Island Hopper Songwriter Fest: Where to Eat, Stay and Play

Where to eat, stay and play for the 5th annual songwriters' festival in Southwest Florida.

Written by SLN Staff Writer
Island Hopper Songwriter Fest: Where to Eat, Stay and Play
A songwriter at sunset. Photo by Brian Tietz

Heading to the 5th Annual Island Hopper Songwriter Fest on The Beaches of Fort Myers & Sanibel? Featuring an incredible 10 days of music (from Sept. 21 through Sept. 30) spans some of the area’s most beautiful and relaxing locales, with events in Captiva Island, Downtown Fort Myers and Fort Myers Beach. Nashville favorites like LOCASH, Midland and Travis Denning will play tentpole shows, while singer/songwriters from around the world will perform throughout the fest.

If you aren’t heading south for the show this year, make a plan for 2019. And if you are, we’ve got you covered for all the must-see, must-eat and must-stay spots in the area. Check out our guide below!


Courtesy of Veranda

The Veranda
Nestled in the heart of historic downtown Fort Myers, The Veranda will take you away from the hustle & bustle of everyday life to a bygone era of Antebellum charm. The Veranda’s romantic setting in two turn-of-the-century homes, combined with our Southern Regional Cuisine, an extensive wine list, and first class service staff will provide you with the most unique dining experience in Southwest Florida.


Courtesy of Doc Ford’s

Doc Ford’s Fort Myers Beach
Doc Ford’s Fort Myers Beach sits on the back of beautiful Estero Bay on San Carlos Island and offers the best waterfront dining on Ft. Myers Beach. Arrive by car or boat, experience live music and watch the largest shrimp boat fleet in the U.S. head in and out of the gulf through Matanzas Pass. With seating inside and out, it’s a view you will never forget.

Courtesy of Heavenly Biscuit’s FB page

Heavenly Biscuit
Heavenly Biscuit is a hidden gem famously known for their cinnamon rolls is a pint-sized, daytime eatery serving biscuit breakfasts, bagels and sandwiches in a cheerful atmosphere.


The Clam Shack
The Clam Shack is a casual family-owned restaurant serving up New England seafood on Sanibel Island in Southwest Florida. Nothing’s better after a day at the beach than fresh seafood. Whether you’re in the mood for some fried Ipswich clams, a crisp buttery lobster roll, traditional fish and chips or a little bit of everything, this spot has you covered.

Bubble Room
The Bubble Room has been a whimsical staple on Captiva Island since 1979. The world-famous restaurant that it is today followed a very modest beginning of just a few tables in the front room of the home of the Farqhuarson family. Today’s famous multi-theme restaurant slowly took shape, with crazy collections throughout the space. In fact, many of the spot’s original flair is still on display today, with actual moving trains on all three floors added for kids of all ages. The Bubble Room is a hoot, from toys to photos to…Christmas decor? The front room was decorated for Christmas and the additional theme of “it’s always Christmas at the Bubble Room” took shape with the introduction of many Father Christmases, the Elf Room and year-round Christmas lights. This is a place you have to see to believe, and it’s got historical value, too! The Bubble Room was one of the first buildings in the area to introduce the bright and cheerful pastel colors now widely used throughout the island.

Courtesy of Farmers Market

The Farmers Market
Serving Southwest Florida since 1952, the Farmers Market Restaurant is the longest-operating restaurant in Lee County, serving the finest southern food you have ever tasted. Using recipes passed down generations, diners keep coming back for fantastic home cooking…away from home.


Courtesy of Hotel Indigo

Hotel Indigo
Located in the River District in a historic property across the street from the federal courthouse, the Hotel Indigo Ft. Myers Downtown River District puts you in the heart of it all, near great shopping (including the Post Office Arcade adjacent to the hotel), historic attractions and local businesses. Fittingly, the hotel is inspired by the area’s creative community, and is a stop on Downtown’s monthly Music Walks featuring local musicians. As the only boutique hotel in the neighborhood, Hotel Indigo is passionate about delivering personalized service and amenities beyond the expected.

Courtesy of Island Inn

Captiva Island Inn
Just steps to Captiva Beach and fabulous restaurants, the Captiva Island Inn provides the perfect location in the heart of the beachside Captiva Village. The Captiva Island Inn’s 16 unique one- and two-bedroom cottages and suites sit squarely between the Captiva Island beach on one side and the bay on the other. Either way you go, the scenery is fantastic.

Courtesy of Jensen’s Resort

Jensen’s Resorts
If your ideal vacation is staying directly on a beautiful beach with nothing between you and the gentle Gulf of Mexico surf, seagulls, shelling and breathtaking sunsets, you’ll love Jensens’ unique Beach Resort Suites. (If a casual, laid-back, family-friendly, affordable Captiva Marina Vacation with boating, fishing, manatees & pelicans steps from your cottage door is more your style, there are also 14 Historic Marina Cottages & Suites from which to choose.

