Insider Tips

 

Key West, Florida, offers a vibrant array of activities that cater to all interests. From historical sites to outdoor adventures, there's something for everyone. Here are some must-do experiences:

Attend Local Festivals

Key West hosts numerous festivals throughout the year, such as Fantasy Fest and the Key West Songwriters Festival, offering unique cultural experiences.

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Book Tours In Advance

Spots for activities like snorkeling, sunset cruises, and jet skiing fill up quickly, especially during holidays and festivals.

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Bring Water Shoes

Some beaches, like Fort Zachary Taylor, have rocky shorelines. Water shoes make swimming and snorkeling more comfortable.

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Catch the Sunrise At White Street Pier

For a serene start to your day, visit White Street Pier to witness a tranquil sunrise over the Atlantic Ocean.

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Choose the Right Neighborhood

Old Town offers vibrant nightlife and historic sights, while quieter areas like Truman Annex provide a peaceful retreat. Our team can help you pick the perfect vacation rental for your needs.

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Ditch the Car

Parking is limited and expensive in Old Town. Walk, bike, or rent a golf cart to navigate the island with ease.

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Duval Loop Bus

This free shuttle runs through Key West’s most popular areas, making it convenient for sightseeing.

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Embrace Mornings

Want to experience Duval Street without the crowds? Visit early for a peaceful coffee or leisurely breakfast at local cafés.

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Explore Beyond Duval Street

While Duval Street is a must-see, don't miss the quieter neighborhoods like Bahama Village, where you can find local eateries, shops, and cultural sites.

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Happy Hour a Must

Many bars and restaurants offer great deals between 4–6 p.m. It’s the perfect time to sample fresh seafood and refreshing cocktails.

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Pack Light (and Casual)

Key West is laid-back — flip-flops, swimsuits, and casual attire are perfect almost everywhere.

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Reef-Safe Sunscreen

Protect both your skin and the local marine life. Reef-safe sunscreen is required at many snorkeling and diving spots.

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Rent a Bike

Rent a Bike: Navigating the island on two wheels is a convenient and enjoyable way to explore, allowing you to access hidden gems and avoid parking hassles.

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Reserve Your Table

For popular dining spots, especially during peak season, book ahead to avoid long waits.

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Timing Is Everything

The famous Sunset Celebration at Mallory Square begins about two hours before sunset. Arrive in time to enjoy local performers, artisans and prime waterfront views.

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Try Local Favorites

Don’t miss a slice of authentic Key lime pie or conch fritters at iconic local spots. Ask our team for recommendations near your rental!

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Use Our Concierge Services

Looking for the best excursions or dining reservations? Our team is here to help you live like a local while enjoying the comforts of your home away from home.

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Visit During Shoulder Seasons

Visit During Shoulder Seasons: For milder weather and fewer crowds, plan your trip in the spring (May to June) or fall (September to November).

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Visit Lesser-Known Spots

Simonton Street Beach is a local favorite for a quiet sunset, while Indigenous Park offers peaceful nature trails.

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