Frequently Asked Questions

Key West Transportation



    Yes! You’ll want to have transportation while your in Key West to make your experience more fun and enjoyable.

    Why is a Golf cart the best choice for transportation in Key West?
    Since Key West has a lot more to see than just Duval Street, having a fun and safe way to get around to all the best spots will provide additional opportunities for fun. There are beaches & parks for swimming & snorkeling, restaurants & bars, museums and historic houses, and the popular Southernmost Point. Because some point of interest are close but others are spread out on the island,  walking around the island to see everything can be very challenging when it’s hot outside. So, if you want to see as much as you can without wearing yourself out, rent a golf cart.

    Can golf carts really be fun and safe?

    Absolutely! When cruisin’ around with your family and friends to check out ALL the best spots, you’ll really enjoy having the shade from the canopy and feeling the salty breeze. Additionally, riding in a golf cart makes sightseeing much easier because you have more visual area than riding in a car. The best part is that golf carts are easy to drive, and are street legal with all the required safety additions. They’re safer for families who want to travel together than bikes, and the best way to get around for those who have mobility issues.

    Where should I go on a golf cart?

    Some of my favorite spots to take a golf cart ride to are Ft Zachary Taylor State Park to enjoy the view of the historic Key West Harbor, Higgs Beach Park for snorkeling off the beach, and Salute on the Beach! for lunch and a glass of wine. I have a lot more special spots that I can share with you depending on your interests.  😎

    Where can I rent a golf cart?

    Directly from me, a local in Key West. Let me set up the perfect rental for you and your group. My free concierge service is available to anyone and there are no hidden fees. Golf cart rentals are available in gas & electric versions, and can come with 4, 6 or 8 seats. Additionally, you can rent golf carts for 3, 5, 8 hours or daily and it will also include Free Delivery!

    Call Me directly for best rates: Bethany @ 305-290-2049 or DM for me more info.

    Looking for more recommendations or help planning your Key West vacation?
    Use our FREE Vacation Planner:

    Check out our vacation planner for help planning your Key West vacation:

Uncategorized FAQ

  • Havana Day Trip

    Do I need advanced reservations? Absolutely. This is a very popular, small group excursion with very limited availability. Booking as far in advance as possible is recommended.

    Can I go any day of the week on the Day Trip to Havana? No, Havana Day Trips depart on Tuesdays & Fridays only. You can inquire about private Havana Day Trips, which fly most week days, depending on availability.

    What’s included in the Havana Day Trip? An amazing day full of rich culture & history. Airfare, Visa & all required documentation, all transportation, private guide in Cuba, entry to all museums & points of interest, all US & Cuban government taxes, lunch & drinks.

    Are there any additional fees or costs beyond the $1195 trip cost? No, the Havana Day Trip is an all-inclusive trip. There will be no additional costs.

    How many seats are there on the airplane? We have two aircraft, a 5 passenger & a 10 passenger plane. The size of the plane is determined by the amount of passengers on the trip.

    Is there a passenger weight limit on the airplane? No, there is not a weight limit per se, but there is a size consideration. The aircraft are small, so if you require additional space, please purchase an additional seat. Additional seats would be sold at the full ticket purchase price.

    What time is check-in for the Havana Day Trip? 7:00 am sharp. Please do not be late.

    Where do we check in at the Key West airport? Signature Flight Support, private terminal building at the Key West Airport. 3471 S Roosevelt Blvd, Key West, FL 33040 Map & Directions

    Where do we park at the Key West Airport?

    Driving Directions: Turn into the main entrance of Key West International Airport. At the first stop sign, stay on the ground level towards arrivals. Drive under two walkways.

    Parking a car: follow the signs to Short Term Parking. From the parking lot, look for the old control tower. The private terminal building is located just to the right and past the old control tower. The Signature Flight Support logo will be found on the outside of the building.

    Dropping off: as you drive under the second walkway, get in the right lane and drive straight past the regular baggage claim and stop at the old control tower. The Signature Flight Support private terminal building is located just to the right and past the old control tower. The Signature Flight Support logo will be found on the outside of the building.

    What’s the weather like in Havana? Very similar to Key West temperatures. In the city, it can feel hotter. The summer months are warm & humid.

    What should I wear on the trip? Loose fitting, breathable fabrics, closed-toe shoes, hat, & sunscreen. A small umbrella can be helpful during the warmer months for shade.

    Can I bring my cellphone to Havana? Yes, but cell service may be limited to none. Great for taking photos during your trip.

    Can I bring snacks and drinks on the trip? You can bring prepackaged foods that are sealed. Please, no fruits, vegetables, or beverages. Water will be provided for you. You can purchase additional beverages throughout the day.

    Can I bring back cigars & rum from Cuba? NO. US Customs does not allow the import of any tobacco or alcohol from Cuba. But you can enjoy them during your Day Trip to Havana.





  • What are the Best Dog Parks in Key West?

    What are the Best Dog Parks in Key West?

    Higgs Beach Dog Park & Dog Beach 🐶

    Higgs Beach Dog Park Key West has two fully enclosed areas.
    Key West Dog Parks

    Dog Beach Key West is the only dog-friendly beach
    Key West Dog-Friendly Beach

    Higgs Beach Dog Park on Atlantic Blvd has 2 fully enclosed play areas with unlimited fresh water for pups. Across the street, you can take a wonderful leashed walk on Knight Pier (White St Pier) & Higgs Beach for a great oceanfront scenery.

    Dog Beach is next to Louie’s Backyard on Vernon Street. It’s the only dog-friendly public beach where dogs can swim & play. The area is small, but for “water dogs” it’s paradise. BYO fresh water for your pup.

  • Yours First FAQ Question

    Yours relevent questions answer.

OKW Business Practices

  • How long has OKW been in business?

    We have been providing Free Concierge Services in Key West since 2007

  • Is the Concierge Service Really Free?

    Absolutely! Our Premium Concierge Call Center Service is complimentary and free of charge. We do charge for provisioning, deliveries, special events and Luxe Concierge Services.

  • Is OKW a franchise?

    No 🙂 We are a homegrown local, family owned business.

  • How long has OKW been in business?

    We have been providing Free Concierge Services in Key West since 2007