Are you looking for the best sunset cruise in Key West?
You’re in the right place because the 13 best sunset cruises in Key West are all listed here.
Being based in Southwest Florida, Key West is a skip and a jump away, and I’ve taken many weekend trips to experience the Southernmost City.
Going on a sunset sail in Key West is one of my favorite things to do here because nothing beats watching the sun slip slowly into the horizon from an open sailboat.
With miles and miles of beautiful coastline, magical coral reefs, fascinating marine life, and incredible views that extend from ocean to sky, not to mention great food and drinks, there’s something about sunset tours in Key West that makes it an experience like no other.
If you’re looking to experience the magic of twilight on the tranquil waters of the ocean, then you’re in for a treat!
I’ve rounded up 13 of the best sunset cruises in Key West that feature amazing views, comfortable vessels, and top-notch service so you can have a memorable and unique experience and make the most out of your getaway.
Get ready to sail into a world of vibrant colors and mesmerizing horizons!
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In This Post:
Top 3 Picks: Sunset Cruises in Key West
#1 TOP PICK
⭐️⭐️⭐️⭐️⭐️
Private Sunset Cruise Around Key West
✔️ Private charter boat tour
✔️ See several of Key West’s top attractions
#2 PICK
Small Group Key West Sunset Sail
✔️ Small group tour
✔️ Unlimited beer, wine, and soft drinks
✔️ Includes gourmet cheeses and other appetizers
#3 PICK
Key West Sunset Sail Aboard Schooner
✔️ Includes hors d’oeuvres
✔️ Beer, wine, champagne, and other non-alcoholic drinks included
13 Best Sunset Cruises in Key West
1. Two Hour Private Sunset Cruise Around Key West
⭐️ RATING: 5/5 stars | ⏳ TOUR LENGTH: 2 hours | ⛵️ Book it!
Experience the magic of a famous Key West sunset on this two-hour private sunset cruise around Key West!
You’ll have the entire boat to yourself, allowing for a serene and relaxing experience while escaping the hustle and bustle of Duval Street and Mallory Square.
Your captain will take you around eleven of the most breathtaking spots on the island, including Florida Keys National Marine Sanctuary, Fort Zachary Taylor Historic State Park, Southernmost Point, and more, where you can soak up stunning views of colorful sunsets reflected off crystal-clear waters.
“Our private sunset tour was amazing and relaxing! Captain Tim talked about history of the area before taking us to see mangroves. The kids had an amazing time out in the open ocean before heading back and watching a beautiful sunset! Highly recommend!” – Nellyholland (Read more reviews)
This two-hour private sunset tour is just the right length to unwind, soak up the scenery, and make unforgettable memories.
This is undoubtedly one of the best sunset cruises in Key West, and it’s the perfect way to uncover some of Key West’s top attractions while relaxing and savoring the moment.
✅ Check Prices and Availability: Two Hour Private Sunset Cruise Around Key West
2. Small Group Key West Sunset Sail With Wine
⭐️ RATING: 5/5 stars | ⏳ TOUR LENGTH: 2 hours | ⛵️ Book it!
This small group Key West sunset sail with wine promises a unique and luxurious experience aboard a 65-foot schooner.
You’ll have the chance to explore some of Key West’s best spots and catch beautiful views of the magnificent sunset while sampling up to eight different wines and/or five different beers from around the world.
“By far the best sunset cruise we have ever taken!! Rocky made delicious snacks that paired nicely with the wine. The captain and crew did a great job and went out of their way to show us all a good time. I would highly recommend this cruise to everyone! We will go again our next trip down.” – Robin (Read more reviews)
The crew members have also prepared an array of gourmet cheeses, accompanied by mouthwatering appetizers like summer sausages, crackers with brie, and crisp green apples drizzled with golden honey to munch on while taking in the views.
This small group sunset sail is perfect for couples, friends, and families looking to make the most of their weekend in Key West or for celebrating a special occasion.
✅ Check Prices and Availability: Small Group Key West Sunset Sail With Wine
3. Key West Sunset Sail Aboard Schooner
⭐️ RATING: 5/5 stars | ⏳ TOUR LENGTH: 2 hours | ⛵️ Book it!
Hop aboard a marvelous replica of the 1851 historic Schooner America and embark on this Key West Sunset Sail Aboard Schooner.
Discover some of the city’s most amazing sites while sailing in style, from the historic Fort Zachary to the vibrant Mallory Square, the charming Sand Key Lighthouse, and more.
