SUN & WATER: A FLORIDA INSIDER’S TRAVEL GUIDE

From Orlando theme parks to the Florida Keys, polo fields, hidden beaches, and offshore fishing traditions

Introduction: Florida as a Collection of Worlds

Florida is not one destination—it is several layered into one state.

In a single trip, you can move from Disney fireworks to offshore marlin fishing, from polished resort dining in Orlando to barefoot beach bars in the Keys, from snorkeling coral reefs to watching polo matches in Wellington.

This guide collects years of practical travel notes, reservations, routes, and local favorites across Orlando, Fort Myers, the Florida Keys, and South Florida’s equestrian and polo country.

It is designed less as a brochure and more as a working field guide—built around experience, timing, and the places that consistently deliver.

CHAPTER 1 — ORLANDO: RESORTS, PARKS, AND FAMILY BASE CAMP

Getting There: Airfare & Timing

Airfare for three people was approximately $1,400 in August 2016 for December travel on United, reflecting peak holiday pricing patterns.

Car Rental Strategy

Two main approaches:

1. Costco + Alamo (Preferred Value Option)

  • Premium car rental: about $400 for 13 days (around 2023 pricing)
  • Historically around $1,300 in earlier years
  • Strong value when booked early through Costco travel

2. Membership Fast-Track Rentals

  • Budget or Hertz using personal membership programs
  • Useful when flexibility or upgrades are needed

Where to Stay: Caribe Royale Orlando

A long-time family base in Orlando:

  • Caribe Royale Orlando
  • Address: 8101 World Center Drive
  • Phone: 407-238-8000

Past stay example:

  • 2016: 2 nights for $360
  • Comparable suite pricing in 2023: approximately $225 per night

This property works well for:

  • Disney access
  • Spacious suites
  • Resort-style downtime between park days

Disney & Theme Park Strategy

Key priorities:

  • Disney parade or special event tickets
  • Discovery Cove snorkeling day experience
  • Visit Celebration, the planned Disney town:
    • Walkable shopping
    • Model community architecture
    • Scenic driving tours through residential areas

Dining Near Disney Springs

Raglan Road Irish Pub

Located in Disney Springs:

  • Fish and chips
  • Scallops
  • Irish beer selection
  • Live pub atmosphere

Discovery Cove

A signature Orlando experience:

  • Snorkeling in controlled reef environments
  • Dolphin encounters
  • Tropical lagoon experience

Surf & Water Sports Near Orlando

Surf Lessons & Parks

  • Disney Typhoon Lagoon surf experiences available through Disney programs

Best Nearby Surf Beaches

  • Cocoa Beach (~1 hour, ~$3 tolls)
    • Beginner-friendly waves
    • Cocoa Beach Pier area has softer surf
  • Satellite Beach / Melbourne
    • Better for intermediate to advanced surfers
    • Rock-bottom breaks
  • New Smyrna Beach
    • Most consistent surf in Florida
    • Reliable waves year-round

Surf Rentals

  • Cocoa Beach Surf Company (near Ron Jon’s)
  • Quiet Flight (preferred over Ron Jon’s)
  • Board rentals typically under $20/day

CHAPTER 2 — FORT MYERS & SOUTHWEST FLORIDA

Local Food & Markets

Sun Harvest Citrus

  • 14601 Six Mile Cypress Pkwy
  • Fort Myers, FL
  • Known for citrus products and “orange ice cream”

Fleamasters Flea Market

  • Local shopping and produce sourcing

Restaurants & Dining

  • Fat Katz Sports & Bistro
    • 10080 Daniels International Court, Fort Myers
  • Skip One Seafood
    • 17650 San Carlos Blvd, Fort Myers Beach
  • Sweet Melissa’s
    • Sanibel Island fine dining
  • Lido Beach Restaurant
    • Famous for grouper sandwiches and lobster rolls
  • The Salty Crab
  • Key Lime Shack
    • Fort Myers Beach favorites
  • Owens Fish Camp
    • Sarasota (516 Burns Lane, 941-951-6936)

