Sailing in The Crossings, FL


Two-Hour Sunset Sail for Two, Four, or Six from Florida Keys Sailing (Up to 50% Off)

Florida Keys Sailing

Marathon

On an air-conditioned boat, passengers can bring coolers of food or drinks and even take the helm, if they wish

$200 $104

$95 for a Learn to Sail Package from Key Lime Sailing Club ($200 Value)

Key Lime Sailing

Key Largo

Two-hour introductory sailing class aboard a 22-foot single-masted Catalina teaches students trimming, tacking, and jibing

$200 $95

$379 for a Three-Hour Sailing Trip for Up to Six Guests from Let's Go Sailing Today ($595 Value)

Let's Go Sailing Today

Northeast Coconut Grove

Guests spend up to three hours cruising Biscayne Bay aboard the “Dream Catcher,” a 40’ Beneteau sailboat

$595 $379

$599 for a Five-Hour Sailing Charter for Up to Six with a Bottle of Wine from Carlin Sailing ($1,130 Value)

Carlin Sailing

Dinner Key Marina

Glasses of French wine complement a five-hour sojourn across waters lined by city views, mangroves, and local wildlife

$1,130 $599

$199 for a Private Sailing Lesson from Captain Tyler Martin's Sailing Vessel Resurgam ($495 Value)

Captain Tyler Martin's Sailing Vessel Resurgam

Captain Tyler Martin's Sailing Vessel Resurgam

Private lessons on S/V Resurgam can target specific areas of sailing knowledge or the basics

$495 $199

$29 for a 3-Hour Weekday Island Adventure Miami Day Cruise and Tour from Tropical Sailing Up to $50Value)

Tropical Sailing

Bayside Marketplace and Marina

40 ft. catamaran cruises along Miami’s hot-spots for 3 hours during cruise, stopping at a sandbar, & participating in water activities

$50 $29

$25 for Treasure Hunt Sailing Adventure for Two from Bluefoot Pirate Family Adventures (Up to $50 Value)

Bluefoot Pirate Family Adventures

Bluefoot Pirate Family Adventures

Face painting and water-cannon fights on family-friendly treasure hunt aboard 49-passenger ship

$50 $25

$29 for a Three-Hour Weekday Island Adventure Miami Catamaran Cruise from Tropical Sailing ($50 Value)

Tropical Sailing

Bayside Marketplace and Marina

Three-hour catamaran cruises stopping at an island or sandbar where guests have free use of kayaks, paddleboards, and a water trampoline.

$50 $29

Two-Hour Sunset or City Cruise or Morning, Afternoon, or Sunset Sailing Charter from 44% Off)

Miami Yachting Company

South Pointe

The captain and crew use decades of experience to show off secret hideaways and lagoons, plus the homes and yachts of notable residents

$1,300 $734

$499 for a Four-Hour Sailing Charter for Up to Six from Ra Charters ($1,000 Value)

Ra Charters

RA Charters

Guests board a 45-foot, double-masted charter and embark on a tour of Biscayne Bay

$1,000 $499

Eco-Adventure Airboat Tour for One, Two, or Four at Everglades Safari Park (20% Off)

Everglades Safari Park

Everglades

Guests take airboat tour of Everglades National Park; tickets host alligator show, trail access, and chance to hold baby alligator, Snappy

$25 $20

Hop-On, Hop-Off Trolley Tour for One, Two, or Four from City View Trolley Tours (32% Off)

City View Trolley Tours

Key West

Riders hop on and off at nine stops along a scenic route through the streets of Key West

$28 $20

Pirates Adventures Water Tour for One or Two from Miami Aqua Tours (35% Off)

Miami Aqua Tours - Dabun

Bayside

Narrated sightseeing tours cruise past Miami landmarks, with sweeping views of the skyline

$27 $18

Everglades Airboat Tour for One, Two, or Four at Coopertown Airboat Tours (Up to 29% Off)

Coopertown Airboat Tours

Everglades

Airboats travel nine miles through the Everglades, gliding past stretches of sawgrass, alligator holes, and wetland wildlife

$23 $17

Sightseeing Boat Cruise for One, Two, or Four from Bayride Tours (Up to 34% Off)

