(800) 814 COOL Questions? Call Us Now!

Key West Sunset Cruises

When are you traveling?
Filter
Languages Clear
Time of Day Clear
1
6
16
Duration Clear
0
16
0
0
0
Price Clear
$0 $500+
Specials Clear
13
10
0
4
1
Features Clear
1
9
16
1
11
Accessibility Clear
2
7
14
Families Clear
6
7
3
Rating Clear
14
15
15

Key West Tours

Attractions

Guides

Calendar

16 Results
Sort by:
Featured
  • Key West Wind & Wine Sunset Sail
    Likely to Sell Out

    Key West Wind & Wine Sunset Sail

    1,456

    Wind & Wine has been the #1 rated sunset sail on City Boat Tours for over a decade. In our opinion, this is the best...
    Read More

     2 hours (approx.)  Free Cancellation  Instant Confirmation
    $109
    $99
    Details
    $109
    $99
    Details
  • Key West Sunset Cruise: Dinner, Live Music & Drinks Included
    Likely to Sell Out

    Key West Sunset Cruise: Dinner, Live Music & Drinks Included

    1,544

    Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar....
    Read More

     2 hours  Free Cancellation  Instant Confirmation
    from
    $92.95
    Details
    from
    $92.95
    Details
  • Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar

    Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar

    3,252

    Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran...
    Read More

     2 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $79.95
    Details
    Best Rate
    $79.95
    Details
  • Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location
    Special Offer

    Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location

    121

    Looking for the perfect way to end your day? Join us aboard a 45ft Corinthian powercat, and ride in comfort with this relaxing, catered cruise...
    Read More

     2 hours (approx.)  Hotel pickup offered  Free Cancellation  Instant Confirmation
    $99
    $89
    Details
    $99
    $89
    Details
  • Key West Schooner Sunset Sail with Hors D'oeuvres and Full Bar

    Key West Schooner Sunset Sail with Hors D'oeuvres and Full Bar

    1,528

    Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and...
    Read More

     2 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $99.95
    Details
    Best Rate
    $99.95
    Details
  • Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
    Likely to Sell Out

    Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

    1,528

    Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key...
    Read More

     2 hours  Free Cancellation  Instant Confirmation
    from
    $116.10
    Details
    from
    $116.10
    Details
  • Sunset Sail in Key West with Beverages Included
    Likely to Sell Out

    Sunset Sail in Key West with Beverages Included

    847

    Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention...
    Read More

     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $79
    Details
    from
    $79
    Details
  • Sunset Sail Cruise in Key West
    Likely to Sell Out

    Sunset Sail Cruise in Key West

    232

    Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's...
    Read More

     2 hours  Free Cancellation  Instant Confirmation
    from
    $95
    Details
    from
    $95
    Details
  • Key West Private Wind & Wine Charter

    Key West Private Wind & Wine Charter

    1,456

    The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on City Boat Tours three years running. See the sunset...
    Read More

     2 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $3,499
    Details
    Best Rate
    $3,499
    Details
  • Classic Key West Schooner Sunset Sail with Full Open Bar
    Likely to Sell Out

    Classic Key West Schooner Sunset Sail with Full Open Bar

    174

    There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This...
    Read More

     2 hours  Free Cancellation  Instant Confirmation
    from
    $109
    Details
    from
    $109
    Details
  • Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

    Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

    156

    “The Key West Cocktail Cruise is the best thing to happen to Sunsets since cameras and sunglasses!” This is not your average Key West pleasure...
    Read More

     2 hours  Instant Confirmation
    from
    $65
    Details
    from
    $65
    Details
  • Private Sunset Cruise around Key West
    Likely to Sell Out

    Private Sunset Cruise around Key West

    51

    Embark on a tour around the island of Key West. Your guide will be talking you through many points of interest around the island. Make...
    Read More

     2 hours  Free Cancellation  Instant Confirmation
    from
    $400
    Details
    from
    $400
    Details
  • Private Key West Sunset Sail
    Likely to Sell Out

    Private Key West Sunset Sail

    45

    2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for...
    Read More

     2 hours  Instant Confirmation
    from
    $695
    Details
    from
    $695
    Details
  • Bimini Charters - Private Luxury Catamaran 3-hr Sunset Sails
    Likely to Sell Out

