Formerly Carefree Vacations
email
phone 1.800.266.3476
3271-3280 of 8167 results

Land Offers

Italy
8-Nights Rome and Tuscan Highlights
Italy
Trafalgar
Vacation Offer ID 1519214
Reference this number when contacting our travel specialist.
From $2,574
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Promotions

Special Promotion: 2026 on Sale | Save 10%* on select 2026 premium departures

Valid for new bookings deposited Now – July 31, 2025 for travel January 1, 2026 – December 31, 2026.

*Promotion may not be combinable with any other offers, promotions, or discounts, and is subject to availability. Other restrictions may apply. 
Italy
6-Nights Italy: Tuscany & Umbria
Italy
Country Walkers
Vacation Offer ID 1533737
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Promotions

Exclusive Amenity: Receive $50 Gift Code to Use at New Headings Online Outdoor Gear Shop

Valid on new bookings deposited now – December 31, 2025 for travel anytime. 

Other restrictions may apply. Contact your travel advisor about this Signature Exclusive Amenity.
Italy
8-Nights The Amalfi Coast - Privately Guided
Italy
Alexander+Roberts
Vacation Offer ID 1461324
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From $7,599
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Promotions

Exclusive Amenity: Receive $200 Per Couple or $100 Per Person on any Pre or Post Stay Extension to an Alexander+Roberts Small Group Journey, Small Ship Journey, or Private Journey

Valid on new bookings deposited now – December 31, 2025, for travel anytime. 

Other restrictions may apply. Contact your travel advisor about this Signature Exclusive Amenity.

Special Promotion: Ask your travel advisor about additional savings when you Pay-in-Full.

Valid for new bookings deposited Now – December 31, 2025 for travel from Now – December 31, 2026.

Valid on any Small Group, Small Ship, or Private Journeys.

*Promotion may be combinable with other offers, promotions, or discounts, and is subject to availability. Other restrictions may apply. 
Italy
8-Nights Country Roads of Umbria & Tuscany - Classic Group
Italy
Insight Vacations
Vacation Offer ID 1517258
Reference this number when contacting our travel specialist.
From $3,495
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Promotions

Special Promotion: 2026 on Sale | Save 10%* on select 2026 premium departures

Valid for new bookings deposited Now – July 31, 2025 for travel January 1, 2026 – December 31, 2026.

*Promotion may not be combinable with any other offers, promotions, or discounts, and is subject to availability. Other restrictions may apply. 
Italy
5-Nights Italy: The Dolomites, Bolzano to Ora
Italy
VBT Bicycling Vacations
Vacation Offer ID 1540314
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Promotions

Exclusive Amenity: Receive $50 Gift Code to Use at New Headings Online Outdoor Gear Shop

Valid on new bookings deposited now – December 31, 2025 for travel anytime. 

Other restrictions may apply. Contact your travel advisor about this Signature Exclusive Amenity.
Italy
16-Nights Grand Italian Experience
Italy
Trafalgar
Vacation Offer ID 1519186
Reference this number when contacting our travel specialist.
From $5,079
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Promotions

Special Promotion: 2026 on Sale | Save 10%* on select 2026 premium departures

Valid for new bookings deposited Now – July 31, 2025 for travel January 1, 2026 – December 31, 2026.

*Promotion may not be combinable with any other offers, promotions, or discounts, and is subject to availability. Other restrictions may apply. 
Italy
6-Nights Italy: Puglia’s Undiscovered Coast
Italy
VBT Bicycling Vacations
Vacation Offer ID 1538589
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Call for pricing
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Promotions

Exclusive Amenity: Receive $50 Gift Code to Use at New Headings Online Outdoor Gear Shop

Valid on new bookings deposited now – December 31, 2025 for travel anytime. 

Other restrictions may apply. Contact your travel advisor about this Signature Exclusive Amenity.
Italy
9-Nights Great Italian Cities
Italy
Trafalgar
Vacation Offer ID 1519188
Reference this number when contacting our travel specialist.
From $3,102
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Promotions

Special Promotion: 2026 on Sale | Save 10%* on select 2026 premium departures

Valid for new bookings deposited Now – July 31, 2025 for travel January 1, 2026 – December 31, 2026.

*Promotion may not be combinable with any other offers, promotions, or discounts, and is subject to availability. Other restrictions may apply. 
Italy
9-Nights Best of Italy: Rome, Florence, and Venice
Italy
Avanti Destinations
Vacation Offer ID 1233759
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Italy
8-Nights Country Roads of Umbria & Tuscany - Small Group
Italy
Insight Vacations
Vacation Offer ID 1517259
Reference this number when contacting our travel specialist.
From $3,273
Request a Quote View Details
Promotions

Special Promotion: 2026 on Sale | Save 10%* on select 2026 premium departures

Valid for new bookings deposited Now – July 31, 2025 for travel January 1, 2026 – December 31, 2026.

*Promotion may not be combinable with any other offers, promotions, or discounts, and is subject to availability. Other restrictions may apply.