Weekend Getaway

Florida Island Hopping: the Gulf ICW

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October 2013
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By
Capt. Jeff
Werner

Fort Myers Beach, Florida

Fort Myers Beach, is a barrier island on the Gulf of Mexico that lies just south of the junction that marks the western end of the Okeechobee Waterway and the beginning of the Gulf Intracoastal Waterway. Fort Myers Beach has a rich history dating back 2,000 years to the Calusa Indians.

The best spot to dock on Fort Myers Beach is the Pink Shell Resort & Marina (855-482-1947, pinkshell.com). Experience their newly built floating docks adjacent to Bowditch Point on the north end of the island.

Begin your tour of the island with a bit of time travel at the Mound House (239-765-0865, moundhouse.org). Walk inside a Calusa Indian shell mound and discover the indigenous culture that Ponce de Leon met as he searched for the Fountain of Youth. Tour the William Case House which was built atop of the shell mound and has been restored to its 1921 grandeur.

A peaceful trail walk through an unspoiled mangrove canopy and oak hammock along the Back Bay awaits you at the Matanzas Pass Preserve (239-765-6794). Observe the flora and fauna native to Southwest Florida at this unique park which includes the Estero Island Historic Cottages.

Since the 1950s, Fort Myers Beach has been home to a large fleet of shrimp trawlers that harvest pink gold from the Gulf of Mexico. Dinghy over to San Carlos Island to visit the shrimp boats. Take a self-guided walking tour of working shrimp fleet and don't forget to buy some fresh pink shrimp right at the shrimp docks.

Day 1- Sanibel and Captiva, Florida

If you enjoy shelling, then the beaches of Sanibel Island offer the best location to pursue that hobby in Southwest Florida. If you are new to shelling you will soon learn the Sanibel stoop. As you walk along the beach bending down in hope of finding that rare junonia shell. And if you just want to learn more about shells, visit The Bailey-Matthew Shell Museum on Sanibel (3075 Sanibel Captiva Rd, 888-679-6450).

The only marina on Sanibel is appropriately named Sanibel Marina (239-472-2723, sanibelmarina.com) and is just about a mile away from the Sanibel Lighthouse and across San Carlos Bay from Fort Myers Beach. The marina is also home to Gramma Dot's Seaside Saloon, a local's choice for lunch or dinner (239-472-8138).About 10 miles north on the Gulf Intracoastal Waterway is the island of Captiva. According to local folklore got its name because the pirate Jose Gaspar kept his female captives there for ransom. Dock your boat at the Yacht Harbor at South Seas Island Resort (888-777-3625, southseas.com) and you can enjoy the amenities of one of the Top 10 Beach Resorts for Families. End your day watching a fabulous sunset over the Gulf of Mexico from the resort's beach.

A visit to Captiva is not complete without dinner at The Bubble Room (15001 Captiva Dr., 239-472-5558). Words cannot describe the eclectic nature of this restaurant, seeing is truly believing. From the uniforms of the servers to the restaurant's décor chock full of memorabilia, it is always a night to remember. And do save room for dessert!

Day 2- Cabbage Key, Useppa Island and Cayo Costa

Cruising about 15 miles further north on Gulf Intracoastal Waterway are three unique islands clustered together, each with their own ambiance.

Useppa Island (239-283-1061, useppa.com) is a private island club with Old Florida charm. In the early 1900s it was the center of tarpon sportfishing in Southwest Florida and was owned by wealthy Florida land owner and entrepreneur Barron Collier. The guests at his private retreat included Hollywood stars, tycoons and political bigwigs. Call ahead for dock space at the marina, lunch at the elegant Collier Inn and a tour of the island. You may want to join the club!If your tastes are a bit more laid back, dock at Cabbage Key (239-283-2278, cabbagekey.com) for lunch or dinner. Have a cheeseburger, and discover why it is rumored that after eating here, Jimmy Buffet was inspired to write his song Cheeseburger in Paradise. And if you get bored, try to count the dollar bills plastered all over the bar and restaurant by patrons throughout the years.

