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    • Day Trip to Havana!
    • Golf Cart Rental
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    • Dolphin Watch & Snorkel
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    • All Male Private Boat Charter
    • All-Male Sail, Snorkel, Paddle Adventure
    • Ghost Trolley Tour
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    • Jet Ski Tour
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    • Wine Tasting Sunset Sail
    • Paddle the Mangroves
    • Parasailing
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    • Sail, Kayak, Snorkel Eco Tour
    • Schooner Sunset Sail
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  • Live Like A Local Key West Vacation Special

    4 Day | 3 Night Package $2,795
    Single or Double Occupancy
    Live Like A Local Vacation Special includes:

    1. Waterfront accommodations located in the historic district.

    2. Premium golf cart rental to cruise around town.

    3. Private boat charter to explore sandbars and remote islands.

    4. Classic schooner sunset sail.
    Reserve Today More Details
    Key West vacation
    • Accommodations
      Old Town Resort
    • Transportation
      Golf cart
      Performance Golf Cart
    • Dining
      Best Local Recommendations
    • Adventures
      On the Water
    Additional Package Details

    Here’s what your vacation will look like:

    Day 1:

    Arrive Key West Airport
    Pickup Golf Cart at OurKeyWest Lounge & Galleria
    12:00pm Head to Lunch*
    4:00pm Check-in at your Resort
    4:15pm Enjoy the famous Key West Sunset Celebration*
    6:00pm Dinner*
    7:30pm- Check out Hank’s Hair of the Dog Saloon*

    Day 2:
    8am: Breakfast*
    9:30-11:00am Key West Custom’s House Exhibition*
    11:00am Early Lunch*
    12:30pm Arrival for your Private 4-hour Boat Charter
    1:00-5:00pm Private Boat Charter
    6:00pm Dinner*
    7:30pm- Hang with the locals at the Green Parrot Bar*

    Day 3:
    8:00am Breakfast*
    9:30am Bike Tour*
    1:00pm Lunch*
    2:30-4:00pm Shopping/ Siesta*
    4:00pm Check in for Sunset Sail
    4:30-6:30pm Sunset Sail
    7:00pm Dinner*
    8:30pm Show at La Te Da*

     

    Here’s a more in depth look at the important stuff:

    Accommodations:  Situated within a working cruise ship port just steps from Key West’s famous Mallory Square and one block from Duval Street, this luxurious resort in the heart of Old Town Key West has it all, from enticing, globally-inspired waterfront cuisine to a sparkling pool surrounded by lush plant life. Dining, dancing, historical architecture, and wonderful galleries are all at your doorstep.**

    Transportation: Golf carts are a fun way to discover all the best spots in Key West. Take this 4 seater golf cart anywhere on the island to enjoy dining, parks, beaches, or even a Duval cruise.

    Dining: We’ll infuse your vacation with fun, locally-inspired dining experiences that will take you on an exciting culinary journey.

    Adventures:

    • Sunset Sail: This public sunset sail features an array of fine wines and upscale beers from around the world, complemented by bountiful hors-d’oeuvres that will arouse your palate. All this while sailing under a cloud of canvas aboard a beautiful, Key West Schooner.
    • Private Boat Charter: Guided by a local captain, you will enjoy a private 4-hour day exploring the beautiful, crystal clear waters surrounding Key West. With this private charter, you get to choose how you spend your time on the water! Dolphin watching, snorkeling, relaxing on the sandbar and even visiting secluded beaches!

    *Recommendations only.

    **Package estimates are based on arrival dates, availability and room type. Exact prices will be determined prior to purchase.

