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Top 10 Best North America Sailing Trips

Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 22
 

2 Hour Chesapeake Day Sail on Catamaran Epiphany

(5 of 9 reviews)

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel offers cushioned seating and panoramic views of the Chesapeake Bay. Glide... More

Free Cancellation
Start From $245.00
 
2 Hour Chesapeake Day Sail on Catamaran Epiphany

2 Hour Chesapeake Day Sail on Catamaran Epiphany

  • North America
  • Superb9 reviews5

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. ....

    Free Cancellation
    Start From $245.00
 
 

kayaking in Huatulco

(5 of 6 reviews)

The geographical position favors us to observe whales, dolphins, turtles and much more while sailing in the kayak in calm waters, we have contact with the most 95% of the time on the tour, so it is highly recommended for biologist... More

Free Cancellation
Private Tour
Start From $76.59
 
kayaking in Huatulco

kayaking in Huatulco

  • North America
  • Superb6 reviews5

The geographical position favors us to observe whales, dolphins, turtles and much more while sailing....

    Free Cancellation
    Private Tour
    Start From $76.59
 
 

Private Catamaran: Snorkel, Swim and Dolphin Watching

(5 of 1 review)

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take you to some of the best spots the area has to offer while you are visiting the Emerald Coast.... More

Free Cancellation
Private Tour
Start From $465.00
 
Private Catamaran: Snorkel, Swim and Dolphin Watching Likely to Sell Out

Private Catamaran: Snorkel, Swim and Dolphin Watching

  • North America
  • Superb1 review5

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion....

    Free Cancellation
    Private Tour
    Start From $465.00
 
 

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

(5 of 124 reviews)

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the North side of the island. During the day, this is generally filled with exciting winds for gre... More

Free Cancellation
Private Tour
Start From $485.00
 
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail Likely to Sell Out

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

  • North America
  • Superb124 reviews5

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind....

    Free Cancellation
    Private Tour
    Start From $485.00
 
 

Cozumel Private Snorkeling and Charter Experience

(4.9 of 29 reviews)

We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On this tour, you'll have your own completely private charter visiting the famous 'El Cielo' and other amazing destinations to give you... More

Free Cancellation
Private Tour
Start From $850.00
 
Cozumel Private Snorkeling and Charter Experience Likely to Sell Out

Cozumel Private Snorkeling and Charter Experience

  • North America
  • Superb29 reviews4.9

We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On th....

    Free Cancellation
    Private Tour
    Start From $850.00
 
 

St Augustine Nights of Lights Tour with Live Music and Sunset Opt

(4.6 of 70 reviews)

Fury’s Nights of Lights cruises offer a one-of-a-kind way to experience St. Augustine’s holiday magic from the water, giving guests sweeping, unobstructed views of the illuminated bayfront, the Bridge of Lions, and Castillo de... More

Free Cancellation
Private Tour
Start From $82.69
 
St Augustine Nights of Lights Tour with Live Music and Sunset Opt Likely to Sell Out

St Augustine Nights of Lights Tour with Live Music and Sunset Opt

  • North America
  • Superb70 reviews4.6

Fury’s Nights of Lights cruises offer a one-of-a-kind way to experience St. Augustine’s holiday ....

    Free Cancellation
    Private Tour
    Start From $82.69
 
 

Baltimore Harbor Evening Sail on the Unforgettable

(4.6 of 5 reviews)

Enjoy a beautiful time on the water as you sail through beautiful Baltimore Harbor, take in the gorgeous scenery of the skyline as the city lights up. Treat yourself and a loved one on this elegant sailing experience.  It's BYOB,... More

Free Cancellation
Private Tour
Start From $75.00
 
Baltimore Harbor Evening Sail on the Unforgettable Likely to Sell Out

Baltimore Harbor Evening Sail on the Unforgettable

  • North America
  • Superb5 reviews4.6

Enjoy a beautiful time on the water as you sail through beautiful Baltimore Harbor, take in the gorg....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

Romantic Dinner on a Spanish Galeon in Cancun

(4.3 of 23 reviews)

