Menu

Top 10 Best North America Sailing Trips

Found 685 Sailing Trips activities in North America. Sort by Popularity. - Page 12
 

Sunset Cruise San José del Cabo

(4.9 of 8 reviews)

Experience the exclusivity and privacy of San José del Cabo, where stunning sunsets paint the sky, creating the perfect backdrop for relaxation and adventure. Spectacular sunset views: Watch the sky light up with vibrant colors ... More

Free Cancellation
Start From $99.00
 
Sunset Cruise San José del Cabo

Sunset Cruise San José del Cabo

  • North America
  • Superb8 reviews4.9

Experience the exclusivity and privacy of San José del Cabo, where stunning sunsets paint the sky, ....

    Free Cancellation
    Start From $99.00
 
 

Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster & Beef menu.

(4.4 of 7 reviews)

Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out of ideas to celebrate love with your partner? Imagine to reconquer your true love. In Cancun you have an incredible opportunity to ... More

Free Cancellation
Start From $95.00
 
Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster & Beef menu.

Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster....

  • North America
  • Exellent7 reviews4.4

Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out o....

    Free Cancellation
    Start From $95.00
 
 

Experience Oceanside Sailing with Whales and dolphins!

(5 of 11 reviews)

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and most comfortable sailboats in the Oceanside harbor. We cater to guests from many of the five star hotels in the area. We serve an up... More

Free Cancellation
Private Tour
Start From $130.00
 
Experience Oceanside Sailing with Whales and dolphins!

Experience Oceanside Sailing with Whales and dolphins!

  • North America
  • Superb11 reviews5

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and mo....

    Free Cancellation
    Private Tour
    Start From $130.00
 
 

12pm Turtle Canyon Snorkel Adventure

(4.8 of 272 reviews)

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

Free Cancellation
Private Tour
Start From $96.30
 
12pm Turtle Canyon Snorkel Adventure

12pm Turtle Canyon Snorkel Adventure

  • North America
  • Superb272 reviews4.8

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....

    Free Cancellation
    Private Tour
    Start From $96.30
 
 

1 hour Private Navigation in Transparent Boat Arco de Los Cabos

(4.4 of 33 reviews)

Get to know the famous Arch of Los Cabos in private mode, where only you and your loved ones will be on the boat, together with the guide and captain, you will be able to enjoy incredible rock formations, tropical fish, reefs, the... More

Free Cancellation
Private Tour
Start From $498.67
 
1 hour Private Navigation in Transparent Boat Arco de Los Cabos

1 hour Private Navigation in Transparent Boat Arco de Los Cabos

  • North America
  • Exellent33 reviews4.4

Get to know the famous Arch of Los Cabos in private mode, where only you and your loved ones will be....

    Free Cancellation
    Private Tour
    Start From $498.67
 
 

Private Key West Sandbar and Paddle by Boat

(4.9 of 31 reviews)

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats and wildlife refuges as well as spot an abundance of marine birds and sea life. Padd... More

Free Cancellation
Private Tour
Start From $600.00
 
Private Key West Sandbar and Paddle by Boat

Private Key West Sandbar and Paddle by Boat

  • North America
  • Superb31 reviews4.9

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch

(4.9 of 41 reviews)

Let yourself be carried away by the wind on an unforgettable adventure through the wonderful Lagoon of 7 Colors. A unique experience to enjoy with family or friends, open bar and lunch. Without engine noises, the sounds of nature... More

Free Cancellation
Private Tour
Start From $63.47
 
Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch

Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch

  • North America
  • Superb41 reviews4.9

Let yourself be carried away by the wind on an unforgettable adventure through the wonderful Lagoon ....

    Free Cancellation
    Private Tour
    Start From $63.47
 
 

Come Sailing with us at Navy Pier: Sail Beautiful Lake Michigan

(5 of 60 reviews)

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

Free Cancellation
Private Tour
Start From $507.96
 
Come Sailing with us at Navy Pier: Sail Beautiful Lake Michigan Likely to Sell Out

Come Sailing with us at Navy Pier: Sail Beautiful Lake Michigan

  • North America
  • Superb60 reviews5

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....

    Free Cancellation
    Private Tour
    Start From $507.96
 
 

Deluxe Turtle Snorkeling Escapade at Waikiki

(4.8 of 5 reviews)

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More

Free Cancellation
Private Tour
Start From $110.00
 
Deluxe Turtle Snorkeling Escapade at Waikiki Likely to Sell Out

Deluxe Turtle Snorkeling Escapade at Waikiki

  • North America
  • Superb5 reviews4.8

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....

    Free Cancellation
    Private Tour
    Start From $110.00
 
 

Windjammer Classic Day Sail from Camden, Maine

(4.7 of 335 reviews)

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations on a modern windjammer. With wide ... More

Free Cancellation
Private Tour
Start From $59.95
 
Windjammer Classic Day Sail from Camden, Maine Likely to Sell Out

Windjammer Classic Day Sail from Camden, Maine

  • North America
  • Superb335 reviews4.7

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

(4.7 of 3 reviews)

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the sky transform into a palette of golden hues as the sun dips be... More

Free Cancellation
Private Tour
Start From $63.00
 
Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms Likely to Sell Out

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

  • North America
  • Superb3 reviews4.7

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....

