Weekend Getaway

Historic Hampton Roads Boating Itinerary

Mid-Atlantic
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October 2017
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By
Bob
Ruegsegger

When the English Colonists who established Jamestown sailed through a watery passage into the New World in 1607, there were no charts, lighthouses, or daymarks. They often used familiar English sobriquets as names for the places and rivers that they "discovered" in Virginia -- Cape Charles, Cape Henry -- but Captain John Smith's map of Virginia, in use for seventy-five years, also recorded many of the native tags given by the indigenous people, including the Chesapeake Bay.

These days, the area at the confluence of the James River, Elizabeth River, and the Chesapeake Bay -- collectively known as Hampton Roads -- is still a great place to explore by water.

Norfolk and Portsmouth are on opposing banks of the eastern branch of the Elizabeth River, and the shipyards and marinas lining both sides make this a splendid starting point for a cruising adventure in the region. On the Norfolk bank are the Waterside Festival Marketplace, Waterside Marina (757-625-3625), and Town Point Park. The naval museum, Nauticus, which has the World War II-Era Battleship Wisconsin as its centerpiece, is adjacent to Town Point Park and is an easy five-minute walk from Waterside Marina. Also, a former 1873 church now turned into a tavern, the Freemason Abbey Restaurant, is only a four-block trek from Town Point Park.

The Elizabeth River Ferry provides a convenient, interesting, and inexpensive means of crossing the river from Norfolk to Portsmouth. A one-way ride costs $1.75 and runs every 30 minutes. Portsmouth boasts a plethora of boatyards and marinas. Tidewater Yacht Marina (757-393-2525), located at mile marker 0 on the Intracoastal Waterway (ICW), houses some of the best marine facilities in Hampton Roads along with Ocean Marine Yacht Center (757-321-7457). Both are set in the heart of Portsmouth's Olde Towne, a charming historic maritime district with the country's oldest operating U.S. Naval Hospital and loads of shopping and dining options. The Naval Shipyard Museum, Portsmouth Lightship Museum, and the Children's Museum of Virginia are also nearby, and the Olde Towne Courtesy Shuttle provides passenger service within the Olde Towne district.

Cruisers who like to explore should check out this Historic Hampton Roads boating itinerary.

DAY ONE - Waterside/Olde Towne to Lynnhaven Inlet

Lynnhaven Inlet, on the Chesapeake Bay side of Virginia Beach, is approximately 22 nautical miles from Waterside and Olde Towne. The voyage requires sailing down the Elizabeth River, around Lambert's Point and into Hampton Roads. Along the way, cruisers will sail past the Norfolk Naval Base, over and under the Hampton Roads Bridge-Tunnel and the Chesapeake Bay Bridge-Tunnel, and under the Lesner Bridge into the Lynnhaven River.

Lynnhaven Bay was the site of a notorious 18th-century pirate battle, and Lynnhaven oysters gained renown worldwide for their succulence and distinctive flavor. Long Bay Pointe Marina (757-321-4550) is located on Wolfsnare Creek, a tributary of the Lynnhaven River. This first-rate boating resort is about five minutes from the Chesapeake Bay and ten minutes from the Atlantic Ocean. The 215-slip marina with floating docks can accommodate boats from 20 to 200 feet. Amenities include a tackle shop, fish-cleaning facilities, climate-controlled restrooms, showers, laundry facilities, and easily accessible parking. Restaurants are located on the premises.

First Landing State Park, the site where English colonists first came ashore in 1607, is within walking distance. The park features 20 miles of hiking and bicycling trails and a mile and a half of beach.

Cape Henry and its two lighthouses are located ten miles east of Lynnhaven Inlet via Shore Drive (Route 60), on the Joint Expeditionary Base-Fort-Story. The Old Cape Henry Lighthouse, built in 1792, is open to visitors for a fee.

DAY TWO - Virginia Beach to Cape Charles

Passing through Lynnhaven Inlet into the Chesapeake Bay on a northerly heading will put sailors on course to Cape Charles. An easterly bearing will put the crew on a course to Cape Henry -- and the Atlantic Ocean.

