Custom Montauk Itinerary Planning
Montauk Planned Just for You.
A custom, insider designed itinerary so every moment of your trip feels easy, well planned and worth the time and money you’re spending.
$75 USD Made for you Itinerary
Some people come for the surf, some for the beaches, some for long summer weekends that turn into late nights. Others visit in the quieter months, when the town slows down and the landscape feels more raw and reflective.
Planning a trip to Montauk isn’t difficult but the details (& getting it right) matter more than people expect. Transportation, seasonality, where you stay, and how much you try to fit in can completely change how the trip feels.
If you’ve been saving restaurants, beaches, and things to do but aren’t sure how to turn it into a plan that actually works for your timing, budget and travel style, this is where I can help.
I offer Custom Montauk Itinerary Planning designed to take the stress and second-guessing out of planning so your trip feels planned just for you.
What This Service Is & Who It’s For:
Instead of generic recommendations you’ll receive a thoughtful itinerary tailored to:
- how long you’re staying
- your trip priorities
- your budget
- food preferences
- whether or not you’ll have a car
- what you actually want your days to feel like
Imagine Your Trip…
- You show up and everything feels effortless and perfectly planned just for you
- Every restaurant, beach, and activity matches your vibe
- You feel like you know Montauk & not just like a tourist
- Your trip feels curated and worth every dollar you’re spending
That’s the difference between spending hours researching a trip… and having it designed for you.
This is a great fit if you:
- Want insider, local-level recommendations without spending hours researching
- Care about the feel of your trip, not just checking places off a list
- Are visiting Montauk for a weekend or short stay
- Want help deciding where to stay and how to structure your days
- Want restaurant recommendations tailored to you
- Care about balance more than checking off every activity
- You don’t want to spend hours researching and second-guessing decisions
- You want help turning ideas into a clear, realistic plan
This may not be the right fit if you:
- Prefer to plan every detail yourself
- Enjoy a fully spontaneous, unstructured approach
What’s Included in a Custom Itinerary & Price:
Custom Montauk Itinerary – $75 USD
A fully personalized and insider designed itinerary is built around your timing, travel style, budget and priorities, and includes:
- A fully customized Montauk itinerary tailored to you
- Up to two rounds of edits to refine the final itinerary
- A flexible, day-by-day outline that’s easy to follow
- Guidance on where to stay based on location, vibe, and logistics
- Dining and activity suggestions tailored to your preferences
- Transportation notes and seasonal context
- Local input, tips and recommendations
Limited Availability
To keep each itinerary custom and highly personalized I only take on a limited number of clients each month.
Once my calendar is full, I close bookings until the next availability opens.
Sample Itinerary:
How it Works:
Step 1: Share Your Trip Details
Once you book, you’ll receive a short questionnaire that covers the essentials: when you’re visiting, who you’re traveling with, if it’s a special occasion and what matters most to you on this trip.
I’ll also ask about preferences like:
- The kind of food you enjoy or any food preferences
- How much time you want to spend at the beach vs doing activities and sightseeing
- Whether a spa day or fishing trip is part of your ideal trip
- If you’re more drawn to Montauk’s local, laid-back side or the more classic Hamptons feel
- Hotel budget and preferences (luxury, boutique, standard)
- & more!
This gives me a clear picture of how you want your trip to feel.
Step 2: Receive Your Custom Itinerary
Using your responses I’ll create a day-by-day Montauk itinerary tailored to your timing, travel style, and priorities. You’ll receive your Custom Itinerary within 7 business days of submitting your questionnaire.
If I’m booking your hotel through Fora Travel, I’ll also recommend and select accommodations that align with your itinerary, location needs, and overall vibe.
Step 3: Review & Refine
You’ll receive your itinerary to review and can request up to two rounds of edits. This ensures the final plan feels exactly right for you.
Step 4: Enjoy Your Trip
You’ll arrive in Montauk with a solid plan in place that also feels intentional, flexible, and easy to follow. You’ll have the luxury to enjoy your trip without second-guessing the details.
Hotel Booking, at No Extra Cost:
In addition to itinerary planning, I’m a certified Travel Advisor with Fora Travel.
If you’d like, I can also handle booking your hotel at no additional cost to you. Through Fora’s network of 2,000+ partner properties worldwide, I’m often able to secure extra amenities that aren’t available when booking on your own, such as:
- Welcome amenities
- Room upgrades, subject to availability
- Daily breakfast for two
- Property credits (often $100+ for dining or spa)
- Early check-in or late check-out, when available
Hotels compensate advisors directly, which means you receive added value and personalized planning without paying more.
A Few Things to Know:
- This service focuses on planning before your trip.
- It does not include real-time support, reservations, or activity bookings.
- It’s designed to help you feel confident before you arrive.
Talk to a Local:
Whenever Brent and I travel, we always talk to the locals to get their personal recommendations because after traveling around the world we KNOW how valuable local insight can be.
Not just for recommendations (although those are great too!) but for the details you’d never find online:
- where to go at the right time of day or for the right occasion
- what’s actually worth it vs just popular on the internet
- the spots that don’t show up on “top 10” lists
- small details that could save you time or money
That’s what I bring into every itinerary I create. The best trips aren’t built from Google searches – they’re built from real experience.
Why Work With Me:
I’ve lived in Montauk my entire life and have traveled around the world. I know how valuable local knowledge and insight can be to a trip.
I understand how much the experience changes depending on when you visit, how long you stay, and what you experience.
Montauk in July feels completely different from Montauk in October and a weekend trip feels different than a longer summer stay. Those details matter and they’re often what make or break a trip.
Ready to Start Planning?
If you’re planning a trip to Montauk and want help creating the perfect plan and itinerary, you can request a custom itinerary below.
Frequently Asked Questions:
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Do you book hotels or activities for me?
I do not book restaurant reservations or activities on your behalf. I focus on planning and structuring your trip and as a Travel Advisor with Fora Travel, I can assist with hotel recommendations and bookings when it makes sense.
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Is this only for first-time visitors to Montauk?
Not at all. Many people who already know Montauk still want help refining their plans. Choosing the right area to stay, celebrating a special occasion, balancing busy days with downtime, or planning around seasonality or transportation.
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Can you help if I’m visiting without a car?
Yes. This is one of the most common reasons people reach out. I’ll plan your days around what’s realistically walkable or accessible based on where you’re staying and how you’re arriving.
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How far in advance should I request an itinerary?
Four weeks+ ahead is ideal especially for summer visits. If your trip is coming up soon, you’re still welcome to reach out and I’ll let you know what’s possible.
What Travelers Are Saying:
A few words from travelers I’ve helped.
“Working with Ariana was a treat! She was quick to respond, and obviously very knowledgeable of the area [Montauk, NY]. She provided us with an incredible itinerary which we did not need to stray from hardly at all. Would highly recommend her services for anyone looking to do a similar kind of trip!”
— James
“Ariana was fantastic! We looked at several options in the Hamptons and after listening to what we were most interested in doing, Ariana gave us a couple of excellent options and Baron’s Cove was perfect. She provided us with several suggestions of things to do and places to eat during our short stay and all recommendations were 100% on target.”
— Charles
Ready for Your Curated Montauk Trip?
If you’re feeling overwhelmed trying to plan your Montauk trip or just want a clear plan built around your priorities, I’d love to help!