37 days in Caribbean Itinerary

37 days in Caribbean Itinerary

Created using Inspirock Caribbean journey planner

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San Juan, Puerto Rico
— 7 nights
Fly
2
Isla de Vieques, Puerto Rico
— 4 nights
Fly
3
The Bottom, Saba
— 2 nights
Ferry
4
Philipsburg, St. Maarten-St. Martin
— 7 nights
Fly
5
Punta Cana, Dominican Republic
— 6 nights
Fly
6
Seven Mile Beach, Cayman Islands
— 3 nights
Fly
7
Havana, Cuba
— 6 nights
Fly

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San Juan, Puerto Rico

— 7 nights

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Popular historic sites such as Old San Juan and Holocaust Memorial Monument are in your itinerary. Give yourself a bit of retail therapy at Plaza Las Americas and Estudio de Arte Samuel Lind. Change things up with these side-trips from San Juan: Puerto Rico Premium Outlets (in Barceloneta), El Yunque Rain Forest (in El Yunque National Forest) and Palmer (Maji Lina Gallery & Art Center & Coqui International). There's lots more to do: get to know the fascinating history of Sitio Histórico de San Juan, pick up a one of a kind souvenir at El Alcazar, buy something for everyone on your list at Santurce POP, and kick back and relax at Condado Beach.

To see photos, other places to visit, maps, and more tourist information, go to the San Juan trip site.

Cairo, Egypt to San Juan is an approximately 18.5-hour car ride. You can also fly. The time zone difference moving from Eastern European Standard Time (EET) to Atlantic Standard Time (AST) is minus 6 hours. When traveling from Cairo in December, plan for a bit warmer days and warmer nights in San Juan: temperatures range from 34°C by day to 28°C at night. Wrap up your sightseeing on the 10th (Tue) to allow time to travel to Isla de Vieques.

Things to do in San Juan

Shopping · Museums · Historic Sites · Parks

Side Trips

Isla de Vieques, Puerto Rico

— 4 nights

Isla Nena

For sixty years until 2003, most of the Isla de Vieques was closed off to the public, with the US Navy using the island's beaches and surrounding waters for drills and testing of new military machinery, such as bombs.
Head to Serenity Point Yoga & Visionary Arts Space and Siddhia Hutchinson Fine Art Galleryfor plenty of shopping. And it doesn't end there: contemplate the waterfront views at Sun Bay Beach, see some colorful creatures with a scuba or snorkeling tour, stroll through Vieques National Wildlife Refuge, and explore the ancient world of El Hombre de Puerto Ferro.

To see traveler tips, more things to do, and other tourist information, go to the Isla de Vieques tour itinerary builder website.

Fly from San Juan to Isla de Vieques in 2 hours. Alternatively, you can do a combination of car and ferry; or do a combination of shuttle and ferry. In December, daytime highs in Isla de Vieques are 34°C, while nighttime lows are 28°C. Wrap up your sightseeing on the 14th (Sat) to allow time to travel to The Bottom.

Things to do in Isla de Vieques

Outdoors · Parks · Beaches · Shopping

The Bottom, Saba

— 2 nights
Your day by day itinerary now includes The Bottom. Start off your visit on the 15th (Sun): explore the activities along Saba National Marine Park, contemplate the waterfront views at Tide Pools at Flat Point, and then visit The Bottom. On the 16th (Mon), you'll have a packed day of sightseeing: get a taste of the local shopping with Saba Trail Shop, take in the awesome beauty at Mount Scenery, and then take in the architecture and atmosphere at Sacred Heart Church.

Plan a The Bottom trip in moments using our itinerary builder.

You can fly from Isla de Vieques to The Bottom in 6.5 hours. In December, The Bottom is slightly colder than Isla de Vieques - with highs of 26°C and lows of 24°C. Finish up your sightseeing early on the 16th (Mon) so you can catch the ferry to Philipsburg.

