5-day Romantic trip for 2 to New York City, NY from Portland, OR

Here’s a complete 5-day romantic itinerary for a trip to New York City from Portland, Oregon. I'll  include budget-friendly and luxury options for transportation, accommodation, dining, and activities. Need help planning your next getaway? Contact me at www.DiamondTravelAgent.com and I will help you plan your next break.

---

Day 1: Arrival & Evening Stroll

• Travel

• Budget-Friendly: Fly economy on airlines like Delta, Alaska Airlines, or JetBlue. Tickets: $250–$400/person round-trip if booked in advance.
• Luxury: Fly first class or business class on airlines offering premium amenities like Delta One. Tickets: $1,200–$2,000/person round-trip.
• Arrive at JFK, LaGuardia, or Newark. Use subway or shared shuttles for budget transport, or book a private car service for a luxury experience.

• 
  

  Hotel Check-In

  • Budget-Friendly: Pod Times Square Hotel or Hampton Inn Manhattan-Times Square. $150–$250/night.
  • Luxury: The Plaza Hotel or The Ritz-Carlton Central Park. $900–$2,500/night.
    

• Evening Activity

  
  • Walk along the High Line (free) for a romantic view of NYC’s skyline. End at Chelsea Market for casual dining.
  • Luxury option: Dinner at Le Bernardin (Michelin-starred French restaurant). Prix fixe menu: $150+/person.
    

---

Day 2: Iconic Landmarks & Broadway

• Morning
  

  • Visit Central Park. Rent a rowboat at Loeb Boathouse ($20/hour) or take a private horse-drawn carriage ride (luxury: $150+).
  • Stop by Bethesda Terrace and Bow Bridge for photos

• Lunch

• Budget-Friendly: Grab a slice of NYC pizza at Joe's Pizza or dine at Shake Shack ($10–$20/person).
• Luxury: Lunch at Tavern on the Green in Central Park. $60+/person.

• Afternoon

• Explore The Metropolitan Museum of Art.
• Budget-Friendly: Admission is “pay what you wish” for NY residents; suggested donation for visitors is $30.
• Luxury: Private tour ($100+).

• 

  Evening

  • Budget-Friendly: See a Broadway show from the TKTS booth for discounted tickets ($50–$100/person).
  • Luxury: Premium seating for a hit musical like Hamilton or Phantom of the Opera ($200–$500/person).
    

---

Day 3: Lower Manhattan & Dinner Cruise

• 
  Morning
  
  • Take the Staten Island Ferry (free) for views of the Statue of Liberty and Manhattan skyline.
  • Luxury: Book a private yacht tour ($500+ for a couple).

• Lunch

• Budget-Friendly: Dine at The Halal Guys or Eataly Downtown ($10–$20/person).
• Luxury: Lunch with views at One Dine in One World Trade Center. $50+/person.

• Afternoon

  • Visit the 9/11 Memorial (free) and One World Observatory ($44/person).

• Evening

  • Budget-Friendly: Sunset picnic at Brooklyn Bridge Park with views of Manhattan.
  • Luxury: Dinner cruise around Manhattan with Bateaux NYC ($200+/person).

---

Day 4: Shopping & Nightlife

• Morning

  
  
  
  • Stroll through SoHo and Greenwich Village for boutique shopping.
  • Budget-Friendly: Street shopping or visit the Union Square Greenmarket.
  • Luxury: High-end shopping on Fifth Avenue or a private styling session.

• Lunch

  • Budget-Friendly: Try a NYC deli like Katz’s Delicatessen ($20–$30/person).
  • Luxury: Dining at Eleven Madison Park (tasting menu $335/person).

• Afternoon

  
  • Visit Top of the Rock for panoramic views.
    • Budget-Friendly: $40/person.
    • Luxury: VIP priority access ($100/person).

• Evening

  • Budget-Friendly: Discover NYC’s jazz scene at Smalls Jazz Club ($25 cover).
  • Luxury: VIP experience at Blue Note Jazz Club or rooftop cocktails at 230 Fifth.

---

Day 5: Departure

• Morning

  • Relax with brunch at Bubby’s Tribeca (budget: $20–$30/person) or The Polo Bar (luxury: $60+/person).

• Afternoon

  
  
  
  • Walk across the Brooklyn Bridge, enjoying views and taking photos.
  • Optional: Visit DUMBO for iconic NYC views.

• Departure

  • Budget-Friendly: Subway or shared ride to the airport ($10–$20/person).
  • Luxury: Private car service ($100+).

---

Estimated Costs for 2 People

• Budget-Friendly: ~$2,000–$2,800 total (including flights, mid-range accommodation, and dining).
• Luxury: ~$10,000–$15,000 total (including first-class flights, luxury hotels, and upscale dining).

Would you like more detailed information on any of these options? 

Here’s an enhanced version of the 5-day romantic New York City itinerary with additional excursions for both budget-friendly and luxury preferences:

---

Day 1: Arrival & Evening Stroll

• As previously planned.

---

Day 2: Iconic Landmarks & Broadway

• Morning

  • Additional Excursion: Take a guided pedicab tour of Central Park to cover more iconic spots in less time.
    • Budget-Friendly: Group tours ($35–$50/person).
    • Luxury: Private pedicab ride with personalized stops ($100+).

• Afternoon

  • Additional Excursion: Walk to the Roosevelt Island Tramway for a scenic ride ($4 round trip with a MetroCard). Enjoy views of Manhattan and the East River.

---

Day 3: Lower Manhattan, Statue of Liberty & Dinner Cruise

• Morning

  • As previously planned.