Cape Charles, on Virginia's Eastern Shore, is 25 nautical miles from the mouth of Lynnhaven Inlet. The cruise to Cape Charles will involve passing through the Chesapeake Bay Bridge-Tunnel at some point. While small craft may pass under the bridge trestles, larger craft must pass over either the Thimble Shoals Channel Tunnel or the Chesapeake Bay Tunnel Channel. On the Eastern Shore side of the bridge tunnel, larger vessels can pass under the North Channel Bridge.

The town of Cape Charles was founded by Alexander Cassatt and William L. Scott in 1864. It was the southern terminus of the New York, Philadelphia, and Norfolk Railroad. The outgrowth of railroad tracks from Maryland to Cape Charles opened markets in the Northeast to Eastern Shore produce and seafood. By employing steamboats and railroad barges, the newly established port created a link to Norfolk. Cape Charles grew rapidly and quickly became the economic and domestic hub of Northampton County.

These days, Cape Charles is the gateway to the ecosystem of the Virginia Coast Reserve, a coastal barrier biosphere comprised of mainland watersheds, lagoons, and tidal marshes. Because of where it's situated, it also serves as a kind of convenience store for super yachts in need of fuel and provisions as they cruise the Atlantic coast.

Cape Charles Yacht Center (757-331-3100) is a full-scale service facility, with short-term and long-termboat slips and dry storage. All types of mechanical systems are designed, serviced, and installed on site. Guests also get complimentary shuttle service to all Cape Charles attractions. The 75-ton Marine Travel Lift (a 650-ton lift is currently under construction), gently and expeditiously removes and returns bigger craft to the water, and the deep-water floating docks can easily accommodate large yachts for transient or longer visits.

DAY THREE - Cape Charles to Hampton

Hampton is in the heart of the Hampton Roads region, about 22 nautical miles from Cape Charles on Virginia's Eastern Shore. The entrance to the Hampton River is just beyond Old Point Comfort, where the channel passes between Fort Monroe National Monument and Fort Wool and over the Hampton Roads Bridge-Tunnel.

Bluewater Yachting Center (757-723-6774) is adjacent to Blackbeard's Point on the port side at the mouth of the Hampton River -- where Blackbeard's severed head was posted on a pole as a warning to other pirates in 1718. The full-service marina offers diesel and premium gasoline, a full parts department, and factory-trained technicians. It also has a swimming pool, a coin-operated laundry, bicycle rentals, and the ever-popular Surfrider Restaurant.

A complimentary water shuttle is available on demand to transport guests from the marina to the center of downtown, where the Hampton History Museum illuminates the city's past, from the native Kecoughtan Indians through the 20th century. The Hampton Carousel was built in 1920, and its 48 intricately carved horses and two elegant chariots were recently restored. The Virginia Air & Space Center serves as the official visitor site for Hampton's NASA Langley Research Center.

Hampton has had a reputation for hospitality since Captain John Smith and his men were welcomed and treated kindly by the Kecoughtan people during the winter of 1608-1609. The four-centuryold tradition continues to this day. The Hampton River Waterfront has five marinas all on its own, and is an ideal stopping point for boaters traveling the Chesapeake Bay or the Intracoastal Waterway. If you can, hit the town during the annual, nationally acclaimed Blackbeard Pirate Festival in June --it's a swashbuckling good time.

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Chesapeake Bay Calendar of Events
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Summer is here, and it’s time to soak up the sun, visit bustling beaches, learn about boating history and relish the small-town charm around the Chesapeake Bay. Read on for hidden gems and tried-and-true events along the Bay, all the way from Havre de Grace to Cape Charles. Whether you’re a fan of watersports, arts and crafts, street festivals, or coastal cuisine, you’ll find something worth docking for a while.

July

Yorktown Market Days, Fun in the Sun Market

Yorktown, VA

July 16 - Fun in the Sun Market;

August 6 - National Farmers Market Week

Experience a coastal Hampton Roads market on the York River. Check out local produce, meats, seafood, gourmet dog treats, art and more every Saturday this summer, and stop by one of the dates above for a themed, family-friendly extended market.

