Table of Contents
- Introduction
- Best Time to Go
- How to Reach Long Island
- Top Islands and Places
- Classic Tourist Circuits
- Things to Do and Activities
- Festivals and Seasonal Events
- Sample Itineraries
- Where to Stay
- Estimated Costs
- Local Food, Shopping, and Culture
- Tips for Different Travelers
- FAQs
- Conclusion
Introduction
Island hopping from Long Island blends iconic beaches, lighthouse views, quiet preserves, and charming harbor towns into one easy, ferry-fed adventure. From the car-free boardwalks of Fire Island to the serene lanes of Shelter Island and the dramatic bluffs of Block Island, you can craft a coastal escape that feels far away—without leaving New York’s backyard.
This guide covers the best islands to visit, how to link them by ferry, when to go, what it costs, and ready-made itineraries for weekends and weeklong trips.
Best Time to Go
- Peak beach season: Late June–early September for warm water, full ferry schedules, lifeguards, and open restaurants. Expect higher prices and crowds.
- Shoulder sweet spots: Late May–mid-June and September for calmer beaches, easier bookings, and mild weather. Some services may run reduced hours.
- Off-season: October–April sees quiet towns and limited ferries; great for lighthouse walks, winery visits, and budget stays (but not ideal for swimming).
How to Reach Long Island
Arriving
- By train: LIRR from NYC Penn Station or Grand Central to Babylon, Sayville, Patchogue, Greenport, and Montauk (seasonal direct trains on summer weekends). Off-peak fares typically range about $15–$30 one way depending on distance and time.
- By car: I-495 (Long Island Expressway) to South Shore (for Fire Island ferries), North Fork (Greenport/Orient), and the Hamptons/Montauk. Summer weekends can be congested—start early.
- By air: Fly into JFK or LaGuardia (NYC), or Long Island MacArthur (ISP) for proximity to South Shore ferries.
Getting around for island hopping
- Fire Island ferries: Passenger ferries from Bay Shore (Kismet, Ocean Beach, Ocean Bay Park), Sayville (Cherry Grove, Fire Island Pines, Sailors Haven), and Patchogue (Davis Park, Watch Hill). Parking lots are available near terminals for a fee.
- Water taxis: Fire Island Water Taxi connects many communities along the barrier island in season.
- Shelter Island ferries:
- North Ferry: Greenport ↔ Shelter Island Heights.
- South Ferry: North Haven (near Sag Harbor) ↔ Shelter Island South.
- Block Island (RI): Seasonal passenger ferries from Montauk (Viking Fleet) to Block Island. Other year-round options depart Point Judith, RI, and seasonal from New London, CT.
- Cross Sound: Orient Point ↔ New London, CT (for onward trips to Fishers Island via separate ferry from New London).
- Bikes: Ideal for Fire Island, Shelter Island, and Block Island; most ferries allow bikes for a small fee.
Top Islands and Places
Fire Island
Car-free communities, dune-backed beaches, and classic boardwalks define this 32-mile barrier island. Families love Ocean Beach; nature lovers head to Sailors Haven and Watch Hill; LGBTQ+ travelers flock to Cherry Grove and Fire Island Pines.
- Highlights: Fire Island Lighthouse, Sunken Forest (Sailors Haven), lifeguarded beaches, sunset dining in Ocean Beach.
- Good to know: Most towns are pedestrian/bike only; bring a wagon for luggage. Limited medical services—pack essentials.
Shelter Island
Nestled between the North and South Forks, Shelter Island is a tranquil escape of cedar-shingled inns, quiet roads, and nature preserves.
- Highlights: Mashomack Preserve (2,000+ acres of trails), kayaking in Coecles Harbor, sunset at Crescent Beach.
- Access: Ferries from Greenport (North) and North Haven (South). Cars allowed; bikes encouraged.
Montauk and the Hamptons
Where the Atlantic meets dramatic bluffs. Montauk combines surf beaches, fishing charters, state parks, and the historic Montauk Point Lighthouse.
- Highlights: Ditch Plains surfing, Camp Hero and Shadmoor trails, whale-watching in season, lighthouse climbs.
- Connection: Seasonal ferry link to Block Island from Montauk Harbor.
Greenport and the North Fork
A maritime village with a working harbor, galleries, and wine country at its doorstep.
- Highlights: Greenport’s waterfront and carousel, Little Creek Oyster Farm tastings, nearby vineyards and farm stands.
- Connection: North Ferry to Shelter Island; Cross Sound Ferry from nearby Orient Point to New London, CT.
Block Island (Rhode Island)
A classic New England island reachable seasonally from Montauk. Expect moors, lighthouses, and pretty beaches.
- Highlights: Mohegan Bluffs, Southeast and North Lighthouses, Great Salt Pond kayaking, biking quiet lanes.
