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3-Day Dog-Friendly Key West Itinerary

Viewed by 240 travelers

Day 1: Arrival and Exploration

Key West, Florida

9:00AM

Breakfast at Sarabeth's

Start your vacation with a delicious breakfast at Sarabeth's, known for its dog-friendly outdoor seating and amazing fluffy pancakes.
Head east along Fleming Street from your lodging to reach the restaurant.
USD20, 1 hour

10:30AM

Explore Dog Beach

After breakfast, take your furry friend to Dog Beach, the perfect spot for them to splash around and meet other dogs while you soak up the sun.
From Sarabeth's, head south on Whitehead Street until you hit the beach.
Free, 2 hours

1:00PM

Lunch at The Green Parrot

Grab lunch at The Green Parrot, a local favorite with a pet-friendly patio where you can enjoy a Cuban sandwich while your dog lounges at your feet.
Take a leisurely stroll back up Whitehead to Southard Street.
USD15, 1 hour

2:30PM

Visit Fort Zachary Taylor Historic State Park

Post lunch, visit this beautiful park where you can both enjoy walking trails and lovely beach areas.
Drive or bike to the state park entrance at 601 Howard England Way.
USD6 per vehicle, 2 hours

5:00PM

Sunset Celebration at Mallory Square

Wrap up your day at Mallory Square where you can enjoy the local performers and stunning sunset views with your pup by your side.
Drive or walk to Mallory Square, located at the waterfront.
Free, 2 hours

7:30PM

Dinner at The Lobster Shack

Finish off with dinner at The Lobster Shack, which offers a dog-friendly patio and fantastic seafood dishes.
A short walk back towards Duval Street.
USD25, 1.5 hours
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Day 2: Adventure and Relaxation

Key West, Florida

8:00AM

Breakfast at Blue Heaven

Start your day with breakfast at the quirky Blue Heaven, famous for its outdoor seating and delicious Key Lime pie pancakes.
Head east on Thomas Street from your hotel.
USD18, 1 hour

9:30AM

Snorkeling Trip

Enroll in a dog-friendly snorkeling tour where your pet can either keep you company on the boat or stay at a nearby pet-sitting service while you explore the underwater beauty.
Meet at the designated tour spot on Front Street.
USD75 (plus pet-sitting fee if necessary), 3 hours

1:00PM

Lunch at Conch Republic Seafood Company

Refuel with a hearty lunch at Conch Republic Seafood Company, which has dog-friendly outdoor dining and serves fresh conch fritters.
A short walk along the waterfront.
USD20, 1 hour

2:30PM

Visit the Ernest Hemingway Home and Museum

After lunch, take a stroll to the Ernest Hemingway Home where leashed dogs are welcome to explore the gardens while you admire the historic site.
Walk up Whitehead Street to the museum location.
USD14, 1.5 hours

4:00PM

Relax at Dog Park

Visit the dog park at the end of your day, a great place for your dog to run free and socialize.
Head to the dog park at 2626 North Roosevelt Blvd.
Free, 1 hour

6:00PM

Dinner at Santiago's Bodega

Enjoy dinner at Santiago's Bodega, which offers a cozy atmosphere and an outdoor patio perfect for dining with your dog.
Drive back towards downtown along the boulevard.
USD30, 1.5 hours
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Day 3: Fun and Leisure

Key West, Florida

8:00AM

Breakfast at The Cafe

Savor a healthy breakfast at The Cafe, featuring a pet-friendly patio and vegan options that everyone can enjoy.
Take the scenic walk along the water from your accommodation.
USD15, 1 hour

9:30AM

Kayaking at Key West Kayak Tours

Join a kayak tour that allows pets, where your dog can enjoy the beautiful waters of Key West right alongside you.
Meet at the kayak rental location on the harbor.
USD50 (plus fee for dog gear if required), 2.5 hours

12:00PM

Lunch at Louie's Backyard

Have a delightful lunch on the beachfront patio at Louie's Backyard, known for its relaxing vibes and seafood dishes.
Head south along the coast to the restaurant.
USD28, 1.5 hours

1:30PM

Relax at the Beach

Enjoy a relaxing afternoon at the nearby Higgs Beach, where your dog can play and frolic in the sand.
Exit from Louie's and take the coastal path to the beach entrance.
Free, 2 hours

3:30PM

Visit The Southernmost Point Buoy

Take a stroll to the iconic Southernmost Point Buoy for a photo op, where dogs are welcomed to accompany you for this must-see landmark.
Walk up Whitehead Street to the landmark.
Free, 1 hour

5:00PM

Dinner at the Dog House

End your trip with dinner at the fun and casual Dog House, known for its hot dogs and inviting ambiance, perfect for you and your dog.
Take a quick walk back to your lodging area.
USD10, 1 hour
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