Classic Harbor Line - Key West
Schooner Sunset Sail with Food & Drinks
- 4.9 (335 reviews)
- 2 hours
- Free cancellation
My pick: My classic pick: $123, 2 hours under sail, 4.9 from 335 reviews, drinks and a food plate included.
Sunset Cruise Key West
By Rowan Ellis · Updated · Affiliate links, explained in my disclosure
Fury Water Adventures
Reef Snorkeling with Drinks and Sunset Option
4.5 (609) · from $49
A sunset cruise in Key West is a two-hour sail with a drink or a longer snorkel that ends in the golden hour. I compared five evening trips, from $49 to $134, and the best-rated one is a schooner. Prices are in US dollars, checked in October 2026, and the booking links are affiliate links, as I explain on my about page. For the full list of trips, see my overview of boat tours in Key West.
My pick for a classic evening is the Classic Harbor Line schooner sunset sail: $123, 2 hours, rated 4.9 from 335 reviews, with drinks and an hors d’oeuvres plate included.
Sunset Cruise Key West Florida
A sunset cruise in Key West, Florida works because the island faces open water to the west, so the sun drops over the horizon with nothing in front of it. The Sunset Watersports listing says it heads straight out to sea for unobstructed views of the sunset. Old Town’s Mallory Square, 0.6 kilometers from the seaport by my measurement from the place data, is where the crowd gathers on land.
The timing moves a lot through the year, and it is the first thing I would check. The times below are my calculation from sunrise-sunset.org for the island’s coordinates, shown as local clock time for the middle of each month. They include the shift to daylight saving time in March and the return to standard time in November. You can check any date with the NOAA solar calculator.
| Month | Sunset (mid-month) | Month | Sunset (mid-month) |
|---|---|---|---|
| January | 6:01 PM | July | 8:19 PM |
| February | 6:22 PM | August | 8:02 PM |
| March | 7:37 PM | September | 7:32 PM |
| April | 7:50 PM | October | 7:01 PM |
| May | 8:04 PM | November | 5:41 PM |
| June | 8:18 PM | December | 5:42 PM |
Key West Sunset Cruise Schooner
The schooner is the traditional way to see a Key West sunset cruise, and the Classic Harbor Line trip is the best evidence I have for it. The America 2.0 has teak decks, mahogany trim and 3,600 square feet of canvas, according to the listing, and it sails for 2 hours with complimentary alcoholic and non-alcoholic drinks and an hors d’oeuvres plate. Champagne is included if you choose that option. It has 4.9 from 335 reviews, the highest rating in my whole Key West list for a trip with more than 300 reviews.
Reviewers say the wind cooperated and the boat sailed out past the reef before turning back, and another says the swells got big but the captain kept everyone calm. It is $123, so it is not the cheapest, but the rating and the sailing make it the one I would book for an anniversary. Gratuity is not included.
Key West Sunset Cruise Dinner and Open Bar
There is no sit-down dinner cruise in my data, and I will not dress a buffet up as one. The Sunset Watersports signature cruise is the closest thing to an evening with food: $80, 2 hours, rated 4.6 from 513 reviews. It leaves from the historic seaport, and the listing describes an unlimited open bar with rum runners, champagne, margaritas and draft beer, plus finger foods such as meatballs, hummus, cheese and crackers, and live music.
That makes it the social option. It is the one I would choose for a group of friends, and the one I would skip if I wanted quiet. Tips and transport to the meeting point are not included. The listing does not give a meeting point in the text I have, so check the booking page for the exact dock.
Sunset Watersports Key West
Key West Signature Sunset Cruise with Open Bar, Food & Music
- 4.6 (513 reviews)
- 2 hours
- Free cancellation
My pick: The party evening: $80, 2 hours, open bar, finger food and live music, 4.6 from 513 reviews.
Sunset Cruise Key West Catamaran
The catamaran sunset in my data is a snorkel trip. The Fury reef snorkeling trip runs on a 65-foot catamaran and offers a sunset slot as well as morning and afternoon: $49, 3 hours, rated 4.5 from 609 reviews. You snorkel first, then the crew serves rum punch on the sunset trip, according to the listing. It departs from the Fury booth behind the Opal Key Hotel at 241 Front Street.
The Sunset Watersports dolphin and snorkel sunset cruise is the second option with a snorkel: $80, 3 hours, 4.4 from 573 reviews. It heads out to the islands of the Key West National Wildlife Refuge, looks for dolphins and then stops at the reef. Both are good if you would rather be active than sit. For the reef details, see my snorkeling tour page.
Fury Water Adventures
Reef Snorkeling with Drinks and Sunset Option
- 4.5 (609 reviews)
- 3 hours
- Free cancellation
My pick: The cheapest sunset: $49, 3 hours, snorkel first, rum punch on the sunset slot, 4.5 from 609 reviews.
Sunset Watersports Key West
Dolphin Watching and Snorkeling Sunset Cruise
- 4.4 (573 reviews)
- 3 hours
- Free cancellation
My pick: Dolphins, reef and sunset in 3 hours: $80, 4.4 from 573 reviews.
Sunset Cruise Key West Adults Only
I did not find a trip in my data that is labeled adults only. The party-style cruise has an open bar, so it suits adults, but the listings do not set an age rule that I can quote. If a child-free evening matters to you, ask the operator before you book, and read the booking page for age limits. The quietest evening in my list is the schooner, and the longest is the Danger Charters afternoon excursion.