- Note: Services are seasonal; book peak dates early.
Long Beach and South Shore Parks
Easy-entry barrier island beaches for day hops.
- Highlights: Long Beach boardwalk, Jones Beach concerts, Robert Moses State Park (Field 5 and Lighthouse boardwalk).
Fishers Island (extension)
Quiet and residential with limited visitor services; accessible via ferry from New London, CT (not from Long Island directly).
- Good to know: Minimal services for day-trippers; check schedules and visitor information in advance.
Classic Tourist Circuits
South Shore + Fire Island Day Hop
- Base: Bay Shore, Sayville, or Patchogue.
- Plan: Morning ferry to your chosen Fire Island town; beach time and lighthouse or Sunken Forest visit; sunset dinner; last ferry back.
North Fork + Shelter Island Loop
- Base: Greenport.
- Plan: Morning tasting at a North Fork winery; hop the North Ferry to Shelter Island; hike Mashomack; beach and lunch; return to Greenport for harbor strolls.
Montauk + Block Island Escape
- Base: Montauk.
- Plan: Early ferry to Block Island; rent bikes; explore Mohegan Bluffs and lighthouses; late-afternoon ferry back. Add a Montauk lighthouse hike the next morning.
Cross-Sound Extension (Orient–New London–Fishers Island)
- Base: Greenport/Orient Point.
- Plan: Cross Sound Ferry to New London; connect to the Fishers Island Ferry for a quiet day of biking and beachcombing; reverse route back.
- Note: Check schedules carefully for same-day returns.
Urban Add-On: Governors Island via NYC
- Plan: LIRR to Brooklyn/Manhattan, then NYC Ferry to Governors Island for car-free biking, art, and harbor views.
- Note: Not on Long Island proper but a fun first/last-day add-on.
Things to Do and Activities
- Beaches: Lifeguarded swimming at Robert Moses, Jones Beach, and popular Fire Island towns; calmer bays on Shelter Island.
- Biking: The best way to explore Fire Island, Shelter Island, and Block Island; rentals available seasonally.
- Hiking: Sunken Forest boardwalks; Mashomack Preserve trails; Montauk’s Shadmoor and Camp Hero cliffs.
- Lighthouses: Fire Island Lighthouse and Montauk Point Lighthouse (check climb hours); Block Island’s Southeast and North Lighthouses.
- On the water: Kayak/paddleboard Peconic Bay and Great South Bay; sailing charters from Greenport; fishing trips from Montauk.
- Wildlife: Birding along dunes and marshes; whale-watching cruises from Montauk in summer.
- Wine and farms: North Fork vineyards, cideries, and u-pick farms June–October.
Festivals and Seasonal Events
- Montauk Music Festival (May): Local and touring acts across venues.
- Greenport Maritime Festival (September): Tall ships, parades, and harbor heritage.
- Block Island Race Week (June, biennial): Sailing regatta and island buzz.
- Fire Island Pride season (June): Events centered in Cherry Grove and the Pines.
- North Fork harvest events (September–October): Winery crush parties and farm festivals.
Sample Itineraries
2-Day Weekend: Fire Island + North Fork
- Day 1: Morning ferry to Fire Island (Ocean Beach or Sailors Haven); beach and Sunken Forest; sunset dinner; ferry back and overnight near Bay Shore or Sayville.
- Day 2: Drive/train to Greenport; harbor stroll and oyster tasting; North Ferry to Shelter Island; Mashomack hike and Crescent Beach; return to Greenport.
3–4 Days: Montauk + Block Island
- Day 1: Arrive Montauk; lighthouse visit; sunset at Ditch Plains.
- Day 2: Early ferry to Block Island; bike loop to Mohegan Bluffs and lighthouses; beach time; return ferry.
- Day 3: Kayak or whale-watching in Montauk; relax at Kirk Park Beach; dinner in the harbor.
- Day 4 (optional): Hamptons village stop or vineyards on the drive back.
5–7 Days: Complete Coastal Circuit
- Day 1: Long Beach boardwalk + Jones Beach; overnight near South Shore.
- Day 2: Fire Island Lighthouse + Ocean Beach; overnight South Shore.
- Day 3: Greenport town + winery; ferry to Shelter Island for sunset; overnight Greenport or Shelter Island.
- Day 4: Mashomack Preserve + bayside paddle; afternoon ferry back; drive to Montauk.
- Day 5: Montauk state parks and lighthouse; beach time.
- Day 6: Day trip to Block Island.
- Day 7: Leisure morning; farm stands on North Fork en route home.
Where to Stay
- Montauk: Beach hotels and motels near the ocean or harbor; great for sunrise walks and early ferries. High summer rates; book early.
- Greenport: Boutique inns and waterfront hotels within walking distance of dining and the North Ferry.
