Sail Into Serenity: A Full-Day Private Catamaran Charter on the Chesapeake
All Ages • 8 Hours • 2- 12 Passengers
Morning in Annapolis begins with the quiet shuffle of dock lines and gulls gossiping over breakfast. The catamaran waits with an easy confidence—broad, stable, inviting—its twin hulls promising a day that stretches beyond the horizon. You step aboard to the scent of salt and sun-warmed fiberglass, and the Bay greets you with a patient pulse. The breeze presses a palm against the sails and the boat answers, sliding out past the red-brick shoulders of town and the shining domes of the Naval Academy. Annapolis recedes; open water takes over.
Trail Wisdom
Choose Non-Marking Footwear
Wear boat shoes or clean sneakers with light-colored soles to protect the deck and keep your footing secure.
Plan Your Menu
Bring easy, finger-friendly foods and a small cooler; the crew can help stow it, but space is limited.
Time the Breeze
Summer seabreezes often kick in after lunch; schedule sailing-intensive segments for mid to late afternoon.
Mind the Captain’s Fee
Budget for the direct-to-captain fee at the dock: $400 (≤6 passengers) or $500 (7–12).
Local Knowledge
Hidden Gems
- •Anchor for a swim in a quiet Back Creek cove near Eastport
- •Photograph Thomas Point Shoal Lighthouse from the water’s calmer lee side
Wildlife
Osprey, Bottlenose dolphin (summer)
Conservation Note
Oyster reef restorations are improving Bay health—avoid single-use plastics, use marina pump-outs, and never discard anything overboard.
Annapolis has been a sailing hub for centuries; the U.S. Naval Academy, founded in 1845, continues that maritime legacy on the Severn River.
Seasonal Guide
spring
Best for: Steady sailing winds, Cool, clear afternoons
Challenges: Chilly mornings, Changeable weather fronts
April–May brings reliable breeze and thinner crowds. Pack layers and a windbreaker; water temps remain cool.
summer
Best for: Warm swims, Afternoon seabreezes
Challenges: Heat and humidity, Chance of pop-up thunderstorms, Jellyfish in late summer
June–August is prime for swimming and sunset sails. Start earlier, hydrate often, and watch afternoon storm cells.
fall
Best for: Crisp air and golden light, Consistent winds
Challenges: Shorter daylight, Cool evenings
September–October often delivers the best sailing of the year—clear skies, sailable breeze, and fewer boats.
winter
Best for: Quiet waterways
Challenges: Cold temperatures, Limited charter availability
November–March is off-peak; some operators pause trips. If sailing, dress for windchill and bring hot drinks.
Photographer's Notes
What to Bring
Polarized SunglassesEssential
Cuts glare, helps you spot wildlife, and reduces eye fatigue on bright water.
Light WindbreakerEssential
Even mild days feel cooler underway; a packable shell blocks breeze and spray.
Non-Marking Deck ShoesEssential
Grippy, light-soled shoes keep you steady and protect the deck from scuffs.
Dry Bag (10–15L)
Safeguards phones, cameras, and an extra layer from spray and splashes.
Common Questions
Is the captain’s fee included in the booking price?
No. The captain’s fee is paid directly at the time of charter: $400 for six or fewer passengers, $500 for seven to twelve.
Can we bring our own food and drinks?
Yes. This is a private charter—bring your preferred snacks, lunch, and beverages. Use cans over glass when possible.
What happens if weather looks bad?
The captain monitors conditions and may adjust timing, route, or reschedule for safety. Light rain is often manageable; thunderstorms mean delays or cancellation.
Is there a restroom on board?
Yes. The catamaran has a marine head; please follow crew instructions on use and disposal.
Will I get seasick on a catamaran?
Catamarans are more stable than monohulls. If you’re sensitive, take preventive medication in advance and focus on the horizon while underway.
Can we swim during the charter?
Usually yes, conditions permitting. The crew will anchor in a protected cove and provide a safe boarding ladder. Bring towels and a change of clothes.
What to Pack
Polarized sunglasses for glare; light windbreaker for breeze underway; non-marking deck shoes for grip and to protect the deck; compact cooler with finger foods and plenty of water to stay hydrated.
Did You Know
Chesapeake Bay is the largest estuary in the United States, fed by more than 150 rivers and streams, including the Susquehanna, Potomac, and James.
Quick Travel Tips
Park early near the marina to allow time for loading; bring soft-sided coolers to save space on board; check the marine forecast the night before and the morning of your trip; tip your captain and crew for great service, typically 15–20%.
Local Flavor
After docking, head to Eastport’s Boatyard Bar & Grill for a cold beer and a crab cake sandwich, or sip small-batch brews at Forward Brewing. If you’re in the mood for a classic Annapolis brunch, Iron Rooster delivers comfort fare steps from the waterfront. Round out the evening with a stroll past the Naval Academy seawall or a quick stop at the Annapolis Maritime Museum to keep the nautical theme going.
Logistics Snapshot
Closest airport: BWI (Baltimore/Washington International), ~25 miles from Annapolis. Departure area: Annapolis/Eastport marinas near Back Creek. Drive time from downtown Annapolis: 5–10 minutes. Cell service: Generally strong near town; can be spotty farther out on the Bay. Parking: Marina or nearby street parking—arrive early, especially on weekends. Permits: None required for passengers. Captain’s fee is paid directly at the dock.
Sustainability Note
The Chesapeake’s health depends on us—pack out all trash, choose reef-safe sunscreen, and keep lids tight so nothing blows overboard. Respect no-wake zones to protect shorelines and nesting osprey.
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