I'm on a boat, I'm on a boat Everybody look at me, 'Cause I'm sailing on a boat I'm on a boat, I'm on a boat Take a good hard look at the motherf*ing boat (boat, yeah)
Grab your nautical-themed Pashminas, everyone; we’re going to charter a yacht in Key West! What the what? That’s right, with a high enough credit limit, you too could be ‘on a boat like Leo.’
Here’s a look at the types of yachts you can charter in Key West and what’s involved in getting one.
What Is a Yacht Charter?
Did you know you can just pick up the phone and rent a yacht? As the saying goes, all it takes is money! That’s a saying, right?
While the price of a yacht charter might look shocking at first, it’s important to remember everything you get. By staying aboard, you won’t have to worry about hotel rooms or resort costs. You will probably still eat and drink ashore, but you will have access to the boat’s galley to cook food. On a crewed yacht charter, the cook might prepare delicious food for you! You also won’t have to worry about booking snorkel trips or other excursions since you’re living an adventure every day on a yacht charter.
You can charter a yacht anywhere from a few hours to a few weeks. For an overnight trip, you can explore more of the Keys by visiting other marinas or anchoring for the night in secluded coves. Every day, you can pick from a variety of activities like snorkeling, scuba diving, fishing, lobstering, sandbar hopping, or just taking relaxing sails along the island chain.
There are two types of yacht charters you’ll find in Key West: crewed and bareboat.
Crewed Charters
Crewed yacht charters typically provide a captain, but sometimes, you also get a cook. It depends on the yacht size and how long you’re going out. Crewed charters usually include food and some beverages, but policies differ depending on your company. The overall goal is always for the trip to be all-inclusive — just step off the plane and onto your own private yacht for an island getaway.
In Key West, a popular crewed charter option is to rent the yacht for a few days but only have the captain aboard for day trips. Each evening, you’ll return to the marina and use the boat like your hotel room. If you’ve ever dreamed of watching the sunset from your own yacht, this provides a glorious little taste of the yachting lifestyle.
Bareboat Charters
A bareboat charter does not come with a crew or provisions — you’re just renting a ‘bare’ boat. That means you’ll be responsible for all the things a boat owner would be, like navigating safely, planning for the tides, not running aground, avoiding bad weather, and not getting lost. It also means you’ve got to dock the boat when you get back without crashing into anything!
If you think it sounds shady to hand someone your credit card and be given the keys to a yacht in return, know that it’s not quite that easy. Charter companies require that you have some documented experience in similar-sized boats before they’ll let you take theirs out. Even if you’re a seasoned boater, the company may make you go out for a few hours with their captain to check you out in the boat. If you don’t have quite enough experience, they may be able to get you a captain to spend the first day or two of your trip getting you up to snuff.
Regardless of your experience, most companies will spend time with you going over the boat and its systems. They’ll also review your itinerary to make sure you know everything you need to. Remember, on a bareboat trip, you’ll be responsible for buying all your food and beverages. Be sure to review our five killer cocktails to make on the boat.
Training Charters
If you are new to boating but dream of the bareboat yacht charter lifestyle, you could choose to combine your vacation with some training.
There are several different training programs out there for power and sail. If you dream of sailing yachts, ASA (American Sailing Association) has a course curriculum designed to prepare you to take bareboat charters anywhere in the world. You can take these classes at any sailing school or find a school that combines the vacation with the training. Over the course of a seven-day sailing vacation, you’ll go through the courses necessary to become a bareboat captain.
Sail Away Key West and Offshore Sailing School are two such providers on the island.
Key West Boat Rentals
Generally, when you’re looking for a “boat rental,” you’re looking for something for day trips — not for overnights. Boat rentals in Key West are usually center console or pontoon boats between 20 to 25 feet long, and they’re usually rented by the half or full day.
There are a ton of boat rental places on the island, and generally, you don’t need very much boating experience to rent one. You are, however, required to have taken the Florida safe boater course (or your state’s equivalent) if you were born after 1988.
Types of Boats You Can Charter in Key West
Both powerboats and sailboats are available for charter. Charter company fleets vary considerably from company to company and location to location. Some places specialize in renting the newest, sleekest charter boats, while others find good ol’ boats that can be offered at lower prices.
Monohulls vs. Catamarans as Charter Boats
Catamarans make up the overwhelming majority of the Key West charter fleet — and most other charter fleets, actually. Catamarans, both sail and power, are popular because of the amount of space and accommodations that they have. The interior of a 45-foot catamaran is about the same as a 60 or 70-foot monohull. A catamaran this size will have four separate staterooms, each with a private bathroom, meaning you could comfortably divide the cost of your charter among four couples. Plus, cats have huge windows, large patio tables, and lots of outdoor living space. They also have the added benefit of having a much shallower draft, which is great for exploring the Keys.
Catamarans are bigger and more expensive than monohulls, however. If you’re looking for a cheaper ride during your stay, you might do well to find a company that charters a monohull.
Key West Yacht Charter Destinations
Where you go on a yacht charter in Key West depends on how long you’ve booked your charter for. If you’re only going for one or two nights, you’ll have to stick close to the island to ensure you can get the boat back on time. Never fear; there are plenty of incredible sandbars and reefs for exploring.
Three or four-day charters can explore more of the Lower Florida Keys. You might check out places like Little Palm Island Resort, Looe Key, and Bahia Honda State Park.
Five or six-day trips can get you to the Middle or Upper Keys. Places like Marathon, Islamorada, and Key Largo are possible options. For the entire 100-plus-mile stretch of the Keys, there are tons of reefs, sandbars, and little towns to check out and explore.
The longer you’re on the water, the more likely weather will play a major factor in your trip. Strong winds may be unfavorable for travel, or they may limit you to one side of the islands. The seas that can be kicked up on the ocean side can make for very long and uncomfortable travel days, so every captain must pick their destinations with a close eye on the weather.
The most asked-about yacht charter destination in the Keys is probably the Dry Tortugas. Dry Tortugas National Park is about 70 miles west of Key West, far out in the Gulf of Mexico. It’s a beautiful place, but there aren’t many places to stop and very little protection from the weather. Most companies recommend you have a five or six-night charter booked if you intend to call on the Dry Tortugas.
Another option for longer charters is a one-way trip from Key West to Miami or vice versa.
Florida Yacht Charters has a great list describing the various activities and destinations you can see on a Key West yacht charter.
Booking a Yacht Charter in Key West
Here are some companies to check out, whether you’re looking for crewed or bareboat yacht charters in Key West. Some of the major charter companies operate here seasonally, so you can also check with The Moorings and Sunsail to see if they are operating out of Key West for your desired itinerary.
Florida Yacht Charters https://floridayachtscharters.com
Blue Ocean Yacht Charters https://blueoceanyachtcharters.com
Luxury Yacht Charters https://luxuryyachtcharters.com
Key West Yacht Rental (90′ motor yacht)
Calypso Sailing https://calypsosailing.com/charters
Or, You Could Save a Few Thousand...
Truth is, you don’t need to charter a yacht to have a great time on the water in Key West. Every day, I take visitors out on Key West sandbar charters and private cruises. We see dolphins doing flips and all sorts of…stuff. So grab your swim trunks and flippie-floppies, and spend the day exploring Key West by water with Casual Monday Charters.
Plus, we’ll be back by dark, so you can spend the night on terra firma, safe from the Kraken and wonky boat toilets.
Call Captain Zak today and book a private charter to see what all the commotion is about.
