Explore the Keys

Marathon Bagel

Right behind the house and SO good — everyone's favorite. Closed Mondays.

Sparky's Landing

Waterfront dining with a laid-back Keys vibe and the best happy hour around — $0.45 wings and peel-and-eat shrimp. Often has live music.

Burdine's Waterfront

Great tiki bar upstairs, right on the water — there are usually dolphins or manatees below. Famous fries and Key lime pie.

Island Fish Company

The longest tiki bar in the Keys, bayside at MM 54 — fresh seafood, frozen drinks, and unbeatable Florida Bay sunsets. Open for breakfast, lunch, and dinner.

Porky's Bayside

Waterfront tiki-hut on the bay — BBQ smoked daily, fresh seafood, breakfast through dinner, live music at night, mini golf, and deep-fried Key lime pie. Pet-friendly.

La Isla Tacos

Made-to-order tacos, burritos, and seafood baskets from a food truck with a tiki-bar patio.

Coast to Coast Pizza

The best pizza in Marathon, hands down. Call ahead.

Driftwood Pizza, Pasta & Subs

Pizza, pasta, subs, and calzones — an easy go-to for pizza night.

Conch Custard

Newer ice cream stop for Italian ice and gelato.

Irie Island Eats

A hidden little paradise for fresh, locally sourced bowls and wraps, with cute leafy "Keys" outdoor seating.

Lighthouse Grill

Beautiful marina and lighthouse views at Faro Blanco, with a pool-side setting.

Lazy Days South

Excellent food, right on the water with indoor and outdoor seating. The best place to bring your fish and have them cook your catch.

Frank's Grill

Authentic Italian — no water view, but the food is excellent. We often call ahead for takeout so we get the view right from home.

Florida Keys Steak & Lobster House

No view, but an extensive menu and consistently delicious dinners.

Sunset Grille & Raw Bar

Fun spot at the foot of the Seven Mile Bridge with a pool in the middle. Sunday pool party and live music.

Sweet Savannah's

Ice cream, baked goods, and custom cakes.

The Stuffed Pig

Open for breakfast, with excellent food and cute outdoor seating — a local favorite.

Clouds in My Coffee Catering

Private chef Leigh Ann will cook for you right at the villa.

The Lorelei

Tables in the sand and beautiful bayside views. Look for the giant mermaid on US-1 at MM 82.

Morada Bay

Pierre's or the Beach Café, with tables right in the sand — one of the most beautiful settings ever.

Marker 88

Beachfront dining and amazing sunsets — seafood, prime steaks, and more.

Square Grouper

A newer Islamorada spot for great drinks, salads, and sandwiches — one of our favorites.

Moondog Café

My favorite place to eat in Key West.

Blue Heaven

A Key West institution in Bahama Village — an open-air courtyard with roaming roosters, a famous brunch, and mile-high Key lime pie.

The Boathouse

A local favorite for happy hour — half-off appetizers and drink specials down by the Historic Seaport.

Latitudes

One of the most beautiful settings in the Keys — elegant beachfront dining on private Sunset Key, reached by a short ferry. Lovely for a sunset dinner; reservations required.

Overseas Adventures

My absolute favorite thing to do in the Keys.

Captain Hook's Marina & Dive Center

Family-owned marina at Vaca Cut with boat rentals, snorkel and dive trips, sunset cruises, dive instruction, bait and tackle — and cool fishing shirts.

Captain Pip's Marina & Hideaway

Boat rentals on Florida Bay near the Seven Mile Bridge, plus kayak, paddleboard, and bike rentals, snorkeling, and sunset cruises.

Cat Boat Rentals

Catamaran boat rentals out of the World Wide Sportsman at Bayside Marina in Islamorada.

Epic Daze Sportfishing — Capt. Todd Picariello

Born and raised in Marathon, Captain Todd is the absolute best — beautiful boats and a first-class day on the water.

Snorkel Sombrero Reef

Boat out to the vibrant reef beneath the Sombrero lighthouse — one of the best snorkels in the Keys. Trips leave daily from town.

Kayak & Paddleboard

Paddle the mangrove creeks and shallow flats. Rentals and guided eco-tours available nearby.

Old Seven Mile Bridge & Pigeon Key

Walk or bike the restored historic bridge out to Pigeon Key, once home to the crews who built the overseas railroad.

Publix — Gulfside Village

The main grocery stop for provisioning the kitchen when you arrive.

Winn-Dixie

Another full grocery in town for stocking the villa — produce, deli, and everything for the week.

Bait & Tackle

Local shops for bait, tackle, licenses, and honest advice on where the fish are biting.

West Marine

Boating and fishing gear, safety equipment, and just about everything for a day on the water.

Bayshore Clothing

Family-owned island-lifestyle shop since 1988 — men's, women's, and kids' apparel, SPF sun-protection wear, jewelry, and Keys gifts. Across from the Marathon Airport.

T-Shirt & Sandal Factory

Sandals, tees, beachwear, hats, and sunglasses from all the big brands — an easy stop for anything you forgot to pack.

World Wide Sportsman (Bass Pro Shops)

The Bass Pro Shops flagship in Islamorada — fishing and outdoor gear, apparel, a saltwater aquarium, and a walk-aboard replica of Hemingway's Pilar, with the Zane Grey Lounge upstairs.

Shell World

An 18,000-sq-ft Keys landmark since 1972 — shells, coral, jewelry, home décor, resort wear, and every kind of souvenir. A fun browse on the way up or back.

Ocean Gardens & Gifts

A nautical gallery and treasure hunt — marine antiques, shells, coral art, jewelry, and coastal décor, indoors and across the garden grounds.

Sombrero Beach

The town's main public beach: soft sand, calm swimming water, shaded pavilions, a playground, and free parking.

Coco Plum Beach

A quiet local stretch with shallow water and a protected sea-turtle nesting shoreline.

Curry Hammock State Park

Just east of town: a swimming beach, kayak launch, and nature trails. A favorite for windsurfing.

Bahia Honda State Park

Some of the best beaches in the Keys — soft sand, easy snorkeling, and views of the old rail bridge. Worth the short drive south.

Smathers Beach

Key West's longest public beach — a wide strip of sand along the Atlantic, popular for swimming, sunbathing, and watersports.

The Turtle Hospital

Guided tours of the world's only state-licensed sea-turtle hospital. Meet the rehabbing patients — book ahead.

Dolphin Research Center

Meet the resident dolphins and sea lions through demonstrations and interactive programs.

Florida Keys Aquarium Encounters

Touch tanks, stingray and tarpon feedings, and a coral-reef snorkel tank. A hands-on hit with kids.

Crane Point Museum & Nature Center

Tropical hardwood-hammock trails, a nature museum, and the Wild Bird Center, all bayside in town.

National Key Deer Refuge

A large refuge protecting the tiny Key deer, who often walk right up to visitors. About 20 minutes south.

Locals only: there are always Key deer hanging around the Winn-Dixie parking lot on Big Pine Key.

Islamorada

The sportfishing village up US-1, with beachfront dining and sunsets. See the Eat section for our Islamorada restaurant picks.

Key West

About an hour down. Rent a golf cart or scooter — parking is scarce and pricey (often $20+), so once you park, leave the car. The free Duval Loop bus is an easy way around Old Town, and the Old Town Trolley is a fun hop-on tour.

Bahia Honda State Park

A beautiful public beach with kayaking and snorkeling, and views of the old Bahia Honda rail bridge.

Dry Tortugas National Park

Reachable only by boat or seaplane: Fort Jefferson and some of the bluest water you'll ever see.