First Time Stay for Three Months

Question

I just booked a three month stay in Key Largo next January until the end of March. It’s my first time visiting the area and I’ve just started my research so am happy to receive any tips and advice for a long term stay. I’m a foodie so looking for good eats, happy hours and live music. I walk a lot and play pickleball and will be travelling with my service dog. I plan to do several day trips to other areas throughout the Keys. TIA for any suggestions you may have.

Answer

Spending January through March in Key Largo is a fantastic choice—quiet enough to feel relaxed, yet full of great food, outdoor activities, and easy access to the rest of the Keys. Since you're staying for three months, you’ll have plenty of time to settle into a routine, explore hidden gems, and enjoy the area like a local.

Key Largo is very walkable in many areas, but it's also spread out along US-1, so having a car is helpful for errands, beaches, and day trips. It’s an extremely dog-friendly community, and many restaurants offer outdoor seating where your service dog will be welcomed. The winter months also have the best weather: warm days, low humidity, and minimal rain.

Below are detailed recommendations for food, happy hours, live music, outdoor activities, pickleball, day trips, and general long-term stay tips.

Foodie Favorites
- Key Largo Conch House – Great for breakfast, brunch, and island-style comfort food with lots of seafood options.
- Sundowners – Sunset dining on the bay, known for fish tacos, conch fritters, and a relaxed waterfront atmosphere.
- Snook’s Bayside – Excellent food plus nightly sunsets; good spot for live music, too.
- Lazy Lobster – Locals love this place for seafood, lobster specials, and casual vibes.
- The Fish House – A Key Largo classic for fresh catch, blackened fish dishes, and Key lime pie.
- Key Largo Fisheries Backyard Café – Top-notch seafood, casual picnic-table dining, usually very dog-friendly.
- Sal’s Ballyhoo’s – Famous for hogfish, conch salad, and old-school Keys charm.
Happy Hours & Live Music
- Gilbert’s Resort – Iconic tiki bar on the water, almost always has live music on weekends and a fun, lively atmosphere.
- Jimmy Johnson’s Big Chill – Large waterfront bar and restaurant with excellent happy hour specials and live entertainment.
- Sundowners – Good happy hour and frequent acoustic performances.
- Snook’s Bayside – Daily live music and sunset views.
- Skipper’s Dockside – Laid-back vibe with regular live music, good cocktails, and a dog-friendly outdoor area.
Walking, Outdoor Activities & Pickleball
- John Pennekamp Coral Reef State Park – Great for walking trails, beaches, kayaking, and snorkeling boat trips. Your service dog is allowed in most outdoor areas.
- Dagny Johnson Key Largo Hammock Botanical State Park – Perfect for long nature walks, birdwatching, and quiet forested paths.
- Rowell’s Waterfront Park – Open waterfront park, great for dog walking and relaxing by the bay.
- Jacobs Aquatic Center – They often have small community events or fitness classes if you enjoy swimming workouts.
- Pickleball – Popular courts can be found at the Key Largo Community Park. Many snowbirds gather there in winter, so it’s a great place to meet people.
Day Trips to Other Keys
- Islamorada (20–30 mins south) – Breweries, art village, great restaurants, and beautiful beaches. Check out Morada Bay Beach Café for a beachside lunch.
- Marathon (1 hour) – Home to Sombrero Beach, Turtle Hospital tours, and Crane Point Hammock.
- Big Pine Key (1.5 hours) – Look for Key deer at the National Key Deer Refuge; Bahia Honda State Park has the best beaches in the Keys.
- Key West (2 hours each way) – A full-day adventure. Enjoy Duval Street, Mallory Square, the Southernmost Point, and plenty of live music. Very dog-friendly, too.
- Key Largo to Flamingo in Everglades National Park (45 mins to Homestead entrance) – Excellent for birding, walking trails, and wildlife photography.
Dog-Friendly Suggestions
- Most waterfront restaurants in the Keys offer pet-friendly outdoor seating.
- Parks like Rowell’s and local beaches accommodate dogs on leash.
- If you want dog-friendly boat tours, several operators in Key Largo and Islamorada welcome service animals (you can call ahead to confirm).
Long-Term Stay Tips
- Grocery shopping: Publix is your main option; there’s also Winn-Dixie and local seafood markets with fresh catches.
- Traffic: January–April is peak season, so weekend traffic along US-1 can be slow. Plan day trips early.
- Community events: Winter months bring farmers markets, art festivals, and small live-music events—worth keeping an eye on local listings and Facebook groups.
- Weather: Even in winter, bring sun protection. Morning and sunset hours are the best for long walks.
- Water sports: Consider trying snorkeling, kayaking, paddleboarding, or a reef cruise—Key Largo is the “Diving Capital of the World.”

With three months in Key Largo, you’ll have the perfect mix of relaxation, good food, community activities, and day-trip adventures. Locals are friendly, winters are beautiful, and the atmosphere is laid-back and welcoming—especially if you love the outdoors and waterfront dining.

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