Live this unique experience in one of the most romantic cities in the world! Enjoy a magical dinner with the most wonderful scenary. This is the perfect opportunity to enjoy a delicious dinner while you fall in love with the liv... More

Free Cancellation
Private Tour
Start From $95.00
 
Romantic Dinner on a Spanish Galeon in Cancun Likely to Sell Out

Romantic Dinner on a Spanish Galeon in Cancun

  • North America
  • Exellent23 reviews4.3

Live this unique experience in one of the most romantic cities in the world! Enjoy a magical dinner ....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Amazing Snorkeling Experience + Real Mexican Tacos

(4.2 of 15 reviews)

This is the classic snorkeling experience when you come to Cancun, it is a must tour in your Itinerary. When you do this experience you feel a connection with nature, it is like taking a little bit of Cancun with you back home. Se... More

Free Cancellation
Private Tour
Start From $39.00
 
Amazing Snorkeling Experience + Real Mexican Tacos Likely to Sell Out

Amazing Snorkeling Experience + Real Mexican Tacos

  • North America
  • Exellent15 reviews4.2

This is the classic snorkeling experience when you come to Cancun, it is a must tour in your Itinera....

    Free Cancellation
    Private Tour
    Start From $39.00
 
 

Vancouver Sailing Tour - Learn the Ropes

(5 of 2 reviews)

Escape to the open waters of Vancouver on a sailing adventure that offers the best of the city’s scenic vistas. This 2.5-3 hour sailing experience takes you through the picturesque False Creek and English Bay, where you’ll be ... More

Free Cancellation
Private Tour
Start From $181.51
 
Vancouver Sailing Tour - Learn the Ropes Likely to Sell Out

Vancouver Sailing Tour - Learn the Ropes

  • North America
  • Superb2 reviews5

Escape to the open waters of Vancouver on a sailing adventure that offers the best of the city’s s....

    Free Cancellation
    Private Tour
    Start From $181.51
 
 

Private Fishing & Snorkeling Boat Charter (Up to 12 pax)

(4.3 of 18 reviews)

Set sail on the ultimate private marine adventure departing from Nuevo Vallarta! Perfect for families or friend groups (1 to 12 passengers), your party will be assigned one of our 4 private vessels based on your group size. This c... More

Free Cancellation
Private Tour
Start From $1,219.00
 
Private Fishing & Snorkeling Boat Charter (Up to 12 pax) Likely to Sell Out

Private Fishing & Snorkeling Boat Charter (Up to 12 pax)

  • North America
  • Exellent18 reviews4.3

Set sail on the ultimate private marine adventure departing from Nuevo Vallarta! Perfect for familie....

    Free Cancellation
    Private Tour
    Start From $1,219.00
 
 

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

(4.9 of 204 reviews)

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat enjoying the fresh air and best that San Diego has to offer. On your adventure yo... More

Free Cancellation
Private Tour
Start From $119.00
 
Luxury Sailing Tour of San Diego's Bay and Coastal Waterways Likely to Sell Out

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

  • North America
  • Superb204 reviews4.9

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling

(4.9 of 113 reviews)

Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Vallarta´s Bay. You will be able to Sail, Snorkel, Swim and even Paddelboard in Los Arcos National Park, capturing beautiful views ... More

Special Offer
Free Cancellation
Private Tour
Start From $927.89
(Saving 10% ) $1,030.99
 
-10% Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling Likely to Sell Out

Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling

  • North America
  • Superb113 reviews4.9

Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Va....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $927.89
    (Saving 10% ) $1,030.99
 
 

Shallow Water Snorkeling and Dolphin Watching in Key West

(4.6 of 472 reviews)

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s weather refunds of course. Premium drinks & snacks included! Enjoy a premium sha... More

Special Offer
Free Cancellation
Private Tour
Start From $108.91
(Saving inf% ) $0.00
 
-inf% Shallow Water Snorkeling and Dolphin Watching in Key West Likely to Sell Out

