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Popular Sunset & Dinner Cruises Charters in Upper Keys  , United States. Good availability and great rates. Read unbiased reviews and choose the best deal for your trip.

Sunset & Dinner Cruises in Upper Keys- BoatBooker

Upper Keys

Upper Keys, United States

upper-keys

Enjoy one of the most special times of being out on the water: sunset. During this trip you can relax while sipping your favorite drink, listening to the sounds of nature or your favorite music, and watching the magical moment the sun dips below the horizon into the water as we say goodbye to another day in paradise. A sunset in Islamorada is hard to beat, and the best place to watch it is floating along the waters of the Florida Bay.

Departure time varies due to the time of year & what time the sun sets

United States

Island Ryder Charters

Islamorada

Experience Islamorada Like Never Before! There is no better way to immerse yourself in the natural beauty and vibrant marine life of Islamorada than by setting sail on a private charter. Whether you&rsquo;re looking to explore the stunning waters and wild

The Florida Keys are famous for their stunning sunsets, and here, they’re right outside our marina’s back door! You can enjoy the view from Florida Bay or, on calm evenings, head to Alligator Lighthouse to watch the sunset over the open ocean. For a truly unique experience, snorkel as the sun dips below the horizon—it’s absolutely magical. Please note, all trips are weather dependent to ensure your safety and enjoyment.
Sunset trips depart one hour before sunset.

Snorkeling here in Islamorada is a must do!

Bamboo Charters

Bamboo Charters has been running adventure trips in Islamorada since early 2001. Snorkeling and Sandbar adventures are two of our most popular activities. We also offer Eco tours, sunset cruises and we can even stop at local waterfront restaurants and bar

Choose from any of the activities we offer during your private boat charter including, but not limited to:

Snorkeling
Sandbar charters
Sunset cruises
Cruising through the mangroves
Wildlife watching
Birdwatching
Lobstering
Sightseeing
Going to lunch by boat
Bar hopping by boat

Not sure? Just request Captain’s Choice and let the captain decide!

Not seeing what you’d like to do on the boat? Simply tell us your request, and we’ll do our best to make it happen!

Islamorada Private Charters

Islamorada Private Charters &ndash; Luxury Catamaran Experience Set sail aboard the stunning Islamorada Private Charters, a custom-built 2019 catamaran offering an unforgettable adventure in the heart of the Florida Keys. This spacious dual-console vessel

A sunset cruise in Islamorada, Florida, offers a breathtaking experience as you sail into the warm, golden hues of the setting sun. Aboard a comfortable boat, you'll glide through the crystal-clear waters of the Florida Keys, taking in panoramic views of the coastline and lush islands. Whether you're sipping a refreshing drink or enjoying the company of loved ones, this trip is a must-do!

Salty Bowline Charter Co.

Set sail in style aboard the Salty Bowline Charter Co. newest boat in their fleet, a 2022 Contender Bay Center Console located in the heart of Islamorada. This beautiful boat was restored in 2026 with new upholstery, engine upgrades, and brand new top of 

Set sail on a private 2-hour charter for up to six guests and explore the breathtaking waters of Islamorada. Our authentic catamaran Tiki boats offer the perfect blend of adventure and comfort complete with a MODERN BATHROOM ONBOARD Unwind while you cruise through paradise, taking in stunning views and keeping an eye out for dolphins, manatees, and other incredible marine life.

Cruise start times can be modified to fit your schedule with advanced notice. Message Capt Merv with any questions

Nautical Tiki Islamorada

Experience the ultimate island escape aboard the Nautical Tiki Islamorada, a stunning 2023 Beach Cat Tiki Catamaran, perfect for unforgettable adventures in the heart of Islamorada. This spacious vessel comfortably accommodates up to six guests, providing

Perfect for couples, small families, or groups who want a quiet sunset without the crowds. Short and sweet 1‑hour private cruise to catch the best light and photos.

Island Adventures

Spend a private day on the water in Islamorada with Island Adventures, a fully restored 19 ft Hurricane deck boat perfect for up to 6 guests. This isn&rsquo;t a crowded party boat or a rigid group tour. It&rsquo;s your own small-group trip built around wh

Day of fun on our beautiful waters. Pick and choose. We can choose from a trip to the reef, snorkeling, a boat tour around the islands, stopping at the sand bar, or looking for turtles, dolphins, manatees, 

and other marine life. Available for parties 1 to 6.

Custom Charters

Custom Charters invites you to explore the stunning waters of Islamorada aboard a sleek 2017 Sea Fox 266 Center Console. This versatile vessel comfortably accommodates up to six guests and is powered by twin 150 HP Yamaha outboards, cruising at up to 40 k

Set sail on a serene 1-hour sunset cruise around Key Largo’s bay. Discover how locals live and marvel at wildlife, including dolphins, manatees, birds, and iguanas as the sun dips below the horizon. Bring a drink and soak in the peaceful, stunning views.

Sunshine Watersports Boat Charter

Key Largo

Set off on an unforgettable adventure with Sunshine Watersports Boat Charter, a sleek and spacious 2021 Cobalt 25 SC Dual Console based out of Key Largo. Powered by a 300 HP Mercury outboard, this vessel cruises comfortably at up to 35 knots, perfect for 

The Hurricane is equipped with a stylish “sea deck” – perfect for photos – and a top-of-the-line JL Audio speaker system with wireless Bluetooth.
The built-in bimini top provides shade over the back half of the boat, ensuring comfort on sunny days. Upon pick-up, cooler space, ice, and water will be available for your convenience. Guests are welcome to bring their own food and beverages on board.
Included in your charter:  Stand-up paddle-board  • 9x5 floating water mat  •  Floats, Snorkel Gear & More!

Islamorada Private Sandbar & Snorkel Charters

Experience the best of Islamorada on your own private boat charter. Perfect for families, couples, and small groups looking for a relaxed, unforgettable day on the water. Cruise to the famous Islamorada sandbars, snorkel in crystal-clear waters, or explor

Experience the magic of the ocean in the golden afternoon light. Begin with guided snorkeling in clear, calm waters, then unwind at a stunning sandbar. As the day ends, enjoy a breathtaking sunset cruise on the way back.
Optional onboard BBQ (extra fee): grilled hot dogs, burgers, and sides.
Snorkeling gear is provided, safety is our priority, and all ages are welcome. Don’t miss this perfect sunset adventure!

A Fishing Guru – Contender 39 ST

Experience the ultimate adventure aboard A Fishing Guru, a 2023 Contender 39 ST Center Console based in stunning Islamorada. Perfect for up to six guests, this high-performance vessel is powered by three 425 HP Yamaha outboard engines, reaching speeds of 

Sunset & Dinner Cruises in Upper Keys

Top Sunset & Dinner Cruises in Upper Keys