Romantic Big City Weekend Best Done in Medium Sized City

A romantic big city weekend to celebrate a special occasion is always a treat. The hustle and bustle of the city, exploring history and culture, and finding new restaurants energize the senses and can increase the joy factor in any relationship. Thanks to the urban renewal in many medium sized cities in the last decade, this experience can be achieved with less hassle and expense. Let’s face it, you don’t need the city that has EVERYTHING for a long weekend. You only have two or three days, so a city with two or three days’ worth of places to explore and things to do will work just fine.

Indiana State Capitol, along the Cultural Trail through Indianapolis

Being within driving distance is a plus, but parking in a city needs to be factored into the plan. There aren’t many legal places to park in a city for free. With only a couple of days, you don’t want to spend a lot of time trying to get there. You want to go far enough to feel like you went somewhere, yet be close enough to not spend the majority of the weekend driving.

Hotel rates in cities fluctuate tremendously based on supply and demand. A major convention or sporting event can raise prices to crazy levels. However, a large convention hotel on a weekend with nothing going on may offer enticing discounts and specials to lure the leisure traveler. Be flexible, and take the special deal on the weekend it is available. You may find yourself in a premium property at a very average price. While there may not be a big event in town during your stay, restaurants, museums and other attractions are always open, and less crowded on the “off” weekends.

I did some research to compare three JW Marriott Hotels in New York, Chicago and Indianapolis on the same weekend to demonstrate the value proposition of the smaller city. New York is the largest city in the United States with just under 8.5 million residents. Chicago has a current population of around 2.7 million and ranks #3. Further down the list, Indianapolis is #14 in size with a population just under 850,000.

JW Marriott Indianapolis, view from the Canal District

Because of the supply and demand variable, one of these hotels can be sold out on a weekend where another hotel is offering deep discounted packages. The lesson here: Timing is everything. Check the special offers and packages on each hotel’s local website. That is where you will find additional amenities added to the room packages to entice guests on a slow weekend, or to encourage you to book directly with the hotel.

I found the JW Marriott Essex House at 160 Central Park South in New York City to offer its lowest priced room, a room for two with one queen bed, in the $400-$600 range per night. Add a breakfast for two package for an up charge of $100 per night. Parking in the Big Apple is $65 for cars and $70 for SUVs per night, with no in and out privileges during your stay. Clearly, driving into NYC is discouraged. There is also no pool at the Essex House.

At the JW Marriott Chicago, 151 West Adams Street, I found rates as low as $249 per night for a low level room with no view. Valet parking in Chicago is $68 per day or $45 per day for off site parking. There is an indoor pool at the JW Chicago, which can be a romantic, relaxing amenity after a long day of sightseeing. I am not a huge fan of driving into Chicago, although I have done it.

My choice for the best romantic getaway destination for a big city weekend is the JW Marriott at 10 S. West Street in Indianapolis. Boasting the largest JW Marriott in the world, this 1005 room hotel was built in 2011 for the 2012 Super Bowl. Everything is fresh and new. There is definitely a convention focus at this property, but when room occupancy indicates a slow weekend, the ingenious staff pulls out the Hoosier Hospitality to entice guests. Checking the weekend specials will give you room rates from $159 to the low $200’s per night.

Many specials include features like room upgrades, champagne and chocolate strawberries, breakfast included, late checkout or tickets to local attractions. With 33 floors overlooking the city on one side and White River State Park on the other side, there is a high probability of getting a room with a fabulous view. Parking at the hotel will run $37 per day or $42 per day for valet parking, with in and out privileges. We found a public lot across the street at White River State Park for $10 per day. A state of the art indoor swimming pool, hot tub and fitness room were amenities we enjoyed early in the morning and late in the evening around our other activities.

Indianapolis City View from our Room on the 33rd Floor

What is there to do in Indy? We didn’t get into our car all weekend, as the hotel sits amidst the White River State Park, the NCAA Hall of Champions, the Eiteljorg Museum, the Indiana Museum, and much more. A skywalk takes you to Circle Centre Mall without needing to go outside, if shopping is on your agenda. The Indianapolis Cultural Trail makes a great guide for a hike through the city, or you can bike the trail by renting bikes within a block of the hotel through the Indiana Pacers Bike Share Program. The hotel concierge can assist with restaurant reservations, with lots of options within walking distance.

Enjoying our Segway Tour of Indianapolis on Big City Weekend — Enjoying our Segway Tour of Indianapolis

My favorite activities? The one hour Segway Tour through Segway of Indiana which started next to the Visitor’s Center at White River State Park and the Old World Gondola ride in the Canal District. Not only did we fill our weekend, but we left so many things unexplored. We will go back again, and won’t have any trouble filling another weekend with completely different experiences.