“Outstanding trip. Captain Amber and her crew did an amazing job of looking after the passengers. Food and drinks provided were excellent and far exceeded our expectations. Would highly recommend.” – Lois (Read more reviews)
As you soak up the beautiful views, savor complimentary hors d’oeuvres and sip on a wide selection of refreshing alcoholic and non-alcoholic beverages.
Snacks, drinks, and a gorgeous sunset — what more could you ask for from a sunset sail in Key West?
✅ Check Prices and Availability: Key West Sunset Sail Aboard Schooner
4. Sunset Sail Key West Jolly II Rover
⭐️ RATING: 5/5 stars | ⏳ TOUR LENGTH: 2 hours | ⛵️ Book it!
Ready for an unforgettable adventure around Key West? Jump onboard the Jolly II Rover, the only square-rigged topsail schooner in the area, for this sunset sail Key West Jolly II Rover tour.
You’ll embark from the Key West Historic Seaport at the corner of Elizabeth Street and Greene Street, ready to explore some of Key West’s most iconic sites with snacks and ice-cold water in hand.
As you glide through the waters on this vintage schooner with red sails, you’ll be treated to breathtaking views of Man O’ War Harbor, Christmas Tree Island, Fort Zachary Taylor State Park, and more.
“Awesome sunset cruise! Amazing crew! Fun time! Would highly recommend! The crew was very knowledgeable and very interactive and engaging! Money well spent!” – James (Read more reviews)
Your journey continues with a leisurely cruise along the coastline, revealing the grandeur of the mansions on Sunset Key. Keep your eyes peeled for Mallory Square, the iconic Navy Mole, and dolphins and sea turtles frolicking around you in their natural habitat.
You’ll then head out into the vastness of the open Atlantic Ocean, where you’ll witness a breathtaking sunset that sets Key West apart each and every day.
✅ Check Prices and Availability: Sunset Sail Key West Jolly II Rover
5. Key West Dolphin Watch Sunset Sail
⭐️ RATING: 4.5/5 stars | ⏳ TOUR LENGTH: 2.5 hours | ⛵️ Book it!
If you’re looking for a unique way of watching the sunset in Key West, this 2.5-hour Key West dolphin watch sunset sail is just what you need!
This tour allows you to explore some of Key West’s most spectacular sites while keeping your eyes peeled for dolphins, sea turtles, stingrays, and other marine life.
“We had a wonderful experience. Saw lots of dolphins and enjoyed the lovely sail. Booze was free flowing and snacks were great ! A fun knowledgeable crew. This is the way to see Key west!” – Rene (Read more reviews)
As you board the luxury catamaran, prepare to unwind and indulge. Watch the sun slowly dip below the horizon as you savor mouthwatering tapas, including delectable shrimp cocktail, perfectly paired with a glass of wine or champagne.
When it comes to the best sunset cruises in Key West, this one certainly has everything you need for a sublime experience.
✅ Check Prices and Availability: Key West Dolphin Watch Sunset Sail
6. Key West Sunset Party Cruise With Live Music
⭐️ RATING: 4./5 stars | ⏳ TOUR LENGTH: 2 hours | ⛵️ Book it!
Welcome aboard a 65-foot luxurious sailing catamaran on this Key West sunset party cruise with live music!
Get ready to set sail on this spacious catamaran and be serenaded by Key West’s most talented singers and songwriters while you find your perfect spot to relax or hit the dance floor.
“We had an amazing time! Drinks were good, food was delicious, but the music and the crew made the night memorable!!” – Tom (Read more reviews)
You’ll also munch on mouthwatering appetizers while sipping on refreshing beer, margaritas, wine, and champagne and marveling at stunning views of island’s coastline.
With drinks, unlimited appetizers, and live music from the island’s best singers and songwriters, this is the best sunset cruise in Key West for party and music lovers!
✅ Check Prices and Availability: Key West Sunset Party Cruise With Live Music
7. Key West Sunset Tiki Boat Tour
⭐️ RATING: 5/5 stars | ⏳ TOUR LENGTH: 2 hours | ⛵️ Book it!
This Key West sunset tiki boat tour is one of the coolest sunset cruises in Key West to experience the beauty of the island from the water.
With a small group of just six people, you’ll have the perfect chance to bask in the beauty of the Key West harbor while enjoying your favorite drink (BYOB) and toasting to the stunning sunset.
Marvel at the hidden gems of Key West as you pass by luxury houses, Sunset Pier, and Mallory Square, and capture the perfect picture of the elusive “green flash” as the sun sets on the horizon.
