Welcome to two unforgettable “New”s: New York City and New London. Across eight days, you’ll mix bucket-list landmarks and little neighborhood secrets with coastal strolls, galleries, and a dash of casino sparkle—without torching your budget. Expect skyline sunsets, ferry rides, jazz haunts, and seaport history you’ll still be chatting about years from now.

New York’s layered story—Lenape homelands, Dutch trading post, immigrant gateway—unfolds in every neighborhood, from the brownstones of Harlem to the shipyards of Red Hook. New London, once a whaling powerhouse, now thrives with indie art, maritime heritage, and easy day trips to Mystic’s working seaport and nearby Foxwoods. You get big-city electricity and small-city warmth in one sweep.

Practical notes: This plan favors free or low-cost highlights, local eats, and subway- or train-friendly routes. Book flights via Trip.com or Kiwi.com. For overnights, browse VRBO New York City, Hotels.com New York City, and for the coast VRBO New London or Hotels.com New London.

New York City

New York City is a living museum and a 24/7 stage. By day, wander Central Park meadows, the High Line’s elevated gardens, and harbor ferries; by night, street eats, jazz, and indie concerts keep the pulse going. You’ll balance signature sights with local favorites that feel tailor-made for a romantic, budget-conscious trip.

• Top sights (low-cost/free): Central Park, the High Line, Brooklyn Heights Promenade, DUMBO waterfront, Roosevelt Island Tram (metro fare), Staten Island Ferry (free skyline views).
• Concerts & nightlife: Bowery Ballroom, Brooklyn Steel, Webster Hall, Village jazz clubs—many offer affordable weeknight tickets or late sets.
• Foodie gems on a budget: Vanessa’s Dumpling House (handmade dumplings), Mamoun’s Falafel (late-night staple), Xi’an Famous Foods (spicy hand-pulled noodles), Time Out Market stalls (varied, view-rich seating).

Stay: Budget-first picks include Pod 51 Hotel (compact rooms, Midtown East) or apartment-style comfort at Residence Inn by Marriott New York Manhattan/Times Square. If you’re splurging for one night, check iconic The Plaza Hotel. Browse wider options on Hotels.com or VRBO for kitchenette-equipped stays.

Getting there: Fly into JFK/LGA/EWR via Trip.com or Kiwi.com. From the airport, use public transit to keep costs low.

Day 1: Arrival, Midtown Ease, and a Sunset Stroll

Morning: Fly into NYC. If you can, aim for an early arrival to maximize daylight. Drop bags at your hotel and grab a pick-me-up at Culture Espresso (artful cappuccinos, house-baked cookies).

Afternoon: Stretch your legs through Bryant Park and the New York Public Library’s marble halls—both free. For a late lunch, try Xi’an Famous Foods (bold cumin lamb noodles; share a bowl to save).

Evening: Ride the Roosevelt Island Tram at golden hour (standard subway fare) for river and skyline views perfect for couples’ photos. Cap it with a thin-crust slice at Joe’s Pizza or a budget-friendly plate at Los Tacos No. 1 (stand-and-mingle vibe).

Day 2: Central Park Romance and the High Line

Morning: Coffee and a croissant at Zibetto Espresso Bar, then wander Central Park: Bow Bridge, the Ramble, and the Conservatory Water. In warm months, rent a rowboat (seasonal) for a classic date moment.

Afternoon: Walk Fifth Avenue window displays and detour to the Paley Park pocket waterfall for a quiet pause. Head to Chelsea to enter the High Line; snack from nearby Chelsea Market (split a taco trio or a hand roll to stay on budget).

Evening: Watch sunset from the High Line’s 10th Ave overlook, then dinner in Greenwich Village: Mamoun’s Falafel (cheap, satisfying) or Saiguette (Vietnamese—order a shared banh mi and noodle soup). Consider a late jazz set in the Village; weeknights often have lower covers.

Day 3: Harbors, Ferries, and Brooklyn Lights

Morning: Bagels at Ess-a-Bagel (share a loaded one) and head downtown. Pay respects at the 9/11 Memorial pools (free), then walk to Battery Park for Lady Liberty views.

Afternoon: Ride the free Staten Island Ferry for skyline photos. Return, cross the Brooklyn Bridge on foot, and explore DUMBO’s cobblestones and Manhattan Bridge photo spot. Grab budget bites at Time Out Market’s top-floor seating for panoramic dining.

Evening: Stroll the Brooklyn Heights Promenade as the skyline lights up—romantic and free. Nightlife in Williamsburg: check weeknight shows at Baby’s All Right or Brooklyn Steel; many gigs have sub-$30 tickets if booked early.

Day 4: Queens Food Crawl and Harlem/Village Jazz

Morning: Hop to Jackson Heights for a global breakfast: Tibetan momos from Lhasa Fast Food or Colombian pastries from La Pequeña Colombia. Coffee at Sweetleaf in LIC before riverside views at Gantry Plaza State Park.

Afternoon: If you’re artsy, MoMA PS1 (check for pay-what-you-wish hours) or explore Bushwick’s street art by foot (free). Snack stop: Vanessa’s Dumpling House—share a sesame pancake and dumplings for under $10.

