31 days in Bahamas & Caribbean Itinerary

31 days in Bahamas & Caribbean Itinerary

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Route & dates

31 days in Bahamas & Caribbean Itinerary

Start: Philadelphia, United States
Fly:  6​h 45​min
1
Nassau, Bahamas
— 5 nights
+3
Fly + bus + foot + bus:  8​h 30​min
2
Ocho Rios, Jamaica
— 6 nights
bus + Fly:  7​h 15​min
3
Havana, Cuba
— 6 nights
Fly:  6​h
4
Punta Cana, Dominican Republic
— 6 nights
Fly:  4​h 30​min
5
San Juan, Puerto Rico
— 6 nights
Fly:  6​h 45​min
End: Philadelphia, United States


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5
nights
Nassau, Bahamas

On a trip to Nassau you can immerse yourself in a dynamic city atmosphere or spend your days lazing on the soft golden sands.
Your inner history buff will appreciate Christ Church Cathedral and St. Francis Xavier Cathedral. Take a break from the city and head to Arawak Cay and Jaws Beach. There's lots more to do: enjoy the sand and surf at Western Esplande Beach, admire the masterpieces at Junkanoo World Museum & Arts Centre, get engrossed in the history at The Heritage Museum of the Bahamas, and view the masterpieces at The National Art Gallery of The Bahamas.

To see photos, maps, other places to visit, and more tourist information, use the Nassau trip planner .

Philadelphia, USA to Nassau is an approximately 7-hour flight. You can also do a combination of train and flight; or do a combination of train and flight. Traveling from Philadelphia in June, you can expect nighttime temperatures to be somewhat warmer in Nassau, with lows of 76°F. Cap off your sightseeing on the 6th (Thu) early enough to travel to Ocho Rios.

Things to do in Nassau

Outdoors Parks Beaches

Side Trips

Paradise Island, Love Beaches
Find places to stay Jun 1 — 6:
Highlights from your plan
Parasailing & Paragliding
Arawak Cay ©
Arawak Cay
Western Esplande Beach ©
Western Esplande Beach

6
nights
Ocho Rios, Jamaica

A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
Step out of the city life by going to Burwood Beach and Silver Sands Public Beach. Get some historical perspective at Good Hope Plantation and Our Lady of Fatima Catholic Church. Step out of Ocho Rios to go to Montego Bay and see Greenwood Great House, which is approximately 1h 55 min away. Pack the 7th (Fri) with family-friendly diversions at Rainforest Adventures. There's much more to do: brush up on your knowledge of spirits at Appleton Estate, take in nature's colorful creations at Shaw Park Gardens & Waterfalls, admire the sheer force of Little Dunn's River Falls, and kick back and relax at Bamboo Beach Club.

For ratings, maps, traveler tips, and other tourist information, refer to the Ocho Rios trip planner .

You can do a combination of flight and bus from Nassau to Ocho Rios in 8.5 hours. Expect a daytime high around 90°F in June, and nighttime lows around 78°F. Finish up your sightseeing early on the 12th (Wed) so you can travel to Havana.

Things to do in Ocho Rios

Outdoors Theme Parks Parks

Side Trips

Greenwood Great House, Good Hope Plantation, Appleton Estate, Silver Sands Public Beach, Burwood Beach
Find places to stay Jun 6 — 12:
Highlights from your plan
Scuba & Snorkeling
Burwood Beach ©
Burwood Beach
Silver Sands Public Beach ©
Silver Sands Public Beach

6
nights
Havana, Cuba

Havana
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Step off the beaten path and head to Fusterlandia and Palacio De Los Capitanes Generales. Get some cultural insight at Plaza de Armas and La Iglesia de San Agustin o San Francisco el Nuevo. Explore the numerous day-trip ideas around Havana: Matanzas (Cuevas de Bellamar, Callejon de las Tradiciones, & more) and Cardenas Cathedral (in Cardenas). There's still lots to do: take in the spiritual surroundings of Church and Convent of St. Francis of Asisi, see the interesting displays at Museo Napoleonico, wander the streets of Central Havana, and don't miss a visit to Calle Obispo.

To find where to stay, ratings, photos, and more tourist information, you can read our Havana vacation maker site .

Traveling by combination of bus and flight from Ocho Rios to Havana takes 7.5 hours. Traveling from Ocho Rios in June, plan for little chillier nights in Havana, with lows around 72°F. Wrap up your sightseeing on the 18th (Tue) early enough to travel to Punta Cana.

Things to do in Havana

Neighborhoods Historic Sites Museums

Side Trips

Matanzas, Cardenas Cathedral
Find places to stay Jun 12 — 18:
Highlights from your plan
Central Havana
Central Havana
Palacio De Los Capitanes Generales ©
Palacio De Los Capitanes Generales

6
nights
Punta Cana, Dominican Republic

Punta Cana ©
In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.
Get in touch with nature at Juanillo Beach and Parasailing & Paragliding. Your cultural itinerary includes sights like Basilica Catedral Nuestra Senora de la Altagracia and Parroquia de San Dionisio. Venture out of the city with trips to Cueva de las Maravillas (in El Soco), Playa Mariposa (in La Romana) and National Park of the East (in Bayahibe). There's lots more to do: identify plant and animal life at Indigenous Eyes Ecological Park & Reserve, tee off at Hard Rock Golf Club, and look for gifts at Don Lucas Cigars.

To see other places to visit, photos, and more tourist information, read Punta Cana trip site .

Traveling by flight from Havana to Punta Cana takes 6 hours. Alternatively, you can do a combination of flight and shuttle. You'll lose 1 hour traveling from Havana to Punta Cana due to the time zone difference. Expect a daytime high around 87°F in June, and nighttime lows around 76°F. Cap off your sightseeing on the 24th (Mon) early enough to travel to San Juan.

Things to do in Punta Cana

Outdoors Parks Golf

Side Trips

Higuey, Cueva de las Maravillas, National Park of the East, Playa Mariposa
Find places to stay Jun 18 — 24:
Highlights from your plan
Juanillo Beach ©
Juanillo Beach
National Park of the East ©
National Park of the East
Cueva de las Maravillas ©
Cueva de las Maravillas

6
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Take a break from the city and head to Waterskiing & Jetskiing and La Mina Falls. Visit Paseo de la Princesa and Parroquia Sagrado Corazon de Jesus for their historical value. Get out of town with these interesting San Juan side-trips: Kayaking & Canoeing (in Fajardo), Zipline (in Rio Grande) and Luquillo (Monkey Threads & Balneario Luquillo). There's lots more to do: Head underground at La Cueva del Indio, view the masterpieces at The Poet's Passage, find your balance on the water with some of the best stand-up paddleboarding in the area, and relax and rejuvenate at some of the top local wellness centers.

For more things to do, traveler tips, reviews, and more tourist information, use the San Juan trip itinerary planner.

Fly from Punta Cana to San Juan in 4.5 hours. Alternatively, you can do a combination of shuttle and flight; or do a combination of bus and ferry. In June, plan for daily highs up to 89°F, and evening lows to 78°F. Finish up your sightseeing early on the 30th (Sun) so you can travel back home.

Things to do in San Juan

Outdoors Parks Adventure

Side Trips

Fajardo, Arecibo, Luquillo, Cascada La Mina (La Mina Falls), Zipline
Find places to stay Jun 24 — 30:
Highlights from your plan
Paseo de la Princesa ©
Paseo de la Princesa
Waterskiing & Jetskiing
Zipline

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