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The 16 Best Cruises And Boat Tours in Key West
Key West is a place where the water is as much a part of the landscape as the streets and architecture. It’s a city built on water, and there’s no better way to see its charm than from the deck of a boat or on a sailing adventure. Whether it’s a peaceful sunset cruise, an active snorkeling day, or a lively party sail, this island offers a range of options to suit different interests and budgets.
What makes Key West special for cruise lovers? The combination of calm Gulf waters, vibrant sunsets, and historic landmarks visible from the water creates unforgettable moments. With options like intimate champagne sails, lively sunset parties with live music, or full-day expeditions to Dry Tortugas, there’s no shortage of ways to enjoy the ocean. Below, we’ll explore the best cruises and boat tours in Key West, helping you find the perfect water adventure.
Quick Overview
Our list covers a variety of water experiences:
- Romantic adults-only sunset cruises with champagne (Tour #1)
- Classic sailing trips with live music or hors d’oeuvres (Tour #3, Tour #7)
- Family-friendly snorkel and sailing combo adventures (Tour #4)
- Unique private sunset sails for groups (Tour #13)
- Full-day trips to Dry Tortugas with snorkeling (Tour #11)
- Dolphin-watching sunset sails with tapas (Tour #8)
- Party cruises with live music and open bars (Tour #6)
- Reef snorkeling and sailing adventures (Tour #10)
- Elegant schooner sunset sails with full open bars (Tour #12)
- Romantic wine and sunset sails (Tour #14)
- Family-friendly reggae sunset sails with rum punch (Tour #14)
- Shorter catamaran sunset cruises with drinks (Tour #9)
- Classic schooner sunset sails with open bar (Tour #12)
- Special group private sails with wine and snacks (Tour #13)
- Evening beer and cocktail sails with live music (Tour #16)
Now, let’s explore each option in detail.
1. Adults only Sunset Cruise from Key West with Champagne
This 2-hour cruise offers a peaceful, adult-focused way to experience a Key West sunset. Limited to just 14 passengers, the small group size ensures a personalized and relaxed atmosphere. You’ll enjoy house champagne, fine wines, and cold beers, complemented by a gourmet cheese buffet featuring berries, seafood dip, and fresh-baked bread. The cruise takes place on a comfortable catamaran, perfectly suited for a tranquil late afternoon sail.
What makes this tour stand out? The intimate setting and the option to purchase bottles of Moët & Chandon for a celebratory toast. Guests emphasize the romantic, peaceful vibe and attentive crew. If you’re seeking a quiet, sophisticated evening with excellent drinks and spectacular sunset views, this cruise delivers.
Bottom Line: Best for couples or adults wanting a refined, quiet sunset experience with top-tier drinks and gourmet snacks.
2. Sunset Sail in Key West with Beverages Included
For around $79, this 1 hour 30 minute sail offers a quick but memorable way to catch the sunset. Limited to 24 passengers, it offers good vantage points for photos and a chance to escape larger crowds. The crew attentively serves a selection of alcoholic and non-alcoholic beverages throughout the trip as you glide through Key West Harbor. You’ll get to see the famous Sunset Celebration from the water, adding a fun twist to the sunset tradition.
Guests praise the calm sailing experience and the friendly crew. The cruise fits well into a busy evening, especially if you’re short on time but want a scenic, relaxing sail.
Bottom Line: An excellent choice for those seeking a short, intimate sunset experience with drinks and great photo opportunities.
3. Key West Schooner Sunset Sail with Bar & Hors d’oeuvres
This 2-hour cruise takes you aboard a replica of the 1851 Schooner America. As you sail past landmarks like Fort Zachary and Mallory Square, you’ll enjoy complimentary hors d’oeuvres and included drinks—beer, wine, and champagne. The cruise provides a historic sailing experience combined with spectacular views of the sunset over the Atlantic.
Guests rave about the professional staff and the leisurely pace, making it ideal for relaxing after a day of sightseeing. The nostalgic schooner adds a charming touch, and the delicious snacks and drinks make for a well-rounded experience.
Bottom Line: Perfect for travelers looking for a classic sailing experience with good food, drinks, and great scenery.
4. Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail
At number 4, this full-day adventure packs sailing, snorkeling, and kayaking into one trip. Visiting the Key West National Wildlife Refuge, you’ll see colorful coral reefs and marine life like turtles and fish. The tour includes a buffet lunch with unlimited beer, wine, and soft drinks, making it excellent value for an active day.