Where to Dock: Riverwalk Landing

Spirit of America

Havre de Grace, MD

July 2

Enjoy this beautiful town through a mid-century Americana lens at the Independence Day festival. You won’t want to miss the Patriotic Pooch contest, 50s throwback entertainers and best of all, derby races on Pennington Avenue.

Where to Dock: Tidewater Marina

Sea Glass & Beach Crafts Market at Annmarie

Solomons, MD

July 2

Kick off the holiday weekend at the Annmarie Sculpture Garden & Arts Center’s annual beach-themed market. Browse all things crafty and sea glass at over 50 booths!

Where to Dock: Solomons Harbor Marina

Kent County Waterman’s Day

Rock Hall, MD

July 3

For the first time since 2019, stop by and celebrate watermen who dedicate their lives to working on the Chesapeake! Enjoy a day of family fun, including anchor tosses and a raffle, culminating in the infamous boat docking.

Where to Dock: Haven Harbor Marina Resorts

Tuckahoe Steam & Gas Association’s 49th Annual Show

Easton, MD

July 7-10

Calling all car, truck and train enthusiasts! This multi-day show will be packed with steam and gas engines; antique tractors, trucks and cars; live steam train models; and even a horse pull.

Where to Dock: Easton Point Marina

Chesapeake Stand Up Challenge

Annapolis, MD

July 9 

Sponsored by the Eastport Yacht Club, this open water race has something for all levels. Experienced paddlers can fight it out in the seven-mile Challenge, and recreational paddlers will enjoy the 3.5-mile Challenge or one-mile Just for Fun race.

Where to Dock: Eastport Yacht Center

Plein Air Easton Art Festival

Easton, MD

July 17-24

Plein air painters express their craft from life instead of the studio, so you’ll see artists from across the country painting all around town. Also attend lectures and workshops, and buy art and other goods downtown all week. 

Where to Dock: Easton Point Marina

14th Annual Hampton Heat

Hampton, VA

July 23

Dock at the transient slips in downtown Hampton, then join the landlubbers at Langley Speedway, one of NASCAR’s best weekly tracks, for the annual Hampton Heat races.

Where to Dock: Bluewater Yachting Center

Southern Maryland Boat Club Bash on the Bay

Leonardtown, MD

July 29-31

Since the Calvert Marine Museum opened an exhibit on the golden era of powerboat racing in 2013, this vintage boat club has put on several races a year. Make your way to the historic Leonardtown Wharf to see vintage powerboats in action.

Where to Dock: Combs Creek Marina

2022 Snakehead Summer Slam

July 30

Annapolis, MD

Things are sure to heat up at the fourth of five tournaments in the 2022 Snakehead Championship Series at Anglers Sport Center. Anglers in kayak/shoreline and boating divisions will be up for all kinds of prizes, including one from the Coastal Conservation Association Maryland’s Great Chesapeake Invasive Count.

Where to Dock: Podickory Point Marina

Annapolis Yacht Club Two Bridge Fiasco Race

Annapolis, MD

July 31

Cruise to the southern Chesapeake to witness this pursuit style race starting between the Chesapeake Bay Bridge and Severn River Bridge. Look out for all types of boats in the competition, and even a foiler or two if you’re lucky.

Where to Dock: Annapolis Yacht Club

August

Annual Chesapeake Bay Balloon Festival

Cordova, MD

August 5-7

Embrace the Eastern Shore summer lifestyle at this family-friendly festival. Feel the adrenaline rush of hot air balloon rides and keep the thrill going on the mechanical bull and bouncy house on land.

Where to Dock: Easton Point Marina

A Day of Celebration & Remembrance of Harriet Tubman

Cambridge, MD

August 6 

Celebrate Harriet Tubman’s life, bicentennial and antislavery activism on the Underground Railroad just miles from where she lived as a child. Join the commemorative parade through the streets of Cambridge and enjoy local vendors and entertainment at the festival.

