Sail When And If: Your Gateway to Adventure in Key West
Experience the breathtaking beauty of Key West with Sail When And If, your premier boat tour agency for unforgettable ocean adventures.
Sail When And If in Key West offers an unforgettable sailing experience amidst stunning ocean views. Perfect for tourists seeking adventure, relaxation, and the beauty of the Florida Keys.
A brief summary to Sail When And If
- Monday 9 am-9 pm
- Tuesday 9 am-9 pm
- Wednesday 9 am-9 pm
- Thursday 9 am-9 pm
- Friday 9 am-9 pm
- Saturday 9 am-9 pm
- Sunday 9 am-9 pm
Local tips
- Book your tour in advance, especially during peak tourist seasons to secure your spot.
- Bring sunscreen and a hat to protect yourself from the sun while enjoying your sailing experience.
- Don't forget your camera to capture the stunning sunsets and marine life you encounter.
- Wear comfortable clothing and shoes suitable for being on a boat.
- Inquire about seasonal wildlife sightings, as certain times of the year offer unique opportunities to see dolphins or manatees.
Getting There
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Bicycle
If you are near downtown Key West, rent a bicycle from one of the numerous rental shops. Head south on Caroline Street towards the Southernmost Point, then turn right onto Whitehead Street. Continue straight until you reach South Street, then take a left onto South Street. Follow it as it curves into Shrimp Road, and you will find 'Sail When And If' at 7009 Shrimp Rd on your left.
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Walking
From the famous Mallory Square, walk south on Wall Street towards Duval Street. Turn left onto Duval Street and head east until you reach the intersection with South Street. Turn right onto South Street and walk until you reach Shrimp Road. Turn left onto Shrimp Road, and 'Sail When And If' will be on your right at 7009 Shrimp Rd.
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Public Transit (Bus)
To reach 'Sail When And If' using public transit, look for the Key West Transit bus service. Board the bus at a nearby stop heading towards the Stock Island route. Request to get off at the stop closest to Shrimp Road. From the bus stop, walk south on Shrimp Road for about 5 minutes, and you will arrive at 7009 Shrimp Rd.
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Taxi or Rideshare
If you prefer a quicker and more direct route, use a taxi or rideshare service like Uber or Lyft. Enter 'Sail When And If' or the address '7009 Shrimp Rd, Key West, FL 33040' into the app. The driver will take you directly to your destination without any hassle.
Discover more about Sail When And If
Iconic landmarks you can’t miss
Key West Seaplane Adventures
2.2 km
Discover the breathtaking beauty of Key West from above with unforgettable seaplane adventures, a unique perspective on Florida's stunning landscapes.
The Real World: Key West House
2.6 km
Explore The Real World: Key West House, a cultural landmark embodying the vibrant spirit of Key West, Florida.
Key West Visit
4.2 km
Experience the vibrant culture, stunning sunsets, and endless adventures waiting for you in Key West, Florida, the ultimate travel destination.
Rest Beach
4.9 km
Discover the serene beauty of Rest Beach in Key West, a perfect spot for relaxation, sunbathing, and breathtaking sunsets.
Key West Veterans Memorial Garden at Bayview Park
5.0 km
Discover a serene tribute to heroes at the Key West Veterans Memorial Garden, a tranquil oasis of reflection and remembrance amid lush landscapes.
African Cemetery
5.1 km
Explore the African Cemetery in Key West, a serene and historic site honoring the rich cultural heritage and memory of African ancestors buried here.
Battery Inman
5.1 km
Explore Battery Inman, a serene historical landmark in Key West, Florida that combines rich history with stunning ocean views and beautiful gardens.
Hidden Key West Walking Tours
5.8 km
Explore the hidden treasures of Key West with immersive walking tours that unveil the island's rich culture and history.
USS Maine Memorial
5.8 km
Explore the USS Maine Memorial in Key West, Florida – a historical landmark honoring naval bravery and sacrifice during the Spanish-American War.
Holy Names Cemetery
5.9 km
Explore the serene beauty and rich history of Holy Names Cemetery, a hidden gem in Key West offering tranquility and reflection.
The Mansion On The Sea
6.1 km
Experience a luxurious stay at The Mansion On The Sea, a prime hotel in vibrant Key West with stunning ocean views and elegant accommodations.
The Cable Hut
6.2 km
Explore The Cable Hut, a historic landmark in Key West, where maritime history and communication technology come together in a charming setting.
Bishop Albert Kee Statue
6.2 km
Explore the Bishop Albert Kee Statue in Key West - a stunning tribute to leadership, art, and the Episcopal Church's rich history.
Weddings + Events at the Ernest Hemingway Home
6.4 km
Discover the enchanting Ernest Hemingway Home, the perfect wedding venue in Key West, blending history, beauty, and romance for your special day.
Ridley House - Key West Historic Inns
6.5 km
Discover the historical elegance of Ridley House, a charming hotel in Key West, offering a unique blend of comfort and rich heritage.
