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Your Next Vacation Voyage: Three Itineraries

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Choosing a Starting Point... South Florida

After the year we’ve had, we all deserve to take some time for a much needed getaway. Since everyone has spent months being stuck at home and plans continue to get cancelled, we’ve decided to plan out some dreamy vacations. And since the weather is dropping below freezing all over the US, it’s the perfect time to take advantage of the beautiful weather the Sunshine State — and beyond — has to offer.


There are more registered boats in Florida than any other state, with tens of thousands of out-of-state boats visiting Florida waters every day. Florida easily accommodates this traffic with over 2,000 miles of coastline, making it the perfect boating destination in the United States. As the southernmost part of the continental United States, Florida is also a great starting point for longer, non-domestic travel by boat.


We’ve put together a few possible itineraries for your next boating excursion that starts and ends in the Sunshine State. With travel options that can be as short as a single day trip or as long as a couple weeks, these routes around the Atlantic and Caribbean are worth checking out before planning your next seafaring vacation.

Since all of our destinations are further south, we suggest starting off in South Florida. Particularly the cities of Fort Lauderdale and Miami are the most popular places to port due to its extensive coastline, intricate channels, and exciting on-land attractions. Fort Lauderdale has more than 300 miles of inland waterways and is home to over 40,000 yachts. Miami, only about 25 miles south of Fort Lauderdale, is also a common starting point due to the beautiful waters and fun, bustling atmosphere. If you decide to port in one of these two cities, be sure to allot some extra time to experience these amazing destination spots.


If your party enjoys scuba diving or deep-sea fishing, the Florida Keys might be perfect for you. Key Largo is popular among divers for it’s coral reefs and shipwrecks, while Islamorada boasts being the sportfishing capital of the world. Cushion your trip with a couple days on the front- or back-end to take advantage of the beautiful waters and extraordinary sunsets that the Florida Keys have to offer.

Popular marinas in South Florida include:

 

 

  • IGY Marina Fort Lauderdale
  • Sunrise Harbor Marina Fort Lauderdale
  • Miami Beach Marina
  • Sunset Harbor Yacht Club Miami
  • Key West Harbor
  • Marina Key West
 
Swimming Pigs in Bahamas

The Island Route:
Bahamas, Turks & Caicos

If you’re looking to take a short trip, maybe over the weekend, the Bimini Islands in the Bahamas are the perfect destination. They are the closest Bahamian islands to the United States — only about 50 nautical miles from Fort Lauderdale or Miami. Commonly referred to as simply ‘Bimini’, the two main islands, North Bimini and South Bimini, are known for the beautiful beaches and incredible ecosystems that have developed around the several old, off-shore shipwrecks.

 

Bimini is also rich with both history and legend; it is rumored that Ponce de León sailed to Bimini in the 1500s in search of the Fountain of Youth. Many have also found inspiration on the white sandy beaches for famous works including Ernest Hemingway, Dr. Martin Luther King Jr., and Jimmy Buffet.

 

We recommend at least two days for this trip, though the actual sailing can take as little as two hours each way, depending on the boat. Since you’ll have to travel through the Gulf Stream to reach the Bahamas, we also recommend checking weather conditions on the water within a day of your departure. Due to the strength of the Gulf Stream current, we recommend an indirect route that won’t have your crew fighting the course of the water the whole way to Bimini. The easiest way to get past the Gulf Stream is to cross it straight east from Miami before heading south to the Bahamas in calmer waters.

Once you’re there, we suggest taking the time to really explore the shoreline before diving into the water to explore the ocean life. The deep waters surrounding Bimini and many other Bahamian islands also make this destination ideal for fishing. Bimini is perfect for a weekend fishing trip, or an ideal stop on a fishing tour that can include other spots in the Bahamas like Grand Bahama, Nassau, Exuma, and Andros Island. The Bahamas are also an idyllic place to explore the water by scuba diving, snorkeling, kayaking, and so much more.

Don’t forget these important items while you pack:

 

  • Valid passport, properly stamped and dated
  • Medications, including ones for seasickness
  • Personal floatation devices (PFDs) for everyone on board
  • Gear for fishing, including fishing license and cooler

 

 

  • Sunscreen and lightweight, long-sleeve shirts and pants to block harmful UV rays
  • Sunglasses, preferably polarized for more protection
  • First aid kit
  • Equipment for snorkeling, scuba diving, etc.
Caribbean Sunset

The West Caribbean Route:
Havana, Cuba & Tulum, Mexico

Most cruise lines make the same popular stops along the western Caribbean including Grand Cayman, Cozumel, or Costa Maya. For a more unique and less tourist-filled destination, we suggest a weeklong trip to Havana with an optional, more ambitious second stop (for those who can handle multiple days at sea) in Tulum. 

 

Both boast their own eclectic energy and offer a wide variety of activities for all to enjoy. And even if you plan to spend most of your time on or near the water, Havana and Tulum both have some of the most beautiful white sand beaches (with stunning turquoise waters) in the area.

