Private Sunset Cruise around Key West - Watching the Sunset from Mallory Square and the Water

Private Sunset Cruise around Key West

Experience a private sunset cruise in Key West for $350, lasting about 2 hours, with personalized guides, scenic stops, and wildlife sightings.

Set sail on a private sunset cruise around Key West for approximately 2 hours, priced at $350 per group (up to 6 people). This tour begins at 5950 Peninsular Ave and is led by a knowledgeable captain who finds the quietest spots for watching the sunset, ensuring an intimate and peaceful experience. The tour includes stops around Sunset Key and Mallory Square, offering stunning views of the islands, waterfront mansions, and beaches. A cooler full of chilled water keeps everyone refreshed, making it a perfect choice for romantic evenings or relaxing outings.

The cruise is highly praised, earning a perfect 5.0 rating from 48 reviews and a 98% recommendation rate. The majority of reviews highlight Captain Donnie’s friendly demeanor, expert navigation, and engaging commentary. Booking typically occurs about 34 days in advance, so early planning is recommended. This tour suits those looking for a personalized, scenic experience on the water with the chance to see marine wildlife like dolphins.

Key Points

Private Sunset Cruise around Key West - Key Points

  • Private tour for up to 6 guests at $350 enhances intimacy and flexibility.
  • Approximately 2 hours long, offering ample time to enjoy sunset views and sightseeing.
  • Stops at Sunset Key and Mallory Square highlight scenic islands and lively sunset-watching crowds.
  • Captain Donnie’s expertise ensures visits to the quietest spots for sunset viewing.
  • Wildlife sightings, including dolphins, are possible during the cruise.
  • Comfort and convenience are prioritized with a cooler of chilled water provided.

The Personal Touch of a Private Sunset Experience in Key West

This private sunset cruise offers a personalized experience that large group tours can’t match. With a capacity of up to 6 people, the $350 fee provides an exclusive way to enjoy the natural beauty of Key West from the water. The two-hour duration balances enough time for multiple scenic stops and relaxing sunset viewing without feeling rushed. It’s an ideal option for romantic couples, small groups of friends, or families seeking a peaceful escape.

The tour begins at 5950 Peninsular Ave and concludes back at the same point, making logistics straightforward. The mobile ticket feature adds convenience, and most travelers find the experience suitable for a wide range of ages and physical abilities. The warm and friendly guidance from Captain Donnie enhances the experience, and reviews consistently praise his knowledgeable narration and personable approach.

Exploring Sunset Key and Its Oceanfront Mansions

Private Sunset Cruise around Key West - Exploring Sunset Key and Its Oceanfront Mansions

A key highlight of this cruise is the opportunity to cruise around Sunset Key, where you can admire the luxurious waterfront mansions and beautiful beaches. Captain Donnie takes you to the quietest spots to observe the sunset, avoiding crowds and offering a more tranquil experience. Watching the sky change colors over Sunset Key provides a breathtaking backdrop for memorable photos and peaceful reflection.

This stop offers a rare vantage point for appreciating Key West’s exclusive island and its natural beauty, with the added bonus of informative commentary about the area. The calm waters and soft lighting during sunset make this part of the cruise especially relaxing and picturesque.

Watching the Sunset from Mallory Square and the Water

Private Sunset Cruise around Key West - Watching the Sunset from Mallory Square and the Water

Cruising past Mallory Square allows guests to see the lively scene that many associate with Key West’s famous sunset celebrations. From the boat, you’ll witness street performers, live music, and crowds waiting eagerly for the sunset spectacle. Captain Donnie’s route ensures you get a spectacular view of all the activity happening on land, combined with a unique water-level perspective.

This combination of scenic viewpoints makes the cruise ideal for those who enjoy both nature’s beauty and the vibrant local culture. It’s a great way to experience the energetic atmosphere of Key West’s sunset without the crowds on land.