    Bimini Charters - Private Luxury Catamaran 3-hr Sunset Sails

    4

    Rent your own private yacht and savor the beautiful Key West sunset away from the crowds. Do it all on a luxury catamaran reserved just...
    Read More

     3 hours  Free Cancellation  Instant Confirmation
    from
    $775
    Details
    from
    $775
    Details
  • Sunset Cruise

    Sunset Cruise

    15

    Come see for yourself why Marathon Mermaid is voted the #1 thing to do in Marathon! Watching the sunset by water is a must-do when...
    Read More

     2 hours  Free Cancellation  Instant Confirmation
    from
    $84.69
    Details
    from
    $84.69
    Details
  • Private Romantic Sunset Cruise
    Likely to Sell Out

    Private Romantic Sunset Cruise

    New To The Site!

    Embark on an unforgettable journey as the sun dips below the horizon, casting vibrant hues across the endless expanse of the ocean. About Our Sunset...
    Read More

     3 hours  Instant Confirmation
    from
    $895
    Details
    from
    $895
    Details
Filter

Frequently Asked Questions

The answers provided below are based on answers previously given to customers' questions.

Q: What are the best options for Key West Sunset Cruises?

A: According to verified reviews on City Boat Tours and TripAdvisor, the best Key West Sunset Cruises are:

Q: What are the best kid-friendly options for Key West Sunset Cruises Tours?

A: According to verified reviews on City Boat Tours and TripAdvisor, the best kid-friendly Key West Sunset Cruises are:

View all kid-friendly Tours →

Q: Which Key West Sunset Cruises have Instant Confirmation?

A: Key West Sunset Cruises with Instant Confirmation include:

View all Tours with Instant Confirmation →

Q: Which Key West Sunset Cruises have Free Cancellation?

A: Key West Sunset Cruises with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

Q: I need a ride! Which Key West Sunset Cruises include Hotel Pickup?

A: No problem. These Key West Sunset Cruises include Hotel Pickup:

View all Tours with Hotel Pickup →

Q: Got any more Key West trip ideas?

A: We sure do. Check out our curated lists of hand-picked Key West Tours.

View all Key West Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Key West?

A: Based on our sales data over the past year, the most popular styles of tours and activities in Key West are:

View all tour styles in Key West →

Language
Currency
Activity name

Currency

Activity name

Lowest Price Guarantee

Activity name

We guarantee the lowest price on all the tours available to book on our site. We'll refund the difference if you find the exact tour cheaper online until 48 hours before your tour starts.

We Make It Easy!

Gather your information

Locate your City Boat Tours Booking Number and the proof of the lower price you found.

Send it to us

Email [email protected] with the documents, your name, and your home address.

We'll review

We'll review your materials and get in touch as soon as possible.

Receive your refund

If everything checks out, we'll refund you the price difference.

Refund Terms & Conditions

The following conditions apply to all lowest price guarantee refund requests:

  • The lowest price guarantee is available to any customer who makes a qualifying purchase through our website. The qualifying purchase must be a minimum of US$20 (or equivalent).
  • The lowest price guarantee covers retail and prepaid rates available to the general public. This does not include discounts or promotions you may receive (or be eligible for) from third-party sites or organizations such as AAA or AARP or special offers made as part of a membership program, corporate discount, daily deal, group, or rewards program.
  • City Boat Tours promotions cannot be combined with the lowest price guarantee.
  • If you find a lower retail or prepaid rate for the same tour, offered on the same date, time and priced in the same currency as your original purchase, on any other website between the time you book on City Boat Tours and 48 hours before your trip starts, we will refund the difference.
  • The lowest price guarantee does not apply where a lower overall price is found by breaking down the purchased tour into one or more parts sold separately.
  • City Boat Tours reserves the right to verify the lower price details. Examples of acceptable forms of verification include a web screenshot or a web address.
  • All refund decisions will be made at the sole discretion of City Boat Tours.

Sorting, ranking, and search results

Activity name

City Boat Tours wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through City Boat Tours over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

Cool Support

Ask us anything!

Activity name

Cool Robot