Cayo Costa is both a Florida State Park (941-964-0375) that is accessible only by water, and a barrier island with nine miles of pristine beaches and primitive campsites. Anchor for the night at Pelican Bay. If you enter from the north at Pelican Pass you will find deep water and a snug harbor for the night.

Day 3- Boca Grande

Just five miles to the north across Charlotte Harbor is Gasparilla Island with the town of Boca Grande as its heart. Boca Grande looks like a quaint Midwestern town dropped down onto a sandy island, which gives it a uniqueness. Katherine Hebpurn made Boca Grande her winter home and for the former Presidents Bush and their families it is a favorite Christmas holiday destination. The south end of Gasparilla Island at Boca Grande Pass is nexus of professional tarpon fishing tournaments. You may want to try your hand at catch and release with one of the many local fishing charter captains.

You can tie up at Whidden's Marina (941-964-2878, whiddensmarina.com) or Boca Grande Marina (941-964-2100, bocagrandemarina.net) depending on the draft and LOA of your yacht.

While dinner at the Main Dining Room of the Gasparilla Inn is a must, you can also enjoy lunch at Inn's Pink Elephant Restaurant (500 Palm Ave., 877-403-0599). And at the end of the day take a stroll along Lighthouse Beach to search for a fossil shark's tooth, which is a lucky find for beachcombers, and who knows it just may be your lucky day!

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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.

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.

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!

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.

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.

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.

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. 

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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!

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.

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.

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Find a Heavenly Hideaway - Secluded Atlantic Beaches
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Some of the best summer getaways require only the bare essentials: a few towels, sunscreen, and a cooler of cold drinks and snacks. If venturing away from the crowds, unplugged and ready to unwind, is what you’re dreaming about, Marinalife has found idyllic places for you. The following beaches will help you reconnect with nature and discover your happy place in the sun.

DAMARISCOVE ISLAND, ME

As the first island to be inhabited by European fishermen in the 1600’s, Damariscove Island lies six miles from Boothbay Harbor. Because of nesting birds and a fragile ecosystem, the northern half of the 210-acre hourglass-shaped island is restricted. On the southern portion, trails wind along the water’s edge through coastal tundra. The freshwater pond, salt marsh and a cobble beach are perfect for picnicking. At the head of the harbor, a small museum showcases Damariscove’s rich history. A stone pier on the working waterfront welcomes local fishermen. Tie-ups are not permitted here, but the tiny, protected harbor has two courtesy moorings.

BOSTON HARBOR ISLANDS, MA

Many of the three dozen islands spread over 50 square miles of the greater Boston Harbor basin were populated in the 1800s and later deserted during urban migration. Partial foundations and stone walls remain as relics of long-gone days.

Each spot of land has its own appeal. Anchor off Great Brewster Island and trek to the top of 100 foot bluffs for a view of lighthouses across the harbor. The rugged New England coastline and tidal pools of Grape Island, and gorgeous wildflowers on Rainsford Island make brag-worthy photos. Four islands within the park offer moorings, but reserve a spot well in advance. Spectacle Island has a lifeguarded beach as well as breathtaking views from the top of North Drumlin. Graceful granite archways of Civil War era Fort Warren greet visitors to Georges Island. Peddocks Island is appealing for being off the beaten path. Once home to Native Americans, militiamen and prisoners of war, it was used for shooting scenes for the film Shutter Island.

FIRE ISLAND, NY

When cruising the Great South Bay, be sure to visit Fire Island, a thin slice of land off the south shore of Long Island. A home for diverse plants, animals and people for centuries, it has pristine beaches, ancient maritime forests, high dunes and frequent glimpses of wildlife.

Activities on this car-free beach haven include hiking the 40-acre maritime Sunken Forest at Sailors Haven, climbing 182 steps to the top of the Fire Island Lighthouse and soaking up nature on Fire Island National Seashore. Take care not to disturb the piping plover, an endangered migratory shorebird that burrows its nests in the sand of the park beaches. Anchor offshore and wade in, or tie up to the floating dock at Talisman (Barrett Beach). Sailors Haven and Watch Hill Marina are in the park itself.

