Add dates
Key Biscayne

Sailing trips & boat tours

Our most recommended Key Biscayne Sailing Trips & Tours

South Beach: Miami Skyline and Bay Cruise on 1920s Yacht

1. South Beach: Miami Skyline and Bay Cruise on 1920s Yacht

Step aboard the only vintage yacht offering sightseeing cruises from South Beach, Miami. Let your captain guide you around the many islands of Biscayne Bay, where the rich and famous have their homes. See places the bigger cruises don't have access to and enjoy some snacks. Depart from South Beach Marina, where you'll have the chance to see multi-million dollar yachts from up close. Take a laidback boat ride with light tour narration and chill music. Bring your own bottle of wine or champagne to sip on as you admire the views and taste a delicious cheese platter. Take a seat in the polished wood interior or on the outside leisure deck for the most incredible panoramic views of the shore. View the southernmost tip of South Beach, Fisher Island, the Miami Skyline, Downtown Miami, Key Biscayne, and the Port of Miami. Learn how Star Island, San Marco Island, Belle Isle, Grove Isle, Di Lido Island, and Brickell Key were all manmade as development projects, but are now home to some of the world’s most wealthy and famous. Finally, see the iconic Flagler Monument built on an otherwise unpopulated island.

Miami: Hobie Cat Sailing

2. Miami: Hobie Cat Sailing

The Hobie Cat is a small sailing catamaran. They are very simple to sail, so there's nothing to worry about, even if it's your first time. Before you know it, you will be sailing on your own in the beautiful Key Biscayne. The waters are always calm so it's a great place for sailing whatever level you're at.  You will receive you a short lesson on the beach and learn how to operate the Hobie cat. Before you know it, you will be sailing on your own in the bay of Key Biscayne.

North Bay Village: Private 22-Foot Bayliner Charter

3. North Bay Village: Private 22-Foot Bayliner Charter

Get to know the islands, virgin beaches, and sandbar of Biscayne Bay with this private charter of a 22-foot bayliner. Choose from a 2-hour or 4-hour charter option. Sail form North Bay Village aboard a comfortable ship and look for colorful marine life with the help of the included snorkeling gear. Meet your captain and cruise to the destinations of your choice. Sunbathe on the ship's ample deck and paly your own tunes through the Bluetooth sound system. Feel the sea breeze in your hair as you take in views of the skyline of Miami and the golden sands of Miami Beach. Admire unobstructed views of the city's hottest districts like South Beach, Downtown, and Brickell. Discover how the rich and famous live as you cut through the water in front of top-tier celebrity homes. Keep an eye tour for dolphins and manatees along the way. Cruise in confidence with captains that are certified by the US Coast Guard. Bring your own food and drinks to compliment the included bottle of champagne. Uncover the world under the waves with high-quality snorkeling gear.

  • Water activities
2 activities found
Sort by:

Frequently asked questions about Key Biscayne Sailing Trips & Tours

What are other things to do than Sailing Trips & Tours that are worth visiting in Key Biscayne?

The other unmissable things to do in Key Biscayne are:

What are the best Key Biscayne Sailing Trips & Tours?

Which Key Biscayne Sailing Trips & Tours are taking additional COVID-19 precautions?

These Key Biscayne Sailing Trips & Tours are taking additional COVID-19 precautions:

Other Sightseeing Options in Key Biscayne

Want to discover all there is to do in Key Biscayne? Click here for a full list.

What people are saying about Key Biscayne

Overall rating

3.9 / 5

based on 12 reviews

What an amazing experience!!! Captain Bob and Connor know how to show a great time and loaded with fun information Too!!!!! Gorgeous boat and beautiful scenery… what more could you want. Simply incredible….

Fue una gran experiencia, nos instruyeron muy bien para usar el velero, definitivamente regresamos.