Sails, Sunsets, and Sangria – Key West Cruises Worth Missing Dinner For

Sunset cruises in Key West are basically a rite of passage like getting sunburned on your first day or realizing your “waterproof” sandals aren’t. There’s no better way to vibe with the Conch Republic than bobbing around at golden hour with a drink in hand and your worries somewhere back on shore

Key West is easily one of the most fascinating places in the U.S. — laidback, quirky, and full of island charm. With its lovely atmosphere and Caribbean vibes it’s the perfect place to escape the busyness of life for a while. However, if you’re looking to make your stay extra memorable, then you should explore taking one of the seven sunset cruises in Key West below.

Time to Chill (Like Really Chill)

Not all cruises are created equal. Use the handy chart below to find the one that best fits your vibe, whether that’s reggae and rum or tapas and “I’m definitely spotting dolphins first.”

We’ve rounded up the top options to help you pick your perfect cruise match — check out the chart below for a quick side-by-side.

Sure, you could save a few bucks and watch the sunset from Mallory Square, which is always a nice experience. Alternatively, you could sail past Mallory Square and Sunset Key and have an uninterrupted sunset experience out on the Florida Keys that you’ll remember forever.

10 Best Sunset Cruises in Key West

Below are the 10 best sunset cruises in Key West. Most cruises last about two hours and depart from either Opal Key Resort & Marina, Key West Bight Marina, or Garrison Bight Marina.

1. Snorkel and Sunset Sail

Best For: Adventure seekers who want to snorkel and sip rum in the same outing.

Jam to reggae beats and snorkel at North America’s only living coral reef, and enjoy a sunset sail tour. Unlimited rum punch, beer, wine, and sparking wine are provided, after snorkeling of course. At three hours long, this is the lengthiest tour on the list.

🥤🤿 Snorkel and Sunset Sail ➡️ Check Availability

2. Sushi Cruise

Best For: Foodies and couples who prefer chilled vibes over party boats.

Sip, snack, and say goodbye to the sun like a sushi-loving sea god. This isn’t a party barge—it’s more like your cool friend’s boat with better snacks.

🍥⛴ Sushi Cruise ➡️ Check Availability

3. Cocktail Cruise With Open Bar

Best For: Social butterflies looking for unlimited drinks without breaking the bank.

This cocktail cruise with an open bar is one of the most affordable ways to enjoy unlimited drinks on a sunset cruise in Key West. Visitors looking for a small group experience, a fun atmosphere, and comfortable seating are sure to enjoy the voyage! Light snacks including breads and spreads are also provided.

🍹🛥️ Cocktail Cruise With Open Bar ➡️ Check Availability

4. Classic Sunset Cruise With Live Music

Best For: Party lovers and groups who want music, mingling, and open bar energy.

When you think of a Key West sunset cruise this tour is most likely what you envision. This large catamaran has plenty of space to stretch your legs while you jam to live music. Moreover, with an open bar and a nice assortment of appetizers, this is the perfect tour for anyone looking to party!

🥳⛵ Classic Sunset Cruise With Live Music ➡️ Check Availability

5. Tiki Bar Tour

Best For: Laidback travelers who want a BYOB cruise with island-style charm.

If your vacation motto is “no shoes, no worries, definitely bring a koozie,” this is your cruise. Bonus points if your adult beverage has a tiny umbrella in it.

Nothing screams laid-back quite like a floating tiki bar cruise around Key West. With only six passengers allowed, you won’t find a more intimate experience unless you charter a boat. Only water and ice are provided. However, passengers are allowed to bring their favorite adult beverages onto the boat. Check out these custom Key West koozies/party huggers to bring on board.

🗿⚓ Tiki Bar Tour ➡️ Check Availability

6. Premium Wine and Tapas

Best For: Wine lovers, romantic duos, and dolphin spotters with gourmet taste.

There’s no better sunset cruise in Key West for foodies and wine lovers than this one. Departing conveniently from Key West Bight Marina, the Premium Wine and Tapas Tour is 2.5 hours long and provides passengers with a plethora of scrumptious tapas and wine. Furthermore, the spacious and luxurious catamaran allows you to take in all the sights and the sunset comfortably. Additionally, the captain is passionate about spotting dolphins.

🐬🍷 Premium Wine and Tapas ➡️ Check Availability

7. Sunset Sail with Live Music, Drinks, and Appetizers

Best For: People who believe sunsets are better with a margarita and a band named Killer Dudes.

This is your sunset, but make it a full-on island soundtrack. Hop aboard this floating jam session-slash-happy hour where the live music is local, the drinks are bottomless, and the appetizers disappear mysteriously fast (because they’re good, not haunted). Great for couples, sunset chasers, or anyone who’s ever said, “This view needs a steel drum.

🛥️ Sunset Party Cruise ➡️ Check Availability

Is it Your First Time in Florida? > Read This

There are plenty of sunset cruises in Key West, but these are the MVPs. Whether you’re chasing dolphins, sipping sangria, or yelling “Arrrr!” on a schooner, there’s something here to float your boat. Just don’t forget sunscreen and your sense of adventure. Welcome aboard!

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