 

Both stops are also rich with ancient history and modern flare.

Havana, Cuba’s capital, is home to beautiful Spanish colonial architecture that dates back to the 16th century, which is a beautiful juxtaposition to its buzzing nightlife.

 

Tulum has become a very trendy destination in the past few years, and for good reason. On the coastline of Mexico’s Yucatán Peninsula, Tulum was once a Mayan port city with rich nautical history. The ancient Mayan ruins are well preserved and make for great exploring once on land. 

As far as travel plans, we suggest leaving from the Florida Keys. Havana measures about 91 nautical miles from Key West as opposed to about 222 nautical miles from Fort Lauderdale. From Key West, the trip takes about 4 hours depending on the type of boat, water conditions, etc. We suggest allocating the first half of your day to make it to Havana, with plenty of time to enjoy the sunset from Havana’s beaches or many waterfront restaurants.

 

From Havana, the trip to Tulum is much longer and can take as much time as 2-4 days. With about 347 nautical miles between the two destinations, you have the option to stay out at sea for the duration of the voyage, or make pit stops along the way along the coast of Cuba, Cancún, or the beautiful island of Cozumel.

Beach of Dominican Republic

The East Caribbean Route:
Dominican Republic

For a longer voyage, taking your time to sail through the Caribbean Sea is a must.

 

The Caribbean is one of the most highly travelled areas in the world, especially by boat, with over 2 million annual travelers. There, you can enjoy warm weather and fair boating conditions year-round, making it a great destination for anyone with flexible travel dates. 

 

To take a vacation in a climate totally different than what you’ll find in the continental United States, we suggest a tropical trip to the Dominican Republic.

 

Puerto Plata, a popular docking point in the Dominican Republic, is about 840 nautical miles from Miami. At a speed of 10 knots, the trip can take a few days. We suggest stopping in the Bahamas, along the northern coast of Cuba, or even at Port-de-Paix in Haiti before arriving in the DR.

 

For smoother sailing, traveling in November or December (after hurricane season) is best. The travel conditions on the water tend to be calmer. Plus, who wouldn’t want a long holiday trip to somewhere warm and sunny? After a year like 2020, you deserve it.

With this trip especially, it’s important that you have an experienced crew and plan for many variables. For example, provisions will need to be carefully planned – we suggest doubling the amount of necessary food, water, and supplies just in case there are unforeseen delays or hiccups during travel.

Your Next Vacation Voyage:
Three Itineraries

anchor in the water

Choosing a Starting Point... South Florida

After the year we’ve had, we all deserve to take some time for a much needed getaway. Since everyone has spent months being stuck at home and plans continue to get cancelled, we’ve decided to plan out some dreamy vacations. And since the weather is dropping below freezing all over the US, it’s the perfect time to take advantage of the beautiful weather the Sunshine State — and beyond — has to offer.


There are more registered boats in Florida than any other state, with tens of thousands of out-of-state boats visiting Florida waters every day. Florida easily accommodates this traffic with over 2,000 miles of coastline, making it the perfect boating destination in the United States. As the southernmost part of the continental United States, Florida is also a great starting point for longer, non-domestic travel by boat.


We’ve put together a few possible itineraries for your next boating excursion that starts and ends in the Sunshine State. With travel options that can be as short as a single day trip or as long as a couple weeks, these routes around the Atlantic and Caribbean are worth checking out before planning your next seafaring vacation.

Since all of our destinations are further south, we suggest starting off in South Florida. Particularly the cities of Fort Lauderdale and Miami are the most popular places to port due to its extensive coastline, intricate channels, and exciting on-land attractions. Fort Lauderdale has more than 300 miles of inland waterways and is home to over 40,000 yachts. Miami, only about 25 miles south of Fort Lauderdale, is also a common starting point due to the beautiful waters and fun, bustling atmosphere. If you decide to port in one of these two cities, be sure to allot some extra time to experience these amazing destination spots.


If your party enjoys scuba diving or deep-sea fishing, the Florida Keys might be perfect for you. Key Largo is popular among divers for it’s coral reefs and shipwrecks, while Islamorada boasts being the sportfishing capital of the world. Cushion your trip with a couple days on the front- or back-end to take advantage of the beautiful waters and extraordinary sunsets that the Florida Keys have to offer.

Popular marinas in South Florida include:

 

 

  • IGY Marina Fort Lauderdale
  • Sunrise Harbor Marina Fort Lauderdale
  • Miami Beach Marina
  • Sunset Harbor Yacht Club Miami
  • Key West Harbor
  • Marina Key West
 
Swimming Pigs in Bahamas

The Island Route:
Bahamas, Turks & Caicos

If you’re looking to take a short trip, maybe over the weekend, the Bimini Islands in the Bahamas are the perfect destination. They are the closest Bahamian islands to the United States — only about 50 nautical miles from Fort Lauderdale or Miami. Commonly referred to as simply ‘Bimini’, the two main islands, North Bimini and South Bimini, are known for the beautiful beaches and incredible ecosystems that have developed around the several old, off-shore shipwrecks.

