MULTI-DAY YACHT CHARTERS
Don’t just dip into paradise for a day, but awaken to it every morning. Multi-day charters transcend fleeting escapes, inviting you to fully immerse in the Gulf Coast's magic, from dawn swims in hidden coves to starlit nights anchored in privacy and luxury.
Multi-Day Charters
Curated Seven Day Itineraries
Where the Journey Begins
Cruise from serene bays to vibrant islands, where the Gulf's turquoise waters draw you deeper into their spell.
Depart from Sarasota, St. Petersburg or Tampa Bay and drift into the timeless charm of Boca Grande. Dine at Miller’s Dockside, and enjoy a scenery where pastel cottages and swaying palms frame a majestic harbor. Spend the afternoon paddle-boarding through glassy inlets or simply soaking in the hush of Old-Florida refinement as sunset washes the sky in warm amber tones.
The Gulf's Jewel
Immerse yourself in the vibrant rhythm of Key West, where reef-blue waters meet lively waterfront culture. Snorkel vibrant coral gardens by day, tender ashore to storied streets by evening, and let the island’s electric sunset energy carry you into nights filled with music, laughter, and candlelit dining beneath the palms.
Island Vibrance
Culminate the journey in the true spirit of island vibrance.
Linger in the crystalline calm of Marathon, a haven of shallow sandbars and world-class snorkeling. Drop anchor in tranquil turquoise waters, explore thriving reefs, or savor long, slow afternoons as the sea stretches endlessly around you.
Island Vibrance
Culminate the journey in the true spirit of island vibrance.
Conclude on the shell-strewn shores of Captiva Island, where privacy and natural beauty reign. Lounge at the South Seas Resort, enjoy beachcombing at sunrise, secluded swims, and one final golden Gulf sunset create a graceful return to Sarasota, relaxed, restored, and quietly exhilarated.
Island Vibrance
Culminate the journey in the true spirit of island vibrance.
The final morning unfolds as you cruise back home. Enjoy breakfast on deck, the water calm beneath you, the week replaying in quiet flashes, reef dives, sunset toasts, and laughter. You don’t simply disembark; you arrive back changed, relaxed, restored, and carrying the unmistakable imprint of a week lived fully at sea.
Private Island Escape
Your journey begins with a serene run toward secluded shores. Ease into the rhythm of the Gulf with paddleboards at sunrise, kayaks through quiet mangroves, and sunset cocktails on the flybridge as the sky turns molten gold.
Island Energy
Step into the unmistakable energy of Key West. Snorkel vibrant reefs straight from the swim platform, take jet skis for an open-water sprint, then tender ashore for lively streets and waterfront dining under electric sunsets.
Reefs & Open-Water Wonder
Anchor in the crystalline shallows of Marathon, where sandbars become your private playground, SeaBobs carving through turquoise water, inflatables drifting beside the yacht, snorkel gear revealing a world below.
Then venture to Dry Tortugas National Park, home to the legendary Fort Jefferson. Here, history stands against an endless horizon, and reef systems feel brilliantly untouched.
Polished Gulf Calm
Return to the polished calm of Boca Grande for slow mornings and glowing evenings. Paddleboard through still harbors, unwind on expansive sunpads, and savor chef-crafted dinners as Gulf breezes move softly through the decks.
A Refined Finale
Depart Boca Grande beneath soft Gulf light, perhaps after one last paddleboard glide or a final jet ski run along the coast. Cruise north past barrier islands and waterfront estates as lunch is served on deck, the yacht moving effortlessly across open water. The approach to port feels smooth and composed, a refined arrival that mirrors the elegance of the week behind you.
Iconic Destinations for Your Multi-Day Voyage
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Conch Harbor Marina, Key West
Park the boat in the heart of the action where the margaritas are cold, the sunsets are legendary, and the 'Old Key West' soul is right at your dock.
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Faro Blanco Marina, Marathon
Dock beneath the iconic lighthouse for a quintessential Keys stay that perfectly balances classic maritime charm with modern luxury.
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Little Palm Island, Marathon
Trade your cell service for five-star service at this ultra-exclusive, private-island paradise where the only thing on your 'to-do' list is existing.
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Sandestin Golf & Beach Resort
From the greens to the grains of white sand, experience a vibrant resort world where the golf is world-class and the après-beach scene never ends.
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The Dry Tortugas National Park
Journey 70 miles past the horizon to discover crystal-clear snorkeling and a massive 19th-century fortress rising out of the turquoise deep.
Why Choose a Multi-Day Charter?
Escape the ordinary and indulge in a luxury yachting experience like no other. Whether you’re craving a weekend retreat, an island-hopping adventure, or a full week in paradise, this multi-day charters offer the perfect blend of relaxation, adventure, and five-star service.
112’ Superstar stands as a masterpiece of design, engineered for those who demand an extraordinary experience on the water. Beyond its striking silhouette lies a sanctuary of quiet luxury, where expansive social spaces and refined interiors combine.
The flagship seven-day experience aboard Superstar redefines the boundaries of privacy and scale, offering a sanctuary where every detail is choreographed by your dedicated crew. From sunrise over calm anchorages to starlit dinners, the Superstar transforms the ocean into your own private estate.