What sets this apart? The all-inclusive package saves you money and time, while the small group size (limited to 20) ensures attentive service. The experienced crew shares insights about the local habitat, making it both fun and educational. Some reviews highlight the opportunity to see turtles and stingrays.
Bottom Line: Ideal for active travelers wanting a comprehensive day of sailing, snorkeling, and kayaking with all food and drinks taken care of.
5. Key West: Schooner Sunset Sail with Food & Drinks
This 2-hour cruise aboard a classic schooner offers beautiful views of the sunset, with ample opportunity to see wildlife such as dolphins and sea turtles. You’ll enjoy delicious hors d’oeuvres and included beverages like beer, wine, and champagne. Plus, the atmospheric Green Flash phenomenon at sunset is a highlight.
Guests emphasize the professional crew and the relaxing, scenic environment. The romantic setting makes it perfect for couples celebrating special occasions. The comfortable schooner, paired with tasty snacks, provides a refined experience without feeling formal.
Bottom Line: A top pick for romantics and those wanting a traditional schooner experience with good food and drinks.
6. Key West Sunset Sail with Live Music, Drinks and Appetizers
This 2-hour party cruise combines live music with unlimited drinks and appetizers. Set sail from Fury watersports, with a luxurious 65-foot catamaran offering stunning sunset views and lively atmosphere. The local band keeps the energy high as you sip margaritas, champagne, and beer, while nibbling on antipasti, fruit, and hummus.
Guests love the festive vibe and the friendly crew. It’s perfect for travelers wanting to combine sunset sightings with dancing and socializing. The lively music and generous drinks make this a memorable evening.
Bottom Line: Designed for those seeking a fun, upbeat sunset experience with live entertainment.
7. Key West Sunset Sail Aboard Legendary Schooner Appledore
Rated 5 stars by over 200 reviews, this 2-hour cruise features a historic 1851 schooner. As you sail past Key West landmarks, you’ll enjoy complimentary beer, wine, champagne, and cocktails. The crew offers interesting commentary on the sights, and the traditional sailing adds to the experience’s authenticity.
Many reviewers highlight the beautiful sunset and the relaxed, friendly atmosphere. The staff’s knowledge and the classic schooner ambiance make this a favorite among sailors and romantics alike.
Bottom Line: Best suited for those who appreciate historic vessels and a laid-back yet elegant sunset sail.
8. Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
This 2.5-hour intimate sail combines dolphin watching with a relaxing sunset. Limited to a smaller group, you’ll have opportunities to see dolphins up close while enjoying wine and delicious tapas like shrimp cocktail. The luxe catamaran provides comfort, and the dolphin sightings add a special touch.
Guests appreciate the calm environment and the personalized experience. The inclusion of snacks and drinks makes it a sophisticated yet laid-back option.
Bottom Line: Ideal for wildlife lovers and those seeking a luxurious, quiet sunset with marine life.
9. Champagne Sunset Catamaran Cruise in Key West
At 1 hour 30 minutes, this champagne cruise is a shorter, elegant option. You’ll sail on a 69-foot catamaran, enjoying wine, champagne, sangria, or beer, with the chance to spot marine life and island views. A cash bar is available for additional drinks.
Guests call it a fantastic experience with friendly staff. The small size allows for more intimate viewing and relaxing atmosphere, perfect for those wanting a quick yet classy sunset.
Bottom Line: Great for travelers seeking a refined, shorter cruise with premium drinks.
10. Key West Reef Snorkel & Sail Adventure
Number 10 offers a 3-hour snorkeling trip to explore North America’s only living coral reef. The small-group setting (just four participants) makes for personalized attention. The tour includes snorkel gear, water, soda, wine, and craft beer, and chances to see turtles, dolphins, eels, and colorful fish.
Guests rave about the friendly crew and the spectacular reef. The combination of sailing and snorkeling caters well to those who want a mix of relaxation and underwater adventure.
Bottom Line: Perfect for snorkelers keen on exploring coral reefs with expert guidance and a relaxed vibe.
11. Dry Tortugas National Park Day Trip by Catamaran
A day-long expedition, this trip takes you 10 hours to the remote Dry Tortugas. You’ll enjoy snorkeling, a historic fort visit, and cruise past Boca Grande and Marquesas Keys. The state-of-the-art Yankee Freedom III catamaran provides comfort and sightseeing commentary.
