How to Choose the Best Sunset Cruise in Key West
Written by Terrance Davis
Terrance writes for Dwell Key West, highlighting some of the best attractions, sites, and events in and around Florida's Keys.
Key West’s coastal location gives you plenty of opportunity to enjoy the shoreline. Set right along the water, the city offers some of the most stunning views and romantic atmosphere you can find. Key West is home to some incredible sunset sailing experiences that are great for couples, families, groups, or even solo travelers. Follow along with this blog before taking a unique and enjoyable evening as we walk you through some of Key West’s best sunset cruise experiences!
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In this Blog
- What Kind of Key West Sunset Cruise is Right for You?
- Choose a Traditional Sunset Sailing Experience
- Pick a Catamaran Cruise for More Space and Communal Entertainment
- Make a Full Evening Out of a Key West Dinner Cruise
- End Your Evening at Dwell Key West!
- Frequently Asked Questions About Key West’s Sunset Cruises
What Kind of Key West Sunset Cruise is Right for You?
Key West is home to several types of cruises, so choosing the right option for you is important to making the most of your scenic evening. Before setting off, consider your party size, the atmosphere you’re looking for, and what type of group you will be going with. Pick between a romantic evening or a fun night on the shore, with many operators in the area running both motorized boats and sailing vessels. With so many great options, there isn’t necessarily a single best experience; it’s just all about what you’re looking for.
Choose a Traditional Sunset Sailing Experience on a Schooner
Take a ride on a schooner or sailboat for a cruise that focuses on the sailing experience more than anything else. Enjoy a classic nautical experience on the shore with many charters housing custom-built vessels that will give you that rocking feeling that sailing is all about. While they aren’t the focus, many of these tours will feature refreshments and snacks along the way. Explore some of these local charters that specialize in schooner rides for your traditional Key West sunset cruise:
Classic Harbor Line Key West
Schooner America 2.0 is the vessel at this local operator working out of the Key West Bight, behind the Schooner Wharf Bar. Classic Harbor Line has been in business since 2008 and has since worked to offer some of the best sunset sails in Key West.
- Tour Duration: 2 hours
- Starting Price: Adults: $108 | Children Aged 2-12: $54
- Book Here
Schooner Appledore
Set sail on a classic wooden boat, with the option for a possible champagne cruise with this Key West cruise operator. First built in 1978, the Appledore II is an 86-foot-long windjammer made using traditional techniques. With its 110-degree knockdown rating along with its 10.5 knot hull speed, the Appledore II can move quickly and without fail, leaving you with a pleasing ride along the Gulf.
- Tour Duration: 2 hours
- Starting Price: $109.95
- Book Here
Danger Charters
Don’t let the name scare you away! This local Key West cruise provider makes just about any trip on the water an experience that Coastal Living magazine called one of the top two sunset sails in North America. Watch the crew set up the sails for your sunset ride, and enjoy a smooth evening with premium beverages, alcohol, and finger foods. Just remember, these tours only serve guests and customers 13 years old and up.
- Tour Duration: 2 hours
- Starting Price: $115
- Book Here
Pick a Catamaran Cruise for More Space and Communal Entertainment
Spread out and enjoy more room for more people with a catamaran cruise. Catamarans often come with wider decks to accommodate larger groups, usually with amenities like music and drinks to create a more energetic vibe. Catamaran rides are perfect for large groups, families, and special events. This is a great time for those who aren’t too concerned about the sailing experience and instead would rather spend quality time on the water with loved ones.
Agro Navis
This 75-foot-long luxury catamaran was the last commercial sailing vessel built in Key West and now sails its waters year-round, offering peaceful sunset cruises. Trips with this provider are inclusive and feature craft beers, cocktails, and fine wines, along with light meals that can be upgraded for a more complete dining experience.
- Tour Duration: 2 hours
- Starting Price: $111
- Book Here
Fury Water Adventures
Spread out on this comfortable vessel, which offers three viewing levels, giving you plenty of time to relax, chat, hang out, and enjoy the deck with your friends. Along with refreshments including cold margaritas, sodas, and draft beer, cruises will also be accompanied by live music from a band, allowing you to jam out on the shore to your heart’s content.
- Tour Duration: 2 hours
- Starting Price: $63
- Book Here
Sebago Watersports
Sail from Key West’s Historic Seaport aboard this catamaran that was built with comfortable sunset viewing in mind. During the cruise, you can enjoy complimentary champagne, wine, sangria, beer, soft drinks, and bottled water while the crew guides the boat toward clear horizon views. The family-friendly adventure also offers multiple seating areas, covered seating, an onboard restroom, and views of landmarks like Fort Zachary Taylor.
- Tour Duration: 1.5 hours
- Starting Price: $49.95
- Book Here
Make a Full Evening Out of a Key West Dinner Cruise
Have the luxurious evening of your dreams with a full dinner set right on the sea for a true waterfront dining experience. Immerse yourself in an incredible 2-in-1 experience with a cruise that mixes great food with stunning views of the horizon. Many dinner cruises feature champagne and tropical dinner buffets to ensure everyone on board is happy and satisfied.
Sunset Watersports Key West
Climb aboard this sunset cruise for a full evening, including a tropical buffet, live music, and an unlimited open bar. The 65-foot “Party Cat” offers an open sundeck for a great look at the horizon as the sun goes down. You’ll also have access to an air-conditioned cabin, dance floor, full bar, and onboard restrooms. Dig into island favorites on board, including local fish, jerk chicken, pulled pork, salads, and Cuban bread for a lovely dinner with the sunset in the distance.
- Tour Duration: 2 hours
- Starting Price: $79.95
- Book Here
Key West Cruises
Get some of the best views around with this stunning sunset cruise that puts you right at the center of a tropical sunset cruise experience. Along for the ride is a local steel drum performer to really tie together the tropical vibe. Onboard, enjoy an assortment of delicious island-inspired foods, including pulled pork, fried fish, plantains, veggies, and Cuban bread. For an extra $19, you can also upgrade your drink package to include unlimited drinks made with top-shelf liquors.
- Tour Duration: 2 hours
- Starting Price: Adults: $79.95 | Ages 6-12: $39.95 | Children under 5: Free
- Book Here
End Your Evening at a Rental from Dwell Key West!
Featured Stay: FLOR DE CANA @ Azul Mansion Key West
Now that you’ve had your tour of the sunset cruises here in Key West, it’s time to book that trip! Blend sunsets with sailing and communal fun when you take your trip to Key West. Whenever you’re ready, we here at Dwell Key West will have a rental waiting for you.
Our boutique hotel rentals near Duval Street are perfect for your Key West Vacation. With amenities like a fully-functional kitchen or pool access, we’re confident you’ll find the ideal stay in our extensive catalog. There’s no better time to book a trip than now, so what are you waiting for? Browse our available rentals now and book your next trip to Key West directly with Dwell Key West!
Frequently Asked Questions About Key West’s Sunset Cruises
How long do sunset cruises in Key West usually last?
Most Key West sunset cruises last between 90 minutes and two hours. Dinner cruises and private charters may run longer, so always check the scheduled return time before making evening plans.
Are Key West sunset cruises suitable for children?
Many catamaran and dinner cruises welcome families, but age policies vary. Some sailing experiences are reserved for teenagers and adults, so review the operator’s requirements before booking.
Should I book a Key West sunset cruise in advance?
Booking ahead is recommended, especially during holidays, spring break, and other busy travel periods. Reserving early also gives you more choices between schooners, catamarans, dinner cruises, and private charters.
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