Private Land Charters

Experience Island Life, Escalated!

What is a land charter?

Sit back and relax, in the First Class Cabin, while Ali (the co-owner of Kokomo Charters) shows you a day you could only create by living here your whole life. This area has so many hidden gems, that even full time residents haven't seen and experienced.  Let us show you what this incredible place called Sarasota, and her Sister Islands are really about, by way of a Cadillac Escalade ESV Platinum - not only loaded with every option Cadillac offers, but also loaded with accessories that will accompany your experiences along the way like beach chairs, champagne flutes, shark teeth sifters, yeti coolers, and other necessities for an epic day!  We'll pair your route to match your group.

8-Hour Adventures

No rush, no worries, no hurries.  It's our pleasure to show you the secrets of the area.  We got this! 

An Itinerary To Match Your Party

Whether it's hopping tiki bars, beaches, shopping or alligators, trust we will make it work perfectly!

Up to 6 Guests

Very comfortable seating with separate climate zones, generous space and a huge cargo capacity.


Get the Cadillac, the Driver, the Gear, the Freedom and the memories.  Let's go play!

Explore Our Tours


Northern Island Hopping

Explore the Islands of Anna Maria, Longboat and Lido Keys. Uncover a secret beach, shop til you drop and visit the spots that make this area so special and unique.


Southern Island Hopping

Explore the Islands of Venice and Casey Key. Hunt for sharks teeth, drive through millionaire row, or throw back a cocktail at a tiki bar. We promise a fantastic day for everyone!


Tiki Bar hop with sunset endings

Tiki Bars with a twist!  Visit our incredibly fun Tiki Bars and see some awesome sights along the way.  For dessert, you'll have front row seats for the sunset show over the Gulf.


Night Out On The Town - Sarasota Style

This elegant tour promises the perfect night out on the town. Enjoy a great dinner, hit a beautiful spot to catch the sunset, and visit a few of Sarasota's iconic bars for libations.  It's a great night!


garden tour

Choose Jungle Gardens or Selby Gardens for a morning adventure, then fill the afternoon with good food, shopping, beaches and sightseeing.  The possibilities are endless.


Ole' FL Tour

Step back into time with us as we explore Florida's natural beauty and wildlife.  We'll visit areas untouched by man and witness it's pure form as it was way back when.


land & seaRay

Only have one day to play?Travel well along the road less traveled!  Pair the Caddy Tour with a Boat Tour aboard 'Good Vibes,' our 31' Sea Ray and be dropped off dockside!

Copy of DSC05156

Custom Tours

Want something different, but need some help with suggestions?  Call us up.  Trust that Ali's planning skills and local knowledge will get you to exactly where to want to be.

About The Cadillac.

Spread out. Bring Stuff. We've got room!


Ambition on a grand scale. Iconic design, innovative technology, and craftsmanship elevated to a higher degree. The Cadillac Escalade ESV Platinum.  Let's do this!


Why a Private Land Charter?

Because the road less traveled is worth the ride!

Imagine seeing and experiencing the beauty of this area where parking is never an issue, having the right gear to experience these places, no worries about driving, traffic, directions or research - and doing it all First Class!  It's a short cut that will make up the cliff notes to this Paradise, and is truly something amazing to experience!  

Live in the moment.

Below are a few pictures of places we visit.  They are all beautiful, unique and with a history that Ali will explain.

See It. Feel It. Live it.  -  Welcome To Paradise.

Convenient Pickup Zone

Pick up and drop off will be where you're calling home.  If you're outside the shaded area of the map, please contact us as there may be a pickup fee.

Common F.A.Q's

Can children go?
Yes! But be sure to bring a child car seat one is needed, as those are not provided.

During my tour, will we be stopping for a bite to eat?
Yes! On every tour, we will either be stopping for lunch or dinner (dependent on tour schedule), at a unique place that offers incredible water views. Ali makes pick the place.

Can I bring drinks?
Yes!  Every tour includes complimentary water and soda. There will be a cooler and ice in the Caddy if you would like to bring some cocktails, or other special drinks. Please keep in mind though, drinking alcohol in the vehicle is allowed, but it is NOT intended to be a "booze cruise." Thank you for your understanding - let's keep it classy.

Can I bring food?
Yes! Please bring any snacks that you would like, we just ask that you please refrain from eating in the vehicle.  We promise to find the perfect spot for snack time. 

Land Tours available in january - 2020!

We're not quite ready to book our Land Tours just yet, but they will be available for purchase at the beginning of January, 2020. Please give Ali a call at 941-323-5411 to learn more about these Tours, or for reservations in 2020.

Tour You're Interested In
Northern Island HoppingSouthern Island HoppingTiki Bar HopGarden TourOle’ Florida TourLand & SeaRay TourCustom TourUndecided

Gift Cards Available

Select Your Charter


Scroll to Top