     

    Local Key West vacation experts are here to help plan the perfect getaway just for you.
    Reserve Today More Details FAQ's
  • Havana Hemingway Excursion

    4 Day | 3 Night Package $4195
    Single or Double Occupancy
    Havana Day Trip Vacation Special includes:

    1. Waterfront Key West accommodations located in the historic district.

    2. Premium golf cart rental to cruise around town.

    3. Day Trip to Havana.

    4. Classic schooner sunset sail.
    Reserve Today More Details
    Havana Day Trip
    • Accommodations
      Old Town Resort
    • Transportation
      Golf cart
      Performance Golf Cart
    • Dining
      Best Local Recommendations
    • Adventures
      classic car in havana
      Cultural Tour
    Additional Package Details

    Here’s what your Havana Day Trip vacation will look like:

    Day 1:
    Arrive Key West Airport
    Pickup Golf Cart at OurKeyWest Lounge & Galleria
    12:00pm Head to Lunch*
    4:00pm Check-in at your Resort
    4:15pm Enjoy the famous Key West Sunset Celebration*
    6:00pm Dinner*
    7:30pm- Check out Hank’s Hair of the Dog Saloon*

    Day 2:
    8am: Breakfast at SaraBeth’s*
    9:30am Bike/Walking Tour*
    12:00pm Lunch*
    4:00pm Check in for Sunset Sail
    4:30-6:30pm Sunset Sail
    7 PM: Dinner*

    Day 3:
    7:00am Check-in for Havana Day Trip
    8:00am Departure for Havana Day Trip
    6:00pm Arrive in Key West from Havana
    7:30pm Dinner*

    Here’s a more in depth look at the important stuff:

    Accommodations:  Situated within a working cruise ship port just steps from Key West’s famous Mallory Square and one block from Duval Street, this luxurious resort in the heart of Old Town Key West has it all, from enticing, globally-inspired waterfront cuisine to a sparkling pool surrounded by lush plant life. Dining, dancing, historical architecture, and wonderful galleries are all at your doorstep.**

    Transportation: Golf carts are a fun way to discover all the best spots in Key West. Take this 4 seater golf cart anywhere on the island to enjoy dining, parks, beaches, or even a Duval cruise.

    Dining: We’ll infuse your vacation with fun, locally-inspired dining experiences that will take you on an exciting culinary journey.

    Adventures:

    Sunset Sail: This public sunset sail features an array of fine wines and upscale beers from around the world, complemented by bountiful hors-d’oeuvres that will arouse your palate. All this while sailing under a cloud of canvas aboard a beautiful, Key West Schooner.
    Havana Day Trip: Spend a fascinating day in Havana, following in the footsteps of Ernest Hemingway. Join our guided Hemingway Literary Excursion as we explore the cultural and historic connections between Cuba & Key West, and supporting the Cuban people’s newfound entrepreneurial spirit.

    *Recommendations only.

    **Package estimates are based on arrival dates, availability and room type. Exact prices will be determined prior to purchase.

    Local Key West vacation experts are here to help plan the perfect getaway just for you.
    Reserve Today More Details FAQ's
  • The Big Fishing Trip

    4 Day | 3 Night Package $3995
    Single or Double Occupancy
    Professional Fishing Vacation Special includes:

    1. Waterfront accommodations located in the historic district.

    2. Premium golf cart rental to cruise around town.

    3. Two Days of Professional Fishing Charters.

    4. Classic schooner sunset sail.
    Reserve Today More Details
    sport fishing in key west
    • Accommodations
      Old Town Resort
    • Transportation
      Golf cart
      Performance Golf Cart
    • Dining
      Best Local Recommendations
    • Adventures
      Trophy Hunting
    Additional Package Details

    Here’s what your Ultimate Fishing vacation will look like:

    Day 1:

    Arrive at the Key West Airport
    Pickup Golf Cart at OurKeyWest Lounge & Galleria
    12:00pm Head to Lunch*
    4:00pm Check-in at your Resort
    4:15pm Enjoy the famous Key West Sunset Celebration
    6:00pm Dinner*
    7:30pm- Check out Hank’s Hair of the Dog Saloon*

    Day 2:
    7:30am: Check in for 3/4 day private Professional Fishing Charter
    8am – 2 pm Professional Fishing Charter
    2:15pm Lunch*
    Siesta
    6:00pm Dinner*
    7:30pm- Hang with the locals at the Green Parrot Bar*