Where to Dock: Cambridge Yacht Basin

Pirates & Wenches Weekend

Rock Hall, MD

August 12-14

Presented by Main Street Rock Hall, you can dock at a local bayfront marina ready for an immersive, family-friendly weekend. The whole family will love the marketplace on Main Street, pirate and mermaid performers, and costume contests, and there will be no shortage of grub and grog.

Where to Dock: Haven Harbor Marina Resorts

Solomons Dragon Boat Festival 2022

Solomons Island

August 13

Cruise to scenic Solomons Island to watch 30 dragon boat teams compete for glory on the Patuxent River and explore the local vendor village. Arrive the week before and you might catch a Dotting of the Eye Ceremony or even a flash mob.

Where to dock: Solomons Harbor Marina

Leo Wardrup Memorial Cape Charles Cup Regatta

Cape Charles, VA

August 20-21

Make your way to Virginia’s Eastern Shore for two days of racing on the Chesapeake. While you’re there, lounge on the Cape Charles town beach, stroll around the retail district and check out Victorian homes in the historic district.

Where to Dock: Cape Charles Yacht Center & Marine Services

7th Annual Coastal Craft Beer Festival

Virginia Beach, VA

August 27

Spend your Saturday at the waterfront Neptune’s Park, tasting your way through 60+ beers, ciders and seltzers from 30 breweries. Learn about all Virginia breweries have to offer or branch out with some regional or national craft brews.

Where to Dock: Rudee's Inlet Station Marina

September

The Waterfront Festival

Havre de Grace, MD

September 9-10

Cruise to the northern Bay to round out your summer with this annual festival, kicking off with a lighted boat parade. Enjoy fun for the whole family with fresh crab and seafood, beer gardens, live music, hot air balloons and a youth fishing derby!

Where to Dock: Tidewater Marina

2nd Annual Portsmouth Paddle Battle

Portsmouth, VA

September 10 

Whether you kayak or paddleboard as a novice or a pro, or enjoy waterfront live music, food and drink, there’s a place for you in the Paddle Battle on the Elizabeth River. Proceeds will support the Portsmouth Naval Shipyard Museum and Lightship Portsmouth Museum.

Where to Dock: Tidewater Yacht Marina

TrawlerFest Baltimore

Baltimore, MD

September 27-October 1

Close out your summer season with Passagemaker’s annual boat show held at Harbor East Marina in the heart of downtown Baltimore. The show hosts impression in-water selections of new and pre-owned long-rang cruisers, coastal cruisers and of course, tons of trawlers. Free seminars and educational demonstrations are held throughout the weekend.

Where to Dock: Harbor East Marina

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Wickford Cove to Block Island, RI
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Our nation's smallest state has big boating opportunities. Rhode Island's Narragansett Bay is prime for cruising picturesque and protected with many beautiful harbors. While not on everyone's chart plan, Wickford is an historic hamlet with delightfully walkable shady streets lined with beautiful colonial homes. From quiet Wickford, you're set for a straightforward passage out to The Bay, then poised to cross the broad blue expanse of Rhode Island Sound to the fun, boat- and bike-friendly Block Island. This Narragansett tour will have you feeling like a bold explorer while landing at easy modern marinas.

Day 1: Wickford Cove

Wickford Cove is the smallest town in the smallest county of littlest Rhode Island. That's not to minimize its quaint downtown full of waterfront gardens, charming architecture and tremendous yachting heritage. Stroll Wickford's self-guided marker tour of historic seaside homes, then pop into some darling boutiques around the harbor like Serendipity and Pink Parasol.Conclude your walk at Wickford on the Waterfront with a salty cocktail, local oysters or stuffed clams (stuffies in Rhode Island lingo). Tate's Italian Kitchen serves hearty classics across the village's main Brown Street. Moorings can be reserved at Wickford Yacht Club or go to Safe Harbor Wickford Cove for a full-service marina with dock space.

Day 2: Block Island

Wickford to Block Island 29 NMCruising down the western shores of Narragansett Bay under the Jamestown Bridge, passing magnificent mansions then Point Judith Light, you are soon on your way across the open expanse of Rhode Island Sound to Block Island. The farthest island from land on the entire Eastern seaboard, Block Island is even more remote than Monhegan in Maine (10 miles out by comparison).