• Afternoon

  • Visit Ellis Island and the Statue of Liberty.
    • Budget-Friendly: Take the standard ferry ($24.50/person).
    • Luxury: Book a private guided tour, including pedestal or crown access ($75–$120/person).

• Evening

  • Additional Excursion: Stroll through the charming cobblestone streets of Stone Street for a lively outdoor dining scene.
  • Explore Brooklyn Heights Promenade for stunning sunset views of Manhattan.

---

Day 4: Shopping, Museums & Nightlife

• Morning

  • Visit the American Museum of Natural History or the Museum of Modern Art (MoMA).
    • Budget-Friendly: Suggested donations at AMNH or $25 at MoMA.
    • Luxury: Private museum tours or after-hours VIP access.

• Afternoon

  • Additional Excursion: Explore The Edge at Hudson Yards, one of NYC’s newest observation decks.
    • Budget-Friendly: $38/person.
    • Luxury: Champagne experience at The Edge’s Sky Deck ($60+/person).
  • Walk through the futuristic Vessel (free entry with reservation) or book a guided tour of Hudson Yards.

• Evening

  • Additional Excursion: Take a sunset helicopter tour for spectacular aerial views of NYC.
    • Budget-Friendly: $200–$300/person.
    • Luxury: Private helicopter tour ($1,000+ for a couple).

---

Day 5: Brooklyn Adventure & Departure

• Morning

  • Cross the Brooklyn Bridge and explore the trendy DUMBO neighborhood.
    • Stop by Jane’s Carousel ($2/person) and capture photos of the Manhattan skyline from Pebble Beach.

• Afternoon

  • Additional Excursion: Visit the Brooklyn Botanic Garden or Prospect Park for a peaceful retreat.
    • Budget-Friendly: $18/person for the Botanic Garden.
    • Luxury: Private garden tours with curated experiences.

• Late Afternoon

  • Optional Excursion: Tour the New York Public Library and Bryant Park before heading to the airport.
    • Budget-Friendly: Free library tours and casual park dining.
    • Luxury: End with champagne and dessert at the Blue Box Cafe at Tiffany & Co.

---

Additional Excursions to Consider

• Day Trips

  • Budget-Friendly: Take the Metro-North train to Sleepy Hollow or Beacon for a day exploring quaint Hudson Valley towns. ($30–$40/person round trip).
  • Luxury: Private car or guided tour to the Hamptons for a beachside getaway. ($500–$1,000/day).

• Unique Experiences

• Budget-Friendly: Explore NYC street art with a self-guided tour of Bushwick’s murals (free).
• Luxury: Private photography session around NYC landmarks for romantic keepsakes ($300–$800/session).

Here’s a breakdown of estimated costs for the budget-friendly and luxury versions of the itinerary, considering flights, accommodations, food, transportation, and excursions for two people:

---

Budget-Friendly Total Costs (2 People)

Category	Cost per Person	Cost for 2 People
Flights (economy)	$300–$400	$600–$800
Accommodation	$150–$250/night	$750–$1,250 (5 nights)
Meals (casual)	$40–$70/day	$400–$700
Local Transportation	$50–$70 total	$100–$140
Excursions & Tickets	$200–$400 total	$400–$800
Miscellaneous	$100–$200	$200–$400

Total Budget-Friendly Cost for 2 People: $2,450–$4,090

---

Luxury Total Costs (2 People)

Category	Cost per Person	Cost for 2 People
Flights (business/first class)	$1,500–$2,000	$3,000–$4,000
Accommodation	$900–$2,500/night	$4,500–$12,500 (5 nights)
Meals (upscale)	$150–$250/day	$1,500–$2,500
Local Transportation (luxury)	$300–$500 total	$600–$1,000
Excursions & Tickets (premium experiences)	$800–$1,500 total	$1,600–$3,000
Miscellaneous	$500–$1,000	$1,000–$2,000

Total Luxury Cost for 2 People: $10,200–$25,000

---

Key Takeaways

• The budget-friendly trip is great for exploring NYC’s highlights while keeping costs low, ranging from $2,450 to $4,090 for two people.
• The luxury trip includes premium experiences, upscale dining, and high-end accommodation, ranging from $10,200 to $25,000 for two people.

Let me know if you'd like to adjust the plans or dive deeper into specific costs!

---

This expanded itinerary offers a perfect mix of iconic sites, hidden gems, and unique experiences to make your NYC trip unforgettable. Let me know if you'd like even more ideas!

Did you enjoy this post? I’d love to hear your thoughts in the comments! Is there a dream trip or destination you’d like me to write about? Share your ideas below, and let’s make travel inspiration a two-way street!

Make Your Trip Effortless with Diamond Travel Agent!

Planning a trip? Let me, your Diamond Travel Agent, take the stress out of booking accommodations and excursions. With our extensive hospitality connections and exclusive partnerships, we can secure:

• Better Rooms and Rates at top-tier hotels.
• Airfare Discounts on select airlines.
• Discounted Excursions for unforgettable experiences.
• Guaranteed Reservations so you’ll never worry about availability.
• Plus, enjoy perks like free spa days or even complimentary nights at select destinations!

Reach out today at www.DiamondTravelAgent.com, and let’s plan a trip by train that’s smooth, luxurious, and unforgettable. Why settle for average when you can travel like a diamond? 💎

Did you enjoy this post? I’d love to hear your thoughts in the comments! Is there a dream trip or destination you’d like me to write about? Share your ideas below, and let’s make travel inspiration a two-way street!