 

Bimini is also rich with both history and legend; it is rumored that Ponce de León sailed to Bimini in the 1500s in search of the Fountain of Youth. Many have also found inspiration on the white sandy beaches for famous works including Ernest Hemingway, Dr. Martin Luther King Jr., and Jimmy Buffet.

 

We recommend at least two days for this trip, though the actual sailing can take as little as two hours each way, depending on the boat. Since you’ll have to travel through the Gulf Stream to reach the Bahamas, we also recommend checking weather conditions on the water within a day of your departure. Due to the strength of the Gulf Stream current, we recommend an indirect route that won’t have your crew fighting the course of the water the whole way to Bimini. The easiest way to get past the Gulf Stream is to cross it straight east from Miami before heading south to the Bahamas in calmer waters.

Once you’re there, we suggest taking the time to really explore the shoreline before diving into the water to explore the ocean life. The deep waters surrounding Bimini and many other Bahamian islands also make this destination ideal for fishing. Bimini is perfect for a weekend fishing trip, or an ideal stop on a fishing tour that can include other spots in the Bahamas like Grand Bahama, Nassau, Exuma, and Andros Island. The Bahamas are also an idyllic place to explore the water by scuba diving, snorkeling, kayaking, and so much more.

Don’t forget these important items while you pack:

 

  • Valid passport, properly stamped and dated
  • Medications, including ones for seasickness
  • Personal floatation devices (PFDs) for everyone on board
  • Gear for fishing, including fishing license and cooler

 

 

  • Sunscreen and lightweight, long-sleeve shirts and pants to block harmful UV rays
  • Sunglasses, preferably polarized for more protection
  • First aid kit
  • Equipment for snorkeling, scuba diving, etc.
Caribbean Sunset

The West Caribbean Route:
Havana, Cuba & Tulum, Mexico

Most cruise lines make the same popular stops along the western Caribbean including Grand Cayman, Cozumel, or Costa Maya. For a more unique and less tourist-filled destination, we suggest a weeklong trip to Havana with an optional, more ambitious second stop (for those who can handle multiple days at sea) in Tulum. 

 

Both boast their own eclectic energy and offer a wide variety of activities for all to enjoy. And even if you plan to spend most of your time on or near the water, Havana and Tulum both have some of the most beautiful white sand beaches (with stunning turquoise waters) in the area.

 

Both stops are also rich with ancient history and modern flare.

Havana, Cuba’s capital, is home to beautiful Spanish colonial architecture that dates back to the 16th century, which is a beautiful juxtaposition to its buzzing nightlife.

 

Tulum has become a very trendy destination in the past few years, and for good reason. On the coastline of Mexico’s Yucatán Peninsula, Tulum was once a Mayan port city with rich nautical history. The ancient Mayan ruins are well preserved and make for great exploring once on land. 

As far as travel plans, we suggest leaving from the Florida Keys. Havana measures about 91 nautical miles from Key West as opposed to about 222 nautical miles from Fort Lauderdale. From Key West, the trip takes about 4 hours depending on the type of boat, water conditions, etc. We suggest allocating the first half of your day to make it to Havana, with plenty of time to enjoy the sunset from Havana’s beaches or many waterfront restaurants.

 

From Havana, the trip to Tulum is much longer and can take as much time as 2-4 days. With about 347 nautical miles between the two destinations, you have the option to stay out at sea for the duration of the voyage, or make pit stops along the way along the coast of Cuba, Cancún, or the beautiful island of Cozumel.

Beach of Dominican Republic

The East Caribbean Route:
Dominican Republic

For a longer voyage, taking your time to sail through the Caribbean Sea is a must.

 

The Caribbean is one of the most highly travelled areas in the world, especially by boat, with over 2 million annual travelers. There, you can enjoy warm weather and fair boating conditions year-round, making it a great destination for anyone with flexible travel dates. 

 

To take a vacation in a climate totally different than what you’ll find in the continental United States, we suggest a tropical trip to the Dominican Republic.

 

Puerto Plata, a popular docking point in the Dominican Republic, is about 840 nautical miles from Miami. At a speed of 10 knots, the trip can take a few days. We suggest stopping in the Bahamas, along the northern coast of Cuba, or even at Port-de-Paix in Haiti before arriving in the DR.

 

For smoother sailing, traveling in November or December (after hurricane season) is best. The travel conditions on the water tend to be calmer. Plus, who wouldn’t want a long holiday trip to somewhere warm and sunny? After a year like 2020, you deserve it.

With this trip especially, it’s important that you have an experienced crew and plan for many variables. For example, provisions will need to be carefully planned – we suggest doubling the amount of necessary food, water, and supplies just in case there are unforeseen delays or hiccups during travel.