Experience the ocean aboard a classic schooner

This is Seamanship

Sail the Entire Florida Keys

We will sail the length of the Florida Keys between Miami and Key West, stopping at Dry Tortugas National Park and Biscayne National Park along the way. Since sailing is the art of reading and responding to the weather and the ocean, each itinerary differs slightly and our cruise track is subject to change. No matter where we sail, we promise beautiful scenery and an unforgettable experience.

Sample Itinerary

  • Day 1—Sunday

    Arrive to Wonder, move into your bunk, and then gather for a full ship meeting at 3pm to review the weather and voyage plan. Then we prepare for battle.

    We will sail from Stock Island to Key West harbor and battle our sister ship, the Jolly II Rover. This includes firing our ships cannons as we chase one another through the harbor, dodging and dancing amongst the other sunset cruising boats.

    We will then sail west into the sunset and anchor overnight inside the Key West National Wildlife Refuge.

  • Day 2—Monday

    Start the day with a delicious breakfast and endless coffee. We will spend the morning anchored in the Key West National Wildlife Refuge where you will likely have the beach all to yourself.

    After lunch we will get underway for Dry Tortugas National Park, the westernmost island in the Florida Keys. We will arrive in the evening as the sunsets and anchor in the park.

  • Day 3—Tuesday

    Spend the morning and afternoon exploring the national park. After we wrap up with the park, we will prepare to get underway for our major voyage segment to Biscayne National Park. This a roughly 150 mile journey, so will sail through the night and utilize our watch schedule to rotate duty so you get a full sense of what voyaging is like.

    Night sailing takes the magic of the ocean to a new level. You will practice identifying other boat traffic based on their lights and look for constellations as you steer using the stars. The final reward is watching the sun rise with the sails up and feeling that you just had the most exhilarating night of your life while the rest of the world slept.

  • Day 4—Wednesday

    We will spend most of the day sailing as we continue our voyage up the Florida Keys. This is the heart of the voyage where seamanship skills will be taught and practiced. Watches will rotate every four hours, allowing you to get into the rhythm of the ship.

    Sometime in the evening we will drop our anchor in Biscayne National Park and you will get a full night’s sleep. Congratulations—you just sailed over 100 miles.

  • Day 5—Thursday

    We will spend the morning exploring the park, which usually includes both shore and swimming. Biscayne is a mostly underwater national park, so we can tie up to mooring balls at popular snorkel sites. Late in the afternoon, we will get underway for our final voyage segment to the Port of Miami. We will arrive as the sun sets behind Miami’s beautiful skyline.

    The last night of every voyage features a short celebration called a “swizzle” with singing, storytelling, guitar, and maybe a final game of Catan or euchre.

  • Day 6—Friday

    It is time for a final breakfast, coffee, and goodbyes. Guests will depart by 10:00am filled with an amazing sense of accomplishment—you just had one of the best adventures of your life. Just five days ago you joined a ship of strangers who are now your shipmates and friends. There is nothing quite like the bonds formed at sea.

    As you depart, remember: once a shipmate, always a shipmate. If you ever see Wonder in port out in the world, we hope you will come say “Hi” and tell us a story from your voyage—the only problem you will have is picking one.

What You Will Learn

  • Nautical Charts & Navigation

    We give each guest crew member their own small nautical chart of the Florida Keys and explain it during orientation. You will practice plotting positions, using triangles and dividers, and interpreting both paper and electronic charts. We will make regular entries into the ship’s log that include navigational notes.

  • Introduction to Weather

    This will begin in advance of you even showing up to Wonder through our pre-voyage emails. Once you arrive, we will look over the forecast and talk about how the wind affects our voyage plan. We will also talk about global wind circulation, high and low pressure, fronts, squalls, and more. We will teach you how to take hourly weather observations as part of watch.

  • Sail Handling and Sail Physics

    Sails can act like wings, flags, or kites. We will explain the benefits of each, how to identify proper sail trim, and how to set sails on a schooner. Wonder has three types of sails aboard and nine sails in total, allowing for a fuller exploration of sail theory than more common sloop rig sailboats. You will handle the sails frequently, giving you plenty of hands-on experience with the concepts we cover.

  • Stargazing and Celestial Navigation

    We have two sextants aboard and we plan to use them. You will learn the conceptual theory behind determining one’s position from the sun, stars, planets, and the moon. Then, weather permitting, you will have the chance to try taking a sextant reading. We will also do plenty of stargazing during our overnight sail.