ASSATEAGUE, MD

The 37 miles of Assateague Island on the Atlantic coastline is part of a barrier island chain extending from Maine to Texas. Assateague Island National Seashore has inviting miles of sandy beaches, salt marshes, maritime forests and an inviting atmosphere, but the real draw is the wild ponies roaming free along the beaches.


The animals are thought to be descendants of horses brought to several remote islands in the late 17th century by mainland owners trying to avoid fencing laws and taxation of livestock. Assateague’s horses are tough enough to survive the scorching heat, exuberant mosquitoes, temperamental weather and poor-quality food on this remote, windswept barrier island. They are truly wild and best admired from afar.

SANDBRIDGE BEACH, VA

Just a few minutes south of Virginia Beach’s festive three-mile boardwalk is secluded Sandbridge Beach. A spectacular hideaway of pristine sand dunes and dancing sea oats, it’s perfect for unwinding with nature.


The beach sits near Back Bay National Wildlife Refuge, home to sea turtles and various bird species, and False Cape State Park. Both have protected areas but welcome kayakers, hikers and fishermen.

MASONBORO ISLAND RESERVE, NC

Just south of the vibrant coastal town of Wrightsville Beach, one of the great hidden gems of the southeast is Masonboro Island, an essentially pristine barrier island and estuarine system. Masonboro Sound’s nutrient-rich waters are an important nursery area for fish including flounder, pompano, menhaden and bluefish.

The beaches along the north and south sound side of the island are the best landing spots for boats. Trails lead cross-island to the beach where visitors can trek along miles of undisturbed ocean shoreline. Inland on the dunes, grassy flats, marsh grass and eelgrass beds, use care that the vegetation and the habitat of nesting loggerhead and green sea turtles are not disturbed.

HAMMOCKS BEACH STATE PARK, NC

Hammocks Beach State Park, known locally as Bear Island, is an untouched beach area accessible only by boat. Try visiting in the late spring or early fall to avoid sweltering heat and overzealous mosquitoes.

The park rents kayaks, canoes, and paddle boards for exploring the Bear Island Water Trail or just meandering marshy waterways. There are no marked hiking paths, but wander through beautiful maritime forests, secret tide pools and endless mudflats. It’s a great place for shell hunters, bird watchers and dolphin lovers.

MORRIS ISLAND, SC

Morris Island’s secluded 840 acres embody the unique ecosystem of the Lowcountry. Located at the mouth of Charleston Harbor and accessible only by boat, the island is actively protected by naturalists and historians, but is constantly under threat of development.

Some deep drop offs in the channels between sandbars make for great shore fishing around the area. Weekend partiers prefer the northern end, while the southern part has hiking trails, peaceful beaches and prime views of the historic Morris Island Lighthouse.

Morris Island has a violent history. In the 1700s, marauding pirates used it as a hideout. And some of the most heroic and consequential battles of the Civil War took place here. Of all the ghost tales told here, it’s been said that some are whispered by the ghosts themselves.

CUMBERLAND ISLAND NATIONAL SEASHORE, GA

Georgia’s largest and southernmost barrier island is located six miles east of St. Marys. Primal maritime forests, wide marshes and unspoiled beaches hum with the tales of previous residents. Indigenous tribes, missionaries, slaves and affluent tycoons have all passed through here.

Over 9,800 acres of Cumberland Island is designated wilderness. You’ll find more than 50 miles of trails for hiking and birdwatching, as well as 18 miles of beach for swimming and beachcombing. Rent a bike and pedal around the island with a stop at Dungeness Ruins, the remnants of steel magnate Thomas Carnegie’s mansion.

The island is only accessible by boat. As the only commercial establishment on the island, Greyfield Inn offers access to 18 miles of beachfront and dockage to its guests.

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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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