“We had an amazing time with great views of the sunset. Our tour guide was great and provided a lot of information about the areas we were passing. Highly recommend!” – Crystal (Read more reviews)
Take in the sights of Fleming Key and the Key West Historic Seaport, home to the Shrimp Fleet, Turtle Plant, and Ferry Terminal, and enjoy the final leg of the journey back to Garrison Bight while sipping on your favorite cocktails.
The tiki bar boat is equipped with a certified captain, ice, cups, a blender, a Bluetooth TV, and a stereo to keep the party going from start to finish.
✅ Check Prices and Availability: Key West Sunset Tiki Boat Tour
8. Key West Sunset Sail With Full Bar, Live Music, and Hors D’oeuvres
⭐️ RATING: 4.5/5 stars | ⏳ TOUR LENGTH: 2 hours | ⛵️ Book it!
Looking for a luxurious way to soak in the tropical beauty of Key West? Look no further — this Key West sunset sail with a full bar, live music, and hors d’oeuvres is the perfect way to enjoy the golden hour.
You’ll set sail on a sleek 60-foot catamaran featuring local musicians that boasts over 1,500 feet of deck space, providing ample room to unwind and enjoy the stunning scenery.
“The crew was awesome. Great energy. Beautiful views. Perfect sunset sail. Music, snacks and bar were a plus!” – Macy (Read more reviews)
Along the way, you’ll catch glimpses of iconic landmarks like Fort Zachary Taylor State Park, Navy Mole, Mallory Square, and more.
The best part about this sunset sail in Key West is that a variety of mouthwatering appetizers and refreshing drinks, including peel-and-eat shrimp, champagne, sangria, wine, beer, soft drinks, and a full liquor bar are provided.
This Key West sunset sail with a full bar, live music, and hor d’oeuvres offers an exemplary blend of luxury, relaxation, and natural beauty.
✅ Check Prices and Availability: Key West Sunset Sail With Full Bar, Live Music, and Hors D’oeuvres
9. Sunset Sip and Sail With Open Bar, Live Music, and Appetizers From Key West
⭐️ RATING: 4.5/5 stars | ⏳ TOUR LENGTH: 2 hours | ⛵️ Book it!
This sunset sip and sail with an open bar, live music, and appetizers is one of the best sunset tours in Key West and a great way to unwind after a day of sightseeing.
Hop on board this amazing Key West sunset cruise, where you’ll enjoy an open bar with unlimited margaritas, rum runners, mixed drinks, champagne, and more, but you’ll also be treated to live music as you sail the beautiful waters and catch breathtaking sunset views.
You can even upgrade to the premium open bar if that’s your fancy!
“An absolute beautiful cruise and sunset. The food (appetizers) was fabulous. The crew was so professional and friendly and even came around to get us more drinks and offered to take pics of our group with our phones. The live music was wonderful also! Will definitely go out on this again!” – Kimberley (Read more reviews)
While you soak up the atmosphere, grab a glass of wine or a draft beer from the open bar and indulge in delicious appetizers, including bbq meatballs, veggie trays, meat and cracker trays, Jamaican jerk chicken sliders, and more.
Between the awe-inspiring views of Key West’s coastline, live music, an open bar, and delicious appetizers, this Key West sunset sailing is anything but ordinary!
✅ Check Prices and Availability: Sunset Sip and Sail With Open Bar, Live Music, and Appetizers From Key West
10. Key West Sushi Sunset Cruise
⭐️ RATING: 5/5 stars | ⏳ TOUR LENGTH: 2 hours | ⛵️ Book it!
Picture yourself relaxing on the deck, enjoying delectable sushi platters and refreshing beverages while the sun gracefully dips below the horizon — you’ll get to do exactly that on this Key West sushi sunset cruise.
You’ll have front row seats to admire the Southernmost Point and other quintessential Key West landmarks from the water.
And don’t forget the Key West Historic Seaport, Mallory Square, Fort Zachary Taylor Historic State Park, Key West Lighthouse and Keeper’s Quarters Museum, and even the exclusive Sunset Key with its rich and famous residents — all passing by as you soak up the magical atmosphere.
“The trip was amazing. The Captain and First Mate Marta were friendly and funny. They made the entire tour so memorable. The Captain toured us around the harbor and told us many stories. The sushi and alcohol were delicious. I highly recommend this to anyone looking to have a romantic evening cruise and see beautiful sunsets.” – Alexander (Read more reviews)
You’ll also get to pair your sushi and snacks with bottled water, alcoholic beverages, and soda.
Sushi lovers, this is one of the best sunset cruises in Key West for you!
