The Best Key West Sunset Cruises

A local saying in Key West is “see you at sunset.” And the best place to watch the sunset? On the deck of a Sebago boat, of course.

Choose Your Perfect Key West Sunset Adventure

STARTS AT $59.95
BOOK DIRECT & SAVE
JUST $49.95!
Sebago Watersports - Sunset 1 2 1

Experience the world-famous Key West sunset

Sunset
A sunset sail past local Key West landmarks
Sebago Watersports - Sunbathing 1
Reduced capacities and comfortable onboard seating
Drinks
Includes: champagne, beer, wine, sangria, soft drinks and water
STARTS AT $89.95
BOOK DIRECT & SAVE
STARTING AT $59.95!
Catamaran

Stunning sunset sail past Key West landmarks

Live Entertainment
Live music from local Key West musicians
Chef
Chef’s selection of hors d’oeuvres, including shrimp cocktail
Drinks
Complimentary premium open bar including sangria, handcrafted cocktails, and boutique wines
STARTS AT $99.95
BOOK DIRECT & SAVE
STARTING AT $69.95!
Red Dolphin

The best way to see dolphins in Key West

Sebago Watersports - Sunset 1 2 1
A sunset sail with dolphins in their natural habitat
Chef
Chef’s selection of tapas, including cocktail shrimp
Drinks
Includes champagne, premium wine, beer, sangria, soft drinks and water
Red Dolphin
The best way to see dolphins in Key West
STARTS AT $139.95
BOOK DIRECT & SAVE
STARTING AT $109.95!
Sebago Watersports - Sunset 1 2 1

Explore Key West's Top Snorkeling Hot Spots

Sebago Watersports - Sunbathing 1
Relax and sunbathe on our expansive tiki boat
Landscape
Explore Key West’s most sought-after sandbars
Sebago Watersports - Swim 1
Swim in the crystal clear waters of Key West
Sebago Watersports - Glass With Wine
Frozen Margaritas and Piña Coladas, refreshing beer, wine, sangria, soft drinks, and water
Sebago Watersports - Tiki Red 1
5:00 PM trip includes Sunset Sail!

Schooner Sunset Sails

Sebago Watersports - Glass With Wine

2-Hour Sunset Cruise With Premium Drinks

Sebago Watersports - Sunset 1 2 1
A sunset sail past Key West’s most iconic landmarks
Sebago Watersports - Sunbathing 1
Capacity limited to just 36 passengers for a more comfortable, VIP experience.
Drinks
Bottomless drink including champagne, homemade sangria, boutique wine, premium beer, cocktails and filtered water
Food
Chef’s selection of hors d’oeuvres and shrimp cocktail
Sebago Watersports - Catamaran 2

Key West’s best schooner sail

Sebago Watersports - Sunset 1 2 1
A sunset sail past local Key West landmarks
Chef
Chef’s selection of hors d’oeuvres and cocktail shrimp
Drinks
Liquor bar, including champagne, sangria, boutique wine, premium beer, cocktails, soft drinks, and filtered water
Sebago Watersports - Catamaran 2
Capacity limited to just 22 passengers for a more comfortable, VIP experience

Why Sebago Delivers the Ultimate Sunset Experience

End your day in paradise with an evening sunset cruise. These excursions offer breathtaking views of a sunset you won’t get to see anywhere else in the world.

Front Row Seats to Nature's Greatest Show

Sebago’s experienced captains navigate to the best spots on the water for viewing our famous Key West sunsets.

Escape the Crowds - Intimate Groups Only

We intentionally limit the number of guests on each cruise to provide a more intimate setting. More room on the deck means better views and the ability to interact with the captain and crew.

Feel the Wind: Real Sailing, Not Just a Boat Ride

As our boats enter open Key West waters, each captain unfurls the sails so guests can experience authentic sailing while enjoying the sunset views.

All-Inclusive Dining & Premium Open Bar

Along with the spectacular views on this tour, you also get an all-inclusive gourmet dinner with bottomless drinks to go with it!

Join Key West's Legendary Sunset Tradition

In line with the long history of sunset watching in Key West, Sebago Watersports regularly participates in the Mallory Square Sunset Celebration, a longstanding tradition that is now an integral part of everyday life for locals.

As a past meeting place for pirates, merchants, and revelers, Mallory Square now hosts nightly jugglers, musicians, artists, tourists, food vendors, and even psychics — all intent on raising sunset watching to an art form. Experience Key West’s breathtaking sunsets for yourself with Sebago Watersports’ sunset sail tours.

Sebago Watersports - Sebago Watersports Chase Guttman 308 1
Sebago Watersports - Sebago Watersports Chase Guttman 193

What Makes Key West Sunsets Unforgettable?

You may still be asking yourself, the sun sets everywhere, what makes a Key West sunset so special? That question is answered by experiencing it for yourself. The best place to watch the sunset in Key West is on the deck of a Sebago ship, drink in hand. Sebago takes part in this nightly sunset tradition, sailing past Mallory Square where our guests wave to the crowd gathered on the docks and watch the jugglers, musicians and other performers. Then we head for open water and sail into the sunset. As the orange sun sinks lower, casting its reflection on the turquoise sea, Sebago’s experienced captains carefully maneuver their ship to provide their guests with a magnificent view of the sunset. No need to stand on tiptoe to catch a glimpse over the crowds!

Sebago offers a variety of sunset tours on catamarans, historic schooners and even combo dolphin watch tours. There is sure to be one tailored to your interests and schedule. Book a Sebago Key West Sunset Tour and join in the celebration!

FAQs

What makes Key West sunsets special?
Key West is the only place in the US where you can watch the sun set directly over the Gulf of Mexico. Our clear turquoise waters and unobstructed views create amazing orange reflections you can’t see anywhere else.
Everything! You get gourmet appetizers, unlimited drinks (full bar, wine, beer) and live music from local musicians. No extra charges – it’s all-inclusive.”
Yes! Our experienced captains take you to the best viewing spots away from crowds. We limit guest numbers so everyone gets great deck space and clear views.”
Three choices: Land’s End ($69.95) with live music, Dolphin Watch & Sunset ($79.95) to see dolphins too, or Sandbar Safari ($99.95) for swimming and snorkeling plus sunset.”
We sail past Mallory Square so you can see the famous sunset celebration with street performers and crowds, then head to open water for better sunset views.”
Real sailing! Once we reach open water, we raise the sails so you can experience authentic wind-powered sailing while watching the sunset.

Reviews

Discover what our delighted customers have to say about their extraordinary experiences. Read the reviews to find genuine, glowing testimonials and five star ratings that showcase the excellence of our service, products, and overall customer satisfaction.
Key West Sebago

Satisfaction Guaranteed

RED guarantees that your overall experience will meet or exceed your expectations. If not we will refund up to 100 percent of your ticket price or rebook you to an alternative experience complimentary. Please note that there are sometimes subtle variations among our excursions due to factors such as weather, food and beverage menu updates, safety of passengers and other factors which may not qualify.
Booking direct ensures you pay the absolute lowest price for any of our products.  Find it cheaper somewhere else and we’ll match it!

Private Charter Requests

Discover Key West your way! Enter your information below and we will be in touch!

Custom Charter Options

  • Experience amazing Key West Sunsets with customized catering options
  • Morning or Afternoon Snorkels
  • All day adventures or eco-tours
  • Dolphin Watches
  • Parasailing

CONTACT MITCHELL TO CUSTOMIZE YOUR VERY OWN WORRY-FREE DAY ON THE WATER.

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