Overview
Private 2-Hour Key West Sunset Cruise | Luxury Manitou Pontoon | Up to 10 Guests
Leave the crowds behind and experience the magic of a Key West sunset from the water on your own private 2-hour cruise aboard a brand-new Manitou luxury pontoon. Departing from the tranquil Cow Key Channel, you'll enjoy a relaxed and intimate journey through hidden backchannels and open waters — all with a front-row seat to one of nature’s most unforgettable shows.
Cruise in comfort with up to 10 guests, guided by a licensed local captain, and take in stunning views of the sunset-drenched coastline, including iconic sights near Mallory Square — without ever getting caught in the crowd.
Whether you're planning a romantic evening, a family outing, or a fun get-together with friends, this cruise offers the perfect mix of laid-back luxury and scenic beauty.
Reserve your sunset escape now — and experience Key West the way locals love it: peaceful, personal, and absolutely stunning.
What's Included
- Cooler with Ice
- Up to 10 Guests
- Food / BYOB of choice
- Captain Fee
Meeting Location
5016 5th Avenue
Key West, FL 33040, USA
Detailed check-in instructions, including the exact address, are provided with your booking confirmation.
This activity ends back at the meeting point.
What To Expect
Tropical Drift – Key West Sunset Cruise (2 Hours)
Departing from the peaceful waters of Cow Key Channel, Tropical Drift offers a private 2-hour sunset cruise that lets you unwind in style—far from the crowds, but close to the magic of Key West. With a licensed local captain at the helm, you’ll cruise past stunning waterfront homes and quiet channels before gliding toward the historic seaport.
As the sun begins to set, enjoy a scenic pass by Mallory Square, where sunset celebrations come alive—viewed from the best seat in the house: your own private boat. Capture the glowing sky as it reflects on the water in vibrant hues of orange, pink, and gold.
Relax on our spacious boat with a deluxe swim deck, bring your favorite beverages, and toast to the day as you drift beneath Key West’s iconic sunset.
Perfect for couples, families, or small groups looking for a peaceful, picture-perfect evening on the water.
Additional Info
- Confirmation is instant and will be received at time of booking
- Service animals allowed
- Public transportation options are available nearby
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
- Infants are required to sit on an adult’s lap
Frequently Asked Questions (10)
Q: Is boating experience required for a boat rental?
Cancellation Policy
Still have questions?
We're here to help.
Activity code: C-328038P5
Traveler Photos
Additional Info
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Frequently Asked Questions (10)
The answers provided below were previously given in response to questions from City Sky Diving customers.
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Yes, prior boating experience is required.
Feb 2022If you have any doubts about becoming seasick on the water, we recommend taking a Dramamine® Motion Sickness Relief tablet the night before your trip. Some people recommend taking it the night before your cruise and then again that morning so you will not feel so drowsy.
Feb 2023- For a full refund, you must cancel at least 24 hours before the tour start time.
- If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the tour start time will not be accepted.
- Cut-off times are based on the tour local time (EST).
- Cooler with Ice.
- Up to 10 Guests.
- Food / BYOB of choice.
- Captain Fee.
This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Apr 2025There is no minimum age for this tour, so bring your wee one along for an adventure..
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the Tropical Drift - A Key West Sunset Cruise is as follows:
- Service animals allowed
- Public transportation options are available nearby
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Tropical Drift – A Key West Sunset Cruise will be included in your confirmation email from City Sky Diving. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.
Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.
If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.
Oct 2026What's Included
- Cooler with Ice
- Up to 10 Guests
- Food / BYOB of choice
- Captain Fee
Additional Info
- Confirmation is instant and will be received at time of booking
- Service animals allowed
- Public transportation options are available nearby
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
- Infants are required to sit on an adult’s lap
