well worth every penny and highly recommend”

Check sailing dates →Read the whole sail review

Food, Key West Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Key West, Sailing Tours with Drinks in the USA, 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 Food & Drinks

9.Key West: Schooner Sunset Sail with Food & Drinks

★★★★★★★★★★4.9 · 318 reviews · 2 hours · from $122

Sail from Key West aboard the wooden schooner America 2.0 for a two-hour sunset outing. The crew serves alcoholic and non-alcoholic drinks plus a personal hors d'oeuvres plate as you pass Fort Zachary Taylor, Sand Key Reef, Mallory Square, and Sunset Pier. Keep watch for dolphins, turtles, water birds, and the Green Flash.

“Amazing cruise. The crew were fantastic, the cruise very relaxing, and the setting sun beautiful to see. Many thanks, a perfect evening.”

Check sailing dates →Read the whole sail review

Food, Key West Sailing Tours, Party and Music Sailing Cruises, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Key West, Sailing Tours with Drinks in the USA, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Key West Signature Sunset Sail with Live Music, Open Bar & Food

10.Key West Signature Sunset Sail with Live Music, Open Bar & Food

★★★★★★★★★★4.5 · 314 reviews · 2 hours (approx.) · from $72

Sail from 201 William St. aboard the three-deck Sandie Cat for a two-hour Key West sunset cruise with live music, unlimited well drinks, beer, wine, champagne, and light appetizers. The mood can range from relaxed to lively, with open space for sunset views and a return to the same dock.

“We really enjoyed being on the water during sunset. The boat had plenty of seating for all the guests and plenty of room to move around to the best areas for views. The live violin duet was a great accompiment to the views. The free pinot grigio and food were what would be expected on this type of tour, acceptable. Great value for the price.”

Check sailing dates →Read the whole sail review

Key West: Sunset Sailing Trip with Open Bar, Food and Music

11.Key West: Sunset Sailing Trip with Open Bar, Food and Music

★★★★★★★★★★4.5 · 310 reviews · from $80

Sail from Key West’s historic seaport aboard the three-deck Sandie Cat for a two-hour sunset cruise. You’ll get open-bar drinks, light appetizers, live music, and room to move between decks. You may also help raise the sails or take a photo at the wheel.

“So much fun! Enjoyed some great music and tasty snacks! Sunset was priceless- my photo was even featured on our local weather newscast!!”

Check sailing dates →Read the whole sail review

Boston Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in the USA, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Boston: Harbor Champagne Sunset Sail from Rowes Wharf

12.Boston: Harbor Champagne Sunset Sail from Rowes Wharf

★★★★★★★★★★4.8 · 299 reviews · 2 hours · from $82

Spend two hours sailing Boston Harbor aboard Schooner Adirondack III or IV. From Rowes Wharf, you’ll pass the Fish Pier, Fan Pier, Castle Island, the Inner Harbor Islands, and Charlestown Navy Yard as the city turns gold. The crew, including hosts such as Steve or Therese on some sailings, shares local history while drinks are available to buy onboard.

“This sunset champagne cruise was lovely! The crew was attentive and professional and the sunset views of the city were incredible. I would definitely highly recommend this activity!”

Check sailing dates →Read the whole sail review

Oahu Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Oahu, Sailing Tours with Drinks in the USA, Tour Reviews, USA Sailing Tours

Waikiki 3pm Tradewind Sail – Open Bar Included

13.Waikiki 3pm Tradewind Sail – Open Bar Included

★★★★★★★★★★5.0 · 246 reviews · 1 hour 30 minutes (approx.) · from $53

Set out from Waikiki at 3 p.m. aboard the Holokai catamaran for a relaxed 90-minute sail toward Diamond Head Lighthouse. Expect ocean views, trade winds, and possible sightings of whales, dolphins, and turtles. Crew members including Captain Austin, Ryan, Mitch, and Grace have earned warm praise for friendly service. Boarding is from the beach, so wear easy-off shoes.

“Great experience! We saw a few whales and even some turtles! The drinks package was nice but you can have a great time without it. I went solo and enjoyed it but groups and families also had a great time.”

Check sailing dates →Read the whole sail review

Oahu Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Oahu, Sailing Tours with Drinks in the USA, Sailing Trips with a Swim Stop, Tour Reviews, USA Sailing Tours

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

14.Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

★★★★★★★★★★5.0 · 236 reviews · 2 hours (approx.) · from $34Lowest fare aboard

Leave Waikiki Beach behind on a two-hour catamaran cruise from Kewalo Basin Harbor. Sail toward Diamond Head, watch for turtles, dolphins, fish, and whales, then swim from the boat or stay aboard with a cocktail. The crew keeps things relaxed, and the small-group setting, capped at 47 people, feels far calmer than the beach.

“We had such an amazing experience✨ 100% recommend this for everyone. The crew was amazing and did their best to make sure everyone was safe and satisfied.”

Check sailing dates →Read the whole sail review

Miami Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in the USA, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Sunset Sail in Miami: Complimentary Champagne Toast

15.Sunset Sail in Miami: Complimentary Champagne Toast

★★★★★★★★★★5.0 · 232 reviews · 2 hours (approx.) · from $99

Sail Biscayne Bay for about two hours aboard an 80-foot catamaran, raising a complimentary glass of Champagne as Miami turns golden. Depending on the wind, you may see Stiltsville, Key Biscayne and Cape Florida Lighthouse, or sail past PortMiami toward South Beach. The crew, including names such as Terry, Maria, Blue, and Erick, keeps the mood relaxed rather than rowdy.