Sailing trips · PRIVATE SAILING CHARTERS IN THE USA
Every trip has one free day too few. These 15 private sailing charters in the USA justify the slot, priced and timed so you can decide in minutes and get back to the fun part.
Take a private two-hour yacht ride from Miami with only your party aboard. Cruise past Bayside Marketplace and Star Island, play your own music, bring food and drinks, and use the onboard restroom. Captain and fuel fees cost extra, so check the full price before booking.
“We did a night ride. We really enjoyed ourselves seeing the Water seeing all the lights definitely a time to remember.”
Captain Dan takes your private group from a Fort Lauderdale residence along the New River, past yachts and waterfront homes, then toward the Atlantic. Bring food and drinks, learn basic sailing, swim or snorkel when conditions allow, and enjoy a flexible four-hour outing for up to six people.
“Dan was wonderful! Very knowledgeable and interesting conversation about the area and sailing! Great trip! Will definitely recommend!”
Spend four hours aboard the sailboat Daffy with Captain Charlie, cruising Fort Lauderdale’s New River, Intracoastal Waterway, Port Everglades, and the Atlantic coast. Bring your own food and drinks, take a turn at the wheel, and choose between relaxed sailing or remaining docked.
“Captain Charlie relating the history of the immediate riverside area, and in enjoying a relaxing cruise on a picture perfect afternoon were both very worthwhile experiences - plus his wife´s mooring efficiency renewed my rather rusty knowledge in how to moor.”
Take a private two-hour cruise around Miami Bay aboard a Sundancer yacht for up to 10 or 12 people. Bring drinks, use the supplied cooler and ice, and play your own music. Captains including Daniel, Jorge, and Aleksandar have led recent trips, with skyline, Brickell, port, and Bayside views along the way.
“it’s was the best time I had since i’ve been in Miami! I can’t wait to do it again”
Reserve a private 42 to 46-foot yacht in Miami for two or four hours with up to 12 people. Cruise the bay, see Brickell and Fisher Island, play your own music, and bring food and drinks. Fuel, ice, and a cooler are included, while the captain fee is extra.
“The overall experience was good not great. The yacht was clean and comfortable. We were expecting to see more nature and swimming in open waters but this trip is about the sightseeing of Miami skyline and mansions. Really not interested in that. The crew mate Layling Briceno was very helpful and had smile on her face. The captain (Diaz) of the yacht had good knowledge about the boats and city but he was not interested or was proactive to make this trip memorable. We had to ask about the things that could be done and not wasting our four hours just sitting in the yacht.”
Cruise Biscayne Bay aboard a private yacht for up to 12 people with Captain Kadir, Ben, Joseph, or Felipe. Swim at Haulover Beach Park, enjoy mansion views, use the Bluetooth speakers and cooler, and request a restaurant stop during your 2 to 6 hour outing.
“It was a great experience, the boat was super clean, plus it's new. Felipe was very kind to us and explained many things to us on the trip. It was a very fun trip that I highly recommend so far. The most beautiful experience we've had in Miami”
Take a private 48-foot yacht from 5400 Collins Ave around Miami Beach and Biscayne Bay. You can cruise past South Beach, waterfront homes, and the Miami skyline, bring ready-to-eat food, and plan a sunset outing. The boat holds up to 12 people, with fuel, water, ice, and a floating mat included.
“Pedí guía en español el capitán no hablaba español, el barco extremadamente descuidado y viejo, la atención de la tripulación nula”
Spend three private hours aboard a 42-foot yacht with Captain Ryan and, when scheduled, McKay. Bring a picnic, drinks, and a playlist as you cruise from Rainbow Harbor past the Queen Mary, Naples, Alamitos Bay, and Long Beach beaches, with time for swimming near Island White.
“We had an amazing 3hr cruise. We took snacks and bubbles and beer and had music so we were all set. All very safe and the boat itself is stunning. Nothing was too much trouble for Captain Ryan. Definitely recommend. Thank you 🤩”
Take the Beautiful Sundancer 40 around Fort Lauderdale with your own group, choosing two to six hours on the water. Captain Simon may be available, and you can bring drinks, play music, spot mansions and yachts, and stop for photos along the city’s waterways.
“Captain Simon was amazing! Accommodating to our needs and made experience super fun! We definitely will book this again. The boat is super comfy and beautiful!”
Board the private Motor Vessel KARLA at Pier 59 for a two-hour cruise with an English-speaking captain, outdoor and indoor lounges, a retractable canopy, and 360-degree views. The route can include Lady Liberty, Ellis Island, Governors Island, Lower Manhattan, and Brooklyn Bridge, depending on tides and your priorities.
“Overall was a 5* but as a value, I give a 4. Anyway, worth all money the skyline.”
Join a USCG-licensed captain aboard the 35-foot Esprit de Joy for a private afternoon or sunset sail from Ashley Marina. Bring drinks and snacks for up to six people, then watch the Battery, Fort Sumter, Castle Pinckney, Ravenel Bridge, and USS Yorktown pass by from the water.
“Our Captain Will was so kind & knowledgeable! Great way to spend the afternoon”
Hire a private yacht for up to 13 people and cruise Biscayne Bay with a licensed captain. You can pass Miami’s waterfront homes, watch for dolphins, then anchor at Haulover Sandbar for swimming and snorkeling. Water, ice, a cooler, gear, and a floating mat are included.
“I was so excited being that the description was everything I wanted. Upon arrival I seen a boat not yacht pulling up. I started to pray. Hoping this wasn’t what I paid for. This was a nightmare experience and I was extremely disappointed. After the boat arrived I try calling to and there was no answer anymore. I was completely scammed. This is extremely disappointing and very devastating. The boat was dirty with worn out equipment. It had a very bad smell. One bathroom out of order and I didn’t fell comfortably at all.”
You’ll cruise Pittsburgh’s three rivers with a private captain for up to six people, passing Acrisure Stadium, PNC Park, Point State Park, and the skyline. Captains Bob, Ed, and Andy are known for local stories. Bring your own food and drinks, then choose the open cockpit or covered area.
“Great tour! Captain Bob was so knowledgeable about the area and a pleasure to be with! We would definitely do the tour again!”
Join Captain Sam aboard Tantara for a private two-hour sail from Brooklyn Bridge Park. The route passes Governors Island, Lady Liberty, One World Trade Center, and the Brooklyn Bridge, with room for up to six people and time for photos, conversation, and sunset city views.
“The experience is very nice. Sam is a great host, easy going, who let you comfortable. The sightseeing is amazing.”
You’ll sail with Easy Breezy Charters from Goodland Boat Park aboard a spacious catamaran for up to six people. Captain Nick may take you toward dolphins, sunset views, or quiet islands for beach time and shell collecting. The boat has lounge space, netting, a head, and bottled water.
“Absolutely a wonderful experience and must do! Our captain was kind, gracious and down to earth. Highly recommend!”
Pick the boat, the hour on the water or the country.