✅ Check Prices and Availability: Key West Sushi Sunset Cruise
11. Sunset Sail in Key West With Beverages
⭐️ RATING: 5/5 stars | ⏳ TOUR LENGTH: 1.5 hours | ⛵️ Book it!
Experience the tranquil, picturesque scenery and ocean air while setting sail at sunset on this sunset sail in Key West.
This small group sunset tour is simple yet intimate and perfect for couples, friends, and families, and it guarantees you a prime spot at the rail to soak in the beauty of the golden hour and take stunning photos.
“The sunset sail was amazing! The amount of people on the sail was perfect. The captain was very knowledgeable of the area and overall made sure we all had an excellent time!” – Leslie (Read more reviews)
Alcoholic beverages, soda, and water are provided throughout the cruise, allowing you to unwind and relax without worrying about anything.
✅ Check Prices and Availability: Sunset Sail in Key West With Beverages
12. Adults Only Key West Cocktail Cruise With Open Bar
⭐️ RATING: 5/5 stars | ⏳ TOUR LENGTH: 1.5 hours | ⛵️ Book it!
Enjoy an evening out on the town with this Adults-Only Key West Cocktail Cruise, featuring an open bar and stunning sunset views.
You’ll board a 47-foot catamaran and sail around the picturesque Floridian coastline while ending the day with an unforgettable experience.
“My friend and I thoroughly enjoyed our cruise. The sunset was beautiful and it wasn’t overcrowded. Bartender was super friendly and also took pictures of the guests. The cocktails were great with a wide variety and the beer and wine selection was also pretty good! Highly recommend!” – Gwynne (Read more reviews)
Not only will you get to soak in the beautiful scenery, but you’ll also have access to unlimited South Florida craft beer, delectable California wine, and hand-crafted cocktails throughout the entire tour at the open bar.
And to top it off, they’ve got you covered with a selection of fresh bread and mouthwatering spreads, and you’re welcome to bring whatever snacks you’d like.
✅ Check Prices and Availability: Adults Only Key West Cocktail Cruise With Open Bar
13. Key West Sunset Champagne Catamaran Tour
⭐️ RATING: 4.5/5 stars | ⏳ TOUR LENGTH: 1.5 hours | ⛵️ Book it!
The final tour on this list that’s a must-do is the Key West Sunset Champagne Catamaran Tour!
You’ll take in the breathtaking island views and soak up the turquoise beauty all around you as you drink unlimited refreshing beer, a glass of fine wine, a bubbly champagne, a fruity sangria, or a cool soda.
“The crew was absolutely amazing!! Felt very comfortable would highly recommend. Gorgeous sunset. The sangria was so good.” – Luanne (Read more reviews)
Cheers to the picturesque sunset views while being treated to crystal clear waters and an unforgettable and amazing experience with a fun and knowledgeable captain.
✅ Check Prices and Availability: Key West Sunset Champagne Catamaran Tour
Sunset Cruises in Key West: FAQs
How long is the Key West sunset cruise?
The duration of sunset cruises in Key West varies and can range from an hour to several hours, depending on which cruise you choose. Most of the sunset cruises in Key West listed in this post are between 1.5 hours and 2.5 hours.
What is special about sunset in Key West?
Sunsets in Key West are known for their captivating beauty and the ambiance they create. The sky transforms into a spectacular canvas of vibrant colors — a gorgeous blend of oranges, pinks, and purples, reflecting on the shimmering turquoise waters surrounding the island.
The unique geographical location of Key West, being the southernmost point in the United States and nestled between the Atlantic Ocean and the Gulf of Mexico, provides unobstructed views of the spectacular sunset, making it a truly magical experience that stands out.
Can you sail to Key West?
Yes, you can sail to Key West. The Key West harbor is a major destination for cruising and sailing vessels, as it’s conveniently situated between the Atlantic Ocean and the Gulf of Mexico in North America. There are plenty of marinas, boat charters, and harbors located in Key West that make it one of the best places for sailors to explore.
Is 3 nights in Key West worth it?
Yes, 3 nights in Key West is worth it, and it’s the perfect amount of time to explore the city’s main attractions while taking in the iconic Key West vibes.
With 3 nights in Key West, you’ll have enough time to explore Duval Street and its trendy bars, take a snorkeling trip to the stunning coral reefs, partake in the Mallory Square sunset celebration, check out some of the island’s historic sightseeing spots such as Ernest Hemingway Home & Museum, and Truman Little White House, and even go on one of the many sunset cruises Key West has to offer.