Outdoor & Activities

  • Legends Country Club (bocce ball)
  • Englewood Beach (famous for shark teeth hunting)
  • Snook One Charters (Capt. Alan Hedstrom, 239-823-9775)
  • Lovers Key Beach is — as the name implies — a romantic 2-mile coast with awe-inspiring pink and orange skies at sunset. It’s ideal for retired couples to stroll the beach and go shelling, or for retired singles to paddle a tandem kayak at the State Park or visit the Discovery Center.
  • Lee County is also home to chic beach towns known for attracting the rich and famous, like Boca Grande. For an elegant night on the water, retirees can spend some of their savings at waterfront restaurants like Eagle Grille & Miller’s Dockside, where guests watch boats sail by while enjoying fresh local grouper and filet mignon. Sitting right between Tampa’s Caribbean-like coastal charm and the wild, untamed beauty of the Everglades, Lee County gives retirees the best of both worlds, right in their backyard.
    Boca Grande is an exclusive, historic village on Gasparilla Island along Florida’s Gulf Coast. Known as the “Tarpon Fishing Capital of the World,” it offers a relaxed “Old Florida” atmosphere characterized by pristine beaches, upscale dining, and local transit via golf carts and bicycles instead of cars.
  • Historic Downtown Venice and shark tooth searching with beach comb on the Venice public beach

Shopping

  • Silver Eagle Florida (Native jewelry)
    • 850 5th Avenue South, Naples

CHAPTER 3 — THE FLORIDA KEYS: KEY LARGO TO KEY WEST

Key Largo: Diving & Snorkeling Base

Morning Star Charters

  • Small sailboat (max 6 people)
  • ~$75 per person (4-hour trip)
  • Focus: non-typical reef snorkeling

Key Largo Highlights

  • John Pennekamp Coral Reef State Park
    • First U.S. underwater preserve (1960)
    • Coral reef sanctuary zones
    • Excellent snorkeling and photography
  • African Queen boat (Bogart film history)
  • Conch House: conch fritters

Lodging

  • Ocean Pointe Suites (2-bedroom condos with kitchens)
  • Key Lime Sailing Club (hidden gem lodging)

Slow Down, Kick Off Your Shoes: A Lifestyle Guide to Islamorada, Florida

There’s a particular kind of stillness that settles over you in Islamorada. Maybe it’s the lack of high-rises. Maybe it’s the salt in the air, or the way every conversation seems to eventually circle back to what’s biting today. Whatever it is, this string of six islands in the Upper Florida Keys has built an entire identity around one simple idea: let the water set the pace.

Sitting roughly 85 miles south of Miami and 80 miles north of Key West, Islamorada skips the resort-town glitz in favor of something more textured — working art studios, weathered dockside bars, and eighteen miles of shoreline that locals treat like sacred ground. It’s Old Florida with salt-crusted edges, and once you’ve spent a few days there, it’s easy to understand why so many visitors never really leave.

Pines & Palms Resort feels like staying at a friend’s beach house, if that friend happened to have impeccable taste. The oceanfront cottages date back to the 1930s and got a fresh design update in 2025, but the mom-and-pop warmth never left — think poolside tiki bar, breezy porches, and a small boutique stocked with local art. Borrow one of the resort’s bikes and you can pedal into the quaint downtown strip in minutes.

For something more polished, Cheeca Lodge & Spa spreads across 27 oceanfront acres with a nine-hole golf course, three pools, a full spa, and a standout restaurant built around the day’s catch. It’s the kind of place equally suited to a honeymoon or a family reunion.

Islander Resort splits the difference — 24 acres of vintage charm freshened up with modern touches like pickleball courts and a saltwater pool terrace. With more than 100 rooms and villa-style suites, it’s built for travelers who want room to spread out.

Islamorada’s soul lives in its art. The Morada Way Arts & Cultural District is often described as the only real “Main Street” between Miami and Key West — six blocks of studios, galleries, restaurants, and live music that transform a once-sleepy stretch of road into a nightly gathering spot. On the third Thursday of every month, the district throws an Art Walk full of local work, music, and color spilling out onto the sidewalks.

