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A traveling must in Cuba is the Lonely Planet guide book and a little bit of basic Spanish will help. Traveling with surf boards is no problem; just take a couple of rubber straps for the taxi's and trucks. Viazul buses will carry your board for free however the train is cheaper, but they will charge you to carry your board in the luggage car about $20 from Havana to Santiago de Cuba.
Late August ,September, October, November are the best months for surfing the south eastern end of the island from Guadalavaca to Baracoa and December to early March are the best months for the Havana and Pinar del Rio regions . A room in Havana will cost you $25-$30 CUC per night and the rest of the country can be between $15-$25 per night and cheaper again for longer stays.
In Havana try Calle 70 or Play Guanabo east of Havana and Varadero has beach breaks. Santiago de Cuba is a great town cheaper than Havana with great night life. The beaches are 19 kilometres out of town, Playa Marv Verde has a left hand point break and Playa Buey Cabon has a left, you can access these beaches by taxi.
Havana, Santiago and Baracoa all have internet access; www.cnnweather.com and www.magicseaweed.com have swell information so you can check the swell forecast for the Caribbean and Atlantic coasts. Cubavision nightly television has a good weather map with satellite images, wind and weather conditions.
Baracoa is a 5 hour Visal bus trip from Santiago and is one of the best towns in Cuba with good lodgings and cheap seafood. In September, October, November the room prices come down between $10 - $15 per night and by buying Cuban peso's you can eat at Cuban restaurants and the peso food stalls.
There are a few breaks around Baracoa at Rio Toa, Rio Duaba and Yumuri 30 kilometres east of town. You can access Yumuri by hire car or taxi, but a cheaper alternative is to take a taxi to the Punta Del Maisi turn off, then take a truck for $1 or one of the private cars that run to Yumuri for $3.