The Complete Guide to Getting on the Water in Annapolis & the Chesapeake Bay

Captained vs Bareboat: Which is Right for You?

This is one of the most important decisions you'll make when booking a charter. Here's the honest breakdown:

Captained Charters

A licensed captain handles the boat while you relax, learn, or participate as much (or as little) as you want. The captain knows the local waters, can teach you as you go, handles all the navigation and safety concerns, and tells you where to find the best crab cakes afterward.

Bareboat Charters

You rent the boat and captain it yourself. This requires demonstrated sailing experience — charter companies will ask about your certifications and experience level. You'll typically need ASA certification or equivalent experience, plus references.

If you're somewhere in between — have some experience but want a safety net — many captains offer "captain-assisted" charters where they're aboard but you do most of the sailing.

Factor	Captained	Bareboat
Experience needed	None	Significant
Cost (per day)	$600-$1,500+	$300-$800
Stress level	Minimal	You're responsible
Learning opportunity	High (if you want)	Self-directed
Flexibility	Captain's expertise guides plans	Total freedom

Sailing vs Powerboat Charters

Different vibes, different experiences. Neither is "better" — it depends on what you're looking for.

Sailing Charters

There's something meditative about sailing. The quiet (no engine drone), the heel of the boat, the connection to the wind. Sailing is slower but more immersive. You feel like you're part of the environment, not just passing through it.

Pros: Peaceful, authentic, eco-friendly, teaches you about wind and weather

Cons: Weather-dependent, generally slower, can heel (lean) significantly

Powerboat Charters

If you want to cover more ground, get somewhere specific (like a restaurant or beach), or have family members who get nervous about the boat leaning, powerboats are the practical choice. They're more like a floating living room.

Pros: Faster, stable platform, more predictable timing, better for fishing

Cons: Fuel costs, engine noise, less "romantic" for some

For sunset sails and romantic occasions, most people prefer sailing. For fishing trips, family outings with young kids, or when you have a specific destination in mind, powerboats often make more sense.

Learning to Sail in Annapolis

Annapolis is one of the best places in the country to learn sailing. The protected waters, consistent winds, and depth of sailing culture make it ideal for beginners.

Options for Learning

Sailing Schools: The Annapolis Sailing School, J World, and others offer structured ASA certification courses. These typically run 2-4 days and give you credentials recognized worldwide.

Private Instruction: One-on-one lessons with a captain. More expensive per hour but often faster progress. This is what I offer — personalized training on your schedule, on the boat type you're interested in.

Learn-to-Sail Charters: A hybrid approach. You book a charter, but the focus is on teaching rather than sightseeing. By the end, you've had a great day AND learned something.

If you're considering boat ownership, I strongly recommend getting at least ASA 103/104 certification first. You'll save money on mistakes, feel more confident, and get more enjoyment from day one.

Offshore Sailing & Ocean Deliveries

For experienced sailors looking to level up, offshore sailing is the ultimate challenge. The Chesapeake Bay is a natural training ground — protected enough to build skills, but with enough weather and traffic to prepare you for the ocean.

What is Offshore Sailing?

Generally, "offshore" means sailing out of sight of land — beyond the protected waters of the Bay, into the Atlantic. It's a different beast entirely: longer passages, watch schedules, weather routing, and self-reliance.

Ocean Deliveries

Boat delivery is moving a vessel from one port to another. Many sailors get their offshore experience by crewing on deliveries. You're not paying for a charter — you're working as crew, learning from experienced captains on serious passages.

Common delivery routes from the Chesapeake include:

• Fall southbound: Annapolis → Norfolk → Beaufort, NC → Florida (or Caribbean)
• Spring northbound: Florida → Chesapeake (or continuing to New England)
• Bermuda runs: 650 nautical miles offshore — serious ocean sailing

Getting Into Sailboat Racing

Sailboat racing is the fast track to becoming a better sailor. The competition pushes you to understand wind, trim, tactics, and boat handling at a level that casual sailing never will.

Annapolis has one of the most active racing scenes on the East Coast. Wednesday night "beer can" races are a local institution — informal, social, and open to newcomers.

How to Get Started

1. Crew on Someone Else's Boat
Most racing boats need crew, and experience isn't always required for entry-level positions. Show up at the yacht club, ask around, or check online crew boards. Be reliable, show up on time, and be willing to learn.

2. One-Design Classes
Boats like the J/70, J/105, and Melges 24 have active fleets in Annapolis. One-design racing means everyone sails the same boat — it's pure sailing skill, not checkbook racing.

3. PHRF/Handicap Racing
Different boats racing against each other with time corrections. Your boat gets a handicap rating based on its theoretical speed.

4. Offshore/Distance Racing
For the seriously committed: overnight races, ocean races, even transatlantic events. The Annapolis-to-Bermuda race draws serious offshore sailors.

Best Times to Charter on the Chesapeake

The Chesapeake Bay sailing season runs roughly April through November, but each season has its character:

Spring (April - May)

The Bay comes alive after winter. Winds are strongest in spring — great for sailing, but can be challenging for beginners. Water is still cold. Fewer crowds, lower prices.

Summer (June - August)

Peak season. Lighter, more variable winds. Warm water for swimming. Afternoon thunderstorms are common — morning charters avoid the heat and storms. Most crowded, highest prices.

Fall (September - October)

The sweet spot. Stable weather, beautiful colors, comfortable temperatures, fewer boats on the water. Many locals consider this the best sailing season.

Late Fall (November)

Cooler but often gorgeous. Boat traffic drops significantly. Some charter companies close, but dedicated operators (like me) keep running.

What Does Chartering Actually Cost?

Transparency time. Charter prices vary widely based on boat size, duration, and whether a captain is included.

Typical Price Ranges in Annapolis

Charter Type	Duration	Price Range
Sunset Sail (captained)	2-3 hours	$300-$600
Half-Day (captained)	4 hours	$500-$900
Full-Day (captained)	6-8 hours	$800-$1,500
Bareboat (day)	Full day	$300-$700
Bareboat (week)	7 days	$2,000-$5,000
Fishing Charter	4-8 hours	$500-$1,200

What's typically included: Fuel, captain, basic refreshments (water, soft drinks), safety equipment, instruction (if wanted).

What's typically extra: Alcohol, catering, overnight dockage fees, extended hours, gratuity for captain (15-20% is standard).

First-Timer's Checklist

Never been on a charter before? Here's what to know:

What to Bring

• Soft-soled shoes (no black soles — they mark the deck)
• Sunscreen and sunglasses (polarized are best)
• Light layers — it's always cooler on the water
• Hat with a strap or clip
• Seasickness remedy if you're prone (take it BEFORE you board)
• Camera with a strap

What to Expect

• The boat will lean (heel) when sailing — this is normal and safe
• You'll be asked to help with simple tasks — or you can just relax
• The captain controls the schedule based on weather and conditions
• Bathrooms ("heads") on boats are small — your captain will explain how they work
• Cell service is usually fine on the Chesapeake

Ready to Book? Your Next Steps

If you've made it this far, you're ready to get on the water. Here's the honest truth about booking a charter:

Book early for peak times. Weekend sunset sails in summer fill up weeks in advance. Fall weekends go fast too.

Weekdays are easier (and often cheaper). If your schedule allows, Tuesday-Thursday charters are more available and sometimes discounted.

Be clear about your goals. Tell your captain what you want: relaxation, learning, celebration, adventure. A good captain customizes the experience.

Weather flexibility helps. If you can move your charter by a day or two based on weather, you'll have a better experience. Sailing in 20 knots isn't everyone's idea of fun.