Sail overnight, stand watch, experience the ocean, and visit a National Park

This is Seamanship

Program Itinerary

  • Day 1 (Sunday)

    Arrive to Wonder, move into your bunk, and relax at the Perry Hotel Marina. We will have an evening orientation to meet everyone, go over safety procedures, review the weather forecast, divide into watch groups, and cover some introductory sailing concepts. We recommend an early night—the adventure begins in the morning!

  • Day 2 (Monday)

    Start the day with a delicious breakfast (see a sample menu here) and endless coffee. We will get off the dock and spend the day sailing to Marguesas Key, arriving in the early afternoon. We have hidden three bits of “treasure” on the island and invite you to put your new nautical skills to the test to solve each challenge, which will reinforce sailing terminology and seamanship concepts.

    We will spend the afternoon and evening exploring the island, which can include kayaking or paddle boarding in the mangroves, snorkeling, or enjoying the beach. Eat delicious dinner on deck as we watch the sunset at anchor.

  • Day 3 (Tuesday)

    Another great breakfast, more coffee, and weighing anchor to get underway to Dry Tortugas National Park. It is about 43 nautical miles to the park and we will use this time to set and strike all of Wonder’s sails multiple times, giving you lot’s of practice. Once at the park, we will check in and go ashore to explore. Depending on our arrival time, we will either stay at Garden Key to see the fort or head to Loggerhead Key for some of the best beaches in the country.

    More snorkeling, more beach, more kayaking, more exploring, and another perfect sunset—with nothing but ocean to our west, we might get lucky and see a green flash.

  • Day 4 (Wednesday)

    We will begin with a short transit to whichever Key we did not visit the previous day. Today we strongly encourage a midday nap, since we will be sailing at night! We will weigh anchor in the evening and prepare to use the stars as bearings for steering. The ocean looks different at night, so we will hone our chart knowledge, identify other boat traffic based on their lights, and look for constellations. The captain is certified in celestial navigation and used to manage a planetarium, so come ready for stargazing!

    We will sail through the night and utilize our watch schedule to rotate duty so you get a full sense of what voyaging is like. The 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 5 (Thursday)

    Sometime in the morning we will anchor again and rest for a few hours after our night of sailing. In the afternoon, we will get underway for a final time in order to catch the sunset. We will sail past downtown Key West as all the commercial sailboats come out to play. We always challenge our sister ship, the Jolly II Rover, to a short schooner race and then fire cannon volleys at one another.

    This is the chance to put your newly acquired sailing knowledge to the test. We will tack back and forth a few times as we dance around all the other Key West schooners. Then it is 4 miles back to the Perry Hotel Marina for our final night at the dock and dinner on the boat. 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 humans form 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 soulless 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 a National Geographic expedition mixed with a TED Talk mixed with a tropical island cruise.

Brass Tacks

Do I need sailing experience?

Absolutely not. In fact, that is kind of the point. Most of the students on 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.

How much does this adventure cost?

Our private Captain’s Cabin costs $6,000 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 $2,500 and four top bunks that are $2,200. 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.