Budget to Sail the Florida Keys

For an unforgettable vacation, set your own itinerary by chartering a private yacht off the Florida coast. Here’s everything you’ll need to save for to make it the trip of a lifetime.
Budget to Sail the Florida Keys

What do you do for a vacation when you have a skipper who wants to sail, some friends who love the beach, and an entire crew looking for adventure? You charter a sailboat.

If the thought of exploring by boat appeals to you, use this guide to plan and budget for your expenses for a weeklong sailboat charter.

Chartering a yacht

The bulk of the expense is chartering the boat. Think of it like renting an RV, car, and hotel room—combined. Naturally, prices vary depending on the size and condition of the boat.

A monohull has more tendency to heel (tip), but on the other hand, it’s easier to dock in tight spaces than a multihull boat, so it’s a better choice for more adventurous sailors, and a smaller crew.

For less experienced sailors, a good option is a catamaran. The dual hulls of a catamaran increase the living space and make for a smoother ride, so it’s a better choice if you have a big group or if seasickness is a concern—or both. A 44-footer, for example, can easily sleep seven people, with two people in each double berth, and one in the crew quarters (or “cubby hole”). Since the price is usually per charter rather than per person, “the more the merrier!” can be the case if you want to save money.

Besides having the option to split the cost with more people, having a larger crew means there are more bodies available to cook, clean, or help with miscellaneous boat jobs like radioing bridges or tying dock lines—making it worthwhile to opt for an extra-large catamaran.

Set this Goal to charter a catamaran for seven days.

Chartered catamaran

Hiring a captain

If you have a certified skipper aboard (for example, a friend who has completed a catamaran sailing course), you can opt for a bareboat charter, which means you’re completely on your own: Your crew will be responsible for doing all of the actual sailing and maintaining the boat. To bareboat charter, you won’t have to pay a captain, but be prepared to put down a security deposit, and make sure that everyone on board will respect the property you’re renting.

If you aren’t qualified for a bareboat charter or just don’t want the extra stress and responsibility of captaining the ship, you can hire a licensed captain. In addition to the daily rate (around $250) of bringing a pro on board, it’s customary to tip the captain about 20%. Not only will hiring a captain help ensure that you have a safe and relaxing trip, but your captain will likely also serve as a tour guide…and sometimes, if you’re lucky, as a cook!

Set this Goal to pay for a week of sailing with a licensed captain.

Captain hire fees


Once you set sail, there’s no turning back—at least, not without some difficult maneuvering and docking involved. Stock up on food and supplies for the week, including basics like dish soap, paper towels, and marine toilet paper—no consumable goods will likely be provided.

Create a group meal plan, figuring that each of you can prepare dinner one night. To provision more efficiently for your charter, look for foods that involve minimal preparation and minimal waste. Think about the preparation involved—for example, instant oatmeal can’t be cooked when you’re underway; you have to be anchored or on shore power to use the stove. And you don’t even want to know how difficult it is to eat a salad when the wind is blowing your kale all over the deck. Buy bottled water, too; you’ll be glad you did.

The best purchases are lunch meat, cheese, pretzels, jerky, grapes, nuts, tortillas, and other foods that are easy to grab and eat. You can also pack up these snacks and take them to the beach when you get off the boat. If you aren’t bringing a five-star chef along with you, planning to eat basic foods and drink beverages straight from a can or bottle will save you time and effort on your trip.

Set this Goal for provisions per person.

Provisions (per person)

Recreational rentals

If chartering a floating RV isn’t enough for you, many marinas and chartering companies offer rental items to add to the fun. You can rent masks, snorkels, and flippers in hopes of seeing some underwater life—or a stand-up paddleboard (SUP; $175 for the duration of the charter) if you want to try paddleboarding on the ocean. Or go with a kayak; buy an inflatable one and bring your own.

You can also rent an extra-large cooler, which can be a lifesaver for keeping drinks cold when fridge space—and cold air—is at a premium.


Marina fees

One of the wonderful things about sailing is that—much like camping—you can get away from it all. If you don’t mind spending your nights “on the hook” (anchored), you can stay onboard for almost nothing. However, when you’re at sea, access to electricity and fresh water will be limited by your generator power and water tank capacity.

Another option is spending a few nights at a marina, where you can access flushing toilets, showers, and perhaps an air-conditioned office with Wi-Fi. Some marinas offer pools, workout centers, and coffee shops or bars on-site, but find one that fits your budget and needs. This can also be a chance to get your feet back on land, which may be a welcome feeling. If you do plan to stay in a marina, call ahead to make sure they’ll have room for your boat.

If you’re a more adventurous type who doesn’t mind roughing it a little bit, you can spend every night on the hook and save yourself the marina fees.

Marina fees


At its best, sailing is beautiful, elegant, and quiet. With the sails perfectly trimmed and a strong breeze blowing, the boat skims along the water being powered by nothing but the wind and waves.

In reality, though, if you have a specific destination, especially one that’s close to land or in a narrow channel, you’ll have to motor—a lot. You’ll need the motors to maneuver in and out of channels, to get close to land, and to help you gain speed when the wind dies down. Depending on how far you go and how much you rely on the motor and generator, you should plan to gas up your boat at least once.


Beach and park fees

You’ll find plenty of free snorkeling and anchorage spots in the Keys, but if you want to actually set foot on a beach—especially one with public restrooms—it’s wise to bring some cash along for entry fees, amenities, and/or grabbing a ride when you want to get inland.

If you’re willing to set these Goals yourself, you, too, can enjoy smooth sailing (figuratively, at least) by staying on budget while you embark on your own sailing adventure. Bon voyage!

Beach and park fees

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