Bayride Tours

Downtown Miami

Embark on 90-minute tours featuring views of aquatic wildlife and magnificent oceanside mansions

$26 $18

Boat Tour for One or Two from Jet Boat Miami (Up to 38% Off)

Jet Boat Miami

Miami

Jet boat speeds through area waters on a tour that includes views of San Marco and Flagler Memorial Islands

$29.95 $19

Four- or Eight-Hour Single Kayak Rental for One or Two at Big Pine Kayak Adventures (Up to 46% Off)

Big Pine Kayak Adventures

Big Pine Key

Kayakers navigate the Florida mangrove system on self-guided tours

$35 $20

Banana Boat Ride for One or Two, or Banana Boat Ride and Jet Boat Ticket from Jet Boat Miami (Up to 43% Off)

Jet Boat Miami

Miami

Hop aboard a banana boat and enjoy views of downtown Miami as you speed around the bay; jet boat cruises at high speeds with 360 twists

$52 $30

Speedboat Tours from Thriller Miami Speedboat Adventures

Thriller Miami Powerboat Tours

Downtown Miami

A speedboat tour of Biscayne Bay, South Beach, and Miami Gold Coast

$38 $27

Hiking Tours of the Everglades from Everglades Nature Tours (Up to 58% Off). Four Options Available.

Everglades Nature Tours

Big Cypress National Preserve

Lead by a Gladesman with 35+ years’ experience, visitors ramble through the unique Floridian ecosystem on private or group tours

$65 $27

Graffiti, Best of Wynwood, or Wynwood Walls Guided Tour for Two or Four from Wynwood Art Walk (50% Off)

Wynwood Art Walk

Wynwood

Walking tours showcase the works of local artists; stops include outdoor galleries and murals

$50 $25

Scavenger Hunt for Two or Four at 3Quest Challenge (50% Off)

3Quest Challenge

Downtown Miami

With a smartphone, clients progress through a series of checkpoints by collecting and solving clues that will lead to a big, final puzzle

$39.95 $20

Taste of Miami, Golden Beaches, or Grand Miami Tour for One from Miami Jet Helicopter Tours (Up to 23% Off)

Miami Jet Helicopter Tours

Miami Opa-Locka Executive Airport (OPF)

Helicopters soar above iconic Miami locales on three possible tours, affording breathtaking views of secluded islands and Miami landmarks

$95 $75

Trip to Key West or Everglades Adventure Tour from Xcursions USA (Up to 35% Off). Six Options Available.

Xcursions USA

Bayside Marketplace

Luxury buses with free Wifi whisk passengers to Key West and back; Everglades Adventure includes wildlife show and air boat tour

$80 $52

Two-Hour Glass-Bottomed-Boat Cruise for Two or Four on the "Key Largo Princess" (Up to 36% Off)

Key Largo Princess

Key Largo Princess

70 ft. yacht shuttles up to 129 guests, who gaze through 280 sq. ft. glass bottom at vibrant coral-reef state park

$70 $45

Orlando Explorer Pass includes admission to 3 or 5 attractions from 15 options. Pay Nothing at The Gate.

Go City Card

Online Deal

Choose 3 or 5 attractions from 15 popular options and save up to 35% off combined admission. Pay nothing at the gate

$49 $49.40

$18 for $30 Worth of Visits and Activities at Pinto's Farm

Pinto's Farm

Redland Citrus Orchards

At this family-owned farm, families enjoy pony rides, paddleboats, hayrides, a farmer’s market, and more

$30 $18

$29 for a Weekday Boat & City Amphibious Trolley Duck Tour from Miami Pirate Duck Tour

Miami Pirate Duck Tours

Miami Pirate Duck Tours

Captain navigates an amphibious vessel along both land and water during 90-minute tour of city sights

$32 $29

Helicopter Tour for Two, Four, or Six from South Florida Helicopter Charter & Tours (32% Off)

South Florida Helicopter Charter & Tours

Kendale Lakes-Tamiami

Groups board a six- or nine-seat turbine helicopter for an airborne tour of South Florida

$220 $149

South Florida Explorer Pass includes admission to 3, 4, or 5 attractions from 25+ options. Pay Nothing at The Gate.