Water, unsurprisingly, dominates everything else. Charter outfits like Bamboo Charters run family-friendly fishing, snorkeling, and sightseeing trips, often led by guides with real marine-biology chops. Reef systems and snorkeling trails sit just offshore, reachable by boat or kayak for travelers who’d rather explore under their own power.

History buffs have two solid stops: the History of Diving Museum, wrapped in an underwater-themed mural and stuffed with centuries of dive gear, treasure-hunting tools, and a genuine bar of silver you can lift yourself; and the Florida Keys History & Discovery Center, tucked inside the Islander Resort, which walks through the region’s layered past — Indigenous history, Spanish shipwrecks, Henry Flagler’s railway, and the devastating 1935 hurricane — with a small theater and rotating exhibits.

And then there’s Robbie’s, the closest thing the Keys have to a local institution. Part market, part marina, part fish-feeding spectacle, it draws crowds who come specifically to toss bait to tarpon large enough to leap clear out of the water.

Skip the strip malls entirely. World Wide Sportsman, now under the Bass Pro Shops umbrella, is an angler’s fever dream — rods, reels, resort wear, and a working marina with charter guides on standby.

For something more whimsical, Rain Barrel Village is worth the stop for Betsy alone: a 30-foot spiny lobster sculpture that’s become one of the most photographed roadside oddities in the Keys. Behind her sits a cluster of pastel shanties turned artist studios and shops, operating since 1978, where you can watch glassblowers at work and browse handmade ceramics and textiles.

A Literary Footnote: Hemingway’s Islamorada

Ernest Hemingway is inseparable from Key West, but his fishing obsession also left fingerprints further up the island chain. Islamorada has long billed itself as the sportfishing capital of the world, a reputation built in large part on the same offshore waters that drew Hemingway to buy his fishing boat, Pilar, in 1934 and chase marlin, sailfish, and tuna throughout the Keys. Fittingly, a sister ship to the original Pilar now sits on display at World Wide Sportsman, giving anglers a chance to see the kind of vessel that shaped some of Hemingway’s best-known adventures on the water. The connection runs deep enough that Islamorada’s own History of Diving Museum has hosted talks specifically on Hemingway’s time fishing the Keys — proof that his legend still has a current in these waters, even outside Key West city limits.

Eating Like a Local

Sunset and seafood go hand in hand here. Lazy Days delivers laid-back beach-bar energy with surprisingly refined fish dishes — try it “Lazy Style,” topped with tomatoes, scallions, mushrooms, garlic, and Key lime butter.

Lorelei Restaurant & Cabana Bar, marked by a giant mermaid statue, is where fishing guides, longtime locals, and the occasional VIP all end up at golden hour, frozen drinks in hand, while a band plays from the dockside stage.

Chef Michael’s, hidden inside a cottage in the arts district, takes sourcing seriously — signature dishes rotate around whatever local fishermen bring in that day, from hogfish to lionfish to snowy grouper.

Square Grouper Islamorada leans into the town’s smuggling-era history with a name that winks at the past, paired with high-end coastal cooking, jellyfish-shaped chandeliers, and panoramic sunset views over the marina.

When to Go

April hits the sweet spot — warm water, manageable heat, and crowds that haven’t yet arrived in full force. It’s also when Island Fest takes over Founders Park with two days of art shows, a car rally, sandcastle contests, and a cook-off between local chefs.

If solitude is the goal, September through November is quietest — but that’s also peak hurricane season, running officially from June through November, so keep an eye on the forecast.

Getting There and Getting Around

Islamorada sits about 90 minutes by car from both Miami International Airport and Key West International Airport, connected by the scenic Overseas Highway. A rental car is essential for reaching state parks, hidden beaches, and roadside fish shacks scattered along the island chain, though the town center itself is walkable and bike-friendly — several hotels, including Pines & Palms, offer bikes free of charge.

For getting around without a car, Freebee runs a free on-demand electric shuttle service roughly from 7 a.m. to midnight, and Uber and Lyft both operate throughout the Keys. Shuttle companies also run scheduled routes between the two major airports for travelers skipping the rental car altogether.