- Shelter Island: Historic inns and B&Bs; peaceful, central base for North/South Fork exploring.
- Fire Island: Limited small hotels and many weekly home rentals in Ocean Beach, Kismet, and the Pines; ideal for car-free stays.
- South Shore (Long Beach, Bay Shore, Sayville): Convenient for Fire Island ferries and day trips.
Typical high-season rates: budget $150–250; midrange $250–450; upscale $450–800+ per night. Weekly Fire Island rentals often range from ~$2,000–6,000+ depending on size and week.
Estimated Costs
- Ferries (round-trip, adult, approx., subject to change):
- Fire Island: $20–35; bicycle $5–10.
- Shelter Island (car ferries): Vehicle + driver each way ~$18–25; walk-on $2–4; bicycle $3–6.
- Block Island (Montauk seasonal): $80–110 passenger; bicycle $10–15.
- Cross Sound (Orient–New London): Varies by vehicle/foot; foot passengers ~$20–40 each way.
- Parking at ferry terminals: ~$10–25 per day.
- Bike rentals: $25–45 per day.
- Kayak/SUP rentals: $40–60 for 2 hours.
- Meals:
- Casual seafood/lobster rolls: $18–35.
- Sit-down dinner: $25–50 per person (food only).
- Sample daily budget (per person, midrange): $180–320 including ferries/transport, meals, and shared lodging.
Note: Prices fluctuate by season and operator—verify schedules and fares before you go.
Local Food, Shopping, and Culture
- Seafood staples: Oyster tastings in Greenport; clam strips and lobster rolls along the South Fork; dockside fish shacks in Montauk.
- Vineyards and cideries: North Fork tastings ($15–30); many offer lawn seating and live music on weekends.
- Cafés and bakeries: Morning fuel in Ocean Beach, Montauk, and Greenport; grab picnic supplies for beach sunsets.
- Shopping: Nautical boutiques and galleries in Greenport; beachwear and surf shops in Montauk; general stores on Shelter Island.
- Culture: Lighthouse museums, maritime heritage in Greenport, seasonal art shows on Fire Island and the Hamptons.
Tips for Different Travelers
Families
- Choose lifeguarded beaches (Robert Moses Field 5, Ocean Beach) and pack sun tents, snacks, and a wagon for Fire Island boardwalks.
- Mind tides and rip currents; obey flags and lifeguard guidance.
- Strollers do well on boardwalks; bring baby carriers for sandy stretches.
Honeymooners and Couples
- Pick boutique inns on Shelter Island or Greenport with sunset access.
- Book a sunset sail, lighthouse climb, or private vineyard tasting.
- Go midweek in shoulder season for quiet beaches and lower rates.
Friends and Groups
- Fire Island house shares for a social, car-free beach week; coordinate ferries and grocery deliveries.
- Montauk nightlife and live music pair well with a Block Island day hop.
- Designate drivers or rely on rideshares/taxis where available; islands have limited late-night transport.
Packing and Safety
- Essentials: Reef-safe sunscreen, hat, refillable water bottle, bug/tick repellent (especially for Mashomack and wooded trails), light layers for ferries.
- Footwear: Sandals plus sturdy shoes for lighthouse stairs and cliff trails.
- Cash/card mix: Some ferries and small vendors may prefer cash.
- Accessibility: Many ferries and boardwalks (e.g., Fire Island Lighthouse approach) have accessible options—verify specific needs in advance.
FAQs
Q: Can I bring my car to Fire Island?
A: Most Fire Island communities are car-free in season. Park at the mainland ferry terminals and travel by foot, bike, or water taxi once on the island.
Q: What’s the easiest island hop for a first-timer?
A: A day trip to Fire Island (Ocean Beach or Sailors Haven) is the simplest. For a second day, add Greenport plus Shelter Island via the short North Ferry.
Q: Is Block Island doable as a day trip from Long Island?
A: Yes in summer, using the seasonal Montauk–Block Island ferry. Take the earliest outbound and late return to allow biking, lighthouse visits, and beach time.
Q: Do I need to book ferries in advance?
A: For seasonal and popular routes (especially Block Island and peak Fire Island weekends), advance tickets are recommended when available. Arrive early for walk-up lines.
Q: Are there ticks and jellyfish to worry about?
A: Yes—use tick repellent and do tick checks after wooded hikes; jellyfish can appear mid-to-late summer—heed lifeguard advisories and swim at guarded beaches.
Conclusion
Island hopping from Long Island is a flexible coastal adventure: walk car-free dunes on Fire Island, bike tranquil Shelter Island, taste wine on the North Fork, and sail to Block Island’s rugged bluffs—all linked by short ferries. Time your trip for summer ease or shoulder-season calm, plan your hops around ferry schedules, and pack light for breezy beach days and lighthouse sunsets.
