Miami · SAILING
The 11 best sailing trips you can book today, with what each costs, how long it runs and who it suits. Number one is top for a reason; start there.
Spend about 3.5 hours sailing Biscayne Bay with captains such as David or JP on a motor-free Hobie catamaran. Expect sandbars, snorkeling, mangroves, wildlife, Miami views, fresh fruit, and a relaxed group of no more than 10 people.
“We had a wonderful day. It was such a pleasant experience on the small catamaran. Our 14 and 12 year old loved it too. Thank you so much!!”
Spend about two hours on an 80-foot catamaran sailing from downtown Miami. Depending on conditions, you may see Stiltsville, Key Biscayne, Cape Florida Lighthouse, PortMiami, South Beach, and dolphins. Captain Terry and crew members such as Maria, Ivy, Blue, Luther, and Erick have been praised for friendly service.
“Amazing time. Everything was awesome. So much better than those tour boats. This was relaxing and no one was talking in my ear all the time. It was long enough to be able to enjoy, take pictures and think about life. 100 % recommend”
Travel from Miami to Key West by bus, crossing 42 bridges and 32 islands. Enjoy six hours in town, then board a Fury catamaran for reef snorkeling with gear, instruction, and drinks afterward. Hotel pickup is offered, but expect a very long day and weather-dependent water time.
“Awful experience, I did not end up going as I was told I was going to be picked up at YVE hotel in Miami and she kept calling to switch the location. Very disappointing and unprofessional!”
Sail Biscayne Bay aboard a private 40-foot Beneteau with Captain Rodrigo or Captain Steve. Shape a four to twelve-hour trip around swimming, paddleboarding, snorkeling, barbecue, sunset views, Stiltsville, Elliott Key, or even a special proposal. The boat holds up to six people.
“We had a terrific time with Captain Steve. He sailed us around the bay and took us to see Stiltsville, the Lighthouse and gave us some history lessons as well. We all enjoyed the beautiful sights and amazing sunset.”
Spend 3.5 hours sailing Biscayne Bay with a small group of up to five people. Guides including David, Dan, and Captain JP share local insight as you visit sandbars, mangroves, and swim spots. Snorkel with provided gear, watch for dolphins and manatees, and try the boat’s trapeze harness.
“I had a great time! I recommend it to everyone who loves water sports & is searching for an unique experience!”
Board the 53-foot DREAMER at 300 Alton Road for a private-style cruise around Biscayne Bay. Choose sand bars, mansion islands, skyline views, sunset, or moonlight sailing with captain Julian, a first mate, floats, snorkel gear, paddle board, snacks, and Bluetooth music.
“Clean boat, awesome crew, great itinerary suggested by Julian (owner operator). Both Julian and the captain of the boat (Also named Julian) were great for my son and me on our trip. They are wealth of knowledge on the area and very welcoming for our trip. We had an excellent time and we will be back soon with the rest of the family. Wonderful evening — thank you guys !!!”
Board the Caribbean Spirit at 401 Biscayne Blvd for a 3.5-hour sail past Miami’s skyline, waterfront mansions, and historic buildings. You’ll have time to swim and snorkel, with safety gear and snacks included. Departures run near daily, and groups can reach 80 people.
“Great guys !!!! The weather was horrible but we still had fun all because of them nicest best crew I’ve ever had in Florida !!!!!”
Take the helm of a 13-foot Hobie Wave on protected Biscayne Bay, no sailing license required. You can bring up to four people, add a lesson or captain at check-in, and upgrade to a six-person Hobie Getaway. Allow time for paperwork, fees, and a weather-dependent return before sunset.
“Great Hobie Cat rental experience! So much fun to sail a bit. Sailing the Hobie Cat is as easy as pie, even I could do it!”
Join Captain David of Sail Ahead Miami for a private sail around Biscayne Bay, with time near Biscayne National Park, Key Biscayne mangroves, and possible wildlife sightings. The trip includes fruit, snacks, and water, with swimming, snorkeling, and BYOB options depending on conditions.
“Great experience with the captain. Pleasant, friendly and inspirational. Have shared this experience wit other members if my family, children and grand children. We learned a lot about the bay area and coconut grove marina”
Spend three hours on a Miami catamaran with an experienced crew, stopping near Pace Picnic Island for a self-drive jet ski ride, banana boat or towable tube, swimming, floating mats, music, beer, wine, and soft drinks. Bring ID, swimwear, sunscreen, and a boating license if required.
“Poor communication and service delivery On the 17th of April 2024, my son was so excited and looking forward to doing the 3 hour excursion (4pm-7pm) particularly the jet ski! We put the meeting address in the GPS. On arrival, the address had many companies on it, so we went from pier 3, to pier 5 asking for this company. Defeated, we then texted Viator on the app and they told us it was power 1. This should have been communicated way before so that we would waste 30 min looking for the meeting place. We were there at 345pm. We waited, at 4 pm, no sign of anyone, 410pm,…”
Learn to handle a Hobie Wave catamaran after a short beach lesson, then sail your private boat across calm Key Biscayne waters. English, Spanish, and French instruction is available. The one-hour rental suits beginners, families, and small groups, with lessons and larger boats available at check-in.
“Fue una gran experiencia, nos instruyeron muy bien para usar el velero, definitivamente regresamos.”
Pick a shoreline, a neighbourhood or a boat.
