Major city · United States
Southold
Spend 1–2 days in Southold for wineries, historic lighthouse and a beach walk; base in Greenport or a B&B near the vineyards.
Southold sits on Long Island's North Fork, a rural area known for vineyards, farms and small‑town charm. The LIRR reaches Greenport, and the Cross Sound Ferry links Orient to Connecticut. One full day covers a winery tasting route and the Horton Point Lighthouse; a second day adds a beach park or a boat rental.
More
More ways in
Local time, weather, currency, airports
- Weather
- see forecast
- Currency
- USD
- Best months
- Sep–Oct, May–Jun (wine harvest and mild weather)
- avoid Jul–Aug (heat, occasional hurricane risk)
- Airports
- ISP · JFK
- Nights
- 1–2
Not a trip line yet
Rules in force · 7Crossing between the US, Canada and Mexico by land needs …Cannabis is legal in Canada and in many US states, but ta…
- North America ↗Crossing between the US, Canada and Mexico by land needs your passport even on a day trip; rental cars need the company's written permission to cross, and most US and Canadian rental insurance stops at the Mexican border.
- North America ↗Cannabis is legal in Canada and in many US states, but taking any amount across the US, Canadian or Mexican border is a federal crime — including edibles and vapes.
- North America ↗The busiest US and Canadian national parks need timed-entry, campsite or lodge reservations in summer; release dates are months ahead.
- United States ↗Check whether you need an ESTA (Visa Waiver Program) or a visa on the official CBP and State Department sites; apply only through esta.cbp.dhs.gov, not third-party sites, and allow time before you book.
- United States ↗Several popular national parks use timed-entry or vehicle reservations in peak season; check each park's page on nps.gov and book on recreation.gov before fixing your dates.
- United States ↗Medical care is very expensive for visitors; buy travel insurance with high medical cover before you fly.
- United States ↗Tipping is expected: about 15–20% at sit-down restaurants and bars, and a tip for taxis, hotel staff and guides.
Entry rules depend on your passport. Full visa guide
What is in this basic guide9 covered · 4 not yet ▾
In this guide
Not in this guide yet
- Walking areas with bag rules
- Day plans checked against opening hours
- Airport-to-bed timings and the last safe connection
- Field-checked times and prices
Emergency numbers for Southold911 ▾
- Police / Fire / Ambulance911
Tap a number to call from your phone. These are the numbers listed in this guide; a row marked check has not been verified.
EssentialsQuick answers and what things cost
Essentials
Quick answers and what things cost
Quick answers
The questions people ask first about Southold, one line each. Tap a card for the full answer.
- Cash or card?Currency is the US dollar (USD, $).United States-wide
- SIM or eSIMAT&T, Verizon and T-Mobile cover the country; prepaid SIMs at their stores and Walmart/Target (passport required), or an eSIM before you fly.United States-wide
- Tap waterTap water is drinkable nearly everywhere; boil or treat water from streams in parks.United States-wide
- TippingSit-down restaurant: 18–22% of the pre-tax bill.United States-wide
- Plugs & powerSockets A/B. US/Canada (A/B): fits · UK/Ireland (G): adapter · Australia/NZ (I): adapter. 120 V: UK and AU 230 V-only devices need a converter; most chargers are dual-voltage.United States-wide
- SafetySouthold is low‑crime; typical rural caution applies—keep valuables out of sight on beaches and lock car doors.
Show all 12 answers
- RestroomsFree public toilets are scarce in big cities; use cafés, department stores, libraries, stations.United States-wide
- Emergency numbers911 police / fire / ambulance
- Sundays & holidaysFederal holidays close offices, banks and post offices; national parks stay open.United States-wide
- Your embassyFind your embassy's 24-hour line before you fly.
- AirportISP Long Island MacArthur Airport (≈30 min drive north via NY‑24).
- Getting aroundLIRR Main Line – Greenport Branch serves Mattituck, Southold and Greenport stations (hourly).
Cost cheat-sheet
Typical prices for the everyday things, as ranges. Your currency is shown next to the local price.