Unmissable attractions to see
Blu Chi Charters
0.0 km
Explore the beauty of Key West's waters with Blu Chi Charters - your gateway to unforgettable aquatic adventures in the Florida Keys.
Sail Away Key West
0.0 km
Discover the beauty of Key West from the water with Sail Away Key West, offering unforgettable boating experiences and scenic adventures in the Florida Keys.
Blue Ocean Yacht Charters
0.0 km
Discover the magic of Key West with Blue Ocean Yacht Charters, where unforgettable sailing adventures await amidst stunning coastal beauty.
Up The Keys Tours
0.6 km
Experience the best of Key West with Up The Keys Tours, where unforgettable adventures and local charm come together for an exceptional getaway.
Sandy Bottoms Charter
1.1 km
Discover the thrill of fishing in the stunning waters of Key West with Sandy Bottoms Charter, where unforgettable adventures await.
Lazy Dog Adventures
1.1 km
Experience the beauty of Key West with Lazy Dog Adventures – your gateway to unforgettable kayaking and boat tours in the Florida Keys.
Key West Tropical Forest & Botanical Garden
1.4 km
Explore the lush beauty of Key West Tropical Forest & Botanical Garden, a serene oasis showcasing Florida's diverse plant and wildlife.
The Mangrove
2.0 km
Discover the natural beauty and tranquility of The Mangrove in Key West, a must-visit nature preserve for every traveler.
Ghost Key West / Robert the Doll Ghost Tour
2.1 km
Discover the haunted history of Key West with the thrilling Ghost Key West / Robert the Doll Ghost Tour, where legends come to life in the moonlit streets.
Fort East Martello Museum
2.1 km
Discover the captivating blend of history and art at Fort East Martello Museum in Key West, a must-visit for all tourists exploring the island's rich heritage.
Smathers Beach
3.3 km
Discover the idyllic Smathers Beach in Key West, where sun-soaked sands and vibrant activities create unforgettable memories.
Sunset Watersports
3.6 km
Explore the Best of Water Sports at Sunset Watersports in Key West - Jet Skiing, Snorkeling, and More Await You in this Tropical Paradise.
The Key West Nature Preserve
4.3 km
Explore the breathtaking landscapes and diverse wildlife at Key West Nature Preserve, a tranquil haven in Florida's tropical paradise.
Historic Charter Boat Row
4.6 km
Discover Historic Charter Boat Row in Key West - your gateway to fishing adventures and stunning ocean views in Florida's paradise.
Kilo Whiskey Charters
4.6 km
Explore the exhilarating fishing opportunities with Kilo Whiskey Charters in Key West, where adventure meets stunning ocean views.
Essential places to dine
Tavern N Town
1.5 km
Experience exquisite American cuisine infused with Floridian flavors at Tavern N Town in beautiful Key West.
The Blind Pig
1.7 km
Experience the vibrant flavors of Key West at The Blind Pig - where delicious fast food meets refreshing drinks in a lively atmosphere.
Salute! On The Beach
5.3 km
Experience coastal dining at its best at Salute! On The Beach in Key West – where fresh seafood meets vibrant flavors in a stunning oceanfront setting.
Mo's Restaurant
5.3 km
Discover the vibrant flavors of Haitian cuisine at Mo's Restaurant in Key West - where every dish tells a story.
Oasis Mediterranean Cuisine
5.3 km
Discover the vibrant flavors of the Mediterranean at Oasis Mediterranean Cuisine in Key West - where every dish tells a story.
Incas Restaurant
5.5 km
Discover the fusion of Peruvian and American flavors at Incas Restaurant in Key West—where fresh seafood meets tropical charm.
El Siboney Restaurant
5.6 km
Experience authentic Cuban cuisine at El Siboney Restaurant in Key West – where flavorful dishes meet warm hospitality.
Cafe Sole
5.7 km
Discover the flavors of Modern French cuisine blended with Caribbean influences at Cafe Sole - a top dining destination in Key West.
Louie's Backyard
5.8 km
Discover Louie's Backyard: A premier dining destination in Key West offering exquisite cuisine and stunning waterfront views.
Azur Restaurant
5.9 km
Discover authentic Mediterranean cuisine at Azur Restaurant in Key West, where fresh ingredients meet island charm for an unforgettable dining experience.
Mangia Mangia
5.9 km
Experience authentic Italian flavors at Mangia Mangia in Key West—where every meal feels like a trip to Italy!
Milagro Restaurant and Bar
5.9 km
Experience vibrant flavors and lively atmosphere at Milagro Restaurant and Bar in Key West - where local cuisine meets island charm.
The Lobster Shack Key West
6.0 km
Experience fresh coastal cuisine at The Lobster Shack in Key West - a top destination for seafood lovers seeking local flavors.
Abbondanza Italian Restaurant
6.0 km
Experience authentic Italian cuisine in Key West at Abbondanza Italian Restaurant - where every dish tells a story.
Little Pearl
6.0 km
Discover exquisite dining at Little Pearl in Key West, where innovative cuisine meets fresh local flavors in an elegant setting.
