pinterest facebook instagram twitter youtube google my business
  • (305) 294-7358
Key West Time
July 12th
11:10am · 89°F
sharing dinner
west parade
when and if

Key West Local Experiences ~ Let A Local Be Your Guide

When you're looking for that authentic Key West “wow” experience, your best bet is to let a local be your guide. Consider taking your family, friends, or just the love-of-your-life, on a Key West private sunset sailing charter, or a deep water or back country fishing charter. And… if you love to eat (and who doesn't) discover why Key West is becoming an international food destination by tasting exotic island food on a guided walking food tour.

Our selection of Key West Experiences will continue to grow, so be sure to check back to see what's next. And please feel free to contact our Concierge Desk, to discuss creating a customized Key West Experience. VHKW is here to help you make vacation memories that will last a lifetime. Contact our in-house concierge who is at your service 7 days a week, from 9 a.m. to 10 p.m. to make your reservation.

Guided Key West Experiences

Key West Sunset Sailing Charter

key west sailing charters Let us set you up with a perfectly custom charter sailboat ride on the beautiful waters surrounding the Florida Keys. The charismatic crew can fill all of your desires and give you the personalized experience you’re looking for. Day, sunset, or starlight, the beautiful fleet provides the perfect opportunity for a truly local sailing excursion.

Skydive Key West

key west sailing chartersLooking for the ultimate adrenaline rush? Take the plunge with Skydive Key West! The Keys are a very unique place to skydive, and the views from up there are unmatched. No matter if it's your first jump or 50th, you can trust the team at Skydive Key West. They have been jumping out of planes in the Florida Keys for over 20 years. An experience you are sure to never forget.

Key West Art Walk

key west art walk The perfect tour to enjoy local art, history, and culture! Named one of the top 10 walking tours by Trip Advisor, Key West Art Walk takes you deep into Key West with unmatched local knowledge and inside relationships. The handcrafted tour by a Key West native will give you the true inside scoop into the island.


Key West Fishing Charters

key west fishing charters Drop a line and see what's biting with the best fishing captains in Key West. We can arrange fishing trips to the backcountry for light tackle fun as well as offshore deep sea fishing for trophy fish. Venture offshore with your personal fishing guide, and try your luck at catching some of the most sought after game fish on the planet. Feel free to ask about custom charters and we'll arrange your ultimate fishing trip.

Air Adventure Key West

air adventure key west Take flight with a private helicopter tour guided by Air Adventure Key West. Get your adrenaline pumping with this high-flying experience. See the backcountry and sore over the Atlantic Ocean as you spot wildlife and take in the beauty of the Florida Keys. This is a great way to see the islands of the Great White Heron National Wildlife Refuge.

Cruisin' Tiki Key West

key west tour boat chartersWhat if I told you that you could tour the Key West Harbor on a Tiki Hut while sipping cold beverages & enjoying the sunset? When you imagine a tropical island and cold daiquiris, there's always a Tiki Bar in the fantasy. Now you can take that tropical fantasy one step further with a ride on a Tiki Tour Boat! This is fabulously fun and unique way to tour the waters around Key West.

Key West Food Tours

key west food tours Key West Food Tours provides visitors with a unique look at the culinary culture of Key West. The walking tour features an up close and personal take on local delicacies and famous Key West eateries. Get your fill of local knowledge and we promise you won't leave hungry. Along the way your guide will point out sights and local history that you may otherwise miss.

Our in-house concierge is at your service 7 days a week from 9 a.m. - 10 p.m. Whether it's to reserve activities or special events, recommend restaurants, book a customized cruise, shop for groceries, or simply book transportation plus much more, we have the local knowledge to assist you. We're a call, text, or email away.

Live Like a Local!
Contact Us Today to Plan Your Trip in Paradise.

9 a.m. - 10 p.m. 7 days a week
(305) 294-1129 (call or text)

vhkw concierge

Concierge Request Form

Select all that apply.

loaderThank you for your inquiry. We will get back to you as soon as possible.

Key West Vacation Rentals

Golf Club Vacation Rentals

key west golf club

Truman Annex

truman annex








town houses and condos





Sunset Key

sunset key

Rentals For Social Distancing

rentals for social distancing

Fantasy Fest

fantasy fest

Holiday Season

holiday season