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Continued from the December 2010 ASA E-Newsletter

Bareboat Chartering Essentials
Planning an Itinerary

By Captain Lisa Batchelor Frailey , ASA Instructor


“Vacation” and “Itinerary” – are these mutually exclusive concepts? For many sailors, a bareboat charter vacation means freedom from schedules, and a chance to go wherever the wind takes them. After all, “Gentlemen only sail downwind” - don’t they?  For most bareboaters, a charter is an opportunity to do some great sailing, to explore new or favorite ports, and to share the experience with a happy and enthusiastic crew!  Here are some tips for planning an itinerary which optimizes your charter experience according to YOUR priorities, while giving you the flexibility to let the wind take you...

Where to Start?  Assuming you’ve selected your charter boat and location, it’s time to have some fun with research!  There are a number of excellent resources to browse.

  • Charter Company literature is a great first cut. Most charter companies publish recommended itineraries, based on their extensive local knowledge, popular sites and events, and feasibility for charter boats on a specific timeline. Check the brochures or websites for several charter companies in your selected charter area and see where the itinerary recommendations overlap. There is probably a good reason!
  • Nautical Charts allow you to plot navigable courses and distances between destinations, so you can determine if your choices are feasible. This may seem obvious, but is often overlooked in the initial planning stages.
  • Cruising Guides give far more detail on specific sailing areas, including harbors, marinas, landmarks, hazards, etc. Because these guides are designed for bareboat charterers and cruisers, there will be areas described that are accessible to private boats, but “off limits” to bareboat charters. Your charter company will give additional guidance. 
  • Tourist Boards have a vested interest in showing off the best features of an area. While not specifically geared to sailing, you’ll find great information on attractions, with copious photographs. Check out the websites, and order free brochures to assist in your planning.
  • Friends and Family who’ve chartered in the area love to share sea stories of their favorites and recommendations. Let them relive their charter memories while you take notes!

Balance Sea and Shore Time.  Create a balance between the time spent sailing and the time spent moored and/or ashore. If you and your crew live to sail, then 10 hour sailing days may be perfect – the journey IS your destination. But if your crew is sold on the idea of idyllic hours spent snorkeling or lying on the beach, then you’ll want to select destinations with shorter sailing legs, to allow time for non-sailing activities. Consider a combination of short and longer sails, to accommodate your crew’s preferences.

Time is of the Essence.  How many sailing days do you have on your charter?  Most itinerary recommendations are built for a 7-day charter.  Check with your charter company to see when you’re able to depart the dock on day one, and when you need to return the boat on your final day. Most likely, you’ll only have half-days available, so your sailing legs must be planned accordingly. Night sailing is rarely allowed on charter boats; be sure you’re secured well before sunset! 

D Street Calculations.  Remember your navigation basics of Distance, Speed and Time.  Make a reasonable but conservative estimate of boat speed based on type/length of boat and prevailing winds, and use this as your planning Speed. Measure the navigable Distance between proposed destinations on the chart, and calculate your Time en route.  Remember that you can’t sail directly upwind, so increase your distances accordingly.    

Charter Boat Features. The size and features of your boat will influence your itinerary. A longer boat can travel faster, and thus cover more distance between destinations. A heavier-displacement boat can make open-water passages more comfortable. Shallow-draft boats allow you to anchor closer to the beach. Onboard amenities also make a difference. If you have eight crewmembers on a boat with a single head, you may appreciate shower facilities ashore. If galley facilities or cooking inclinations are limited, choose an itinerary where you can dine ashore!  Dockside air-conditioning can also influence your choice of berthing, if evening breezes just aren’t enough.

Who’s Onboard?  Your itinerary will be greatly influenced by your crew composition, their preferences and abilities. Consider the sailing experience and stamina of your crew when determining length of passages between destinations, and the difficulty level of the sail.  If your crew is new to sailing, design your itinerary to build skills AND confidence afloat, while enjoying the pleasures ashore. Sailing with kids onboard adds a wonderful new dimension – but it’s a completely different charter than the one you took with your college buddies. For younger kids, 2-3 hour sailing legs are generally plenty long; focus on activities at anchor or ashore. Poll your crew to see what’s important to them and ensure it’s a “vacation” for all onboard.   

What’s In Port?  Features ashore will have a big influence on your itinerary, and will vary in importance with your crew’s preferences and priorities. In choosing your destinations, consider:

  • Evening berthing – anchorage, mooring or marina? What is most convenient for your crew’s plans, and the weather conditions? Do you need an evening of dockside air-conditioning, a convenient grocery, or hot showers?
  • Attractions – what do you want to do or see ashore? Consult travel and cruising guides to discover the peak attractions, or the things that most interest YOU. These may include food, art, architecture, beaches, shopping, archeology, museums.
  • Meals – if your plan is to dine ashore each evening, then you’ll need to plan your itinerary accordingly. A vacation from the galley may be welcome!

Prevailing Winds & Currents. These conditions can make a big difference. If your sailing area has reasonably predictable prevailing winds (e.g. tradewinds, regional patterns, or sea breezes), you can plan an itinerary to take advantage of the wind pattern. Some like to beat to windward on the first part of the trip (“eat your broccoli first”) and save the downwind segments for later in the trip. Consult cruising guides or climatology websites to assist. If your sailing area winds are primarily driven by synoptic patterns (as in the Chesapeake Bay), you may need to plan your itinerary as the local forecast develops; or at least, allow some flexibility so your entire trip isn’t a windward beat. Consider wind-driven and tidal currents in your planning, as well.

Lay Day.  Build flexibility for a “lay day” (delay in port) into your itinerary, in the event you want to stay put for a day, or even a half day. It’s not supposed to storm on your vacation, but sometimes it does – you’ll want the option to remain in port in that event.  As a charterer, I generally pressed for a new destination every day. But while cruising, I embraced the “radical” concept of remaining in a favorite port more than one night. Why not try this on a charter?

Crowd Control.  In charter-dense areas (e.g. BVI), you’ll often find a “circuit” of sailors who’ve studied the same itinerary recommendations. It can be great fun to encounter the same charter crowd each evening in the harbor.  But if you’d like to jump the circuit, consider skipping a leg or two to get out of synch with the crowd, or start your charter midweek instead of the weekend. You’ll find the harbors less crowed, with less competition for space and moorings. During holidays and festivals, you may need to arrive at an anchorage 2-3 days prior to secure a good spot. If that’s not your idea of fun, choose a different time to charter, or skip those harbors completely.   

Semper Gumby. If you recall the old Gumby cartoon, you’ll appreciate the value of flexibility. However you plan your itinerary, be sure to build in the flexibility to accommodate changing weather, mechanical issues, health and fitness, and crew preferences. An important lesson learned as a veteran of exhaustive compressed-schedule backpacking and sailing trips: Take time to enjoy the voyage and the destinations you discover on vacation – there will always be more to experience on the next trip!


About the Author:  Capt Lisa Batchelor Frailey is an ASA Instructor and co-owner of Sail Solomons Sailing School & Yacht Charters. Lisa is also an independent charter broker with extensive chartering and cruising experience in the Caribbean, Mediterranean, and Chesapeake Bay.

Copyright © 2010, Lisa Batchelor Frailey
All rights reserved. 



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