Ultimate 10-Day Key West Adventure Itinerary

Start your day with a breakfast at Hot Tin Roof Restaurant, offering a delightful start to your morning. Post breakfast, head out for an exciting Key West Dolphin Watching, Snorkeling, and Sunset Cruise. Spend your morning spotting dolphins in their natural habitat and snorkeling in the crystal-clear waters of Key West.

After the cruise, satisfy your hunger with a lunch at Pepe's Cafe, a local favorite with a long-standing history. Then, visit the Key West Shipwreck Treasure Museum to learn about the maritime history of the area and the treasures that lie beneath the sea.

Enjoy a relaxed evening at Schooner Wharf Bar, where you can unwind with a drink and some live music. For dinner, indulge in the fresh seafood at Half Shell Raw Bar, known for its oysters and laid-back atmosphere.

Grab a quick breakfast at Mary Ellen's Bar & Restaurant before heading to the Ernest Hemingway Home and Museum. Explore the house where the famous writer lived and see the descendants of his beloved six-toed cats.

For lunch, visit Island Dogs Bar, a quirky spot with a great menu. Spend your afternoon at the Fort Zachary Taylor, where you can relax on the beach or take a tour of the historic fort.

Dine at Bagatelle, an elegant restaurant with a menu that combines French and local flavors. After dinner, take a leisurely walk to Mallory Square and witness the renowned Key West sunset celebration, complete with street performers and a vibrant atmosphere.

Start your day with an energizing breakfast at The White Tarpon Bar & Restaurant. Post breakfast, head out for the Key West Ultimate Parasailing Experience to get a bird's eye view of the island and its surrounding waters.

After your adventure in the sky, grab a casual lunch at Jack Flats. Spend your afternoon exploring the shops and galleries along Duval Street, stopping for a slice of key lime pie at one of the local bakeries.

For dinner, enjoy the waterfront dining at Boat House Bar & Grill, followed by a fun-filled evening at Key West 2.5-Hour Duval Street Pub Crawl, where you'll experience the lively bar scene and make new friends along the way.

Have a delightful breakfast at McKee's Tiki Bar to start your day. Then, pack a beach bag and head to Smathers Beach for a morning of sun, sand, and relaxation.

For lunch, enjoy the casual atmosphere and fresh seafood at Pirate's Cove Key West. Afterward, take a guided tour of the Key West Lighthouse and Keeper's Quarters Museum to learn about the island's maritime history and enjoy panoramic views from the top.

Dine at Old Town Tavern & Beer Garden, a laid-back spot with a great selection of brews. Cap off the evening with a leisurely stroll along the Edward B. Knight Pier, taking in the sights and sounds of the Key West night.

Start your day with a breakfast at Hard Rock Cafe Key West, where you can enjoy a rock 'n' roll atmosphere. After breakfast, take the Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour to get an overview of the island's main attractions and decide which ones you'd like to explore further.

For lunch, visit Sloppy Joe's, a Key West institution with a lively atmosphere and a menu of classic pub fare. Afterward, spend your afternoon at the Key West Aquarium, where you can see a variety of marine life, including sharks, turtles, and colorful fish.

Enjoy a sophisticated dinner at Tavern N Town, known for its fine dining and extensive wine list. After dinner, if you're in the mood for some entertainment, catch a live performance at a local venue or simply take a leisurely walk through the streets of Key West, enjoying the island's unique vibe.

Start your day with a breakfast at Willie T's, a lively spot with a diverse menu. After breakfast, head out for the Key West Reef Snorkel Morning Tour with Breakfast & Mimosas. Spend your morning exploring the vibrant coral reefs and underwater world of Key West.

After the snorkeling tour, grab a casual lunch at Rams Head Southernmost. Then, spend your afternoon at the Key West Cemetery, where you can take a self-guided tour and learn about the island's unique burial traditions and notable residents.

Dine at Wine-O Bar & Lounge, where you can enjoy a great meal paired with a selection of fine wines. After dinner, take a leisurely drive along the Overseas Highway, enjoying the coastal views and the warm evening breeze.

Start your day with a breakfast at Jack Flats, a local favorite with a diverse menu. After breakfast, visit the Harry S. Truman Little White House for a guided tour, learning about the history of the house and its presidential connections.

For lunch, head to Mel Fisher Maritime Museum [2063], where you can explore the exhibits and learn about the treasures recovered from shipwrecks. Afterward, take a guided tour of the Key West Shipwreck Treasure Museum to delve deeper into the island's maritime history.

Dine at The White Tarpon Bar & Restaurant, known for its fresh seafood and relaxed atmosphere. After dinner, take a stroll through the Key West Historic Seaport, enjoying the sights and sounds of the working waterfront.

Enjoy a breakfast at Southernmost Beach Café, where you can savor your meal with a view of the ocean. After breakfast, head to the Key West Full Day Tour of Key West National Wildlife Refuge for a morning of birdwatching and exploring the diverse ecosystems of the refuge.

For lunch, visit The White Tarpon Bar & Restaurant, a casual spot with a great menu. Afterward, take a guided tour of the Key West Historic Seaport, learning about the island's maritime history and the local fishing industry.

Dine at The White Tarpon Bar & Restaurant, where you can enjoy a delicious meal in a relaxed setting. After dinner, head to Duval Street for a night of bar-hopping and live music, experiencing the vibrant nightlife of Key West.

Enjoy a final breakfast at Blue Heaven, reminiscing about your time in Key West. After breakfast, take a leisurely walk through the Key West Historic District, visiting any spots you may have missed and taking in the unique charm of the island.

For lunch, visit The White Tarpon Bar & Restaurant, where you can enjoy a delicious meal in a relaxed setting. Afterward, take a stroll along the Edward B. Knight Pier, reflecting on your time in Key West and taking in the beautiful ocean views.

Dine at The White Tarpon Bar & Restaurant, where you can enjoy a final meal in Key West. After dinner, head to Mallory Square for one last Key West sunset, joining the crowd to bid farewell to the day and the island.