Things to do in The Bottom

Nature · Parks · Wildlife · Shopping

Side Trips

Philipsburg, St. Maarten-St. Martin

— 7 nights
Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Do your shopping at Caribbean Gems and Harbour Point Village. Take a break from Philipsburg with a short trip to Cupecoy Bay Beach in Cupecoy Bay, about 30 minutes away. There's lots more to do: get some thrills on the water with a speed boat tour, stroll through Loterie Farm, make a trip to Frontstreet, and view the masterpieces at Minguet Art Gallery.

To see ratings, more things to do, traveler tips, and more tourist information, you can read our Philipsburg day trip site.

Traveling by ferry from The Bottom to Philipsburg takes 2.5 hours. Alternatively, you can fly. Expect a bit warmer temperatures when traveling from The Bottom in December; daily highs in Philipsburg reach 34°C and lows reach 28°C. Wrap up your sightseeing on the 23rd (Mon) early enough to travel to Punta Cana.

Things to do in Philipsburg

Outdoors · Parks · Wildlife · Beaches

Side Trips

Punta Cana, Dominican Republic

— 6 nights
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.
For shopping fun, head to La Perla Dominicana or Palma Real Shopping Village. Get out of town with these interesting Punta Cana side-trips: Scuba & Snorkeling (in Bayahibe) and Altos de Chavon (in La Romana). Spend a day of island exploring on the 27th (Fri) at Saona Island. Spend the 29th (Sun) spotting exotic species with a safari tour. There's still lots to do: fulfill a lifelong dream with a swim-with-the-dolphins experience, enjoy the sand and surf at Bavaro Beach, buy something for everyone on your list at Downtown Punta Cana, and make a trip to Jesus Maestro Parish.

For ratings, where to stay, maps, and more tourist information, refer to the Punta Cana visit planner.

You can fly from Philipsburg to Punta Cana in 6.5 hours. In December, daytime highs in Punta Cana are 34°C, while nighttime lows are 26°C. Wrap up your sightseeing on the 29th (Sun) to allow time to travel to Seven Mile Beach.

Things to do in Punta Cana

Outdoors · Tours · Wildlife · Shopping

Side Trips

Seven Mile Beach, Cayman Islands

— 3 nights
Seven Mile Beach is a long crescent of coral-sand beach on the western end of Grand Cayman island. Head to Guy Harvey Gallery and Shoppe and Davinoff's Concrete Sculpture Gardenfor plenty of shopping. There's lots more to do: tour the pleasant surroundings at Stingray City Grand Cayman, sample the fine beverages at Cayman Spirits Co. Distillery, laugh and play at Cayman Turtle Centre: Island Wildlife Encounter, and see some colorful creatures with a scuba or snorkeling tour.

To find reviews, ratings, traveler tips, and other tourist information, go to the Seven Mile Beach sightseeing tool.

Traveling by flight from Punta Cana to Seven Mile Beach takes 8 hours. Due to the time zone difference, you'll gain 1 hour traveling from Punta Cana to Seven Mile Beach. Expect a daytime high around 34°C in December, and nighttime lows around 28°C. Finish your sightseeing early on the 1st (Wed) so you can travel to Havana.

Things to do in Seven Mile Beach

Parks · Wildlife · Outdoors · Theme Parks

Side Trips

Havana, Cuba

— 6 nights

Rome of the Caribbean

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Shop till you drop at L'Antigua Habana and Espacio de Arte Triana & Usich. Popular historic sites such as Malecón of Havana and El Morro are in your itinerary. Explore the numerous day-trip ideas around Havana: Cayo Largo (Playa Paraiso & Sea Turtle Hatchery). There's still lots to do: don't miss a visit to Old Havana, take in the exciting artwork at Estudio Taller Santacana, take in the local highlights with Walking tours, and contemplate the long history of Old Square (Plaza Vieja).

To find photos, reviews, ratings, and tourist information, use the Havana tour itinerary website.

You can fly from Seven Mile Beach to Havana in 4.5 hours. Traveling from Seven Mile Beach in January, expect a bit cooler with lows of 19°C in Havana. Wrap up your sightseeing on the 7th (Tue) early enough to travel back home.

Things to do in Havana

Historic Sites · Shopping · Parks · Museums

Side Trips