Louie’s Backyard
James Beard–nominated Southern coastal cuisine served on a multi‑level deck that kisses the Atlantic.
Insider Tip: Get there early for “golden hour” mojitos; head upstairs for lighter fare and gorgeous views.
Latitudes on Sunset Key
Arrive by ferry, dine alfresco on white linen, and watch the sun sink behind historic Fort Zach.
Insider Tip: Take the ferry to this private island for an unforgettable dinner and sunset.
Café Marquesa
An intimate 40‑seat dining room where locally sourced seafood meets refined Key West hospitality.
Insider Tip: A top pick for special occasions—nothing else on the island compares.
A&B Lobster House
Classic supper-club ambiance overlooking the harbor; famed for butter-poached lobster and an exceptional rum list.
Insider Tip: Follow the jazz upstairs to Berlin’s Cigar Lounge for a perfect nightcap.
Blue Heaven
Bohemian courtyard, roaming roosters, and a legendary lobster Benedict.
Insider Tip: Waiting for brunch? Grab a slice of Key lime pie at the bar—yes, before breakfast.
Dry Tortugas Seaplane
A 40‑minute flight over jade‑green reefs to Fort Jefferson—arrive before the ferry crowds.
Insider Tip: Pack snorkel gear; pilots keep fins on board.
Private Sailing Charter (Danger Charters)
Small-group charters with sandbar snorkeling, backcountry kayaking, and artisan cheese & wine at sunset.
Insider Tip: Ask for the “Wind & Wine” sail—perfect for sunset.
Vandenberg Wreck Dive
Explore one of the world’s largest artificial reefs, 100 feet beneath the surface.
Insider Tip: Nitrox certification extends your dive time.
Backcountry Flats Fishing
Chase bonefish and tarpon in the shallows with veteran guides.
Insider Tip: Peak tarpon season runs April–June. Book early.
Ernest Hemingway Home & Museum
Six-toed cats still roam Papa’s Spanish-colonial estate.
Harry S. Truman Little White House
Presidential retreat where Truman shaped post-war policy.
Key West Lighthouse & Keeper’s Quarters
Climb 88 steps for panoramic island views.
Audubon House & Tropical Gardens
Restored 1840s mansion with original Audubon prints.
Mel Fisher Maritime Museum
Explore treasures from 1622 Spanish galleons, including Atocha emeralds.
Gallery on Greene
Home to fine works by folk-art legend Mario Sanchez and other Key West greats.
The Studios of Key West
Live performances and rotating exhibitions inside a former warehouse.
Rodriguez Cigar Factory
Hand-rolled cigars from Cuban-seed tobacco since 1984.
Kino Sandals
Handmade leather sandals—an Old Town tradition since 1966.
Morning Yoga at Fort Zach Beach
Sun salutations under Australian pines with a sea breeze.
Opal Key Resort Spa Day Pass
Sauna, steam, and cocktails just steps from Mallory Square.
Key West Butterfly & Nature Conservatory
A glass-enclosed tropical oasis with butterflies and flamingos.
Green Parrot
125-year-old dive bar with live blues and no cover charge.
Schooner Wharf
Seafaring vibes, waterfront drinks, and sea-shanty bands nightly.
Little Room Jazz Club
An intimate Duval Street venue with world-class jazz performances.
Nestled just steps from the renowned Duval Street, Casa Catalina is a newly renovated classic conch-style residence, seamlessly blending historic charm with contemporary comforts. This spacious abode, exceeding the typical dimensions of cigar makers’ cottages, boasts a generously sized open-plan layout encompassing the living, dining, and kitchen areas, opening up to a large deck and pool. Casa Catalina provides an ideal retreat for your Key West getaway, offering two bedrooms, two baths, and accommodation for up to six guests. Enjoy the island breeze from your private outdoor space, unwind by the pool, and soak in the laid-back luxury that makes Casa Catalina a one-of-a-kind tropical escape in the heart of Old Town Key West.
Prices start at: $14,700 for 28 nights (+taxes and fees)
Welcome to Brisa Azul (Blue Breeze), a beautifully renovated historic home in the heart of Old Town Key West. Up to 6 guests can unwind in 2 bedrooms plus a cozy den (with convertible sofa), and enjoy 3 full baths, a soaring living area, and fold-away doors leading to a private backyard oasis. Lounge by the heated/chilled saltwater pool, relax under the gazebo with built-in grill and bar area, and take advantage of Wi-Fi, modern appliances, and TVs in every room. Located near the historic Seaport and just a short stroll from Duval Street’s world-class dining and nightlife, Brisa Azul is the perfect base for an unforgettable island getaway with all the modern comforts and tropical charm you could ask for.
Prices start at: $12,600 for 28 nights (+taxes and fees)