Greenwich, Connecticut Travel Guide

Happy Tuesday!! As most of you know if you’ve been following along on social media or my posts from last week – I was just in Greenwich, CT for a week doing makeup for a production of Shrek The Musical. I did a lot of exploring and sightseeing while I was there, so I decided to create a fun travel guide for those of you who are in the area or looking for a beautiful town to vacation in in the near future. There is a TON to do and the town itself is so old fashioned and sweet. I’m also including my full vlog of the trip so you can take a peek at some of my adventures captured on video. Let’s do this.

Greenwich, Connecticut Travel Guide

About Greenwich, CT:

Greenwich is a swanky, high-end town that is home to CEOs, billionaires, actors/actresses (and their families) and more prep schools than you know what to do with. It’s touted as being exclusive, expensive and fairly unaffordable for the average Joe, and they like it that way. HOWEVER, Greenwich is also only 40 minutes away from New York City by train, is an attractive vacation destination for those in-the-know and it’s beaches, mansions, shopping and dining are gaining international attention. Can you do Greenwich on a budget? Let’s find out. I’ve put each item in order of budget, affordable and splurge prices organized by lodging / dining / activities.

Where to stay:

There are quite a few places in Greenwich that are nice places to stay if you are vacationing for a few days. 


Holiday Inn Express & Suites – $120-$199 / night* 

This hotel has free parking, wifi and continental breakfast and a pool! It’s a very standard Holiday Inn Express – there isn’t anything fancy about it but it does the trick!!

Greenwich, Connecticut Travel Guide


Stanton House Inn – $213-$232 / night*

This hotel is walking distance away from the famous Greenwich Avenue where you can find shopping, dining and more. Historic and tastefully decorating, this is a must-stay location if you want to take in everything Greenwich has to offer.

Greenwich, Connecticut Travel Guide


Delmar Greenwich Harbor Hotel – $234-$451 / night*

To get the ultimate luxury Greenwich experience, try a couple nights at the Delmar Harbor Hotel. It is located right on the water, so every room has a beautiful view. The location has a 5-star restaurant, full salon and spa and continental breakfast and shuttle bus services. 

Greenwich, Connecticut Travel Guide

*based on 1 room, 2 adults. non-smoking

What to eat:


Burgers, Shakes & Fries

This is home of the best burgers in Greenwich, apparently! Boasting incredibly quick service, delicious burgers, shakes and fries (obviously) and amazing customer service, this restaurant has it all. It has a 4.5 / 5 star review and is located in central Greenwich. 

Greenwich, Connecticut Travel Guide

Glory Days Diner

This is a classic diner with food exactly as you’d expect! They make their food fresh and boast that nothing is ever frozen before serving. It’s less than $10 per plate and they serve breakfast, lunch and dinner. It has a very old fashioned feel and great customer service.

Greenwich, Connecticut Travel Guide

Firehouse Deli

This restaurant is a hole in the wall but don’t let that fool you into skipping lunch at the Firehouse Deli. Customers guarantee EVERYONE will find their perfect sandwich here. You get a ton of food for the price and most customers take home at least have and can get two meals out of one. Customers RAVE about this spot.

Greenwich, Connecticut Travel Guide

Gofer Ice Cream

This shop has 56 ice cream flavors, several different kinds of ice cream cones and lots of other frozen desserts. All of their ice cream is made in small batches so you get the best quality every single time. They have amazing reviews and most agree that it’s the perfect stop after dinner during the summer.

Greenwich, Connecticut Travel Guide



This is the perfect blend between Mediterranean and seafood. You have the option of eating at a table or the bar and they boast amazing desserts as well as full entrees. You DO need to make a reservation for this location but it’s worth the wait according to dozens of customers! 

Greenwich, Connecticut Travel Guide

Elm Street Oyster House

This is another seafood grill. They often have a full bar and this also requires reservations if you want to eat here. All of their fish is caught right there on the beach in Greenwich so it’s the freshest it can be. In addition to dinner, they also have a fabulous brunch menu and a lively happy hour!

Greenwich, Connecticut Travel Guide

Kneaded Bread, INC.

This is a fan favorite for the locals in Greenwich. They have amazing fresh breads and pastries – the smell alone makes your mouth water walking in! Their ingredients are very fresh and they don’t use preservatives. In addition to baked goods, they have salads, soups and desserts. 

Greenwich, Connecticut Travel Guide


I ate lunch here with my aunt while in Greenwich and loved it. They had AMAZING smoothies. I had a strawberry, lemon and orange smoothie and it was AMAZING. I also took a green juice to go. I would steer away from the juices with celery in it simply because it’s so over powering. Their grilled cheese and soups are also SO YUMMY. It’s the PERFECT lunch spot.