Gaze for Marine Wildlife like Dolphins

Private Sunset Cruise around Key West - Gaze for Marine Wildlife like Dolphins

One of the exciting aspects of this tour is the possibility of spotting marine wildlife, including dolphins. Captain Donnie’s familiarity with the waters allows him to navigate to areas where dolphins and other marine creatures are often seen. While wildlife sightings are not guaranteed, the chance to observe dolphins adds an element of thrill to this peaceful cruise.

Guests frequently praise Captain Donnie’s ability to find wildlife and his enthusiasm when animals appear. This makes the tour not only scenic but also engaging for those interested in wildlife and marine life.

Comfortable, Well-Equipped Boat with Refreshments

The boat used for this private sunset cruise is described as pristine and well-maintained, ensuring safety and comfort. A cooler full of chilled water is provided, helping guests stay refreshed as they enjoy the cool evening breeze and spectacular views.

Since the tour is private, there is no need to worry about large crowds or noise, giving a serene environment for relaxing, chatting, or simply soaking in the scenery. The customized pace and friendly guidance from the captain make this a comfortable and enjoyable experience.

Logistics and Meeting Details for the Cruise

The meeting point for this tour is 5950 Peninsular Ave in Key West, conveniently accessible near public transportation. The activity starts and ends at this same location, simplifying planning for visitors. The ticket confirmation is immediate upon booking, and service animals are allowed.

Travelers should note the booking window, with most reservations made about 34 days in advance. The tour offers free cancellation up to 24 hours before the scheduled time, providing flexibility in case of weather changes or change of plans. Since good weather is essential for the cruise, poor weather may lead to rescheduling or a full refund.

The Expertise and Friendliness of Captain Donnie

Private Sunset Cruise around Key West - The Expertise and Friendliness of Captain Donnie

Reviews consistently emphasize Captain Donnie’s knowledgeable narration, friendly demeanor, and expert navigation. He is praised for making the experience engaging, sharing fun facts about the area, and adjusting cruise times to maximize sunset views. Guests mention his warm personality and attention to safety as major strengths.

This captain’s personalized approach really elevates the experience, making it feel like a guided tour rather than just a boat ride. His local expertise shines through as he leads you to the best spots for sunsets and wildlife sightings.

Who Should Book This Private Key West Sunset Cruise?

This tour is perfect for small groups seeking an intimate, flexible experience on the water. It suits romantic couples, families with children, or anyone wanting to avoid large crowds while enjoying spectacular views. The two-hour duration strikes a nice balance between exploration and relaxation, and the private setting allows for personalized attention.

While the tour provides stunning scenery and wildlife opportunities, it’s important to book in advance to secure preferred times, especially during peak sunset seasons. Ideal for those who value comfort, expert guidance, and scenic beauty in a calm and friendly environment.

Ready to Book?

Private Sunset Cruise around Key West



5.0

(48)

98% 5-star

“Donny is amazing! Highly recommend! He was very knowledgeable and great with the kids. We ended up booking another excursion with him the following…”

— Eileen D, May 2025

Frequently Asked Questions

What is the cost of the private sunset cruise?
The tour costs $350 per group, accommodating up to 6 guests.

How long does the cruise last?
The experience is approximately 2 hours from start to finish.

Where does the tour start and end?
It begins and ends at 5950 Peninsular Ave, Key West.

What are the main stops during the cruise?
Stops include driving past the southernmost point buoy, cruising around Sunset Key to admire mansions and beaches, and passing Mallory Square to see the sunset watchers and street performers.

Is wildlife like dolphins visible on this tour?
Yes, dolphins and other marine wildlife may be seen, depending on the day.

What amenities are provided?
A cooler with chilled water is available for guests’ refreshment.

Can service animals join the tour?
Yes, service animals are allowed.

How is the weather handled?
The tour requires good weather; if canceled due to weather, a full refund or reschedule is offered.

How far in advance should I book?
Most bookings happen about 34 days in advance; early booking is recommended.

Is the tour suitable for children?
Yes, reviews mention that Captain Donnie is great with kids, making it suitable for families.

Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours prior to the scheduled activity.

What makes this tour stand out from others?
Its private setting, expert guide, scenic stops, and wildlife viewing opportunities make it a top choice for those seeking an up-close and personal sunset experience in Key West.