Shallow Water Snorkeling and Dolphin Watching in Key West

  • North America
  • Superb472 reviews4.6

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 wee....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $108.91
    (Saving inf% ) $0.00
 
 

Luxury Whale Watch Cruise to The Arch Los Cabos

(4.6 of 151 reviews)

Whale season is from mid-December thru mid-April, you can book this tour all year round but to travel only during the Whale Season (Dec 15 thru April 15th). Enjoy 2 hours spectacular adventure looking for whales, who travel thousa... More

Special Offer
Free Cancellation
Private Tour
Start From $95.00
(Saving inf% ) $0.00
 
-inf% Luxury Whale Watch Cruise to The Arch Los Cabos Likely to Sell Out

Luxury Whale Watch Cruise to The Arch Los Cabos

  • North America
  • Superb151 reviews4.6

Whale season is from mid-December thru mid-April, you can book this tour all year round but to trave....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $95.00
    (Saving inf% ) $0.00
 
 

4 hours - Private 48ft Yacht all inclusive in Tulum and Playa del Carmen

(5 of 487 reviews)

We are a Yacht private rental company with more than 15 years of experience in the hospitality industry in Playa del Carmen, Puerto Aventuras and Tulum. Our services are provided with high quality standards to ensure maximum satis... More

Special Offer
Free Cancellation
Private Tour
Start From $1,299.00
(Saving inf% ) $0.00
 
-inf% 4 hours - Private 48ft Yacht all inclusive in Tulum and Playa del Carmen Likely to Sell Out

4 hours - Private 48ft Yacht all inclusive in Tulum and Playa del....

  • North America
  • Superb487 reviews5

We are a Yacht private rental company with more than 15 years of experience in the hospitality indus....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,299.00
    (Saving inf% ) $0.00
 
 

Private Sailing Tour through the Ten Thousands Islands

(4.9 of 156 reviews)

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos where built in the early 80s and are known through out the sailing community as the fastest, driest, beachable catamaran on the ma... More

Special Offer
Free Cancellation
Private Tour
Start From $450.00
(Saving inf% ) $0.00
 
-inf% Private Sailing Tour through the Ten Thousands Islands Likely to Sell Out

Private Sailing Tour through the Ten Thousands Islands

  • North America
  • Superb156 reviews4.9

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $450.00
    (Saving inf% ) $0.00
 
 

Whale-Watching Pirate Ship Cruise in Los Cabos

(4.7 of 119 reviews)

Go whale-watching in Cabo San Lucas aboard a real pirate ship called the Bucaneer Queen. Sail the Pacific Ocean and the Sea of Cortez in search of these amazing creatures. You will be accompanied by an experienced bilingual guide ... More

Special Offer
Free Cancellation
Private Tour
Start From $99.00
(Saving inf% ) $0.00
 
-inf% Whale-Watching Pirate Ship Cruise in Los Cabos Likely to Sell Out

Whale-Watching Pirate Ship Cruise in Los Cabos

  • North America
  • Superb119 reviews4.7

Go whale-watching in Cabo San Lucas aboard a real pirate ship called the Bucaneer Queen. Sail the Pa....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $99.00
    (Saving inf% ) $0.00
 
 

Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling

(5 of 189 reviews)

Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical waters alongside colorful sea life. The bilingual crew is happy to accommodate any special occasion or request. This unforgettable ex... More

Special Offer
Free Cancellation
Private Tour
Start From $850.00
(Saving inf% ) $0.00
 
-inf% Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling Likely to Sell Out

Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling

  • North America
  • Superb189 reviews5

Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical water....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $850.00
    (Saving inf% ) $0.00
 
 

Sunset Catamaran Sail in Cocoa Beach

(4.9 of 185 reviews)

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the beauty of Floridaâ... More

Special Offer
Free Cancellation
Private Tour
Start From $56.49
(Saving inf% ) $0.00
 
-inf% Sunset Catamaran Sail in Cocoa Beach Likely to Sell Out

Sunset Catamaran Sail in Cocoa Beach

  • North America
  • Superb185 reviews4.9

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $56.49
    (Saving inf% ) $0.00
 
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