Robbie’s Marina

  • Tarpon feeding experience
  • Admission ~$1
  • Fish buckets ~$3
  • Famous “Scarface” tarpon story (historic resident fish tradition)

Other Activities

  • Rain barrel art shops
  • Cheeca Spa
  • Catch-and-cook restaurants
  • Marina fish viewing (3–4 PM daily catch arrivals)
  • Island rentals and private stays

Marathon

  • Sombrero Beach
  • Turtle Hospital (turtle releases)
  • Aquarium Encounters
  • Dolphin Research Center (Grassy Key)
  • Stone crabs and Key West pink shrimp

Lower Keys

  • No Name Pub
  • Sugarloaf Marina kayaking
  • Mahi mahi fishing opportunities

Key West

Top Experiences

  • Conch Train tour
  • Hemingway House
  • Mallory Square sunset
  • Dry Tortugas / Fort Jefferson (Yankee Freedom ferry)
  • Sunset sailing (America 2.0)

Food Highlights

  • Key lime pie (including chocolate-dipped versions)

Travel Notes

  • Ft. Myers to Key West boat: ~3.5 hours, $125/person, 5-hour visit option
  • Driving: ~5 hours without stops

CHAPTER 4 — POLO & SOUTH FLORIDA EQUESTRIAN LIFE

Florida Polo Club Network

Major clubs include:

  • International Polo Club Palm Beach
  • Grand Champions Polo Club
  • Palm Beach Polo Club
  • Sarasota Polo Club
  • Vero Beach Polo
  • Everglades Polo Club
  • Wellington-based clubs (Escue, El Rey, Santa Clara, South Forty, etc.)

Wellington: Polo Headquarters

Dining

  • Bonefish Mac’s Sports Grille (10880 Forest Hill Blvd)
  • Riggins Crabhouse (pier dining, Lantana)

Equestrian & Polo Shopping

  • US Polo Assn. store
  • Nano’s Mallets (Wellington)
  • DerDau (boots/leather goods)
  • The Tackeria (best polo ball pricing)
  • Polo Gear showroom (team discounts available)
  • Tato’s Mallets
  • La Martina store

Polo Venues

  • International Polo Club Palm Beach
  • Wellington polo barns and training facilities

Nearby Attractions

  • Lion Country Safari (drive-through wildlife park)

Hotels Near Polo Grounds

  • Royal Inn Hotel (Royal Palm Beach)
    • ~$134/night (2016)
    • Budget option near equestrian areas

CHAPTER 5 — FISHING & MARINE LIFE (STATEWIDE)

Deep Sea Fishing Culture

Florida’s offshore fishing includes:

  • Marlin
  • Mahi mahi
  • Tuna

Charter insights:

  • Experienced captains often matter more than boats
  • Early morning departures (3:00–6:00 AM common)
  • 8-hour trips recommended for success

Key Charter Operators

  • Die Hard (high-intensity early departures)
  • Action (value-focused)
  • Ho’okela (experienced captain reputation)
  • Start Me Up (fast, reliable boats)
  • Reel Lucky / Lucky Strike II
  • Hinatea, Kai Akua, No Problem, Desperado

Bottom Fishing Options

  • Strike Zone (includes lunch)
  • Marjorie Ann (4-hour private trips)
  • Hokua catamaran trips
  • Sunset fishing (Ho’okela)

CHAPTER 6 — TRAVEL NOTES & TRADITIONS

Across Florida trips, several recurring themes emerge:

  • Costco provisioning runs on arrival
  • Surf gear, liquor, and Christmas meal supplies
  • Holiday traditions (Santa photos, themed beachwear)
  • Banana bread, pie stops, and roadside food culture
  • Mixing structured resort days with spontaneous exploration

Conclusion: Florida as a Network of Experiences

Florida is not one story—it is many overlapping ones.

Orlando delivers structured entertainment and resorts. Fort Myers offers coastal seafood culture. The Keys provide diving, fishing, and slow-water living. Wellington represents equestrian tradition. And everywhere in between are beaches, markets, marinas, and local characters that define the state’s rhythm.

The best way to experience Florida is not to rush it—but to move between its worlds intentionally, letting each region reset the pace of the trip.

And like all great travel systems, the real value is not just in the destinations—but in the traditions that repeat each year.