- CoffeeCoffee at a café$3–$5
- Taxi, about 5 km (3 mi)Taxi, about 3 mi (5 km)Taxi (5 km (3.1 mi))Taxi (3.1 mi (5 km))$25–$35
- Budget bedInn double room, a night, per roomUS$150
- Mid-range bedInn double room, a night, per roomUS$220
- High-end bedInn double room, a night, per roomUS$350
A day, not counting the bed: Budget US$70 · Mid US$150 · High US$250
Prices in local money; change the currency in the header to see yours next to them. Every price and the budget calculator →
DecideWhat it is known for, and when the weather works
Decide
What it is known for, and when the weather works
At a glance
What the city is known for, how you fly in, and where to find the phrases.
- Airports
- ISP Long Island MacArthur Airport (≈30 min drive north via NY‑24) · JFK John F. Kennedy International (≈1 h 15 min by car, LIRR to Ronkonkoma then eastward)
Best months at a glance
From the guide's best and avoid lists
Jan
not flagged
3°C (37°F)37°F (3°C)
Feb
not flagged
4°C (39°F)39°F (4°C)
Mar
not flagged
9°C (48°F)48°F (9°C)
Apr
not flagged
15°C (59°F)59°F (15°C)
May
Best
21°C (70°F)70°F (21°C)
Jun
Best
26°C (79°F)79°F (26°C)
Jul
Avoid
29°C (84°F)84°F (29°C)
Aug
Avoid
28°C (82°F)82°F (28°C)
Sep
Best
24°C (75°F)75°F (24°C)
Oct
Best
18°C (64°F)64°F (18°C)
Nov
not flagged
12°C (54°F)54°F (12°C)
Dec
not flagged
6°C (43°F)43°F (6°C)
Best: May–Jun, Sep–Oct. Avoid: Jul–Aug. Month by month →
Warmest Jul (29°C (84°F)84°F (29°C)), coolest Jan (−3°C (27°F)27°F (−3°C) low), wettest May (10 rain days), driest Feb (7). Averages, not a forecast.
Weather and climate
Southold: next 7 days
Loading forecast…
Forecast: Open-Meteo (CC BY 4.0), model data for this point.
Air quality
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Model estimate (CAMS via Open-Meteo), not a street-level station; readings near busy roads run higher.
Jan
3°C (37°F)37°F (3°C)
−3°C (27°F)27°F (−3°C)
8 rd
Feb
4°C (39°F)39°F (4°C)
−2°C (28°F)28°F (−2°C)
7 rd
Mar
9°C (48°F)48°F (9°C)
2°C (36°F)36°F (2°C)
9 rd
Apr
15°C (59°F)59°F (15°C)
7°C (45°F)45°F (7°C)
9 rd
May
21°C (70°F)70°F (21°C)
13°C (55°F)55°F (13°C)
10 rd
Jun
26°C (79°F)79°F (26°C)
18°C (64°F)64°F (18°C)
9 rd
Jul
29°C (84°F)84°F (29°C)
21°C (70°F)70°F (21°C)
9 rd
Aug
28°C (82°F)82°F (28°C)
20°C (68°F)68°F (20°C)
9 rd
Sep
24°C (75°F)75°F (24°C)
16°C (61°F)61°F (16°C)
9 rd
Oct
18°C (64°F)64°F (18°C)
10°C (50°F)50°F (10°C)
9 rd
Nov
12°C (54°F)54°F (12°C)
5°C (41°F)41°F (5°C)
9 rd
Dec
6°C (43°F)43°F (6°C)
0°C (32°F)32°F (0°C)
8 rd
High / low, both scales · rd = rain days
Arrive & moveAirports are listed under At a glance; this is how to move once you are in
Arrive & move
Airports are listed under At a glance; this is how to move once you are in
Getting around
LIRR Main Line – Greenport Branch serves Mattituck, Southold and Greenport stations (hourly). Rent a car for winery hops; the Cross Sound Ferry runs 30‑45 min from Orient to New London (check schedule). Bicycles are common in Greenport; town roads are paved and well‑signed.
Nearest full guides
Straight-line distance, not travel time
See & doDay-trips, door to door
See & do
Day-trips, door to door
Day-trips
Orient Beach State Park
goDoor to door: ≈30 min total
Drive or bike east on NY‑25 from Greenport (≈15 min)
Beach, fishing pier and sound views; free entry.
