One of my favorite moments, basking in the sunflower fields. Complete with a little red wagon.
Cooling down after the Gurney’s beach party. These yellow umbrellas were numero uno on my Hamptons Bucket List of places to see.
The view from Seamore’s restaurant (part of Breaker’s Montauk.)
A peaceful brunch at Baron’s Cove Inn in Sag Harbour over looking the marina.
Sunset at Ditch Plains beach wearing a Summersalt swimsuit.
At a local farm stand with lots of flowers and a beautiful array of fresh fruit, flowers and vegetables.
Liz and I doing our best Vogue impression in East Hampton.
Love this gravel driveway we discovered while walking around town.
My signature Hamptons look was a striped Eliza J dress, Mansur Gavriel handbag, and wide brim sun hat. 
All smiles at the beach. The dress is by Tobi.
Taking in the sunset at the Montauk Lighthouse. 
Lunch at the Lobster Roll. If any of you watch the show “The Affair”, you’ll know this restaurant.
I am so excited to share my Hamptons Travel Guide with you all! A trip to the Hamptons has been on my travel list for YEARS. There is just something about this New York hot spot summer destination that has always had me curious. Plus, I’ll never pass up a trip to NYC, so when the opportunity came up to go with my friends Liz and Danny I just couldn’t say no!
For those of you who do not know where or what the Hamptons are… They are a string of seaside communities collectively known as “The Hamptons” and also known as Long Island. They are approximately a three-hour drive east of Manhattan. Since the summer is prime time in the Hamptons, flights, and hotels are not cheap. I ended up using my Delta miles and got the flight for free (otherwise it would have cost me about $700 for a non-stop flight to New York!) This highlights a key reason why are flights so expensive right now – high demand for popular destinations during peak seasons can drive up prices significantly. I literally checked out of the Westlake Village Inn, switched out a few things in my suitcase and headed to the airport.
It was such a last minute trip decision that we did not even have a hotel booked for our first night. So I eagerly searched for places during my flight. A lot of places get booked up and their prices soar. Since this was a “fun creative” trip we wanted to stick to a budget and not go crazy. We were able to book one night at the Breakers Montauk. A cute little spot that reminded me of glamping. Each room is its own little bungalow. There isn’t a front desk so if you need anything, they have to bring it from a sister property about 10 minutes away. Forget room service btw. However, there is a cute pool and a restaurant called Semore’s open around noon-10pm.
The second spot we stayed was Montauk Soundview. Definitely a step up from Breakers, but still a budget spot with little luxury comforts. We had booked these two places to save a bit of money cooking ourselves, but we never ended up using of the kitchenette at either hotel. We spent 3 full days in the Hamptons exploring and taking photos. Here are a few highlights:
Places to See:
Seven Pounds Orchard: You pay for what you pick. We drove out to a quaint little farm in Southhampton to take photos in the sunflower fields. Since it is August the fields still have quite a few fields in them, however, I am not sure how much longer the sunflower season lasts.
Montauk Lighthouse: the park closes at 5;30 so make sure you get there before then! We were a bit late so we walked down a short path down to the back and shot these photos. There is also a little beach to walk down and enjoy the view. Fun Fact: The Montauk Lighthouse is the oldest lighthouse in the US.
Flying Pond Beach: (East Hampton) Not the best place for swimming (the current looks a bit strong) but it’s a beautiful east coast beach for sitting out and enjoying the view.
Ditch Plains Beach: popular beach spot in Montauk. Beautiful spot to watch the sunset. Lots of families here and either it’s a dog-friendly beach, or no one cares.
Young Jackie on the South Fork Exhibit: This free exhibit is all about the young Jackie Kennedy and is being held at the Clinton Academy Museum until October 8th. This exhibit is a series of photographs of her as a young girl at various horse shows and with her family.
East Hampton Walking Tour: I love to learn about the history of the places I travel to and walking tours are one of my favorite ways to do that. You can pick up a pamphlet at the Jackie Kennedy Exhibit and it shows you 40 walking points along the main road through East Hampton. Some of the buildings are from the 1770’s!!! They even had a little school house set up as it was in 1776!
Places to Eat:
The Surf Lodge: $$$ A hot spot with lots of good people watching. Get there early and try to get a spot out on the patio. Just be prepared to spend a bit of money. Entrees, 2 drinks each, and an appetizer to share was $220.
The Lobster Roll:$$ Liz is a huge fan of the show “The Affair” and wanted to eat here. Lots of fish and fried options. I ordered the veggie patty (not a huge sea food fan.) Always a long wait, but they have lots of tables. Try to go at an off time.
Joni’s Diner: $ Simple breakfast spot in Montauk. We ordered pick up from here and brought it to our hotel. They may deliver, not sure, but they do get very busy in the morning!
Fresh farm stands: $these little spots by the side of the road are a great place to get fruits, veggies, nuts, and baked goods to snack on.
Baron’s Cove in Sag Harbor: $$ This is a great brunch spot over looking the marina. Try to reserve a table on the balcony.
Gurney’s Resort Montauk: $$$ We sat out on the patio and enjoyed wine with a charcuterie board. Definitely a hot spot in Montauk. On Saturday’s they have their beach parties where you can purchase a cabana or a launch chair. This is where all the 20-30 somethings hang out and party. I highly recommend grabbing an ice cream cone from their to go counter. The vanilla/raspberry mix was soooo good!
1770 House: We did not get to eat here as they were not open for dinner quite yet. However, it did come highly recommended to us!
Bridgehampton Inn: $$ We had brunch here Sunday morning as we were leaving the Hamptons. It was a quiet spot with good food. I’m sure it is only a matter of time before it becomes more popular and crowded on the weekends.
Weather: The weather was perfect. A bit humid and warm at times, but nothing to complain about (especially if you’ve ever been to Thailand.) It rained one day that we were there. The sky cleared up that evening and we were able to go out and enjoy our day.
Transportation: Definitely rent a car! We almost took the Jitney (bus) out to the Hamptons, but we were so glad we opted to rent a car instead. We rented from Budget for about $26 a day and picked it up at JFK. Having our own car allowed us the freedom to drive all around Long Island and not at the mercy of taxi’s and ubers. I hear Uber just came to the Hamptons and the taxis out there charge PER HEAD. Not ideal. We definitely saved money having our own car.
Things I would do differently:
- Go earlier in the summer or in the off season. Less expensive and less crowded.
- Have all hotels books in advanced
- Have itinerary booked in advance. That way you are not spending time looking up places to go while you’re already there.
- Check opening and closing times. The Hamptons have a small town feel. Some places close earlier than you think!
- Plan extra time for picking up a rental car and avoiding rush hour from NYC! (Budget has low prices, but that made for an hour wait time.)
- Check the weather and pack accordingly! I did not do this and could have used some proper rain shoes and an umbrella for the days it rained.
- Spend more time in Sag Harbor. There were more museums I wanted to see here and we just did not have time.
Shop My Looks:
Check out my other recent travel guides and follow me on Instagram @Laura_Lily to see where I’m off to next!
Getaway to the Westlake Village Inn
Even though I have not made it out to the Hamptons in a few years this makes me want to!
xx Kelly
Sparkles and Shoes
Thank you, Ladies ! The Hamptons and you have the style of the good old times !