Restaurant in Portland, United States
Floating Waterfront Vessel
DiMillo's On the Water at 25 Long Wharf is Portland's most recognizable waterfront dining option, housed on a converted ferry boat with Casco Bay views that do most of the heavy lifting. It works best for groups, celebrations, and out-of-town guests where setting matters as much as the food. Book a window table or ask about private dining for a second visit.
DiMillo's On the Water at 25 Long Wharf is Portland's most recognizable waterfront dining destination, and for returning visitors the real question is not whether to go back but how to get more out of it. The setting — a converted ferry boat moored on Casco Bay — is the single strongest argument for booking. If you have been once and sat in the main dining room, the private and group dining options are worth investigating for a second visit, particularly if you are planning around a celebration or a gathering where the view matters as much as the food.
This is a venue that works leading when you match your expectations to what it actually delivers: a reliably crowd-pleasing seafood experience in one of New England's most visually arresting dining rooms. It is not competing with Le Bernardin in New York City or The French Laundry in Napa on technique or ambition. What it offers is a strong sense of place, a menu built around Maine seafood, and a room that earns its keep on atmosphere alone.
For groups, DiMillo's has a clear structural advantage over most Portland alternatives: the boat itself creates natural event space, and the waterfront setting does a lot of the work when you are hosting out-of-town guests or marking a milestone. If you are planning a birthday dinner, rehearsal event, or corporate outing where the wow factor of the location matters, DiMillo's private dining options are worth a direct inquiry. The main room can feel busy and loud during peak summer evenings, which makes a more contained private space a practical upgrade for any gathering where conversation is the point. For intimate dinners of two or three, the bar area or a window table in the main room on a weekday evening is a better call than committing to a private booking.
Summer in Portland is the peak window. Casco Bay views read leading in the longer evening light of June through August, and the lobster-forward menu aligns naturally with the season. If you are visiting now, expect the room to be full on weekend evenings. Booking ahead is easy , this is not a venue where you need to plan weeks in advance the way you would for Atomix in New York City or Smyth in Chicago , but walk-in availability on a Saturday night in July is unlikely.
For deeper context on what Portland's dining scene offers beyond the waterfront, the Pearl Portland restaurants guide covers the full range, from Langbaan to Berlu. If you are building a full trip itinerary, the Portland hotels guide, Portland bars guide, and Portland experiences guide are worth checking alongside.
Reservations: Easy to secure; book online or by phone, and same-week bookings are generally possible outside peak summer weekends. Dress: Smart casual is the practical standard , the setting has enough spectacle that guests tend to dress up slightly, but there is no formal requirement. Budget: Pricing is not published in our database, but expect mid-to-upper casual dining rates consistent with Maine waterfront seafood; lobster dishes will push the per-head cost higher. Groups: Private dining inquiries are leading directed to the venue directly for current availability and minimums. Getting there: 25 Long Wharf is walkable from downtown Portland; street parking and garage options are available nearby on the Old Port.
Smart casual covers it. The waterfront setting on a converted ferry boat means guests tend to dress up slightly more than they might for a casual seafood shack, but there is no formal dress code. A nice layer is practical in summer evenings when the water breeze picks up.
The menu centers on Maine seafood, so lobster-forward dishes are the obvious call, particularly in summer when the catch is at its peak. Specific dish recommendations are outside what our database confirms , check the current menu directly before you go, as seasonal rotations affect availability.
Workable but not ideal. The bar area is the most comfortable option for a solo visit , it gives you a view and something to watch. The main dining room skews toward groups and couples, so a solo diner at a full table can feel slightly under-served by the atmosphere. For solo dining with more personality, Langbaan or the counter at Ken's Artisan Pizza are better fits.
For a more food-forward experience at a similar or slightly lower price point, Kann and Nostrana both deliver more culinary ambition. If you want a lively room with drinks as the anchor, Multnomah Whiskey Library is worth considering. For a neighbourhood dinner with less tourist traffic, Coquine is a strong alternative. See the full Portland restaurants guide for a broader comparison.
Yes, with the right framing. The setting does the heavy lifting , a boat on Casco Bay at dusk is a genuinely strong backdrop for a birthday or anniversary. If you want the occasion to feel more curated, request a window table or ask about private dining options when you book. For a special occasion where the food itself is the centrepiece, venues like Kann will deliver more on the plate.
A seafood-focused menu means strong options for pescatarian diners, but specific allergen protocols and vegetarian or vegan accommodation are leading confirmed directly with the restaurant before you book. Our database does not include current dietary policy details.
Yes, and this is one of its stronger suits relative to Portland peers. The venue's footprint on a converted ferry boat supports larger parties, and private dining space is available for events. For specific group minimums, menu options, and current availability, contact the venue directly. For groups where the meal itself matters as much as the setting, Nostrana and Kann are worth comparing.
| Venue | Price | Value |
|---|---|---|
| DiMillo's On the Water | — | |
| Kann | — | |
| Nostrana | — | |
| Ken’s Artisan Pizza | — | |
| Coquine | — | |
| Multnomah Whiskey Library | — |
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