Evening: Soulful date night with jazz—Harlem’s historic clubs or a Village basement spot. Eat beforehand at Red Rooster (split appetizers) or trattoria-style pasta in the Village to keep it affordable.

Day 5: Galleries, Greenwich Strolls, and a Concert

Morning: Coffee at Café Grumpy and browse Chelsea’s free contemporary galleries. Wander the West Village’s leafy blocks and Washington Square Park—ideal for people-watching buskers and chess matches.

Afternoon: Soho window-shopping, then a late lunch at Prince Street Pizza (square slice) or by-the-slice spots nearby. Rest at your hotel before a big night out.

Evening: Catch an indie concert at Bowery Ballroom, Webster Hall, or a BK warehouse venue—standing-room tickets are often <$35. Post-show, split a carton of hot, peppery noodles from Xi’an Famous Foods or a falafel wrap for a budget midnight snack.

New London

New London’s waterfront blends 19th-century whaling lore with a lively indie arts scene. Bank Street glows with murals, cozy cafés, and small stages; just beyond, Fort Trumbull’s ramparts and the Arboretum offer quiet green escapes. It’s a soft landing after NYC’s tempo—romantic, walkable, and easy on the wallet.

• Top sights: Fort Trumbull State Park, Hygienic Art galleries, New London Waterfront Park, Connecticut College Arboretum, lighthouses and beaches in season.
• Food & drink: Muddy Waters Café (river views), Captain Scott’s Lobster Dock (seasonal rolls), On the Waterfront (classic New England plates), Engine Room in Mystic (craft burgers, whiskey, music).
• Nearby: Mystic Seaport Museum, Olde Mistick Village, and Foxwoods for dining, shows, and the included Hard Rock experience.

Stay: Search walkable stays near Bank Street or the waterfront via Hotels.com or harbor-view rentals on VRBO. Mystic or Groton options are a short drive or train hop away if prices are better.

Getting there from NYC (morning departures): Trains or buses typically take ~2.5–3 hours. Expect ~$25–$45 per person each way if booked in advance; search schedules and fares on Omio (trains) or Omio (buses). You can also return to NYC or fly onward via Trip.com or Kiwi.com (consider nearby airports like Providence or Hartford).

Day 6: Arrive New London, Waterfront Wanders, and a Playful Challenge

Morning: Depart NYC around 8–9 a.m.; arrive late morning. Drop your bags and grab coffee at Muddy Waters Café (river-facing deck if the weather’s kind).

Afternoon: Explore the Waterfront Park, check Hygienic Art’s current exhibits, then dive into a lively, interactive city game with the Nutty New London Scavenger Hunt. It’s guided remotely with prompts that nudge you into landmarks and photo ops—great couple bonding and very budget-friendly.

Evening: Dinner at On the Waterfront (buttery baked cod or a shared seafood pasta). Nightcap at The Oasis Pub—often hosting local bands and DJs with low or no cover.

Day 7: Mystic Day Trip and Hard Rock Foxwoods

Morning: Short hop to Mystic. Start at Mystic Seaport Museum—wooden shipyards, sailmaking demos, and a recreated 19th-century seaport feel tailor-made for slow, hand-in-hand wandering.

Afternoon: Lunch in Olde Mistick Village: split a chowder-and-fish combo or wood-fired pizza; browse artisan shops. Return via Foxwoods for a lighthearted late lunch/early dinner at the Hard Rock Cafe Foxwoods prix-fixe—music memorabilia, hearty plates, and a predictable price point make it easy on the budget.

Evening: Check the Foxwoods events calendar for free/low-cost music or comedy, or head back to New London for a sunset walk by the pier and a scoop from a local creamery.

Day 8: Beachy Morning, Art Stop, and Departure

Morning: Seasonal option: Ocean Beach Park for boardwalk sips and sand time; off-season, roam Fort Trumbull’s river views and the Connecticut College Arboretum’s quiet paths.

Afternoon: Brunch at Hot Rod Cafe (wings, waterfront views) or Captain Scott’s Lobster Dock (in season; split a roll and chowder). Depart by train/bus back to NYC (~3 hours) or fly out via Trip.com or Kiwi.com from Providence/Hartford/New York.

Evening: If you’re lingering, toast the trip with a final sunset at the pier and a cozy dinner back on Bank Street before your departure window.

Where to Sleep (quick links)

• New York City budget-to-comfort: Pod 51 Hotel, Residence Inn by Marriott New York Manhattan/Times Square, browse more on Hotels.com or VRBO.
• New London and nearby Mystic/Groton: Search walkable, waterfront options on Hotels.com or cozy rentals on VRBO.

Getting Around and Between Cities

• Flights: For your inbound/outbound searches, use Trip.com or Kiwi.com for competitive fares.
• NYC ⇄ New London: Expect ~2.5–3 hours each way. Typical advance fares range ~$25–$45 per person. Compare schedules and prices on Omio (trains) and Omio (buses).
• Local transit: NYC subways and buses run round-the-clock; New London/Mystic are walkable with local buses and inexpensive rideshares for evenings.

In eight days you’ll have traced America’s story from skyscraper canyons to a historic seaport, with ferry glides, jazz riffs, and a playful scavenger hunt connecting it all. It’s a romantic, budget-conscious itinerary that still feels rich in flavor, music, and memory—two “New”s, one great love note to the Northeast.