Markets, malls and hidden boutiques
Last Chance Gifts
1.9 km
Explore Last Chance Gifts in Key West for unique souvenirs and local treasures that capture the spirit of the Florida Keys.
Soul House
5.7 km
Explore Soul House in Key West, a unique gift shop offering eclectic clothing, furniture, and home goods that capture the island's spirit.
Southernmost Trolley Stop
6.0 km
Discover unique souvenirs and local treasures at Southernmost Trolley Stop in Key West, the ultimate gift shop for every traveler.
Good Day on a Happy Planet
6.1 km
Explore the vibrant gift shop, Good Day on a Happy Planet, in Key West for unique souvenirs and local artisan treasures.
Southernmost Point Gift Shop
6.1 km
Discover unique souvenirs and local treasures at the Southernmost Point Gift Shop in the heart of Key West, Florida.
Mac's Sea Garden
6.2 km
Explore Mac's Sea Garden in Key West for unique gifts and souvenirs that capture the spirit of the Florida Keys.
Funky Flamingo gift shop
6.2 km
Explore the colorful Funky Flamingo Gift Shop in Key West for unique souvenirs and local artisan crafts that embody the island's spirit.
Local Color
6.2 km
Discover the essence of Key West at Local Color, where unique fashion and local artistry come together in a vibrant shopping experience.
Country Conch
6.2 km
Discover the vibrant spirit of Key West at Country Conch, your ultimate destination for unique gifts and local treasures.
Happy Rooster
6.2 km
Explore Happy Rooster, Key West's vibrant gift shop offering unique souvenirs and local crafts that capture the island's spirit.
Market Place
6.2 km
Discover unique clothing and accessories at The Market Place in Key West, where island style meets vibrant culture.
OurKeyWest Galleria - Gifts, Art, Shopping
6.3 km
Explore the heart of Key West at OurKeyWest Galleria, a vibrant hub for art, gifts, and unique shopping experiences.
Lazy Days of Key West
6.4 km
Discover unique clothing and island-inspired fashion at Lazy Days of Key West, a top destination for visitors seeking style in the heart of the Florida Keys.
Indigo Boutique Key West
6.4 km
Discover unique women's fashion and accessories at Indigo Boutique Key West, where style meets the island's vibrant culture.
Flirt A Unique Boutique
6.4 km
Discover trendy fashion and unique accessories at Flirt A Unique Boutique in Key West, where style meets island charm.
Essential bars & hidden hideouts
Southernmost Point Bar
6.1 km
Experience the vibrant atmosphere of Southernmost Point Bar in Key West, where tropical drinks and local flavors come together in a laid-back paradise.
Bobby's Monkey Bar
6.2 km
Experience the lively atmosphere of Bobby's Monkey Bar in Key West, where good drinks and great company create unforgettable memories.
Speakeasy Inn & Rum Bar
6.2 km
Immerse yourself in the vibrant atmosphere of Speakeasy Inn & Rum Bar, where exquisite rums and cozy accommodations meet in the heart of Key West.
The Rum Bar
6.2 km
Experience the vibrant nightlife of Key West at The Rum Bar, where cocktails and camaraderie come together in a tropical paradise.
Heroes Bar and Liberty Lounge
6.4 km
Discover Key West's lively music scene at Heroes Bar and Liberty Lounge, a top destination for drinks, live performances, and unforgettable memories.
Berlin's Cocktail Bar & Lounge
6.5 km
Discover the charming ambiance of Berlin's Cocktail Bar & Lounge, where exquisite drinks meet a relaxing atmosphere in Key West.
Green Parrot Bar
6.6 km
Discover the lively spirit of Green Parrot Bar, Key West's iconic destination for cocktails, live music, and unforgettable nightlife experiences.
Fat Tuesday Key West Duval St
6.6 km
Discover the vibrant cocktails and lively atmosphere at Fat Tuesday Key West, a must-visit bar on bustling Duval Street.
Whistle Bar
6.7 km
Experience the vibrant nightlife at Whistle Bar in Key West, where cocktails flow and live music ignites the spirit of fun.
The Bull
6.7 km
Discover The Bull, a lively Key West bar with great drinks, energetic vibes, and a rooftop deck for unforgettable sunsets.
Tiki House
6.7 km
Experience the vibrant spirit of Key West at Tiki House, where tropical cocktails and island vibes await you!
Sloppy Joe's Bar
6.7 km
Dive into the lively atmosphere of Sloppy Joe's Bar, a historic Key West gem serving up cocktails, music, and American cuisine in a vibrant setting.
General Horseplay
6.7 km
Discover the vibrant cocktail culture of Key West at General Horseplay, where unique drinks and a lively atmosphere await.
Rick's Bar
6.7 km
Experience the vibrant nightlife of Key West at Rick's Bar, where lively music, creative cocktails, and a friendly atmosphere await every visitor.
Capt Tony’s Saloon
6.7 km
Discover the vibrant history and lively ambiance of Capt Tony’s Saloon, a must-visit bar in Key West offering drinks, music, and local culture.
