37 days in Caribbean Itinerary

37 days in Caribbean Itinerary

Created using Inspirock Caribbean journey planner

Plan created by another user. Make it yours
1
San Juan, Puerto Rico
— 7 nights
2
Isla de Vieques, Puerto Rico
— 4 nights
3
The Bottom, Saba
— 2 nights
4
Philipsburg, St. Maarten-St. Martin
— 7 nights
5
Punta Cana, Dominican Republic
— 6 nights
6
Seven Mile Beach, Cayman Islands
— 3 nights
7
Havana, Cuba
— 6 nights

7
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Popular historic sites such as Old San Juan and Sitio Histórico de San Juan are in your itinerary. Give yourself a bit of retail therapy at Plaza Las Americas and Depigment Art. Change things up with these side-trips from San Juan: El Yunque Rain Forest (in El Yunque National Forest), Estudio de Arte Samuel Lind (in Loiza) and Palmer (Maji Lina Gallery & Art Center & Coqui International). There's lots more to do: browse for treasures at El Alcazar, kick back and relax at Condado Beach, view the masterpieces at La Casa de los Contrafuertes, and explore the galleries of The Poet's Passage.

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 19-hour flight. 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

Side Trips

Rio Grande, El Yunque Rain Forest, Estudio de Arte Samuel Lind, San Patricio Plaza, Puerto Rico Premium Outlets
Find places to stay Dec 3 — 10:
Highlights from your plan
Old San Juan ©
Old San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan

4
nights
Isla de Vieques, Puerto Rico

Isla de Vieques ©
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 Fish Marketfor plenty of shopping. The adventure continues: contemplate the waterfront views at Sun Bay Beach, kick back and relax at Media Luna Beach, explore the galleries of Siddhia Hutchinson Fine Art Gallery, and get a new perspective on things with Boat Tours & Water Sports.

For photos, where to stay, reviews, and tourist information, you can read our Isla de Vieques day trip planner.

You can 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. Cap off your sightseeing on the 14th (Sat) early enough to travel to The Bottom.

Things to do in Isla de Vieques

Outdoors · Parks · Beaches
Find places to stay Dec 10 — 14:
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
Vieques National Wildlife Refuge ©
Vieques National Wildlife Refuge
Scuba & Snorkeling

2
nights
The Bottom, Saba

The Bottom ©
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

Side Trips

Windwardside, Saba, Saba National Marine Park
Find places to stay Dec 14 — 16:
Highlights from your plan
The Bottom ©
The Bottom
Saba National Marine Park ©
Saba National Marine Park
Saba Trail Shop ©
Saba Trail Shop

7
nights
Philipsburg, St. Maarten-St. Martin

Philipsburg ©
Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Do your shopping at Caribbean Gems and Tropismes Gallery. The adventure continues: look for all kinds of wild species at Wildlife Areas, stroll through Loterie Farm, kick back and relax at Great Bay Beach, and contemplate the waterfront views at Mullet Bay Beach.

For where to stay, reviews, maps, and tourist information, read our Philipsburg day trip planning site.

Getting from The Bottom to Philipsburg by ferry takes about 2.5 hours. Other options: 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. Finish your sightseeing early on the 23rd (Mon) so you can travel to Punta Cana.

Things to do in Philipsburg

Outdoors · Parks · Wildlife

Side Trips

Saint-Martin, Sint Maarten, Maho, Orient Bay Beach, Tropismes Gallery
Find places to stay Dec 16 — 23:
Highlights from your plan
Caribbean Gems ©
Caribbean Gems
Speed Boats Tours
Loterie Farm ©
Loterie Farm

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.
For shopping fun, head to La Perla Dominicana or Downtown Punta Cana. 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 Palma Real Shopping Village, 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

Side Trips

Saona Island, Scuba & Snorkeling, Altos de Chavon
Find places to stay Dec 23 — 29:
Highlights from your plan
Saona Island ©
Saona Island
Swim with Dolphins
Safaris

3
nights
Seven Mile Beach, Cayman Islands

Seven Mile Beach ©
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

Side Trips

Grand Cayman, George Town, Cayman Turtle Centre: Island Wildlife Encounter, Davinoff's Concrete Sculpture Garden
Find places to stay Dec 29 — Jan 1:
Highlights from your plan
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Scuba & Snorkeling

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.
Shop till you drop at L'Antigua Habana and Taller de Serigrafia Rene Portocarrero. 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 much more to do: make a trip to Old Havana, steep yourself in history at Finca Vigía, get the lay of the land with Walking tours, and take in the exciting artwork at Espacio de Arte Triana & Usich.

Discover how to plan a Havana trip in just a few steps with Inspirock's itinerary builder.

You can fly from Seven Mile Beach to Havana in 4.5 hours. Traveling from Seven Mile Beach in January, plan for little chillier nights in Havana, with lows around 19°C. Finish up your sightseeing early on the 7th (Tue) so you can travel back home.

Things to do in Havana

Historic Sites · Shopping · Parks

Side Trips

Cayo Largo, L'Antigua Habana
Find places to stay Jan 1 — 7:
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Old Square (Plaza Vieja) ©
Old Square (Plaza Vieja)

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