Read the Wind First
Check the forecast for southwest afternoon breezes common on the Bay. Start upwind so the return leg is easier.
The rigging in Eastport sings before the city fully wakes—halyards ticking against masts, gulls bargaining over breakfast, and the Severn River nudging the docks like a persistent friend. Slide a paddle board off the pier at 326 First Street and the water greets you with a cool palm. The first strokes feel tentative, then confident as your balance clicks. Soon you’re tracing the edge of the channel, sailboats rising like white keys on a piano, the soft dome of the U.S. Naval Academy chapel peeking over the treeline. The river dares you to go a little farther.
Duration1–2 hours
Group SizeSmall Groups
LanguagesEnglish
Rating5.0 (18 reviews)
Trail Wisdom
Trail Wisdom
Work the Shoreline
Hug Eastport’s edges and cross channels decisively to avoid boat traffic and wakes.
Knees Before Feet
If you’re new to SUP, start kneeling to find balance, then stand with a slight bend in your knees and engage your core.
Hydrate and Shield
Bring water and sun protection—UV bounces off the water even on cooler days.
Local Knowledge
Local Knowledge
Hidden Gems
- Back Creek’s quiet marinas for sheltered, beginner-friendly water
- Horn Point breakwater for wide-open Chesapeake views on calm days
Wildlife
Osprey, Cormorant
Conservation Note
The Severn River and Chesapeake Bay rely on healthy eelgrass and clean tributaries; avoid disturbing shorelines, give nesting ospreys space, and pack out everything you bring.
Annapolis’s Eastport neighborhood embodies a working maritime heritage and once staged a tongue-in-cheek “secession” in 1998 to celebrate local waterfront culture.
Seasonal Guide
Seasonal Guide
spring
Best for:Calm morning sessions, Cool, crowd-free paddles
Challenges:Cold water temps, Changeable wind and rain
Crisp mornings and light traffic make spring peaceful; dress for chilly water and keep an eye on passing fronts.
summer
Best for:Warm water, Sunset paddles
Challenges:Boat traffic and wakes, Sea nettles in late season
Long days and warm water are ideal; go early or late to avoid crowds and midday chop.
fall
Best for:Golden light, Mild water temps
Challenges:Shorter daylight, Breezy afternoons
Clear skies and fewer boats set a relaxed tone; time your session for midday or golden hour.
winter
Best for:Solitude, Glass-calm mornings
Challenges:Very cold water, Limited rental availability
Only for skilled paddlers with proper cold-water gear; expect minimal crowds and crisp visibility.
Photographer's Notes
Photographer's Notes
Go early for mirror-like reflections and aim low from a kneel to stabilize shots. A small polarizing filter for your phone cuts glare and deepens blues. Compose with the Naval Academy dome or the Spa Creek Bridge as anchors, and shoot perpendicular to ripples for texture. Use a lanyard or leash for your phone—one splash can end the session.
What to Bring
What to Bring
Sun-Protective Long-Sleeve (UPF)
EssentialShields from intense reflection off the water and reduces sunscreen reapplication.
Water Shoes or Sandals with Heel Strap
Improve grip on the board and protect feet at the launch.
Dry Bag or Phone Pouch with Leash
EssentialKeeps keys and phone safe while allowing on-water navigation and photos.
Light Windbreaker
Cuts breeze on cooler mornings and packs down small on deck.
Common Questions
Common Questions
What to Pack
What to Pack
Water in a squeeze bottle (easy to sip between strokes); UPF shirt or sunscreen (the sun reflects off the water); Dry phone pouch with leash (navigation and photos without risk); Lightweight sandals or water shoes (grip and comfort at the launch).
Did You Know
Did You Know
Annapolis served as the United States capital from 1783 to 1784, where George Washington famously resigned his commission in the Maryland State House.
Quick Travel Tips
Quick Travel Tips
Arrive 15 minutes early for fitting and a quick safety brief; Park in Eastport and expect limited street parking on busy weekends; Paddle mornings for calmer water and lighter boat traffic; Bring a small towel and a change of clothes—your feet will get wet.
Local Flavor
Local Flavor
Post-paddle, refuel like a local: Davis’ Pub for crab cakes and a cold beer, Boatyard Bar & Grill for fish tacos, or a small-batch pour at Forward Brewing. If you’re feeling fancy, O’Learys Seafood sits a short stroll away with Chesapeake-forward plates. Walk the Eastport drawbridge into Downtown Annapolis for ice cream and brick-street wandering.
Logistics Snapshot
Logistics Snapshot
Closest airportBWI (Baltimore
Washington International), ~25 miles. Launch326 First St, Eastport (Annapolis). Drive time from Downtown Annapolis: ~5 minutes. Cell service: Generally strong. Permits: None required for rentals; PFD required on the water. Parking: Street parking in Eastport—arrive early on weekends.
Sustainability Note
Sustainability Note
The Chesapeake Bay is a fragile estuary—keep a respectful distance from wildlife, avoid trampling shoreline grasses, and pack out every scrap. Rinse sunscreen in advance and use reef-friendly formulas to protect eelgrass beds.
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