Horton Point Lighthouse
goDoor to door: ≈20 min total
Drive north on Route 25 to 3575 Lighthouse Rd (≈10 min from Greenport)
Museum entry $5; climb for harbor panoramas.
Cross Sound Ferry – New London, CT
cautionDoor to door: ≈1 h including boarding
Take the ferry from Orient Point (≈30 min crossing)
Limited schedule; plan return or stay in Connecticut.
Eat & sleepWhich area to sleep in
Eat & sleep
Which area to sleep in
Where to sleep
Areas, not hotels: pick the one that fits your arrival time and plans.
Sannino Vineyard B&B
Boutique rooms on a private vineyard; walk to Alvah’s Ln.
The Old Mill Inn
Country‑style inn in Mattituck; easy access to Route 25.
Greenport Inn (downtown)
Close to LIRR Greenport station and waterfront.
PracticalWhat a day costs, what to watch out for, and the pocket card
Practical
What a day costs, what to watch out for, and the pocket card
Cost per day
- Budget
- $70–$120 excl. bed
- Mid
- $120–$200 excl. bed
- High
- $200+ excl. bed
Trip budget
| Inn double room1 × 1 night × US$220 | US$220 |
| Food, local transport, entries2 × 1 day × US$150 | US$300 |
| LIRR round‑trip Greenport ticket2 × US$20 | US$40 |
| Cross Sound Ferry one‑way2 × US$40 | US$80 |
| eSIM data (7 days)2 × US$20 | US$40 |
| Buffer 10%Price creep, a taxi you did not plan, one splurge | US$68 |
| Trip total≈ US$374 per person per day, bed included | US$748 |
2026 estimate in USD; flights and long‑distance rail excluded.
Prices of common things
| Coffee at a café | $3–$5 |
| Glass of local wine (tasting room) | $8–$12 |
| Fish & chips at a waterfront eatery | $12–$18 |
| Taxi (5 km) | $25–$35 |
| LIRR Greenport ticket (one way) | $15–$20 |
2026 estimate; check locally.
Watch out
Safety
- Ferry departures are limited in off‑season; verify times before travel.
- Many wineries close for a few weeks in winter; check opening dates.
- Summer heat can exceed 30 °C (86 °F); bring water and sun protection.Summer heat can exceed 86 °F (30 °C); bring water and sun protection.
Emergency numbers
- Police / Fire / Ambulance
- 911
Pocket card
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SoutholdSouthold
Pocket card · Voykit
My bed tonight
—
—
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À cette adresse, s’il vous plaîtTo this address, please
Emergency
- Police / Fire / Ambulance911
Embassy
US consulate in New York City; nearest US embassy services in Washington, DC.
My embassy: —
Fare anchors (2026 estimate)
- LIRR Greenport round‑trip: about $30 total, check off‑peak schedule
- Cross Sound Ferry Orient → New London: about $40 one‑way, check seasonal timetable
Say or show
- Excusez‑moi — Excuse me / Sorry (excusez‑moi)
- Merci — Thank you (merci)
- Combien ça coûte ? — How much is it? (combien ça coûte)
- Où sont les toilettes ? — Where is the restroom? (où sont les toilettes)
Deep diveWhat this guide covers so far, and its sources
Deep dive
What this guide covers so far, and its sources
Not a trip line yet
This is a basic guide: no airport-to-bed contract, walking clusters or day plans are published for Southold. Airport, fare and schedule details are unverified; check the operators before you fly.
What we know, and what is coming
On this page
- Best months: Sep–Oct, May–Jun (wine harvest and mild weather) · avoid Jul–Aug (heat, occasional hurricane risk) · month by month →
- 2 airports and 3 areas to sleep in
- Weather: a 7-day forecast and monthly averages
- Cost per day in 3 bands
- 3 day-trips, door to door
- 3 things to watch out for, with emergency numbers
Coming as the guide grows
- LIRR tickets to Greenport (check seasonal fare tables).
- Car rental for winery loops (check insurance coverage).
- Bicycle rentals in Greenport for short hops.
Sources
Ask about Southold
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