Courtesy of Island Inn

Island Inn
Imagine 550 feet of unobstructed beach frontage and 10 acres of property that seems to embrace you with a warm sense of community. A variety of accommodations with traditional amenities are available at Island Inn, each perfect to meet the needs of practically any individual, family or group. And the location can’t be beat.

Courtesy of Outrigger

Outrigger Beach Resort
A tropical paradise is yours to discover at The Outrigger Beach Resort. Located on picturesque Fort Myers Beach, this family-friendly hotel greets you with outstanding service and a vibrant Polynesian flair. Enjoy comfort, value, and good old-fashioned fun throughout the resort, from the 144 guest rooms and efficiencies to the two on-site restaurants and beachside Tiki Bar, which features live music daily.

Courtesy of Castways

Castaways Beach and Bay Cottages
Uniquely nestled where paradise meets paradise—at Blind Pass, where Sanibel meets Captiva—discover Castaways Cottages of Sanibel. Here in a true tropical setting with the Gulf of Mexico to the west and Pine Island Sound to the east, you can choose one-, two- and three-bedroom cottages, efficiencies and guestrooms that combine “Old Florida” charm with the wants and needs of the modern beachgoer. Enjoy the privacy of this Gulf-front location, along with a heated pool, private marina, bicycle rentals, kayak rentals, beach chair rentals, the world’s greatest shelling, sunset strolling plus nearby dining and recreational options.


Courtesy of Captiva Cruises

Captiva Cruises
For over 30 years, Captiva Cruises on beautiful Captiva Island has been providing beach and shelling cruises, island hopping, dolphin adventures and the most dazzling sunsets on the Gulf of Mexico to Southwest Florida visitors. Hop aboard and explore the islands of Cabbage Key, Useppa, Boca Grande, Cayo Costa and Pine Island.

Courtesy of Edison and Ford Winter Estates

Edison & Ford Winter Estates
The Edison & Ford Winter Estates boast over 20 acres of botanical gardens, nine historic buildings (including Edison’s Botanic Research Laboratory and the Edison Ford Museum which contains an impressive collection of inventions), artifacts and special exhibit galleries, not to mention the beautiful landscaping throughout the properties.

Courtesy of J.N. Ding Darling

Kayaking at J.N. Ding Darling
Jay Norwood Darling was instrumental in the effort to block the sale of a parcel of environmentally valuable land to developers on Sanibel Island, and at his urging, President Harry S. Truman signed an Executive Order creating the Sanibel National Wildlife Refuge in 1945. The refuge was renamed in 1967 in honor of the pioneer conservationist. The refuge consists of over 6,400 acres of mangrove forest, submerged seagrass beds, cordgrass marshes, and West Indian hardwood hammocks. Approximately 2,800 acres of the refuge are designated by Congress as a Federal Wilderness Area to safeguard and enhance the pristine wildlife habitat of Sanibel Island, to protect endangered and threatened species and to provide feeding, nesting, and roosting areas for migratory birds. Today, the refuge provides important habitat to over 245 species of birds. See it by kayak for a once-in-a-lifetime experience.

Courtesy of Lovers Key website

Bike riding Through Lovers Key State Park
Once a collection of secluded barrier islands reachable only by boat, Lovers Key’s untarnished two-mile stretch of beach is perfect for swimming, shelling or sunbathing. Away from the shore, there’s even more to love as you can hike the trails or kayak the canals of this genuine tropical paradise. A haven for wildlife, the islands and their waters are home to West Indian manatees, bottlenose dolphins, roseate spoonbills, marsh rabbits and bald eagles. The two mile-long beach is accessible by boardwalk or tram. Black Island has over five miles of multiuse trails for hiking and bicycling, and anglers and boaters can launch their vessels from the park’s boat ramp.

Courtesy of Six Mile Cypress Slough

Six Mile Cypress Slough
The Six Mile Cypress Slough Preserve is over 3,500 acres of wetland ecosystem with a Boardwalk trail and Interpretive Center. The cypress slough catches and slowly filters rainwater on its way towards Estero Bay. A myriad of animals like otters, alligators, turtles, wading birds, and more live at the Slough year-round. Others, like migrating birds and butterflies, use the Slough as a feeding area or a winter home.

Koreshan State Park
A unique experience of how some once opted to live, Koreshan State Park is a fascinating journey back in time. In the late 1800’s, the Koreshan religious sect settled the land adjacent to the Estero River and made it their home. Today 11 of the settlement’s original buildings remain, each grandly restored and registered as national historic buildings. The park also offers many outdoor activities, including hiking, camping, picnicking and fishing. The boat ramp on the Estero River provides access to Estero Bay (Florida’s first Aquatic Preserve) and Mound Key Archeological State Park. Canoe and kayak rentals are available at the Ranger Station for guests to enjoy the river’s serenity and see many of southwest Florida’s wildlife species at a more relaxed pace.