112' SUPERSTAR
Four-Person Dedicated Crew
Captain, Mate, & Stewardess delivering attentive service throughout your stay
Private Chef & Curated Dining
Personalized menus and
dishes crafted around your
preferences
All Water Toys Included
Floats, jet skis, and SeaBobs ready whenever the moment calls
Tow-Behind Tender
Effortless access to fishing grounds, snorkeling spots, and hidden coastal escapes
THE CROWN JEWEL OF KOKOMO CHARTERS
Begin your multi-day journey aboard a vessel that defines the "live-aboard" lifestyle. The 112' Superstar is a masterpiece of American craftsmanship, blending the sheer dominance of a superyacht with the refined, intimate comforts of a luxury estate; making it the premier choice for extended stays on the water.
Four-Person Dedicated Crew
Captain, Mate, and Stewardess delivering attentive service throughout your stay
Private Chef & Curated Dining
Personalized menus crafted around your preferences, served in refined onboard settings
All Water Toys Included
Floats, jet skis, and SeaBobs and more, ready whenever the moment calls.
Tow-Behind Tender
Effortless access to fishing grounds, snorkeling spots, and hidden coastal escapes
Available Vessels
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![Multiday Charters – 112' Superstar – "112 foot luxury yacht designed for multiday charters"]()
112' Superstar
Contact our Yacht Broker Concierge for estimated charter rates. Accommodates the primary charterer and up to 8 guests.*
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![Multi-Day Charters – 63' Peace – flagship yacht with expansive deck and overnight accommodations for long charters.]()
63' Peace
Contact our Yacht Broker Concierge for estimated charter rates. Accommodates the primary charterer and up to 4 guests.*
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![Multi-Day Charters – 52' Rally Point – stable catamaran ideal for family-friendly, multi-day yacht experiences.]()
52' Rally point
Contact our Yacht Broker Concierge for estimated charter rates. Accommodates the primary charterer and up to 4 guests.*
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![Multi-Day Charters – 50' Memory Maker – elegant yacht ideal for 3-to-5 day Sarasota to Key West adventures.]()
50' Memory Maker
Contact our Yacht Broker Concierge for estimated charter rates. Accommodates the primary charterer and up to 4 guests.*
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![Multi-Day Charters – 50' Memories, Not Dreams – luxury yacht with spacious interiors for multi-day cruising in Tampa Bay.]()
50' Memories, Not Dreams
Contact our Yacht Broker Concierge for estimated charter rates. Accommodates the primary charterer and up to 4 guests.*
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![Multi-Day Charters – 44' Congetta – sleek modern yacht for upscale private charters in Sarasota and St. Petersburg.]()
44' Congetta
Contact our Yacht Broker Concierge for estimated charter rates. Accommodates the primary charterer and up to 4 guests.*
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![Multi-Day Charters – 42' Wanderlust – catamaran with open layout, perfect for group sailing holidays along the Gulf Coast.]()
42' Wanderlust
Contact our Yacht Broker Concierge for estimated charter rates. Accommodates the primary charterer and up to 4 guests.*
* Vessel rental is offered on a USCG-compliant bareboat (demise) charter basis; as a courtesy, we can provide a curated list of approved captains and crews for you to choose from and fuel costs as part of your quote. You will contract directly with your chosen captain and pay them separately.
THE BEST WAY TO EXPLORE THE COAST
Luxury Accommodations
Spacious staterooms with premium finishes and panoramic views.
Water Toys Galore
Jet skis, snorkel gear, and tenders adventure’s in the Gulf's playground.
Gourmet Chef
Bespoke meals from local bounties tailored for you.
Tender Service
Seamless shore excursions, ensuring every whim is within reach.
Live Aboard in Pure Luxury
Why limit yourself to one hotel view when you can wake up to a fresh Gulf panorama every single morning?
Your luxury master suite becomes your floating home. Enjoy complete privacy at anchor under starlit skies one night, then glide into Florida’s most exclusive marinas the next,step ashore for elite dining, spas, and shopping, before returning to your onboard retreat.
Looking for something different? We also offer 2, 3, and 5-day custom charters to fit your schedule!
YOUR FLOATING PARADISE
This multi-day yacht charters offer all the comforts of a five-star resort on the water.
Dedicated Crew - Your expert captain and attentive team, crafting personalized magic.
Entertainment & Relaxation – Lounge on the sun deck, enjoy onboard WiFi and premium sound systems.
Full Galley & Outdoor Grill – Experience the freedom to cook at sea with a fully equipped galley and outdoor grill.
Exclusive Destinations – Visit hidden sandbars, private beaches, and exclusive marinas.
MULTI-DAY CHARTER BOOKING DETAILS
These multi-day charters provide everything you need for a seamless and luxurious experience:
Private Yacht & Captain
Enjoy a stress-free journey with a professional captain navigating your adventure.
Full Provisions
Includes bedding, linens, kitchenware, non-alcoholic beverages, and water toys for your comfort.
Customizable Add-Ons
Choose options like a first mate, tender, or an overnight stay on the yacht before or after your charter.
Additional Costs
Fuel, docking fees at remote ports, catering, and gratuity are billed separately based on usage.
Book Your Multi-Day Charter Today
Book your multi-day charter and set on a transformative journey, far surpassing fragmented days at the sea. Wake to new views, exploring at your own pace, and returning home refreshed and full of memories that last. Customize your perfect itinerary today.