    Free Cancellation
    Private Tour
    Start From $63.00
 
 

Fort Lauderdale Sailing Charter

(5 of 358 reviews)

Your PRIVATE or SEMI-PRIVATE sailboat charter is hosted by Captain Dan, a licensed captain with 20 years of local sailing experience. For PRIVATE charters, call directly to make arrangements. One to Three passengers bookings are s... More

Free Cancellation
Private Tour
Start From $150.00
 
Fort Lauderdale Sailing Charter Likely to Sell Out

Fort Lauderdale Sailing Charter

  • North America
  • Superb358 reviews5

Your PRIVATE or SEMI-PRIVATE sailboat charter is hosted by Captain Dan, a licensed captain with 20 y....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

4-Hour Sailing Adventure on The Strait of Juan de Fuca

(4.6 of 19 reviews)

Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbacks, Orcas, Sea lions, Seals, Eagles and water birds there is always something to see while you are learning the skills to sail one... More

Free Cancellation
Private Tour
Start From $110.72
 
4-Hour Sailing Adventure on The Strait of Juan de Fuca Likely to Sell Out

4-Hour Sailing Adventure on The Strait of Juan de Fuca

  • North America
  • Superb19 reviews4.6

Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbac....

    Free Cancellation
    Private Tour
    Start From $110.72
 
 

1.5-Hour San Francisco Bay Sailing Tour

(4.8 of 377 reviews)

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with beer and wine. This double-masted, teak-decked, bronze-fitted beauty hold... More

Free Cancellation
Private Tour
Start From $99.00
 
1.5-Hour San Francisco Bay Sailing Tour Likely to Sell Out

1.5-Hour San Francisco Bay Sailing Tour

  • North America
  • Superb377 reviews4.8

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Schooner Apple Jack 2-Hour Day Sail from Boothbay Harbor

(4.3 of 20 reviews)

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we set a c... More

Free Cancellation
Private Tour
Start From $54.95
 
Schooner Apple Jack 2-Hour Day Sail from Boothbay Harbor Likely to Sell Out

Schooner Apple Jack 2-Hour Day Sail from Boothbay Harbor

  • North America
  • Exellent20 reviews4.3

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....

    Free Cancellation
    Private Tour
    Start From $54.95
 
 

Discover Maine's Coastal Charms: Half-Day Scenic Sail

(5 of 3 reviews)

Set sail with us and immerse yourself in the unparalleled beauty of coastal Maine on our half-day excursion. Traverse the serene waters of the Saco River and Saco Bay with its eight gorgeous islands as you uncover their hidden sec... More

Free Cancellation
Private Tour
Start From $270.00
 
Discover Maine's Coastal Charms: Half-Day Scenic Sail Likely to Sell Out

Discover Maine's Coastal Charms: Half-Day Scenic Sail

  • North America
  • Superb3 reviews5

Set sail with us and immerse yourself in the unparalleled beauty of coastal Maine on our half-day ex....

    Free Cancellation
    Private Tour
    Start From $270.00
 
 

Private Sailboat + Captain for a Day Experience

(5 of 548 reviews)

RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY TRIPADVISOR TRAVELER'S CHOICE AWARDS 2022!!! Everyone´s favorite! Enjoy an easy ride around the most relevant landmarks in the lagoon on board of a beautif... More

Free Cancellation
Private Tour
Start From $227.54
 
Private Sailboat + Captain for a Day Experience Likely to Sell Out

Private Sailboat + Captain for a Day Experience

  • North America
  • Superb548 reviews5

RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY TRIPADVISOR TRAVELER'S CHOI....

    Free Cancellation
    Private Tour
    Start From $227.54
 
 

Boat Tour and Snorkel at Pelican Rock

(4.3 of 12 reviews)

The must do activities in Cabo are tour the arch, whale watching and snorkeling. We have put all of those things in one spot in this bucket list level experience. First take a boat tour of all of the landmarks Cabo boasts on the w... More

Free Cancellation
Private Tour
Start From $79.00
 
Boat Tour and Snorkel at Pelican Rock Likely to Sell Out

Boat Tour and Snorkel at Pelican Rock

  • North America
  • Exellent12 reviews4.3

The must do activities in Cabo are tour the arch, whale watching and snorkeling. We have put all of ....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.9 of 102 reviews)

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for... More

Free Cancellation
Private Tour
Start From $125.00
 
2-Hour Oahu Sunset Catamaran Sail Likely to Sell Out

2-Hour Oahu Sunset Catamaran Sail

  • North America
  • Superb102 reviews4.9

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran f....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

San Salvador Spanish Galleon Adventure Day Sail with General Admission

(4.5 of 2 reviews)

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step on board this 16th century Spanish galleon. The San Salvador is a replica of Juan Rodriguez Cabrillo’s ship that arrived at the ... More

Free Cancellation
Private Tour
Start From $119.00
 
San Salvador Spanish Galleon Adventure Day Sail with General Admission Likely to Sell Out

San Salvador Spanish Galleon Adventure Day Sail with General Admi....

  • North America
  • Exellent2 reviews4.5

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step o....

    Free Cancellation
    Private Tour
    Start From $119.00
 
Booking.com
Booking.com
Booking.com