Block Island - weekend warrior - marinalife
Block Island, RI | Greg Burke

Block Island has a vacation vibe, and everything is relaxed, truly on island-time with their moniker of Bermuda of the North. The 1,500 happy humble Block Island residents claim they've been social distancing since 1661, so they've got humor to carry them through the long off-season. Block's pear-shaped 7 x 3-mile island is cool, casual and fun to explore for a few days, yet not so stuffy-chic or celebrity-crushed as Nantucket or Martha's Vineyard.Getting around by bike or moped is the best way to explore Block's entire 16 miles of perimeter roads. Along the undulating country lanes, you may feel transported to Ireland with the lush rolling fields, stone walls, dramatic Mohegan Bluffs and the contrasting blue sea. Passing dozens of unique beaches, you may plan to return later. Highlight sights are Block Island's two impressive lighthouses – North and South East – with the busier main village of Old Harbor in between.Block Island has two boating harbors: the more protected New Harbor in Great Salt Pond, which is preferred by pleasure boaters, and Old Harbor with its primary ferry landing and bustling downtown of shops and grand seaside hotels. Staying at Great Salt Pond overlooking your mooring or dock slip, you should enjoy sunsets, pub fare and a boaters' block party atmosphere at The Oar or Dead Eye Dick's (opens in May). While in the Old Harbor after browsing boutiques, find a perfect chair and cocktail at either grand seaside hotel: Spring House or Atlantic House.For a delicious local dinner, Kimberly's serves littlenecks or calamari followed by lobster mac n' cheese as a beautiful ending to a day of exploring. Live music may be piping out from next door Poor People's Pub to lure you over for a nightcap.Block Island's public moorings in New Harbor are assigned daily by the Harbormaster. Private slips can be reserved at Champlin's Marina, the Boat Basin and Oar House. They book up quickly in prime summer season, which results in boats rafting-up with strangers (friends you haven't yet met!).

Day 3: Newport

Block Island to Newport 25 NMDeparting Block Island, perhaps after fresh coffee and pastries delivered to your boat by enterprising locals, you will be in the company of power boaters and sailing vessels, plus the occasional charging ferry heading to Newport. It's a direct course northeast to the Sailing Capital of Newport.

Bannisters Wharf - weekened warrior - marinalife
Bannisters Wharf, Newport | Greg Burke

No boater worth his Sperry's can miss out on the yachty harbor of Newport, established in 1639. As a visiting boater, contact the Harbormaster or Newport Yachting Center for an affordable mooring or a much pricier dock space in this prime harbor. Water taxis ply the harbor frequently to take you to the town docks.Newport is full of magnificent vessels, lively waterfront pubs lining Bowens and Bannisters Wharfs, and scads of inviting seaside shops on cobblestone streets. Getting off your boat, stretch your sea legs with a scenic 3.5-mile cliff walk by the Gilded Age mansions of our fine affluent families (Rockefeller, Vanderbilt, Dupont, Astor and Morgan). Before sunset, head for Newport rooftop drinks overlooking the harbor at The Vanderbilt or the Hotel Viking to toast your good fortunate in this big little state.

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The Florida Keys
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MAGICAL ASPECTS OF FLORIDA lie beyond the gates of Disney's Magic Kingdom. In fact, a wealth of nature's enchantment unfolds in the 110 miles stretching from Key Largo to Key West, and an abundance of fascinating creatures thrive on the 1,700 islands of the coral cay archipelago.The beginning of the island chain, Key Largo, made famous by the movie starring Bogart and Bacall, is known as the Dive Capital of the World. Wreck divers head for the sunken 510-foot USS Spiegel Grove, while reef lovers choose John Pennekamp Coral Reef State Park. Molasses Reef in Florida Keys National Marine Sanctuary has shallow sections perfect for snorkeling. For a unique day excursion or an overnight stay, dive 20 feet below to the only entrance of the Jules Verne Undersea Lodge at Emerald Lagoon.The world-class and private Ocean Reef Club marina on the northernmost tip of the island has slips to accommodate vessels up to 175 feet.

