Gregory Kiep

Travel Blog

Greg's Insider Guide to Provincetown


As many of you know, Cape Cod is one of my favorite spots, especially Provincetown. Few places in the world have the energy of this magical place - from the shows to the natural beauty to the unique festivities and events that happen throughout the year. There truly is no bad time to visit this destination whether it be a calm September weekend or one of the big festivals like Carnival in August.

I have spent a ton of time in Provincetown and wanted to share a few of my tips and tricks if you are considering making this a vacation destination. Please feel free to reach out to me with questions!

When To Go

There truly is the perfect time to visit Ptown to have the vacation experience you desire. I love September, October, and May which are all on the fringe of the season but still have wonderful shows, events, and places to eat. During the summer months, there are events every weekend like July 4th, Bear Week, Family Week, and the infamous Carnival Week. There is the film festival, art and theatre events, Whale Week, and everything in between. Here is a handy guide to what is coming up. In a few weeks, starting August 15th, is Carnival with the theme "Enchanted Forest." If you are around, make sure you check out the parade - it is pretty amazing.

Where To Stay

Your "home away from home" is an important consideration as you plan your Provincetown vacation and I am here to help! I work with some wonderful hotels in the area that provide some of the most comfortable stays in town. Cape Colony Inn is a large property that offers comfortable and clean accommodations as well as activities onsite for the entire family. Their rooms feature Simmons Beautyrest Pillowtop Mattresses, Keurig® Brewing Coffee Machines, luxurious bathrooms with Beekman 1802 Body Care toiletries, and plenty of space to relax and spend time together. On property, they have a variety of activities including a heated pool, fire pit, volleyball, gas grills, and more!

This year, I am thrilled to announce the newly remodeled Breakwater Hotel which just finished a stunning renovation only a bit over a month ago! This "Cape Cod Chic" property is gorgeous and all rooms feature full view glass doors and large picture windows for a peek at the water – many with south-facing direct water views. Inside, the rooms feature Simmons Beautyrest Pillowtop Mattresses, Keurig brewing machines, flat-panel televisions, mini-fridges, complimentary Wi-Fi, room safe, Beekman 1802 personal care products, local art by kmoe gallery, and the newest and quietest air conditioning in town.

Want to be a bit outside of town in an authentic Cape Cod experience? Truro Beach Cottages offers 10 Iconic waterfront Cape Cod cottages once treasured by fisherman and vacationers alike - revitalized to their original allure. Check them out!

Around Town

There are so many things I could suggest for your trip to Ptown that it is hard to limit. I always say it really offers whatever experience you want - nightlife, beach, shopping, theatre, etc. There are some great sites to help you know what it happening in town or to help you plan your vacation such as ptownie or the Ptown Chamber site. They are both great resources.

I suggest to everyone to check out at least ONE show while you are in town. There are some "summer favorites" like Miss Richfield 1981 and Varla Jean Merman who are Provincetown legends. There are also other great shows like Airotic, a variety of entertainment at the newly opened The Club such as my friends Natalie Joy Johnson & Brian Nash every Wednesday through Sept 4th, and the hilarious and talented NYC Legend, Marti Gould Cummings.

Aside from shows, what else does one do on vacation? If you said eat and drink, you are right :) Some of my favorite places to eat are The Mews (ask about their vodka menu), Canteen with one of the best back yards in town, and Red Inn which is the perfect place for a pre-tea happy hour. For drinks, nothing beats Harbor Lounge to me - it is always one of my first stops. Want a more casual experience? Pop over to The Underground and play a round of pool with the locals.

Gregory KiepComment