That excursion is $134 for 4.5 hours on a shallow-draft schooner, limited to 20 guests. It combines sailing, snorkeling, a kayak and the sunset, with snacks, soda and water and then wine and beer after the watersports. It has 4.8 from only 24 reviews, so the evidence is thin, but the format is unusual. It meets at the Danger Chandlery Store at the Opal Key Resort and Marina.
Danger Charters
Key West Afternoon Sail, Snorkel, Kayak & Sunset Excursion
- 4.8 (24 reviews)
- 4.5 hours
- Free cancellation
My pick: Sail, snorkel, kayak and sunset: $134, 4.5 hours, max 20 guests, 4.8 from 24 reviews.
Compared: Sunset Cruises in Key West
| Operator | Price | Duration | Boat type | Rating | Cancellation |
|---|---|---|---|---|---|
| Fury Water Adventures | $49 | 3 hours | 65-foot catamaran | 4.5 (609 reviews) | Free up to 24 hours |
| Sunset Watersports (signature) | $80 | 2 hours | Sailing cruise | 4.6 (513 reviews) | Free up to 24 hours |
| Sunset Watersports (dolphin and snorkel) | $80 | 3 hours | Sunset One dolphin boat | 4.4 (573 reviews) | Free up to 24 hours |
| Classic Harbor Line | $123 | 2 hours | Schooner America 2.0 | 4.9 (335 reviews) | Free up to 24 hours |
| Danger Charters | $134 | 4.5 hours | Shallow-draft schooner | 4.8 (24 reviews) | Free up to 24 hours |
What to Bring on a Key West Sunset Cruise
Pack for the water even if you plan to stay dry. The Danger Charters listing asks you to bring a bathing suit, hat, sunglasses, a camera and a sweatshirt in the winter months. After dark the wind off the water feels cooler, and the schooner listing mentions the stars emerging, so a light layer is sensible. Bring cash or a card for gratuity: none of the five includes it, and Fury adds an automatic 10 percent service fee for groups of eight or more.
If you also want to see the evening ritual on land, Mallory Square is a short walk from the Old Town piers. The Florida Keys tourism board is the official visitor source for events there. Also look at my pages on dolphin watching in Key West and Key West catamaran tours, since several sunset trips run on the same boats.
How Early to Book
The sunset slot is the one that sells out first in busy months, so I would book a few days ahead rather than on the day. Every trip here has free cancellation up to 24 hours before the start, which removes most of the risk. If the forecast looks poor, move to a morning snorkel instead of paying for a grey evening.
Which Sunset Trip I’d Book
For a sunset cruise in Key West, I’d book the $123 schooner for a quiet, romantic first evening, because 335 reviews back it at 4.9. I’d pick the $80 open bar cruise for a lively group and the $49 Fury snorkel for a cheap, active one. Check the forecast the day before any Key West sunset cruise, and use the free cancellation window if needed. For the rest of my Key West comparisons, go back to the guide to boat tours in Key West or the home page.
Frequently asked questions
How much does a sunset cruise in Key West cost?
The five evening trips I compared run from $49 for the Fury reef snorkeling trip with a sunset slot to $134 for the Danger Charters afternoon excursion. The open bar cruise is $80 and the schooner sunset sail is $123. Tips are not included on any of them, so I'd budget a little extra for the crew.
What time is sunset in Key West?
By my calculation from sunrise-sunset.org for the island's coordinates, mid-month sunset runs from about 5:41 PM in November to 8:19 PM in July, in local time with daylight saving included. The table on this page lists every month. Check your exact date on the NOAA solar calculator, because the table gives the 15th of each month only.
Is there a sunset dinner cruise in Key West?
I did not find one among the 13 trips in my data. The nearest are the Sunset Watersports cruise with finger foods and an open bar, and the schooner sail with an hors d'oeuvres plate. If a sit-down dinner is the point of your evening, I'd book a table separately for after the boat.
Where does the sunset schooner leave from?
The Classic Harbor Line schooner America 2.0 checks in at the ticket booth at 202 William Street, directly behind the Schooner Wharf Bar. The listing asks you to arrive 30 to 45 minutes before departure to get boarding passes. The other sunset trips use piers at the Opal Key Resort or the Old Town seaport.
Can I cancel a sunset cruise in Key West?
All five list free cancellation up to 24 hours before the start for a full refund. Because the evening depends on the sky and the wind, I'd check the forecast the day before and use that window if needed. A reviewer of the schooner notes that the swells can get big, and the crew handled it well.
Tours I compared in Key West
My full review of each one, in the order I rank them:
- Dolphin Watching and Snorkeling Eco Cruise Tour★ 4.6 · from $73
- Reef Snorkeling with Drinks and Sunset Option★ 4.5 · from $49
- Key West Signature Sunset Cruise with Open Bar, Food & Music★ 4.6 · from $80
- Schooner Sunset Sail with Food & Drinks★ 4.9 · from $123
- Dolphin Watching and Snorkeling Sunset Cruise★ 4.4 · from $80
- See Sharks Up Close on a Wildlife Catamaran Tour★ 4.8 · from $99
- Sandbar Excursion & Kayak Tour with Lunch & Drinks★ 4.8 · from $150
- 2-hour Mangrove Kayak Tour★ 4.6 · from $65
- Afternoon Catamaran Sail and Dolphin Watch★ 4.4 · from $50
- Key West Afternoon Sail, Snorkel, Kayak & Sunset Excursion★ 4.8 · from $134
- Catamaran Snorkel with Seafood Boil and Open Bar★ 4.7 · from $70
- Tiki Party Boat Rental★ 5.0 · from $700
- Double Decker Pontoon Boat Rentalfrom $700