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An example plan

Nina & Theo

A night that starts on the water and ends in the piazza — a sunset sail on the bay, a car up to Little Italy, oysters at Ironside, and gelato under the string lights. Planned end to end.

  • Sunset sail → Little Italy
  • 4 stops
  • 5 – 10pm

The evening

Four stops, one unhurried night.

  1. 5:00
    PM

    Golden hour · On the water

    Sunset sail on the bay

    Embarcadero

    A small-group sail out of the harbor as the light goes — drinks in hand, the skyline lighting up behind you. The right way to start a night you've been looking forward to.

    $130 / two

    Book on Viator
  2. 6:45
    PM

    A lift · Black car

    A car to dinner

    Embarcadero → Little Italy

    Five minutes up to Little Italy — because nobody should walk it in heels. The car's waiting at the dock when the sail comes in.

    Waiting at the dock. Swun arranges the car; you just step in.
    Add a car →
  3. 7:30
    PM

    Dinner · Oysters

    Ironside Fish & Oyster

    Little Italy · India St

    $220 / dinner for two

    Reserve on OpenTable
  4. 9:45
    PM

    After · Gelato + the piazza

    Bobboi Natural Gelato

    Little Italy · then Piazza della Famiglia

Why this night

You said Nina lights up the second she's near the water, and that you two are at your best a little out of your routine — so we started you on the bay, not at a bar. The car up isn't a flourish; it's so the night stays easy and nobody's managing logistics in nice shoes. Ironside because you both love a raw bar and a room with some drama — and gelato because the best nights end on your feet, not over a check.

Don't forget the small things

  • A light layer

    The bay cools off the second the sun drops.

  • Flowers at the table

    Waiting at Ironside when you sit down.

  • Cash for Bobboi

    The gelato line moves faster.

A sample plan we built for a fictional couple — so you can see the real thing before you start. The reservation links below are live. Prices are estimates. You book each spot directly — Swun never sits between you and the reservation.

Your turn

Yours won't look like theirs. It'll look like you.

Answer a few questions about the two of you, and we’ll build a night like this — booked, mapped, and ready.

No account needed to start. Two minutes.