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Adult and/or family trips in Maine, the Bahamas, or Chesapeake Bay!












Different Drum Sailing Adventures offers adult and family trips July-September in Maine, on the Chesapeake during the fall, and in the Bahamas November through May.  All trips are customized and designed with your group’s interests in mind.  Most of the year we operate as a hands-on, educational sailing vessel and our adult or family trips can be as educational as you’d like, or more of a laid back, watch the sunset atmosphere! Either way, we’re happy to provide you with an unforgettable, memory filled trip. Looking for a complete, luxury crewed, mint on your pillow, pampered, yachting experience? That's not us! However, there are plenty of companies that provide those services at five times our costs, so the option is yours... 










We offer a 3-tiered price structure to fit different budgets and your group’s interests:

  • Close Hauled: Close Hauled is our most value packed, hands-on option as your group becomes the “First Mate” aboard Boundless!  Since Capt. Jeff will not be hiring a First Mate for your trip, your costs are reduced considerably.  What are the duties of First Mate you ask?  As First Mate your group fixes all meals on board and cleans up afterwards just like being at home.  (Don’t forget your Captain, he needs to eat too!)    There will also be times when you’ll be asked to help raise the anchor, haul the dinghy, and generally be helpful operating Boundless. On your arrival day, you’ll go grocery shopping to stock the boat with fresh food for the week and Capt. Jeff will meet you at the dinghy dock to ferry your goods out to Boundless waiting at anchor. You’ll only purchase fresh food for the week as all condiments are included and already on board.  

       Cost: $4,500/week plus food for up to four people. 


  • Beam Reach: The Beam Reach option includes everything in Close Hauled with the addition of Boundless being fully stocked with food and ready to depart the moment you arrive. This saves you time as you won't have to do the grocery shopping before you arrive and provides convenience at the start of your trip!  Your group/family will still act as First Mate for the week (cooking/clean-up) and meal preferences can be discussed ahead of your trip.  We recommend you do online ordering with one of the local grocery stores (online ordering not available on Bahamas trips) the day before you arrive.  We'll then take a taxi to pickup your order, deliver it to Boundless, and have everything stowed by the time you arrive! Cost: $4,800/week for up to four people plus food. 


  • Broad Reach:  Would you rather watch the sunset sipping a glass of wine while someone else prepares dinner? Our “Broad Reach” option includes the addition of a First Mate on board who will assist Capt. Jeff in the operation of Boundless, and who will also fix meals during the week.  If you’d still like to take the wheel, raise the sails or simply fix a salad while our First Mate is preparing dinner, we welcome all levels of involvement. Cost: $6,400/week plus food for up to four people.

Bringing more than four people? You may bring up to two additional people at $300 per person. Want to bring more than two more? Call us!










Included on all trips: USCG Licensed Captain, boat fuel, gas, propane, Cruising Permit Fee (Bahamas), use of dinghy w/outboard, kayaks (Maine only), bunk/sleeping bags, additional recreation equipment, instruction, and a fully equipped galley (pots, pans, dishes, utensils, stove/oven, cups).

Not included: Groceries, beer/wine, park/museum entrance fees (if any), moorings or marina slips (if requested by group), taxi fare to/from the airport, and personal snorkel gear/ Bahamas trips, (wet suits only needed Jan-mid April).

Options: Some groups prefer to fly/drive in a day ahead and hotel it a night before their trip begins. This allows for a more relaxed beginning, time for grocery shopping if needed, and more flexibility in choosing arrival times.  Additionally, many spend their last night in a hotel or add a night ashore to relax, take long showers, and have time to do more sightseeing in town.   


On all trips, we recommend budgeting for at least 1-2 meals out for variety and to experience the local setting. All trips are 7 days in length including your arrival and departure days. Most groups board Boundless in the morning of their first day and depart the morning or early afternoon of their last day. We can be flexible on your arrival and departure times however, and will be happy to discuss options to fit your schedule.

Instruction/training: Basic knowledge and the experience of sailing, navigation, and marine life come about naturally during a day of travel on board Boundless.  Without going into formalized, daily training, you will learn A LOT during your week with us. If you would like more advanced sail or navigation instruction from Capt. Jeff, it can be provided to whatever level you desire for an additional cost. Let us know if you’d like to make this part of your week, so we’ll be sure to have training materials on board and let us know how many of your group will participate.














S/V Boundless



S/V Boundless is a 46’ blue water cutter/ketch capable of comfortable sailing anywhere.  Boundless has a 13’ 6” beam and draws 6’ beneath the water.  She is powered by a 92 HP Perkins/Sabre diesel engine and has solar panels and a wind generator for charging.  There are berths for up to 9 people, a completely stocked galley with stove/oven, outside grill, refrigerator/freezer, inflatable dinghy with a 15 hp. Yamaha outboard, kayaks (in Maine), and meets all U.S.C.G. safety requirements.  She carries 140 gals. of diesel fuel and 180 gals. of fresh water for conservative showering and cooking.


Boundless has a large center cockpit used for dining, relaxing, or for taking a turn at the wheel while underway.  Below decks is a navigation table, dining table, main cabin, berths, two heads (bathrooms to landlubbers!), galley, V-berth (four bunks), hallway w/bunk, engine room and an aft Captain’s quarters.  There is a TV/DVD player and lots of board games for evening entertainment.


What’s life like on board a 46’ sailing vessel?  We like to call it “Luxury Camping”!  While you will be comfortable for a week aboard, some adjustment from land life is necessary. We think you’ll find the adjustment well worth it in exchange for a vacation week where you’ll see and do things only available on board a sailing vessel.


We do conserve our energy and fresh water consumption but, there’s plenty of power available for normal use and lots of water for drinking and meals.  To conserve our supply, we wash dishes in salt water followed by a fresh water rinse and shower up on deck in bathing suits using seawater followed by a warm, fresh water rinse. Berths are a little narrower than what you’re used to at home, but comfortable.  There's one private cabin and one open location for couples to sleep together and several single bunks. 


What to bring: Passports are required for entering/leaving the Bahamas. On all trips, pack using soft luggage only. Please, no hard suitcases, bags with wheels or telescoping handles. Storage room on board is limited and most people bring too much so, pack light.  Also, do not bring/wear black soled shoes or sneakers as they will leave marks on the boat. A more complete packing list will be sent to you once you’ve signed on. For Bahamas trips, you will need to bring your own mask, fin, snorkel set and a full 3ml wet-suit is recommended for trips January through March. We do not supply alcoholic beverages; however, you may bring your own. Excessive drinking or drunkenness is discouraged aboard and we suggest a limit of 1-2 drinks per day. Boundless is a non-smoking vessel.  If you smoke, you will probably not be happy on your trip, as smoking is not permitted on board and we cannot make accommodations for you to go ashore.

Last thoughts: All of our Family/adult trips are provided on a custom basis, so let's design your perfect getaway week together! If you like to hike, we can make that a central part of your time with us. If you're looking for a week to relax, sit and read while anchored off a deserted beach, we can provide that too! Dates go quickly, so contact Capt. Jeff today to reserve your once in a life-time sailing adventure! 

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Relaxed reading.._
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