Reviewers praise the beautiful beaches and spectacular snorkeling, though some note the long trip and limited time on land. Bring your patience — but the pristine waters and secluded beaches make it worthwhile.
Bottom Line: Best for outdoor enthusiasts and history fans ready for a full day on the water.
12. Classic Key West Schooner Sunset Sail with Full Open Bar
Rated 5 stars by 91 reviews, this 2-hour sail features a full open bar on a majestic schooner. As you glide past landmarks like Sunset Key and the Navy Mole, you can enjoy cocktails, wines, and spirits. The friendly crew makes the experience welcoming and relaxed, perfect for a celebration or romantic evening.
Reviewers highlight the beautiful sunset and the excellent drinks. The open bar means you don’t have to worry about limited beverage options.
Bottom Line: Ideal for travelers who want a classic schooner experience with unlimited drinks and scenic views.
13. Private 2-Hour Wind and Wine Sunset Sail in Key West
This private sailing experience is perfect for groups or special occasions. You’ll set sail just before sunset on a 65-foot schooner, enjoying hors d’oeuvres and a selection of wines and beers. The trip offers a personalized, intimate experience with your party only.
Guests praise the customized atmosphere and the beautiful setting. It’s a great way to create lasting memories with friends or family.
Bottom Line: Best for groups wanting exclusivity and a tailored sunset experience.
14. Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail
This 3-hour trip combines snorkeling at North America’s only living reef with a reggae sunset cruise. Participants can snorkel with gear provided, then relax onboard with rum punch, beer, and wine, all while listening to reggae music. The crew is friendly and accommodating, and the reef offers vivid marine life.
Reviewers highlight the lively atmosphere, the great snorkeling, and delicious drinks. It’s perfect for those who want adventure and relaxation combined.
Bottom Line: Suited for travelers who want a fun, musical reef experience with tropical drinks.
15. 2-Hour Sunset Sailing With Wine In Stock Island
This smaller, intimate sail offers 8 varieties of wine, 5 types of beer, and snacks like charcuterie. Launched from Stock Island, it’s a relaxed way to enjoy the sunset with good company. The skilled crew makes sure everyone has drinks and snacks while soaking up the views.
Guests appreciate the personal touch and the comfortable setting. It’s an excellent choice for wine enthusiasts and those seeking a laid-back experience.
Bottom Line: For wine lovers and travelers wanting a quiet, scenic end to their day.
16. Key West: Sunset Sailing Trip with Open Bar, Food and Music
This 2-hour cruise delivers live music, an open bar, and delicious appetizers. The party atmosphere is perfect for celebrating special occasions or just enjoying the lively spirit of Key West. You’ll sail on a catamaran past iconic landmarks, with music playing and drinks flowing.
Guests enjoy the friendly crew, the dancing on deck, and the spectacular sunset. It’s a lively, fun way to end the day.
Bottom Line: Ideal for travelers who want a festive, energetic sunset experience with food, drinks, and music.
How to Choose Your Perfect Key West Boat Tour
When selecting among these options, consider your budget, available time, and what kind of experience excites you most. Want an intimate sunset with champagne? Tour #1 is perfect. Looking for a full-day reef adventure? Tour #11 offers a comprehensive trip with snorkeling and wildlife. If you prefer live music and a party vibe, Tours #6 and #16 deliver lively entertainment. For a romantic, classic schooner sail, Tours #3 and #7 are top picks.
Think about your interest in wildlife, history, or just relaxing with a drink. Book early for popular sunset slots, especially in peak season. Many tours offer small groups or private options—great for special occasions or just avoiding crowds.
Final Thoughts
From romantic sunset champagne sails to full-day snorkeling adventures, Key West’s boat tours cover a wide range of interests. For those seeking quiet elegance, the Adults only Sunset Cruise or the Legendary Schooner offer refined experiences. If lively evenings with music and dancing are more your style, the Party Cruise won’t disappoint.
For active travelers, the full-day ocean adventure or the snorkel trips provide exciting ways to explore beneath the waves. No matter your preference, booking early ensures you get the best spots for these unforgettable water-based adventures. So, pick your favorite, and get ready to enjoy the stunning waters of Key West.