Greenwich, Connecticut Travel Guide


Blackstones Steakhouse 

This is an incredible restaurant whose staff REALLY treats their customers like family. The location is fabulous and centrally located. It’s a wonderful place to celebrate special occasions. Their menu is full of fresh meat and seafood, imaginative appetizers and delicious desserts.

Greenwich, Connecticut Travel Guide

Thomas Henkelmann

Entrees here are about $45-50 per plate and appetizers cost around $23-27, so this really is a special occasion restaurant. However, you get large portions and impeccable quality. Everything is made fresh. You absolutely need to make a reservation for this location or you won’t be able to get a seat in under 2 hours. 

Greenwich, Connecticut Travel Guide

Gabriele’s Italian Steakhouse

This price point is about the same as Thomas Henkelmann, so it’s definitely a place for a special occasion vs just a random dinner out. They have a large selection of wine, seafood and meats. Gabriele’s is packed solid on holidays and weekends. They also have a HUGE vegetarian menu so they cater to a wide variety of people.

Greenwich, Connecticut Travel Guide

Activities to do:

  1. Greenwich Point Park
  2. Audubon Wildlife Preserve
  3. Greenwich Avenue
  4. LEO Zoological Conservation Center
  5. Crown Greenwich Plaza Theater
  6. Clay Art Center Gallery
  7. Cove Island Park
  8. Bartlett Arboretum



Greenwich, Connecticut Travel Guide

I hope you enjoyed this comprehensive travel guide to one of the most historical cities in the United States! There is so much to do – even on a budget. You don’t have to shell out thousands of dollars to have a fun and relaxing vacation.

Have you been to Greenwich? Let me know what your favorite activity was in the comments below so I can add them to the list!

About The Author

Taylor Mobley


  1. Ruth Ridley | 27th Mar 18

    Oh I loved this recap! Brought back so many memories! I grew up in CT! Greenwich is beautiful!

  2. Carolyn | 27th Mar 18

    I’ve never been here before but I’ll have to keep this guide handy just in case I do. Looks like fun, thanks for sharing!

    • Taylor Mobley | 28th Mar 18

      You are so welcome! It’s a hidden gem of the northeast!!

  3. Deborah | 27th Mar 18

    Oh wow, all the food looks so yummy!!

  4. Julia Comil | 27th Mar 18

    This place is so cute! Love your travel pictures!

  5. lydia | 27th Mar 18

    I have never been to Greenwich, but would love to go sometime! Especially with all the yummy food you talked about. Thanks for sharing girl!

    xo, lydia

  6. Kimmie | 27th Mar 18

    Looks like such a fun trip!! Drooling over that food and those smoothies!

  7. Erica @ Coming Up Roses | 27th Mar 18

    But what about Starbucks? 😉

  8. sharon wu | 27th Mar 18

    i’ve never been to connecticut! never knew there was really much there but clearly i was wrong! looks like you had a blast xx

  9. Nailil | 27th Mar 18

    Everything looks so good, from the food to the accommodations.
    Xx, Nailil

  10. Kileen | 28th Mar 18

    Great post girl! I need to book a trip out with my family and check these out!! I love that you added different budget options!

    cute & little

    • Taylor Mobley | 28th Mar 18

      I know I always appreciate all kinds of budget options. Sometimes we have a lot of money to spare for a trip – and sometimes we don’t. 🙂

  11. Annette Dattilo | 28th Mar 18

    You did such a great job on this post. I now want to go to Greenwhich.

  12. Crystal // Dreams, etc. | 28th Mar 18

    My brother used to live in Connecticut and I know I visited when I was a baby (he’s old enough to be my dad… same parents though, LOL! I get asked that a lot) but I’ve always wanted to go back and explore. This is a great travel guide!

  13. Delia | 28th Mar 18

    I love this travel guide! I would love to go to Greenwich! But I’d choose all the “Splurge” options!

  14. Carmen Edelson | 28th Mar 18

    I’d definitely splurge and go for the Delmar Harbor Hotel! All of the food looks amazing. What a charming place 🙂

  15. Chelsie | 28th Mar 18

    Oh New England – my favorite place in the world. Looks like you had a great trip!

  16. Tonya Tardiff | 29th Mar 18

    So exciting the food looks amazing! I’ve never been to Greenwich this is a great travel guide.

  17. Life of a Sister | 30th Mar 18

    Now I need to go to Connecticut!

  18. Gita | 2nd Apr 18

    Oh wow how beautiful are these photos. I might need to make the trip since it’s not too far off from me.

  19. Kyla | 2nd Apr 18

    It looks so stunning there and I had no idea it was so close to New York! Thanks for the tips!

  20. Talina | 3rd Apr 18

    Wow, this place looks so amazing and the foooddd, omg! Thanks so much for sharing your visit there – I hope one day I can too! xo

  21. Cara Newhart | 3rd Apr 18

    Looks like a super fun trip!!
    I’m always visiting fam when I’m in CT, but ill have to stop by some time and check out some of these spots.

    xo, Cara

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