1. What are the best resort package deals for Jamaica in Winter/Spring 2011?

This winter will see a wealth of all-inclusive hotel stock on the market and all the resort groups have subscriber mailing lists where specials are announced on a regular basis. Couples Resorts offers specials each Wednesday and has an email list where you can sign up to receive alerts as they’re posted. SuperClubs has all-inclusive packages starting as low as $79 USD per person per day at its downscale family-oriented Breezes Trelawny property, while the higher brow Breezes Grand Negril and Breezes Grand Rio Bueno are offering four-night “Bare Bones” packages starting at US$900 per person. Iberostar has rates as low as $135 USD per person nightly, based on double occupancy, at its least expensive property, Iberostar Rose Hall Beach, with this season’s specials at its upscale Iberostar Grand Hotel Rose Hall starting at $250 USD per person.

2. Can you give advice on what to look for—and what to avoid—when searching for a resort deal?

Look for value as prices in Jamaica will vary based on what the tourist is willing to pay. Don’t get duped by hotels publishing an nightly rate of $845 USD per couple, and offering discounts of up to 60% to convince you that $507 USD is a bargain. Booking a week at this rate will cost you US$3,500, which could go far in the villa market, especially when traveling with two or more couples. Then again, it would go even further on a more proactive sojourn around the island when you consider a car rental ($620 USD per week), gas (estimate $300 USD), and a handful of modest hotels every few nights. Remember that all-inclusive packages create an incentive for visitors not to leave the property since you’ve already paid for food and drinks, so it can actually be cheaper to pay for a hotel on a room-only plan and sample a wider selection of cuisine options off property.

3. Where’s the best place to stay for a budget conscious traveler?

Budget accommodations can be found across the island, from rustic cottages in Negril like Westport Cottages and Youth Hostel along Jamaica’s most popular beachfront community, to guesthouses high up in the Blue Mountains like Mount Edge, where $20 USD can afford you a relatively comfortable sleep through the night.

4. Where should you stay if you’re looking to splurge?

Jamaica’s hospitality offering is more geared towards those looking to splurge, with high end suites at some all-inclusive resorts like Sandals Royal Caribbean going for well over 1,000 USD per night for a couple.

Staying at a villa is one of the best ways to feel at home in Jamaica, and the flexibility villa guests enjoy when it comes to menu and activities is limitless. Jamaica also has an excellent offering of villas, perhaps the most diverse in the Caribbean, which can range from affordable when the weekly cost is shared among several guests $500 USD a night, to astronomical at the most ostentatious properties like the Rio Chico, one of the private villas of Sandals founder Gordon “Butch” Stewart, available for rental at $6428 USD a night.

5. What are some of the top music festivals you would recommend?

Conscious reggae lovers won’t want to miss Rebel Salute (January 15), which happens at the Port Kaiser Sports Park in St. Elizabeth. The following week the Jamaica Jazz & Blues Festival (January 23-29) is held just outside Montego Bay at the Greenwood Stadium in Trelawny. Despite the name, it’s only loosely-focused on Jazz and Blues and tends to feature a few big name reggae acts in addition to R&B and classic rock bands. An inaugural three-day reggae festival dubbed Live on the Waterfront (April 22-24) will feature local artists at Pier 1 in Montego Bay. Another highlight of the annual reggae calendar Western Consciousness will be held the following week (April 30) at Paradise Park just outside Savanna-la-Mar in Westmoreland.

6. Where can travelers engage with the history of Jamaica?

Historical sites are scattered all over Jamaica, from ruins of old sugar estate plantations to battle sites where the Spanish and the English clashed. Any serious history buff should spend a good bit of time in Kingston, Spanish Town, and Port Royal, the centers of colonial power which shaped modern Jamaica. The National Gallery holds a permanent collection which gives insight into Jamaica’s changing social and political landscape. The Georgian Society, based in Kingston, is a great resource and schedules somewhat regular tours to historic buildings of the Georgian era in town and around the island.

The most well-preserved Georgian town in the Western Hemisphere is considered to be Falmouth, located in Trelawny within a half-hour’s drive from Montego Bay, where history buffs can benefit from the work a local NGO, Falmouth Heritage Renewal, has been doing over the past 20 years to restore some 34 buildings dating to the high of Jamaica’s colonial slave-based economy and the sugar boom it supported.

7. Where can travelers visit to have a truly local experience?

Treasure Beach along Jamaica’s South Coast in the parish of St. Elizabeth is renowned as the island’s community tourism heartland. This means the tight-knit community has understood since its inception as a tourist destination that many visitors just want to be left alone rather than be bombarded with entertainment, offers, and tours. It’s a low-key place where the local experience is valued by the community members and visitors alike. The local vibe and culture can be soaked up no matter your destination once visitors step outside the boundaries of their resort experience. Unfortunately some hotels actually actively discourage visitors from interacting with the surrounding communities with scare tactics. These are not to be heeded, even if visitors should always keep their head and use common sense.

8. What are some great new restaurants and hotels you would recommend?

Montego Bay’s jerk favorite Scotchies opened a Scotchies Tree in New Kingston. Jo Jo’s Jerk Pit and More in Half Way Tree has quickly become a “vibesy” favorite with a diehard crowd of regulars. The Grog Shoppe Restaurant at Devon House was reborn in late summer under a partnership led by hospitality veterans Gloria Palomino, Tino Caldarelli and Norma Shirley. The most noteworthy new hotel in town is the Spanish Court, where rooms are a bit small but sleek and comfortably appointed.

In Ocho Rios, The Blue House is a wonderful new boutique bed & breakfast which gets rave reviews from guests and immerses visitors in a warm family setting accompanied by great home cooking. For budget vegetarian eats in Ocho Rios, Reggae Pot is a relatively new dependable stop, where “ital” cuisine is served by true-to-the-spirit Rastafarians.

In Montego Bay, three major new resorts have popped up over the past few years, namely Iberostar’s three hotels side-by-side at the eastern edge of the Rose Hall Estate. On Mobay’s Hip Strip, the Altamont West is a comfortable and affordable boutique property that opened relatively recently, and at Freeport, AM Resorts’ Secrets St. James and Secrets Wild Orchid sit adjacent to one another featuring modern décor, excellent food, and west-facing beaches perfect for enjoying sunsets.

Windrush Negril, an intimate bed and breakfast deep on Negril’s West End offers visitors a great escape, with a bocce court, fresh water and salt water pools, and an outdoor kitchen and dining area perfect for entertaining. Moon Dance Cliffs is a new luxury boutique hotel and villa property, also deep on the West End, where hot tubs right outside the villas inspire romance to the sound of crashing waves.