An Ocean City, MD bachelorette weekend on the water means a private pontoon boat for up to 12 guests, a few hours of sandbar floating, a quick stop at Seacrets or another bay-front bar, and a sunset cruise past Assateague Island to look for wild horses. OCA Watersports rents private pontoons (no shared trips with strangers) for 1-8 hour blocks from Pier 23. Bring a cooler, a Bluetooth speaker, and your designated captain, and you are set.

Bachelorettes are one of the biggest weekend groups OCA hosts every summer. The pontoon is the perfect canvas: enough room for 12, a stable deck for the photo group shots, a swim ladder for the cooler-hop into the water, and a bay full of sandbars, bayside bars, and wildlife to fill the time. Below is the full playbook, including the itinerary template most bachelorette groups follow, what to bring, and the details that will save the bride a headache.

Why Ocean City for a Bachelorette?

Group on a pontoon boat enjoying the Ocean City Maryland bay

Ocean City is one of the few mid-Atlantic spots where you can put together a full bachelorette weekend within a 30-minute radius: beach, boardwalk, beach bars, dockside restaurants like Seacrets and Macky's, the inlet, Assateague Island, and the whole bay system. The bay day is almost always the highlight, which is exactly what OCA is built for.

The boat is the part of the weekend nobody else has photos of, and it is what makes the trip feel different from every other bachelorette your friends have already done.

The Standard Bachelorette Itinerary

4-Hour Pontoon Bachelorette Template

11:00 AM — Arrive at OCA dock (12817 Harbor Rd, Pier 23). Park, load the cooler, get the safety briefing, meet your captain.

11:30 AM — Push off. Cruise south through the bay toward Assateague. Group photos with the OC skyline behind you.

12:00 PM — Drop anchor at a bay-side sandbar off Assateague. Float, swim, photos in the shallows, lunch from the cooler.

1:30 PM — Pull anchor, head north toward Seacrets at 49th St. Tie up at the bay-side slips. Two-drink stop max (keep the captain sober).

2:30 PM — Back on the boat. Cruise the bay, take the long way back past the wild horses on Assateague if time allows.

3:30 PM — Return to dock. Group photo with the bride at the bow.

This template works for almost every bachelorette weekend. The variables are how long you sit at the sandbar, whether you stop at Seacrets, and whether you add a jet ski for the bride to ride at the sandbar (more on that below).

What OCA Provides

  • Private pontoon boat for up to 12 guests (your group only, no strangers)
  • 1-8 hour rental window — you pick the duration
  • Full bay access from the Rt 90 bridge in the north to Assateague Island in the south (the largest boating area in all of Ocean City)
  • Temporary boater's license issued at the dock so your designated operator can legally drive
  • Safety briefing before launch
  • Free dock storage for keys and small items
  • Add-on options: Bluetooth speaker, fishing package, crabbing package, tube

What You Bring

  • Cooler with ice, drinks, and food. Stop at a grocery store the morning of (Food Lion at 120th St is closest).
  • Bluetooth speaker (or rent one from OCA for $50)
  • Sashes, banners, hats, customized cups. The bachelorette uniform.
  • Floats and tubes for the sandbar stop. Inflatable swans, donut floats, the works.
  • Sun protection. Reef-safe sunscreen, hats with chinstraps, sun shirts. Sun off the water is intense.
  • Phones in waterproof cases with lanyards. Drop = lost.
  • A designated operator who agrees to stay sober the entire trip.
  • Trash bag. Pack out everything.

The Drinking Rules (Read This)

Yes, passengers 21+ can drink on the pontoon. No, the person driving cannot. Maryland enforces a 0.08 BAC limit on the water and the Maryland Natural Resources Police actively patrol the bay during summer weekends.

The two ways bachelorette groups handle this:

  1. Designate one captain for the whole trip. Maid of honor, sister, anyone willing. They drive, they do not drink. Tip them well at the end of the day.
  2. Rotate captains every hour. Workable if multiple people in the group are confident drivers. Everyone signs off on a no-drinks period before they take the wheel.

Do not skip this. A BUI (boating under the influence) is the same legal weight as a DUI in Maryland.

Add a Jet Ski for the Bride

Bride on a jet ski next to a pontoon boat in the Ocean City Maryland bay

The single best bachelorette upgrade we see at OCA is renting one or two jet skis alongside the pontoon. The bride and one friend ride the skis. The rest of the group rides the pontoon. Everyone meets at the sandbar.

The photos of the bride on the jet ski with the pontoon in the background are the photos that end up in everyone's Instagram. The 70-minute 6 Mile Ride goes south from the OCA dock along Assateague, which is the same direction you will be taking the pontoon. The two groups can ride parallel until you split at the sandbar.

For a full comparison of jet skis vs pontoons (and why so many bachelorette groups book both), see Jet Ski vs Pontoon Boat: Which OCA Rental is Right for Your Group?

Stops Worth Making

Seacrets (49th Street Bay-Side)

The classic OC bay bar. Tie up at the slips, head into the bar, do a round, take group photos at the famous Seacrets sign. About 10 minutes by pontoon from the OCA dock.

Macky's Bayside Bar & Grill (53rd Street)

A few blocks north of Seacrets. Quieter, better for an actual meal, also has dock space for pontoons. A great lunch stop on a longer rental.

The Sandbars off Assateague

The crown jewel of any bachelorette boat day. Drop anchor in 2-3 feet of water, hop off, float with the cooler, take the group photo at the sandbar with the bride in front. We covered the best ones in detail in Best Sandbars in the Ocean City MD Bay: A Pontoon Boat Guide.

Wild Horses on Assateague

If the wild horses come down to the bay-side beach (and they often do), idle 50 yards offshore and let everyone take photos. Even the most jaded bachelorette group goes quiet when a band of horses walks the shoreline. More on the wild horses here.

Pricing and How to Book

OCA Watersports pontoons start at for a 1-hour rental, for 2 hours, for 3 hours (plus tax). The 3-hour block is the most popular bachelorette length. Add jet skis at +tax per ski for 70 minutes.

Pontoon boats are phone reservation only. Online booking is not available for pontoons.

Call 410-629-RIDE (7433) to reserve. Tell us it is a bachelorette and the number in your party. We will help you pick the right time slot for the tide and confirm any add-ons. Summer weekends, especially June and July, sell out 3-4 weeks in advance. Book early.

For jet ski add-ons, book online directly.

A Few Final Tips

  • Coordinate transportation. Park at OCA and walk over from your rental house if you are nearby. Otherwise plan rides home so nobody drives after drinks.
  • Skip the glass. Cans only on the boat. Broken glass on a pontoon is a long, bad afternoon.
  • Pre-make the cooler. Pre-mixed drinks in cans or in plastic cups beat trying to bartend on a moving boat.
  • Capture the dock photo. Always do the full group shot on the bow of the pontoon at the dock before you push off and after you return. Two of the best photos of the weekend.

For broader Ocean City watersports planning, see Best Things to Do on the Water in Ocean City, Maryland and the deals and coupons page for any current promotions before you book.