Drift Through Old Florida: A Chain of Lakes Day Cruise with Harborside Lunch
Tour the southern chain, trace Cypress Gardens history, and break for dockside lunch—lunch cost not included.
Morning slides in soft and glassy over Winter Haven, the lakes wearing a thin veil of mist like a secret they aren’t ready to give up just yet. The pontoon nudges off at 10 a.m., easy as a sigh, and the canal ahead seems to beckon with a quiet handshake. You’re on the Winter Haven Chain of Lakes—dozens of waterbodies stitched together by slim canals—where cypress knees stand like sentinels and ospreys draw perfect circles overhead. The captain points toward the first cut, and the current does its subtle persuading. Here, the water does the routing, urging you north or south depending on the day, stringing together a living museum of Old Florida.
Trail Wisdom
Go Polarized
Polarized sunglasses cut glare so you can spot turtles, fish, and submerged logs in the tea-stained water.
Beat the Storms
Summer afternoons often bring brief thunderstorms—morning departures offer the calmest water and most reliable weather.
Hydrate and Shade Up
Water is provided, but bring extra hydration, sunscreen, and a brimmed hat; the sun bounces hard off open lakes.
Bring a Dry Bag
Protect cameras and phones during canal crossings or sudden squalls; a small dry bag keeps the day stress-free.
Local Knowledge
Hidden Gems
- •The shaded canal near the Cypress Gardens grounds offers the best view of the Florida-shaped Esther Williams pool from the water.
- •Quiet corners around Lake Roy often host basking turtles and hunting anhingas—slow your roll and scan the logs.
Wildlife
Osprey, Great blue heron
Conservation Note
Idle in no-wake zones and give nesting birds a wide berth; shoreline habitats are fragile, and wakes can erode banks and disturb rookeries.
Cypress Gardens opened in 1936 on Lake Eloise, pioneering Florida tourism with elaborate gardens and water-ski shows; the legacy endures at the site of today’s LEGOLAND Florida.
Seasonal Guide
spring
Best for: Mild temperatures, Active birdlife
Challenges: High pollen, Occasional windy fronts
Spring is prime: clear mornings, active ospreys, and comfortable temps for a long, leisurely cruise.
summer
Best for: Warm water scenes, Lush greenery
Challenges: Afternoon thunderstorms, High heat and humidity
Expect bright skies and quick midday storms; start early and plan for intense sun and sticky heat.
fall
Best for: Calmer canals, Fewer crowds
Challenges: Hot spells linger, Variable winds
Autumn brings steadier weather and migratory birds; late afternoons can be beautifully glassy.
winter
Best for: Cool, dry air, Crystal-clear light
Challenges: Chilly breezes on open water, Shorter daylight
Cool mornings and bright skies make for crisp views—pack a light layer for the ride.
Photographer's Notes
What to Bring
Polarized SunglassesEssential
They reduce glare and help you see into the water and along the shallows for wildlife.
Light Sun Hoodie or UPF ShirtEssential
Sun protection is key on open lakes, and a breathable layer keeps you covered without overheating.
Compact Rain Jacket
Afternoon pop-up storms are common in summer; a small shell keeps you dry during quick squalls.
Binoculars (8x)
A lightweight pair brings ospreys, herons, and canal detail closer without leaving your seat.
Common Questions
Where does the cruise start?
Weekday cruises typically depart from Lake Summit; weekend cruises start from Lake Shipp, with the route reversing around the lunch stop at Harborside.
How long is the tour and what’s included?
Plan for about 4.5–5.5 hours on the water with a 12:00–1:00 p.m. lunch stop; ice-cold bottled water is provided, while lunch at Harborside is not included.
Can I bring my own drinks or snacks?
Yes. You’re welcome to bring beverages and snacks aboard; please pack out all trash and use resealable containers.
Is there a restroom on the boat?
Restrooms are available during the lunch stop at Harborside; check with the operator at booking for current onboard facilities.
Is the cruise family-friendly?
Absolutely. The stable pontoon ride, wildlife viewing, and lunch stop make it a great option for families and multigenerational groups.
What happens if the weather turns bad?
In the event of lightning or unsafe conditions, the operator may delay, reroute, or reschedule; summer storms are brief, and safety decisions are made conservatively.
What to Pack
Polarized sunglasses for glare and wildlife spotting; brimmed hat and reef-safe sunscreen for all-day sun; compact rain jacket for quick summer squalls; small dry bag to protect phones and cameras from spray.
Did You Know
The iconic Florida-shaped pool at the former Cypress Gardens—featured in the 1953 Esther Williams film Easy to Love—can still be seen from the water along Lake Eloise.
Quick Travel Tips
Book weekdays for quieter canals and easier parking; arrive 20 minutes early to confirm your departure lake and settle in; bring a credit card for lunch at Harborside and small bills for gratuity; check the forecast and plan for summer storms after 2 p.m.
Local Flavor
After the cruise, check out Grove Roots Brewing Co. in downtown Winter Haven for citrus-forward ales and local food trucks, or grab key lime pie at Harborside if you didn’t at lunch. Swing by the preserved botanical gardens at LEGOLAND Florida for a land-based look at Cypress Gardens’ heritage.
Logistics Snapshot
Closest airports: Orlando (MCO, ~1 hr) and Tampa (TPA, ~1 hr 15 min). Departures: Lake Summit (weekdays) or Lake Shipp (weekends) in Winter Haven—exact dock confirmed at booking. Drive time from downtown Winter Haven: 5–15 minutes. Cell service: Generally strong across the chain. Permits: None required for passengers; parking availability varies by launch.
Sustainability Note
These interconnected lakes support nesting birds and sensitive shorelines—observe idle zones, keep trash secure, and never feed wildlife. Your wake and your waste both matter.