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Discover Your Dream Destination

Aboard one of Stock Island Yacht Company's esteemed yachts, you can travel in style to your heart's desire. One day, you'll be snorkeling the crystal clear waters of Sand Key, and the next, you'll be trying your hand at some of the best sport fishing in the world in The Marquesas Keys. Check out our sample itinerary below and plan your dream vacation.

Sample Itinerary

The Night Before
After settling onto your yacht, relax with an island inspired cocktail or take a swim in the waterfront pool of The Perry Hotel, our 100-room boutique hotel. Prepare for your first big day tomorrow with American Coastal Comfort Food at Matt’s Stock Island Kitchen and Bar, casual fare and creative cocktails at Salty Oyster Dockside Bar and Grill, or Cuban cuisine at DeLuna’s Bar and Grill.

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Sample Itinerary

The Night Before
After settling onto your yacht, relax with an island inspired cocktail or take a swim in the waterfront pool of The Perry Hotel, our 100-room boutique hotel. Prepare for your first big day tomorrow with American Coastal Comfort Food at Matt’s Stock Island Kitchen and Bar, casual fare and creative cocktails at Salty Oyster Dockside Bar and Grill, or Cuban cuisine at DeLuna’s Bar and Grill.

Day 1

Set sail to Sand Key, one of the finest sections of North America’s only living reef. There, you can snorkel its clear waters and see parrot fish, sergeant majors, and even an occasional sea turtle. After lunch, head over to Boca Grande Key and walk along its beautiful deserted beach. Spend the evening at anchor there and enjoy a cozy dinner while your yacht gently sways in the breeze.

Day 2 
Get away from civilization with a sail to The Marquesas Keys, the only true atoll in the western hemisphere. You’ll find some of the best sport fishing in the world among these uninhabited islands. We can even arrange for a local fishing guide to meet you there to try your luck at hooking a tarpon or bone fish. Walk the beach here and you'll come across Cuban "chugs,” small homemade boats used to flee the island. Finish out your evening under a blanket of a million stars enjoying freshly grilled yellowtail or Key West pinks.

Day 3
Start your day with breakfast and a morning swim off the back of your yacht, then kayak or paddle board the mangroves to see great flocks of cormorants and pelicans. Later, spend the day snorkeling the emerald channel that runs through the east Gull Key seeing permit, snook, and redfish.

Day 4
Awake and set sail Key West bound. Stop for a snorkel at Western Dry Rocks, a spectacular spur and groove reef system somewhat off the beaten path of the Key West day charter boats. This reef is teaming with grouper, yellow tail, and blue tang. After lunch head over to anchor off Fleming Key and dingy in to Lagerheads Beach Bar to catch a world famous Key West sunset. Grab a casual bite there or return to your yacht for dinner al fresco under the stars.

Day 5
Rise to meet the day to the sound of waves gently lapping at the side of your yacht. Breakfast in the cockpit and a sail around Key West's Southernmost point puts you up the channel and back to Stock Island Marina Village. Your day isn't through yet. Swim in the pool, grab a cocktail, or take the shuttle into Key West for one last night on the town.

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Experience true luxury on one of our impressive live aboard yachts. Yachts are available for captained or bareboat.

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