Hotel, Motel, Holiday Inn


Step One

To some people, a room is a room.  And we totally get that.  But your room is multi-functional. It’s your home-away-from-home, whether you want it to be comfortable or something totally different and exotic – we got you covered.  Finding the perfect hotel will turn your trip experience way up and also create the feel-good vibe you are looking for. Treat yo’self!


Reliable brands that you know what you are getting

Hilton, Marriott, Sheraton, Radisson


Dark colors, interesting, huge tubs, romantic bar

Kimpton, Night Hotel, Standard


Stay the way the natives do in an apartment rental

AirBnB, VRBO, Craigslist Vacation Rentals

Best Amenities

Luxurious toiletries, above-average pool, sexy minibar

W Hotels, Four Seasons, Harrah’s


Down and dirty or just saving some cash

Quality Inn, Holiday Inn, Travelodge

Hotel Bar

Dark and romantic, good for picking up a date

InterContinental, Thompson, Andaz

Step Two

Okay, so you have picked out the type of room you want. Awesome!  Now, to get the best deal possible

  • Kayak is not only great for flights, it is also a great way to look at many hotels across many websites to compare availability, prices, and room types.
  • TripAdvisor is one of my favorite places to see reviews of the overall hotel.  You can filter reviews down to “couples” or “solo” and tons of key words make it easy to see if they are a fit for you. They also compare various discount sites all from their page like Kayak.
  • And outside of some of these big brands we’ve mentioned, don’t forget about the thousands and thousands of amazing, boutique hotels! While they don’t have a large chain or world-wide reputation, the TLC that small collections put into their properties is not to be underestimated! Check out review sites to see what other people thought.

Step Three

Get that upgrade!  I always book the room with the bed size I want as a base, but the closer it gets to your trip, the easier it gets to turn that standard into a suite – and get some champagne and other treats waiting for your arrival.

  1. Be Shameless!  Email the hotel ahead of time and tell them you are coming in for your birthday/anniversary/other special occasion (don’t like, they know).  Even if they don’t say anything back right away, they will make a note of it for sure.
  2. Ask  if they have any upgrades at check-in.  The agent at the desk will almost always give you a little boost up if they can.  Are you in an interesting industry?  Bring some swag for the agent when you check in.  They love getting in and might send a little something your way back.
  3. The Power of Twitter!  Engage with the hotel 2-3 weeks prior to your trip on social media.  Follow them on Twitter, Facebook, and Instagram and like and comment on things.  Take pictures of your bag and tag them in a “Can’t wait to see my room at the @BostonHilton! #BirthdayTrip #MomandDadsNight #Romance”.  If they see that you are active on social media, you are now their newest – and cheapest – advertising agent.
  4. Tip EVERYONE. If you’re only staying one night, it can seem worthless.  But if this is a place you’ll be back, you want to establish a reputation.  Tip the concierge, tip the bellhop, tip the maids.  I always forget to have singles, especially when first arriving, so plan ahead!

Not Ready to Book?

If you’re not quite ready to commit to traveling yet or don’t have the budget for that super swanky hotel? That doesn’t mean you can’t start thinking about where you want to go for the day when you can afford or get the time to go. Start a bucket list of your dream hotels.

Our Favorite Hotels Our Wishlist


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