Day 1: IslamoradaKey Largo to Islamorada 15 NM

It's a short leg from the diving hub to the Sport Fishing Capital of the World, which boasts the largest charter fishing fleet per square mile on Earth. At dawn, captains head out on deep-sea excursions or idle through mangrove islands and shallow seagrass flats of the backcountry. The silver flashes in the sunlight at Robbie's Marina dock are enormous tarpon, 50 to 100 feet long, doing daily water acrobatics for snacks thrown by visitors into the clear, shallow water.

Islamorada - weekend warrior - marinalife
Islamorada | romrodinka on Canvas

The Keys have a motley past: shipwrecks, pirates, buried treasure, movie stars and especially luscious Key Lime pie. History reaching back to Native American life is outlined at the Keys History & Discovery Center at the Islander Resort.Downtown Islamorada's patchwork of boutiques and galleries is overflowing with original creations of artists, sculptors and jewelers inspired by life on the islands. The Morada Way Arts & Cultural District is a bustling six-block corridor of shops, restaurants and studio spaces. Thirsty shoppers can duck into the welcoming back garden of Florida Keys Brewing Company. Beside the seasonal beer on tap, they serve a Key Lime cocktail so delectable that it could be counted as dessert.Transient dockage to 100 feet is available at Postcard Inn Beach Resort & Marina, a premier facility with 15 sprawling acres of white sand beach. Plantation Yacht Harbor Marina, located in the fabulous Founders Park, is ranked among the top marinas in the world and is a designated Clean Marina.

Day 2: Duck KeyIslamorada to Duck Key 21 NM

Tucked into the secluded and intimate isle of Duck Key, Hawks Cay Resort is a 60-acre destination often named the top family resort in the country. After Hurricane Irma in 2017, a $50 million renovation revitalized the entire property. It's the perfect backdrop for Discovery Channel's popular Saltwater Experience, which is filmed on site.Hawk's Cay guests can do everything or do nothing. Interact and swim with dolphins in their natural environment at the Dolphin Connection or rise early for oceanside yoga before wandering to the spa for a Key Lime Mojito scrub followed by a warm body butter wrap with Key Lime essential oils. Come evening, multiple resort dining choices include the new Sixty-One Prime, a Key-style chop house, and the island casual Angler & Ale.Hawks Cay Marina can accommodate boats up to 110 feet with beams to 20 feet in the resort's back basin.

Day 3: Key WestDuck Key to Key West 52 NM

Before adventuring out in the heat to pet the famous six-toed cats at Hemingway House or view the spartan simplicity of the Truman Little White House, grab a Cuban Café con Leche and wander around town absorbing the laid-back, culturally diverse life of island time.Nightly pub crawls guide visitors along Duval Street's legion of barrooms. Much like the revelers doing the Duval Crawl, the Key West chickens strut the streets and crow at all hours. Colorful roosters and mother hens with tiny chicks weave in and out of traffic and through open cafés around town.

ocean reef club - weekend warrior - marinalife
Buccaneer Island, Ocean Reef Club | Ocean Reef Club

Much quieter winged creatures reside in the Key West Butterfly & Nature Conservatory, a tropical paradise home to hundreds of species of magical butterflies and birds. More of nature's birding and fishing wonders lie just off the western shore. Accessible only by boat, Key West National Wildlife Refuge encompasses 208,308 acres with only 2,019 acres above sea level. Wading birds, pelicans, shorebirds, sea turtles, manatees and dolphins all live within or visit the refuge.There's an eatery on nearly every corner from the quirky Kermit's Key West Key Lime Shoppe to the beautiful Seaside Café at the Southernmost Mansion and Louie's Backyard for fine dining. It's best to experience Key West on a bike or a golf cart so you can catch the quirkiness of the island including the popular drag show at 801 Bourbon Bar and the famous cemetery. And at the end of the day, join the locals for live music at the Green Parrot Bar.Several marinas welcome boaters with a range of pleasant amenities and convenient locations: Conch Harbor Marina in historic Old Town, Stock Island Yacht Club and The Perry Hotel & Marina.

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