  • Watchstanding and Safety

    One of the first things we will do when we get underway are emergency drills. Then, we will teach you how to conduct a boat check, something that happens hourly and is the responsibility of the on-watch. We will cover some of the “rules of the road” for navigating around other vessels. You will become well acquainted with the duties of standing watch, including steering, plotting, lookout, and more.

  • Oceanography

    We will be gazing at the ocean constantly and actually use the ocean conditions to determine wind speed. We will talk about tides, currents, and ocean circulation since all three affect our cruise track. We will get into a bit of Marine Biology as well since we will be exploring some pristine marine environments.

Immersive Adult Education

We gather daily for debriefing a concept that helps you better connect with the ship and the ocean during our voyage. No tests or assignments, just valuable lessons on the deck of Wonder. In addition to our ship meetings, you will learn constantly while you are on watch duty.

As the Oceans & Lakes Campus of the Planet School, Wonder is a living laboratory for how we can reimagine education. We believe that high school should feel more like a purposeful expedition instead of a soul-less slog. Similarly, we aim to create adult voyages that combine adventure, relaxation, learning, nature, and a sense of wonder.

The voyage will feel a bit like throwing a National Geographic expedition, a TED Talk, a tropical island cruise, and a backpacking trip into a blender.

Brass Tacks

Do I need sailing experience?

Absolutely not. In fact, that is kind of the point. Most of the students on our semester-at-sea programs have never set foot on a sailboat and this voyage is designed to mimic that experience.

We will teach you the skills you need to stand watch and, from there, you will have the opportunity to go as deep as you like on a number of topics. Standing watch is where much of the learning happens. We also teach hands-on classes throughout the voyage. As we go through the routines of setting/striking sails, navigating, and steering, you will get ample opportunities to practice new skills alongside a knowledgeable crew member.

And don’t worry, there is ample time to relax and take it all in.

Will I get sea sick?

Probably not. Wonder is larger than the sailboats most people have been on and we are not a racing yacht, so the leaning that sailboats do (called “heeling”) is minimized. For most of the voyage, we will be sheltered from large ocean swells by reefs and the Florida Keys. Swells are what cause the most unpleasant motion since Wonder cuts effortlessly through small waves. We will also be pausing to anchor at intervals that give the body a chance to recover.

If you are prone to motion sickness, we recommend bringing Meclizine (we also stock this aboard). We have ginger, crackers, tea, and other remedies that we stock for our longer multi-week voyages. We have heard mixed reviews of pressure point bracelets: some people swear by them, others throw them away.

  • Our private Captain’s Cabin costs $7,000 and includes two full beds for two passengers. This can be booked by a couple, two friends, or a solo traveler looking for more space.

    We have four bottom bunks that are $3,200 and four top bunks that are $3,000. There is little difference between the top and bottom bunks except for ease of access, so if you’re an “I call top bunk!” kid at heart, then this is your lucky day!

    Every bunk has a fan and a lee cloth, which prevents you from falling out of the bunk if the ship rolls while you’re asleep. Bunks are about the size of a narrow twin bed.

    Every dollar we earn from these voyages supports the Planet School’s tuition-free business model. These rates do not include gratuity for the crew, which is standard practice on sailing voyages at 20%.

    • Meals from Monday morning through Friday morning. Dinner on Sunday evening is not provided, but the Perry Hotel has three great options.

    • Accommodation aboard Wonder that includes bedding, pillow, and a bunk fan.

    • As much coffee, tea, water, and snacks as you like. We cannot serve you alcoholic beverages, but you are welcome to bring beverages and give them to us to store for you.

    • Use of our equipment, including snorkel gear, two kayaks, two paddle boards, hammocks, and more.

    • An automatically inflating PFD fitted with a satellite-enabled Personal Locating Beacon to be worn while you stand watch.

    • A copy of “Ocean of Life” by Callum Roberts for, a blank journal for recording notes and reflections, and a copy of the relevant nautical chart for our voyage so you can plot your journey.

    • A fully licensed, trained, and experienced captain and crew. We actually staff these voyages with two captains to ensure redundancy.

    • Instruction in sailing, navigation, seamanship, sail handling, celestial navigation, meteorology, oceanography, and other related topics while we are underway.

    • Admission to Dry Tortugas National Park

    • All fuel and dockage costs associated with the trip.

    • A crewed 6.5 foot dinghy with outboard engine for going ashore.

    • The commitment to share as much knowledge and passion as we can during the time you are aboard Wonder. We named the boat for a reason: we want to recreate the sense of wonder one feels when discovering something awesomely beautiful in nature. You will see the ocean and the Earth like you never have before and we promise to be there with you, answering every question you have.