Go City Card

Online Deal

Choose 3, 4, or 5 attractions from 25+ popular options and save up to 40% off combined admission. Pay nothing at the gate

$85 $76.50

Select Local Merchants

  • Sailing on Biscayne Bay Coconut Grove
    As Luis Niño programmed the printer for another press run, all he could hear was the ocean—the waves rolling against the boat's hull, the wind whipping across the sails. After navigating waters from the Florida Keys to the Bahamas for years as a recreational sailor, he dreamed of one day captaining his own ship, eventually taking the leap and launching Sailing on Biscayne Bay. Today, Captain Niño and his wife, first mate, and professional photographer Mabel welcome passengers with English and Spanish salutations as they board the Quitasueño, a Beneteau Oceanis 40 Center Cockpit with a teak deck. They charter two- or three-hour, half-day, and full-day sails through Biscayne Bay along Miami, Brickell, and Key Biscayne. Luis and Mabel entertain guests with drinks and snacks and can also arrange a catering menu.
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    Dinner Key Marina
    Coconut Grove, FL US
  • CitySightSeeing Miami
    CitySightSeeing Miami encourages tourists not just to see the sights around them, but also to explore them. Professional bilingual guides educate tourists on historical facts and fun city locations, leaving visitors with a deeper knowledge about Miami. When the urge strikes to linger at a tour stop, guests can hop off their double-decker buses and roam alone. Throughout the day, more buses arrive at each stop in intervals to pick up wandering customers and continue their tours.
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    1200 Anastasia Ave.
    Coral Gables, FL US
  • Elite Marine Canvas & Interiors
    If it's the boater's life for you, you'll want to check out the incredible seaworthy vessels for rent at Elite Marine Canvas-Interiors in Virginia Gardens. Parking is plentiful, so visitors can feel free to bring their vehicles.
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    6111 Northwest 38th Street
    Virginia Gardens, FL US
  • Skip Trent Engines
    Skip Trent Engines knows finding a body shop you trust can be difficult, but they're more than happy to earn it in Homestead. You'll be happy to know that Skip Trent Engines can attend to any scratches and dents on your vehicle as well. Next time you're in need for some A/C repair, you'll definitely want to call into Skip Trent Engines' professional team for some help. The technicians at this bar perform quick, reliable oil changes so you can be in and out in no time. Maintain the pristine condition of your car with tire changes and rotations at Skip Trent Engines. When you need a quick and affordable solution to your vehicle damages, pay Skip Trent Engines a visit. Congratulations! You just found the place to go in Homestead to handle any automotive needs you might have. Skip Trent Engines is ready for your service today.
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    32305 Southwest 200th Court
    Homestead, FL US
  • Loggerhead Club & Marina
    Take your family on a high-seas adventure for the afternoon! Rent one of the many ship-shape vessels available at Loggerhead Club and Marina in Homestead. Parking is plentiful, so patrons can feel free to bring their vehicles.
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    24777 Southwest 87th Avenue
    Homestead, FL US
  • Classic Sail Charters
    Established: 2009 Handicap Accessible: No Staff Size: 1 person Parking: Parking lot Reservations/Appointments: Required Most popular offering: Half-Day and Sunset Sailing Pro Tip: Bring sunscreen, hats, and a smile Q&A with Tony Ireland, Captain What inspired you to start or run this business? Before starting Classic Sail Charters, I volunteered with a community sailing organization that exposed people to sailing who had never sailed before. Most of the participants in the program realized the special calm joy that comes after casting off lines and raising sail. Gliding quietly through the water under sail seems to wash the stress away, and it was apparent in their eyes and faces. After 25 years working in corporate offices, I decided this was for me. What’s your favorite part about your job? Helping people get away from it, and watching the faces light up. Is there anything else you want to add that we didn't cover? Sailing yachts is a sporty activity that requires some mental concentration, as well as some physical strength. When the wind is up and the boat pitches and rolls a bit, it is not the best or safest activity for children under 7, nor is it much fun for the parents. What is the best reaction you’ve ever gotten from a customer? "Thank you, that was wonderful."
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    3600 Southwest 27th Avenue
    Miami, FL US

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