Plus, 3 days allow you to go on an epic Miami to Key West road trip and explore Key Largo and the other keys along the way.
What is the best sunset cruise in Key West?
The best sunset cruise in Key West really depends on what you’re looking for. If you’re interested in private charters with just your group, the two-hour private sunset cruise around Key West is perfect for a more intimate experience.
If you want a more upbeat and party vibe while watching the sunset, then the Key West sunset party cruise with live music is the best option.
And if you just want to enjoy some drinks, snacks, and amazing views, then the adults-only Key West sunset sail with a full bar, live music, and hors d’oeuvres is the way to go.
No matter what type of experience you’re looking for, Key West has a sunset cruise for everyone, and you’re guaranteed to have a great time!
What are the best months to visit Key West?
The best months to visit Key West are from March to May. This is shoulder season, and the weather is perfect — not too hot and not too cold. Plus, the crowds are much more manageable during this time of year. This is also before the start of hurricane season, making it the ideal time to do all of the best things Key West has to offer.
Final Thoughts: Sunset Cruises in Key West
In conclusion, sunset cruises in Key West offer the best experience that combines the magic of nature’s grandeur, the tranquility of the sea, and the joy of delicious drinks and food.
Whether you’re looking for a romantic experience, a party atmosphere, or a quiet escape, Key West has a sunset cruise that will cater to your preferences.
Don’t miss out on this unique experience that truly epitomizes the enchanting beauty and charm of a spectacular Key West sunset.
Sounds like a pretty magical adventure, doesn’t it?
Still unsure which one of the best sunset cruises in Key West is right for you? I recommend this private sunset cruise around Key West with a perfect five-star rating. ⭐️⭐️⭐️⭐️⭐️
Read More About Things to Do in Florida
- Miami to Key West Drive: 25+ Amazing Stops!
- The Ultimate Florida Road Trip: 14 Epic Days!
- Crab Island Destin: Complete Guide + 5 Fun Tours
- 12 Adorable Small Beach Towns in Florida
- 14 Best Beaches in the Florida Panhandle
- 18 Fun Things to Do in Seaside Florida
- One Day in Miami
- 11 Top Beaches in Destin Florida
- 8 Best Dolphin Tours in Destin, Florida
- The Ultimate Weekend in Key West
Key West Travel Planning Guide
🛌 Top hotels and accommodations in Key West:
- Simonton Court Historic Inn & Cottages: (my top pick — it’s in the heart of the historic district/old town and has a delicious breakfast included)
- Courtney’s Place Historic Cottages & Inns: (a few minutes walk to Duval Street and spacious rooms)
- Santa Maria Suites Resort: (includes complimentary daily happy hour and equipped with washers and dryers on-site
- Key West Bed and Breakfast: (cozy and comfortable and a short walk to Duval Street)
🏝️ Top Things to Do in Key West:
- Key West Jet Ski Tour: (a 1.5-hour tour around 28 miles of the Floridian coastline that includes pickup, and the second rider is free on the same jet ski)
- Mangrove Kayak Eco Tour: (2-hour kayak tour around mangrove creeks and a great way to learn about the ecological importance of mangroves and see wildlife up close)
- Key West Hop-On Hop-Off Trolley: (visit 100+ points of interest with the choice of an unlimited one or two day pass)
- Florida Keys Reef Snorkel & Sail Adventure: (small group snorkel tour where you see dolphins, turtles, eels, and more on a sailing yacht)
🚑 Should I buy travel insurance for Key West?
100% YES! Having travel insurance can be incredibly beneficial in a variety of situations. It can cover medical emergencies, trip cancellations, lost or stolen items, etc. It’ll give you peace of mind while traveling, starting at only $5-10 USD per day with Safety Wing.
🚗 What’s the best way to get around Key West?
Renting a car is one of the best and easiest ways to explore Key West and its surroundings. I recommend Discover Cars because you can easily compare the prices and policies of several companies at once so you can find the best deal.
✈️ What’s the best way to get to Key West?
I recommend Skyscanner for finding cheap flights to Key West. They offer an easy-to-use website that compares prices from multiple airlines to help you find the best deal on flights to your trip to Key West and anywhere else in the world.
Disha Smith is the founder of Disha Discovers. She quit her job in 2017 to travel the world to explore new cultures and experience new adventures. She has since been to 95+ countries and counting and has lived in South Africa, Thailand, Croatia, and Australia. She has done all kinds of travel ranging from luxury to budget backpacking, and her mission is to inspire others to discover their own sense of adventure and to help them plan a life full of meaningful experiences through travel.