    • A shower or air conditioning once we leave the dock. Wonder does not have a shower and our air conditioning unit can only run on shore power. The Perry Hotel has showers in the marina that you are welcome to use.

    • Airfare to/from Key West.

    • Ground transportation to/from Wonder.

    • Meals on Sunday, the first day of the trip.

    • Meals on Friday, the last day of the trip, except for breakfast, which we do provide.

    • Access to Wonder before 3pm on Sunday or after 10am on Friday. We need to clean the boat and let the crew rest.

    • Going aloft into the rigging. This requires additional training that is not practical to include in these voyages.

    • Internet or cellular access. There is no cell coverage where we are going. Wonder has a Starlink connection for navigation, ship’s business, and emergencies, but it is not available for guest crew. You should plan to put your phone on Airplane Mode for the entire voyage (and love it).

    • Weather-appropriate attire. You should review our packing list thoroughly.

    • Alcohol. You are welcome to bring your own adult beverages and consume them in accordance with our drug and alcohol policy.

    • Marijuana (in any form) and illegal drugs as defined by the Coast Guard and US Federal Government. While state regulations vary, Wonder is regulated by the Coast Guard as an inspected vessel and maintains a strict drug-free environment. Violating this rule will result in a call to the Coast Guard and immediate removal from the ship.

    • Drunkenness or obvious intoxication while aboard. We permit drinking, but not in excess and not while we are underway. The professional crew are not permitted to drink at anytime. If you are thinking about coming on this voyage and consuming alcohol is important to you, this is probably the wrong ship for you. Fortunately, you’re in Key West and have plenty of other choices.

    • Disrespectful or abusive language towards your shipmates. We also try to keep swearing to a minimum as we cultivate an environment of learning and exploration.

    • Disobeying or circumventing the captain. Orders from the captain are given for everyone’s safety and should be followed expediently. Debriefing on why something happened is encouraged after the fact so we can all learn.

    • Jumping off of Wonder at any time except when explicitly authorized by the captain.

    • Anyone under 16. This is a voyage for adults or 16-17 year olds if attending with their parents.

  • Refund Policy and Our Minimum Booking Requirement

    To reserve your spot, we require a 50% deposit. Your deposit is fully refundable until 12 weeks before the first day of your trip, which is also when the remaining balance is due.

    Every trip needs to have a minimum of 5 guest crew in order to sail. Until we reach our 5 guest crew minimum, your deposit is fully refundable. If we reach the 12 week mark and we have not booked 5 guest crew, your entire payment remains refundable until we reach 5 guests. Due to the uniqueness of this program and few, if any, comparable offerings on the market, we cannot predict demand. We will cancel a trip that has not reached 5 guest crew at two weeks out. During this period, we will be in touch with you and other guest crew to discuss schedules and do our best to fill a boat.

    Trips that reach the guest crew minimum have a very high likelihood of happening. We are running these programs outside of the peak Atlantic Hurricane season and have crafted an itinerary that factors in the seasonal winds of Key West. Rain in the forecast will not cancel a trip. In fact, rain on a trip adds to the adventure. If a tropical storm is developing during your scheduled program and we deem it unsafe to sail, we will cancel the voyage and issue a full refund to you. We will never risk embarking on a voyage if a named storm is developing. Accommodating weather is part of the voyaging process, so we will share updates as we get closer to the date of your program.

    Once we have booked at least 5 guest crew and have collected the remainder of your fee, your full fee is non-refundable if you cancel. We know that sickness, work, life, and family all happen, but we cannot issue refunds regardless of the reason. There are no exceptions to this policy. If we can max out the trip at 10 guest crew and then have a waitlist, we can offer a refund if your spot is filled. We hope you understand this policy and take extra care of yourself so that you can come on an adventure with us! The unique nature of this program requires us to be very strict and black and white in creating our cancellation policy. You will also be required to sign a liability waiver prior to boarding the boat and adhere to our Ship Community policy, Drug and Alcohol Policy, and Safety Policy. Breaking these rules or refusing to sign our liability waiver will result in immediate removal from the vessel at the first safe port, which could be expensive for you. You will not be issued any refund if you are removed from the vessel. All of these policies will be shared with you to review before you are asked to pay the full cost of your ticket, so you will have the opportunity to decline and receive a full refund of the deposit you pay on our website if you choose to book.

  • We will be publishing an updated packing list soon. Here is the list we send crew when we voyage on the Great Lakes. Some of this is not relevant to the Florida Keys (e.g. heavy wool sweaters) but you still need to pack warm gear.