    Day 3:
    7:30am: Check in for 3/4 day private Professional Fishing Charter
    8pm – 2pm Professional Fishing Charter
    2:15pm Lunch*
    Siesta
    7:00 PM Dinner*
    8:00:00-10:30pm Pub Crawl

     

    Here’s a more in depth look at the important stuff:

    Accommodations:  Situated within a working cruise ship port just steps from Key West’s famous Mallory Square and one block from Duval Street, this luxurious resort in the heart of Old Town Key West has it all, from enticing, globally-inspired waterfront cuisine to a sparkling pool surrounded by lush plant life. Dining, dancing, historical architecture, and wonderful galleries are all at your doorstep.**

    Transportation: Golf carts are a fun way to discover all the best spots in Key West. Take this 4 seater golf cart anywhere on the island to enjoy dining, parks, beaches, or even a Duval cruise.

    Dining: We’ll infuse your vacation with fun, locally-inspired dining experiences that will take you on an exciting culinary journey.

    Adventures:

    • Professional Fishing Charters-You will enjoy 2 – 6 hour professional fishing charters aboard a 30’+ custom-built SeaVee center console. They are powered by twin Yamaha outboards, have nice size T-Tops to provide shade & full clean heads. You can choose deep sea, wreck & reef or bottom fishing. All the gear, bait, fuel & captain is included.
    • Pub Crawl-This 2 1/2 hour event begins downtown, moves through the historic seaport and then returns to Duval Street. Everyone will have a choice of a domestic beer or mixed drink at each bar. Enjoy the sites and bars of Key West with our “masters of mixology” as you embark on your party in paradise.

    *Recommendations only.

    **Package estimates are based on arrival dates, availability and room type. Exact prices will be determined prior to purchase.

     

    Give us a call to answer any questions or customize your Trip. You're gonna have a great time on our Island.
    Reserve Today More Details FAQ's
okw magazine spread
FREE WELCOME GIFT BAG
Your Vacation Special includes a complimentary Welcome Gift Bag at check-in, a copy of OurKeyWest Magazine, and a cold beverage at our Welcome Lounge & Galleria in the heart of Old Town Key West.

Planning a Trip to Key West?

Let us know when you're thinking about coming, and we'll help you create the perfect Key West adventure. It's what we do :)

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Lexi Roberts, OKW Concierge specialist
Your Local Concierge,
Lexi Roberts

The staff at Our Key West is exceptional and know the meaning of excellent customer service.

-Del Arnold

These Folks are Super Cool!

-Annie

Their shop is dope.

-Francesca from Pittsburgh

We had such a great time on the Havana Day Trip! This is a must do on everyone's bucket list.

-Steven Michelin

-

Let's Connect!

Party Invites • Fishing Videos • Stories from Havana • Original Music • New Works of Art • Join our Happy Hour
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About Us

Local since 1974, we create guest experiences that emphasize the natural world, art, music, food, history, and local characters. We provide premium concierge services, and serve as market-maker for a select pre-screened portfolio of the island’s best guest activity providers. We have a commitment to the highest hospitality standard, providing personalized guest support daily from 8am to 6pm.

Learn More
Activities
  • Havana Day Trip
  • Fishing Charters
  • Golf Cart Rental
  • Boat Rental
  • Paddle the Mangroves
  • All Day Watersports Adventure
  • Dolphin Watch & Snorkel
  • Key West Bike Tour
  • Bike Rentals
  • Bike Rentals
  • Personal Chef & Catering
  • Sky Dive
  • Key West Private Boat Charter
  • Schooner Sunset Sail
  • Dry Tortugas- Ferry
  • Jet Ski Tour
  • Schooner Sunset Sail
  • Gallery Stroll & Art Tour

Contact Info

Our Key West logo

613 Simonton St
Key West, Florida 33040

(305) 290-2049

PROUD MEMBER OF

Key West Business Guild Key West Attractions Association

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