Trip Planning SOS: Warm and Sunny for 5 days in March

Last week I received an email from a reader named Chris, asking for advice on where to go for a five-day vacation in March. Chris was looking for a place that was nearly guaranteed to be warm and sunny, where she and her husband could relax by the pool or beach. She'd considered an all-inclusive but worried that it would feel like "a week spent at the Olive Garden - mass market and bland." Chris said she and her husband enjoyed snorkeling, hiking, good restaurants, boutique shopping, museums and local cuisine and drinks. Chris said budget was less important than the requirements listed, but that the place had to be easy to get to - no more than one connection away from Chicago.

Based on what Chris and her husband are looking for, here's how I narrowed it down. Since Mexico was an option (and since Chris really wants to make sure it will be warm, not just "warmer than home") I'm assuming that Chris and her husband have passports and are willing to go international. That's good news because, while Florida can certainly get hot during March (especially around Miami) there is always a chance you'll be there for a particularly cool or rainy week. There's a chance of that anywhere, but the odds are generally slimmer the further south you go.  The length of time she wants to be gone for (4-5 days) is short enough to keep me from recommending South America and Central America. It costs more to get there so its best saved for a longer trip.

That leaves the Caribbean and Mexico. Chris was partially right (in my opinion) about the downside to an all-inclusive. In exchange for the ease of having everything included in one price, you lose out on a lot of the local flavor. The experience may not be as exciting as if you stayed at a non-AI and ventured out to explore. Of course, it all depends on the resort. The El Dorado Royale, which is currently running a special, advertises a more intimate, less "spring break woohoo!" type of experience, complete with a foodie-focused food and beverage program. The Riviera Maya, accessed via the Cancun airport, would fit Chris' requirement of being easy to reach. Several airlines run nonstop flights from Chicago to Cancun and most fares will be between $250 and $400.

To see which islands in the Caribbean would be reachable by a nonstop flight, I checked out Budget Travel's nonstop Caribbean tool. I put in Chicago as my home city and found out that the Bahamas, the Cayman Islands, the Dominican Republic, Jamaica, Puerto Rico, St. Martin and the US Virgin Islands all fit the bill.

I don't know that Jamaica would satisfy Chris' requirements for museums and boutique shopping, but it definitely offers excellent snorkeling, physical activity, and a great local flavor. You can do rum or coffee tours, visit waterfalls, watch cliff divers, snorkel, fish, or just relax on the beach while you dine on spicy jerk chicken, fresh grilled lobster, and conch fritters and sip tropical drinks and Red Stripes.

Carl MiKoy via Flickr

One of my favorite places to stay in Negril (about 1.5 hours from the Montego Bay airport) is the Blue Cave Castle. Rooms are basic, but very cheap, starting at just $85 per night. The staff is super friendly, the chefs make some of the best lobster thermador around, and you can wander down the street to several restaurants. For a slightly more luxurious stay, the Rockhouse Hotel is another cliff-side hotel offering stellar service and incredible snorkeling just a few steps out your door.

Puerto Rico may actually be the perfect solution for Chris and her husband. Often dismissed as "not exotic enough" because it is part of the US, Puerto Rico offers the best of both worlds - pristine beaches and a beautiful natural setting plus a lively nightlife, lots of museums and shops, and delicious local cuisine. And best of all, there's no need for a passport or a different currency.

Oquendo via Flickr

Chris and the hubby can divide their stay between time in San Juan and on one of the smaller islands off Puerto Rico. They can spend their time in San Juan exploring the historic Old Town and its protective forts, touring the Bacardi rum factory, and sampling beers at the Old Harbor brewery. They can shop during the day and salsa dance at night, catch a tan on the in-city beach or head to the nearby rainforest. They can zipline through the jungle or spend an evening kayaking in a bioluminescent bay (lit by millions of glowing micro-organisms). They can spend all their time in San Juan or take a ferry or short plane ride to one of the beautiful islands like Vieques, known (but not to many, keeping it relatively undiscovered) for its stunning beaches.

The Verdanza Hotel is located close to Isla Verde beach and just 7 miles from Old San Juan. Rooms are luxurious and cost around $200 per night. A cheaper option is the Coqui del Mar Guesthouse, where rates start at $70 per night. Rooms are basic but stylish and the small hotel is located just steps from the beach.

I can't wait to hear what Chris and her husband decide, whether it be one of these options or another destination entirely. Please let us know, Chris, and happy travels!