A private boat cruise
The centerpiece. A private bachelorette cruise puts the whole crew on one boat with bubbly, dolphins and a gorgeous backdrop. The tiki boat (up to 26) is the crowd favorite for the photos and the vibe.
A beach & sandbar day
Spend the day on the water — beach on a roadless island and anchor on a sandbar for swimming and floating. Easy, fun and very photogenic.
A sunset celebration
Time the cruise for golden hour. A sunset bachelorette cruise gives you the best light for photos and a perfect toast.
Round out the weekend
Add waterfront dining (cruise to dinner by boat), spa time and 5th Avenue shopping. See our full bachelorette weekend itinerary.
From the Helm: Bachelorette weekends: anchoring at Dollar Bay before the sunset leg
Ask us why we pick Dollar Bay for the sandbar stop on a bachelorette charter and the answer’s mostly about depth, not looks — it holds a sandbar shallow enough to stand on at most tide stages without anyone stepping off into a hole, and it sits protected enough that the boat rides steady while ten people move around on one side of it taking photos. Plenty of sandbars around here look just as good in a photo; fewer of them stay forgiving when a group’s shifting weight all afternoon.
Your captain will usually hold that stop until thirty or forty minutes into the charter rather than right after everyone boards, because a group needs a little time to settle in, get a drink in hand and stop fussing with bags before anyone wants to wade in wearing an outfit. Push the sandbar too early and half the group is still finding their sea legs; time it right and everyone’s ready to actually get in the water.
We keep a couple of floats and a boarding ladder specifically for this stop, separate from the gear we use elsewhere on the boat, and we’ll keep whatever cooler the group brought aboard clearly marked apart from our own so nothing gets mixed up once a second round starts circulating. Music stays low at deck level while we’re anchored; we bring the volume back up once we’re moving again and the wind is carrying more of the sound off the stern anyway.
If the wind’s wrong for Dollar Bay on a given afternoon — blowing straight onto that stretch and stacking a chop across it — we’ll run to a more protected pocket farther into the bay instead, trading a little open view for water flat enough that nobody’s holding a drink with one hand and the rail with the other. Guests rarely notice the swap; they just notice the water’s calm enough to actually enjoy the stop, which is the whole point of anchoring at a sandbar in the first place.
None of this is exact science — wind and tide shift which sandbar actually works on a given afternoon, so your captain makes the final call once you’re underway, not from a form filled out weeks in advance. A private charter gives us the room to make that call freely, and our bachelorette tour options are built to leave that kind of flexibility in the schedule rather than lock you into one fixed stop.
That same flexibility carries into the rest of the day — if the group wants a longer stop or an earlier sunset run instead, your captain would rather hear it mid-charter and adjust than stick rigidly to a plan nobody’s attached to anymore.